PRODUCTS

AMINOMETHYLCYCLOHEXANECARBOXYLIC ACID

Aminomethylcyclohexanecarboxylic acid is a synthetic derivative of the amino acid lysine that functions as an antifibrinolytic agent by reversibly binding to lysine receptor sites on plasminogen, thereby inhibiting its activation to plasmin and preventing the breakdown of fibrin clots.
Clinically, Aminomethylcyclohexanecarboxylic acid is widely used to reduce excessive bleeding in conditions such as heavy menstrual bleeding, trauma, surgery, dental procedures in patients with bleeding disorders, and hereditary angioedema, while also gaining importance in dermatology for treating melasma and hyperpigmentation.
The global Aminomethylcyclohexanecarboxylic acid market, valued at around USD 520 million to 1.03 billion in 2024, is projected to reach up to USD 1.86 billion by 2035, driven by rising surgical procedures, demand for non-hormonal treatments, and expanding dermatological applications.

CAS Number: 1197-18-8
EC Number: 214-818-2
Molecular Formula: C8H15NO2
Molecular Weight: 157.21 g/mol

Synonyms: tranexamic acid, 1197-18-8, trans-4-(Aminomethyl)cyclohexanecarboxylic acid, 1197-17-7, Cyklokapron, 701-54-2, 4-(Aminomethyl)cyclohexanecarboxylic acid, Trans AMCHA, Transamin, Amstat, Tranhexamic acid, Tranexamsaeure, Cyclocapron, trans-Amcha, Rikavarin, Tamcha, Amikapron, Anvitoff, cis-Tranexamic Acid, Ugurol, AMCA, AMCHA, cis-4-(Aminomethyl)cyclohexanecarboxylic acid, Frenolyse, Trasamlon, Carxamin, Emorhalt, Tranexan, Mastop, Rikavarin-S, Exacyl, tranexmic acid, Cyclohexanecarboxylic acid, 4-(aminomethyl)-, trans-, trans-Tranexamic acid, 4-(aminomethyl)cyclohexane-1-carboxylic acid, Hexapromin, Transamlon, Hexatron, Spiramin, Tranex, cis-AMCHA, trans-4-Aminomethylcyclohexane-1-carboxylic acid, Acido tranexamico, Acide tranexamique, Acidum tranexamicum, Lysteda, Cyclohexanecarboxylic acid, 4-(aminomethyl)-, cis-, CL 65336, Femstrual, cis-4-Aminomethylcyclohexane-1-carboxylic acid, BAY 3517, Cyclo-F, RP 18,429, Cyclohexanecarboxylic acid, 4-(aminomethyl)-, 4-(Aminomethyl)-Cyclohexanecarboxylic Acid, Tranexamic Acid(Random Configuration), Cyclokapron, Espercil, Haematrix, (1r,4r)-4-(aminomethyl)cyclohexane-1-carboxylic acid, trans-p-(Aminomethyl)cyclohexanecarboxylic acid, cis-4-(aminomethyl)cyclohexane-1-carboxylic acid, CL-65336, DV 79, MFCD00001466, HAKU, DV79, trans-4-(Aminomethyl)-1-cyclohexanecarboxylic acid, trans-4-(Aminomethyl)cyclohexane-1-carboxylic acid, LB1148, MFCD19706018, NSC-291305, trans-1-(Aminomethyl)cyclohexane-4-carboxylic acid, Tranexamic acid (Transamin), DTXSID3045350, Retavase, CHEBI:48669, 37YD696II6, 6T84R30KC1, NSC291305, trans-4-(Aminomethyl)cyclohexanecarboxylic acid ester, 4-aminomethylcyclohexanecarboxylic acid, CL65336, NCGC00016569-01, RP-18429, CAS-1197-18-8, AMH, Tranexamic acid cis-form, Acide tranexamique [INN-French], Acido tranexamico [INN-Spanish], Acidum tranexamicum [INN-Latin], DV-79, Cyklokapron (TN), Rikavarin (TN), Transamin (TN), SR-05000001794, EINECS 214-818-2, trans-1-Aminomethylcyclohexane-4-carboxylic acid, NSC 291305, BRN 2207452, tranexamate, tranexamic-acid, UNII-37YD696II6, UNII-6T84R30KC1, 1ceb, Prestwick_476, ALBB-006013, Spectrum_001391, Tranexamic acid [USAN:USP:INN:BAN:JAN], Prestwick0_000171, Prestwick1_000171, Prestwick2_000171, Prestwick3_000171, Spectrum2_000655, Spectrum3_001189, Spectrum4_000046, Spectrum5_001258, CHEMBL877, Tranexamic acid (Standard), trans-4-(Aminomethyl)cyclohexane-carboxylic acid, Oprea1_786414, SCHEMBL16974, BSPBio_000061, BSPBio_002837, KBioGR_000511, KBioSS_001871, TRANEXAMIC ACID [MI], 3-14-00-00868 (Beilstein Handbook Reference), CIS-4-(AMINOMETHYL)CYCLOHEXANECARBOXYLICACID, DivK1c_000655, SCHEMBL186034, SCHEMBL349408, SPECTRUM1502026, TRANEXAMIC ACID [INN], TRANEXAMIC ACID [JAN], TRANEXAMIC ACID, CIS-, SPBio_000689, SPBio_001982, TRANEXAMIC ACID [USAN], Tranexamic Acid EP Impurity B, BPBio1_000069, CHEMBL292500, GTPL6573, SCHEMBL6885575, SCHEMBL9885628, 701-54-2 (cis+trans), TRANEXAMIC ACID [VANDF], TRANEXAMIC ACID [MART.], CHEBI:94518, HMS502A17, HY-B0149R, KBio1_000655, KBio2_001871, KBio2_004439, KBio2_007007, KBio3_002337, DTXSID50904827, TRANEXAMIC ACID [USP-RS], TRANEXAMIC ACID [WHO-DD], WLN: L6TJ AVQ D1Z -T, GYDJEQRTZSCIOI-KNVOCYPGSA-N, GYDJEQRTZSCIOI-UHFFFAOYSA-N, NINDS_000655, DTXCID401333941, GLXC-10248, HMS1568D03, HMS1921F08, HMS2092P03, HMS2095D03, HMS3712D03, HMS3744G07, Pharmakon1600-01502026, BCP13133, BCP18146, HY-A0102, HY-B0149, SBC83795, Tox21_110500, BBL004469, BDBM50428067, CCG-39692, MFCD00064951, NSC758176, s1875, STK503668, TRANEXAMIC ACID [ORANGE BOOK], AKOS005171632, AKOS015854573, AKOS024257901, TRANEXAMIC ACID [EP MONOGRAPH], TRANEXAMIC ACID [USP IMPURITY], TRANEXAMIC ACID CIS-FORM [MI], AB86495, AC-4687, BS-3867, CS-1965, DB00302, FT29666, IA71533, LB-1148, NSC-758176, TRANEXAMIC ACID [USP MONOGRAPH], 4-(Aminomethyl)cyclohexanecarboxylicacid, 4-Aminomethyl-cyclohexanecarboxylic acid, IDI1_000655, NCGC00016569-02, NCGC00016569-03, NCGC00016569-04, NCGC00016569-05, NCGC00016569-06, NCGC00016569-08, NCGC00016569-09, NCGC00094944-01, NCGC00094944-02, p-(Aminomethyl)cyclohexanecarboxylic acid, AS-80121, BP-12345, DA-78573, FT163756, PD061983, SY011438, SY056656, TS-02090, SBI-0051705.P002, trans 4aminomethylcyclohexanecarboxylic acid, DB-074265, Trans-4-aminomethylcyclohexylcarboxylic acid, trans-p-Aminomethylcyclohexanecarboxylic acid, A0236, A2121, AB00052260, CS-0013687, CS-0055045, NS00006665, trans 4-aminomethylcyclohexanecarboxylic acid, trans-4-aminomethylcyclohexanecarboxylic acid, EN300-91506, Tranexamic acid impurity B;cis-Tranexamic acid, trans-4(aminomethyl)cyclohexanecarboxylic acid, trans-4-(aminomethyl)cyclohexylcarboxylic acid, trans-4-aminomethyl cyclohexanecarboxylic acid, trans-4-aminomethyl-cyclohexanecarboxylic acid, trans-4-aminomethylcyclohexane carboxylic acid, D01136, EN300-121703, P15619, P20836, T71247, Trans-4-Aminomethyl cyclohexane carboxylic acid, trans4-aminomethylcyclohexane-1-carboxylic acid, AB00052260-04, AB00052260_05, AB00052260_06, TRANEXAMIC ACID IMPURITY B [EP IMPURITY], trans-4 -(aminomethyl)cyclohexanecarboxylic acid, trans-4-(aminomethyl)-cyclohexanecarboxylic acid, trans-4-(Aminomethyl)cyclohexane carboxylic acid, trans-4-aminomethyl-1-cyclohexanecarboxylic acid, (trans)-4-(aminomethyl)cyclohexanecarboxylic acid, 4-(Aminomethyl)cyclohexanecarboxylic acid (trans-), 4-trans-(Aminomethyl)cyclohexanecarboxylic acid #, Q418666, trans-?4-?(Aminomethyl)?cyclohexanecarboxylic acid, trans-4- (aminomethyl) cyclohexanecarboxylic acid, trans-4-(aminomethyl)- cyclohexane carboxylic acid, Trans-4-(aminomethyl)-cyclohexane carboxylic acid, trans-4-aminomethyl-1-cyclohexane carboxylic acid, SR-05000001794-1, SR-05000001794-2, SR-05000001794-3, Tranexamic acid 100 microg/mL in Acetonitrile:Water, BRD-K15014948-001-01-2, BRD-K15014948-001-09-5, BRD-K15014948-001-10-3, BRD-K15014948-213-01-3, BRD-K79165417-001-01-7, Q27256710, trans-4-(Aminomethyl)cyclohexanecarboxylic acid, 97%, 4-(Aminomethyl)cyclohexanecarboxylic acid;Tranexamic acid, F8886-7867, Z1741970429, Amchafibrin;trans-p-(Aminomethyl)cyclohexanecarboxylic acid, rel-(1R,4R)-4-(aminomethyl)cyclohexane-1-carboxylic acid, Tranexamic acid, European Pharmacopoeia (EP) Reference Standard, Tranexamic acid, United States Pharmacopeia (USP) Reference Standard, Tranexamic acid, Pharmaceutical Secondary Standard; Certified Reference Material, 4-(Aminomethyl)cyclohexanecarboxylic acid;4-(Aminomethyl)cyclohexanecarboxylic Acid (cis- and trans- mixture);Tranexamic Acid(Random Configuration);Alprazolam Solution, 100ppm;4-(Aminomethyl)cyclohexanecarboxylic Acid (cis- and trans- mixture);TXC;4-(Aminomethyl)cyclohexanecarboxylic Acid (cis- and trans- mixture)>;Cyclohexanecarboxylic acid, 4-(aminomethyl)-

In dermatology, Aminomethylcyclohexanecarboxylic acid has gained popularity as an oral or topical treatment for melasma and hyperpigmentation, as it helps regulate melanogenesis by reducing plasmin activity in skin cells.
Aminomethylcyclohexanecarboxylic acid is generally well tolerated, though side effects such as gastrointestinal discomfort, headaches, and a slightly increased risk of thrombosis in predisposed patients have been reported.
Because of its dual role in hemostasis and dermatology, Aminomethylcyclohexanecarboxylic acid is considered both a critical therapeutic drug in emergency and surgical medicine and an emerging agent in aesthetic and dermatological care.

Aminomethylcyclohexanecarboxylic acid is a synthetic analog of the amino acid lysine.
Aminomethylcyclohexanecarboxylic acid serves as an antifibrinolytic by reversibly binding four to five lysine receptor sites on plasminogen.
This decreases the conversion of plasminogen to plasmin, preventing fibrin degradation and preserving the framework of fibrin's matrix structure.

Aminomethylcyclohexanecarboxylic acid has roughly eight times the antifibrinolytic activity of an older analogue, ε-aminocaproic acid.
Aminomethylcyclohexanecarboxylic acid also directly inhibits the activity of plasmin with weak potency (IC50 = 87 mM), and it can block the active-site of urokinase plasminogen activator (uPA) with high specificity (Ki = 2 mM), one of the highest among all the serine proteases.

Side effects are rare; they include changes in color vision, seizures, blood clots, and allergic reactions.
Aminomethylcyclohexanecarboxylic acid appears to be safe for use during pregnancy and breastfeeding.

Aminomethylcyclohexanecarboxylic acid is an antifibrinolytic medication.
Aminomethylcyclohexanecarboxylic acid was first made in 1962 by Japanese researchers Shosuke and Utako Okamoto.

Aminomethylcyclohexanecarboxylic acid is on the World Health Organization's List of Essential Medicines.
Aminomethylcyclohexanecarboxylic acid is available as a generic drug.

Aminomethylcyclohexanecarboxylic acid is a synthetic derivative of the amino acid lysine that works as an antifibrinolytic agent, meaning it helps prevent the breakdown of blood clots.
Aminomethylcyclohexanecarboxylic acid achieves this by blocking the binding sites of plasminogen and plasmin, enzymes responsible for dissolving fibrin, which is a major component of blood clots.

Clinically, Aminomethylcyclohexanecarboxylic acid is commonly used to treat or prevent excessive bleeding in various situations, such as during heavy menstrual periods, surgeries (especially dental procedures in people with bleeding disorders), trauma, and certain medical conditions like hemophilia.
Aminomethylcyclohexanecarboxylic acid is also frequently used in aesthetic medicine to reduce skin discoloration, such as melasma and post-inflammatory hyperpigmentation, due to its ability to interfere with melanin synthesis.

Aminomethylcyclohexanecarboxylic acid is a monocarboxylic acid.
Aminomethylcyclohexanecarboxylic acid has a role as an antifibrinolytic drug and a hematologic agent.

Aminomethylcyclohexanecarboxylic acid is functionally related to a cyclohexanecarboxylic acid.
Taken orally, Aminomethylcyclohexanecarboxylic acid is indicated for the treatment of hereditary angioedema,6 cyclic heavy menstrual bleeding in premenopausal females,5 and other instances of significant bleeding in the context of hyperfibrinolysis.

Given intravenously, Aminomethylcyclohexanecarboxylic acid is indicated for short-term use (2-8 days) in patients with hemophilia to prevent or reduce bleeding following tooth extraction.
Aminomethylcyclohexanecarboxylic acid is an antifibrinolytic that competitively inhibits the activation of plasminogen to plasmin.
At much higher concentrations Aminomethylcyclohexanecarboxylic acid behaves as a noncompetitive inhibitor of plasmin similar to aminocaproic acid, a similar antifibrinolytic which is 10-fold less potent.

Aminomethylcyclohexanecarboxylic acid binds more strongly than aminocaproic acid to both the strong and weak receptor sites of the plasminogen molecule in a ratio corresponding to the difference in potency between the compounds.
In patients with hereditary angioedema, inhibition of the formation and activity of plasmin by Aminomethylcyclohexanecarboxylic acid may prevent attacks of angioedema by decreasing plasmin-induced activation of the first complement protein (C1).

Off-target antagonism of GABA(A) receptors may be associated with the development of convulsions and hyperexcitability following Aminomethylcyclohexanecarboxylic acid administration1 - the risk appears higher with improper administration or administration during cardiovascular surgery.
Consider EEG monitoring of patients with a history of seizure.
Aminomethylcyclohexanecarboxylic acid competitively and reversibly inhibits the activation of plasminogen via binding at several distinct sites, including four or five low-affinity sites and one high-affinity site, the latter of which is involved in its binding to fibrin.

The binding of plasminogen to fibrin induces fibrinolysis - by occupying the necessary binding sites Aminomethylcyclohexanecarboxylic acid prevents this dissolution of fibrin, thereby stabilizing the clot and preventing hemorrhage.
Aminomethylcyclohexanecarboxylic acid is a medication that is primarily used to treat or prevent excessive bleeding by slowing down the natural process that breaks down blood clots in the body.
Aminomethylcyclohexanecarboxylic acid belongs to a class of drugs called antifibrinolytics, which function by inhibiting the activation of plasminogen to plasmin — the enzyme responsible for breaking down fibrin, the structural protein in blood clots.

By doing so, Aminomethylcyclohexanecarboxylic acid helps to stabilize and preserve clots that have already formed, effectively reducing blood loss in a variety of clinical scenarios.
Aminomethylcyclohexanecarboxylic acid is widely used in medical settings such as cardiac surgery, orthopedic surgery, trauma care, and gynecology, particularly in conditions like menorrhagia (heavy menstrual bleeding), where it can significantly decrease the volume and duration of bleeding.
In trauma cases, especially those involving massive hemorrhage, early administration of Aminomethylcyclohexanecarboxylic acid has been shown to reduce the risk of death when given within a critical time window, such as in battlefield medicine or emergency care.

Aminomethylcyclohexanecarboxylic acid is used to treat heavy menstrual bleeding in women.
This medicine may be used by teenage females, but is not intended for use before the start of menstruation.

Aminomethylcyclohexanecarboxylic acid is an antifibrinolytic agent.
Aminomethylcyclohexanecarboxylic acid works by blocking the breakdown of blood clots, which prevents bleeding.

In the United States, Aminomethylcyclohexanecarboxylic acid is FDA-approved for short-term use in people with severe bleeding disorders who are about to have dental surgery.
Aminomethylcyclohexanecarboxylic acid is used for a short period before and after the surgery to prevent major blood loss and decrease the need for blood transfusions.

Aminomethylcyclohexanecarboxylic acid is used in dentistry in the form of a 5% mouth rinse after extractions or surgery in patients with prolonged bleeding time; e.g., from acquired or inherited disorders.
In China, Aminomethylcyclohexanecarboxylic acid is allowed in over-the-counter toothpaste, with six products using the drug. As of 2018, there are no limits on dosage, nor requirements for labeling the concentration.
0.05% Aminomethylcyclohexanecarboxylic acid in toothpaste is allowed OTC in Hong Kong.

<5% Aminomethylcyclohexanecarboxylic acid in over-the-counter toothpaste is first patented and marketed by Lion Corporation in Japan, where it is still sold.
Presence of unauthorized Aminomethylcyclohexanecarboxylic acid has led to the Canadian recall of a Yunnan Baiyao toothpaste in 2019.
There is not enough evidence to support the routine use of Aminomethylcyclohexanecarboxylic acid to prevent bleeding in people with blood cancers.

However, several trials are currently assessing this use of Aminomethylcyclohexanecarboxylic acid.
For people with inherited bleeding disorders (e.g. von Willebrand's disease), Aminomethylcyclohexanecarboxylic acid is often given.

Aminomethylcyclohexanecarboxylic acid has also been recommended for people with acquired bleeding disorders (e.g., directly acting oral anticoagulants (DOACs)) to treat serious bleeding.
The use of Aminomethylcyclohexanecarboxylic acid, applied directly to the area that is bleeding or taken by mouth, appears useful to treat nose bleeding compared to packing the nose with cotton pledgets alone.

Aminomethylcyclohexanecarboxylic acid decreases the risk of rebleeding within 10 days.
Aminomethylcyclohexanecarboxylic acid metabolism is poorly characterized but does not appear to be a significant means of drug elimination.

According to prescribing information, approximately 1% and 0.5% of an orally administered dose are excreted as a dicarboxylic acid and acetylated metabolite, respectively.
Reported adverse events include seizures, changes in color vision, blood clots, and allergic reactions such as anaphylaxis.
Whether the risk of venous thromboembolism (blood clots) is increased is a matter of debate.

The risk is mentioned in Aminomethylcyclohexanecarboxylic acid literature, and they were reported in post marketing experience.
Despite this, and the inhibitory effect of Aminomethylcyclohexanecarboxylic acid on blood clot breakdown, large studies of the use of Aminomethylcyclohexanecarboxylic acid have not shown an increase in the risk of venous or arterial thrombosis, even in people who had previously experienced thrombosis under other circumstances.

Aminomethylcyclohexanecarboxylic acid is marketed in the US and Australia in tablet form as Lysteda and in Australia, Sweden and Jordan it is marketed in an IV form and tablet form as Cyklokapron, in the UK and Sweden as Cyclo-F.
In the UK Aminomethylcyclohexanecarboxylic acid is also marketed as Femstrual, in Asia as Transcam, in Bangladesh as Intrax & Tracid, in India as Pause, in Pakistan as Transamin, in Indonesia as Kalnex, in South America as Espercil, in Japan as Nicolda, in France, Poland, Belgium, and Romania as Exacyl and in Egypt as Kapron.
In the Philippines, Aminomethylcyclohexanecarboxylic acid's capsule form is marketed as Hemostan and in Israel as Hexakapron.

Beyond its use in bleeding disorders, Aminomethylcyclohexanecarboxylic acid has found applications in dermatology and cosmetic medicine, where it is used both orally and topically to treat melasma, post-inflammatory hyperpigmentation, and sun-induced dark spots.
Aminomethylcyclohexanecarboxylic acid is believed to reduce pigmentation by inhibiting interactions between melanocytes and keratinocytes, and by reducing the vascular component of hyperpigmented lesions.

Pharmacologically, the drug is well absorbed after oral administration, with a peak plasma concentration occurring within a few hours, and it is excreted largely unchanged by the kidneys.
Because of its mechanism of action, Aminomethylcyclohexanecarboxylic acid does not interfere directly with coagulation pathways or platelet function, making it relatively safe in terms of thrombosis risk, although caution is still exercised in patients with a history of clotting disorders.
Aminomethylcyclohexanecarboxylic acid is included in the World Health Organization’s List of Essential Medicines, reflecting its importance in both developed and developing healthcare systems.

With a strong safety profile, minimal side effects in most users, and a wide range of indications, Aminomethylcyclohexanecarboxylic acid has become a cornerstone therapy in the management of bleeding and pigmentation disorders across multiple medical disciplines.
Aminomethylcyclohexanecarboxylic acid might alleviate neuroinflammation in some experimental settings.
Aminomethylcyclohexanecarboxylic acid can be used in case of postpartum hemorrhage; it can decrease the risk of death due to bleeding by one third according to the WHO.

Tentative evidence supports the use of Aminomethylcyclohexanecarboxylic acid in hemoptysis.
In hereditary hemorrhagic telangiectasia: Aminomethylcyclohexanecarboxylic acid has been shown to reduce the frequency of epistaxis in patients with severe and frequent nosebleed episodes from hereditary hemorrhagic telangiectasia.

Aminomethylcyclohexanecarboxylic acid is sometimes used in skin whitening as a topical agent, injected into a lesion, or taken by mouth, both alone and as an adjunct to laser therapy; as of 2017 its safety seemed reasonable but its efficacy for this purpose was uncertain because there had been no large scale randomized controlled studies nor long term follow-up studies.
Aminomethylcyclohexanecarboxylic acid is allowed as a quasi-drug for skin whitening in Japan.

Aminomethylcyclohexanecarboxylic acid is effective in reducing the risk of secondary hemorrhage outcomes in people with traumatic hyphema.
Aminomethylcyclohexanecarboxylic acid did not reduce bleeding or transfusions but did increase complications.

Aminomethylcyclohexanecarboxylic acid is a synthetic antifibrinolytic drug structurally derived from the amino acid lysine.
Aminomethylcyclohexanecarboxylic acid's primary mechanism of action involves the reversible blockade of lysine-binding sites on plasminogen and plasmin molecules, preventing the binding of plasminogen to fibrin and thereby inhibiting fibrinolysis.

This stabilizes blood clots and reduces excessive bleeding.
Unlike traditional anticoagulants, Aminomethylcyclohexanecarboxylic acid does not interfere with clot formation itself, but rather preserves existing fibrin structures by preventing their premature degradation.

Clinically, Aminomethylcyclohexanecarboxylic acid has a broad range of therapeutic applications.
Aminomethylcyclohexanecarboxylic acid is extensively used in surgical settings (such as cardiac, orthopedic, gynecological, and dental procedures) to minimize intraoperative and postoperative blood loss.

Aminomethylcyclohexanecarboxylic acid is a first-line treatment for heavy menstrual bleeding (menorrhagia), where it effectively reduces menstrual blood loss without affecting fertility.
Aminomethylcyclohexanecarboxylic acid is also recommended in cases of trauma and postpartum hemorrhage, where rapid control of bleeding is crucial and has been shown to reduce mortality when administered early.
In patients with hereditary angioedema, Aminomethylcyclohexanecarboxylic acid can help reduce attacks by decreasing bradykinin production, although it is generally considered less potent than C1 esterase inhibitors for this condition.

Beyond hemostasis, Aminomethylcyclohexanecarboxylic acid has gained increasing attention in dermatology and aesthetic medicine.
Both oral and topical formulations are now widely used for the treatment of melasma, post-inflammatory hyperpigmentation, and other pigmentary disorders, due to Aminomethylcyclohexanecarboxylic acid's ability to regulate melanogenesis indirectly through inhibition of plasmin activity in keratinocytes and melanocytes.
By reducing the inflammatory mediators that stimulate melanocyte activity, Aminomethylcyclohexanecarboxylic acid has shown significant efficacy in improving skin tone uniformity, making it a popular option in cosmetic dermatology.

Pharmacologically, Aminomethylcyclohexanecarboxylic acid is well absorbed after oral administration, with peak plasma concentrations occurring within 3 hours, and it is excreted largely unchanged in the urine.
Aminomethylcyclohexanecarboxylic acid has a relatively favorable safety profile, with the most common side effects being mild gastrointestinal symptoms (such as nausea, vomiting, or diarrhea) and headaches.
However, caution is warranted in patients with a history of thromboembolic disease (such as deep vein thrombosis, pulmonary embolism, or stroke), as Aminomethylcyclohexanecarboxylic acid theoretically increases the risk of thrombosis by enhancing clot stability, although large clinical trials suggest this risk is relatively low when used appropriately.

Overall, Aminomethylcyclohexanecarboxylic acid is considered a versatile and essential therapeutic agent that bridges emergency medicine, surgery, gynecology, and dermatology.
Aminomethylcyclohexanecarboxylic acid's ability to both control life-threatening bleeding and address chronic aesthetic concerns like hyperpigmentation highlights its dual role in modern healthcare.
With ongoing research into new delivery methods and expanded indications, Aminomethylcyclohexanecarboxylic acid continues to be an important drug at the intersection of hemostasis, patient safety, and skin health.

Market Overview of Aminomethylcyclohexanecarboxylic Acid:
The global Aminomethylcyclohexanecarboxylic acid market is experiencing steady growth, driven by its broad applications in surgery, trauma care, gynecology, dentistry, and increasingly in dermatology.
Valued at around USD 520 million to 1.03 billion in 2024 depending on scope, the market is projected to reach USD 868 million by 2032 or as high as USD 1.86 billion by 2035, with a CAGR ranging between 5–6%.

Demand is fueled by the rising number of surgical procedures, Aminomethylcyclohexanecarboxylic acid's role as a first-line non-hormonal treatment for heavy menstrual bleeding, and its expanding use in aesthetic dermatology for treating melasma and hyperpigmentation.
North America currently dominates the market thanks to advanced healthcare systems and high adoption rates, while Asia-Pacific is emerging as the fastest-growing region due to expanding healthcare infrastructure and growing consumer interest in skincare.
Despite Aminomethylcyclohexanecarboxylic acid's strong prospects, the market faces challenges such as potential thrombotic risks, regulatory differences across regions, and competition from alternative therapies, but continued innovation in formulations and expanding indications are expected to sustain growth in the coming years.

Uses of Aminomethylcyclohexanecarboxylic Acid:
Aminomethylcyclohexanecarboxylic acid is widely used in medicine for its antifibrinolytic properties, helping to prevent the breakdown of blood clots and reduce excessive bleeding.
Clinically, Aminomethylcyclohexanecarboxylic acid is prescribed in surgical settings (such as cardiac, orthopedic, trauma, dental, and gynecological operations) to minimize blood loss during and after procedures.

Aminomethylcyclohexanecarboxylic acid is a standard therapy for heavy menstrual bleeding (menorrhagia), offering a non-hormonal option that effectively reduces menstrual blood volume while preserving fertility.
In emergency and critical care, Aminomethylcyclohexanecarboxylic acid is a life-saving treatment in trauma and postpartum hemorrhage, where rapid control of bleeding is essential.

Beyond hemostasis, Aminomethylcyclohexanecarboxylic acid is increasingly used in dermatology and aesthetic medicine, both orally and topically, to treat melasma, hyperpigmentation, and post-inflammatory dark spots, due to its ability to reduce melanocyte overactivity by inhibiting plasminogen activation in the skin.
Additionally, Aminomethylcyclohexanecarboxylic acid can be applied in patients with hereditary angioedema to reduce the frequency of attacks.
Together, these uses make Aminomethylcyclohexanecarboxylic acid a versatile therapeutic agent that spans emergency medicine, surgery, gynecology, dentistry, and dermatology.

Aminomethylcyclohexanecarboxylic acid is frequently used following major trauma.
Aminomethylcyclohexanecarboxylic acid is used to prevent and treat blood loss in a variety of situations, such as dental procedures, heavy menstrual bleeding, and surgeries with high risk of blood loss.

Aminomethylcyclohexanecarboxylic acid has been found to decrease the risk of death due to any cause in people who have significant bleeding due to trauma.
Aminomethylcyclohexanecarboxylic acid is most effective if taken within the first three hours following major trauma.
Aminomethylcyclohexanecarboxylic acid also decreases the risk of death if given within the first three hours of brain injury.

Aminomethylcyclohexanecarboxylic acid is sometimes used to treat heavy menstrual bleeding.
When taken by mouth Aminomethylcyclohexanecarboxylic acid both safely and effectively treats regularly occurring heavy menstrual bleeding and improves quality of life.
Another study demonstrated that the dose does not need to be adjusted in females who are between ages 12 and 16.

In a 10-year study, Aminomethylcyclohexanecarboxylic acid and other oral medicines (mefenamic acid) were found to be as effective as the levonorgestrel intrauterine coil; the same proportion of women had not had surgery for heavy bleeding and had similar improvements in their quality of life.
Aminomethylcyclohexanecarboxylic acid is sometimes used (often in conjunction with oxytocin) to reduce bleeding after childbirth.
Death due to postpartum bleeding is reduced in women receiving Aminomethylcyclohexanecarboxylic acid.

Aminomethylcyclohexanecarboxylic acid is sometimes used in orthopedic surgery to reduce blood loss, to the extent of reducing or altogether abolishing the need for perioperative blood transfusion.
Aminomethylcyclohexanecarboxylic acid is of proven value in clearing the field of surgery and reducing blood loss when given before or after surgery. Drain and number of transfusions are reduced.
In surgical corrections of craniosynostosis in children Aminomethylcyclohexanecarboxylic acid reduces the need for blood transfusions.

In spinal surgery (e.g., scoliosis), correction with posterior spinal fusion using instrumentation, to prevent excessive blood loss.
In cardiac surgery, both with and without cardiopulmonary bypass (e.g., coronary artery bypass surgery), Aminomethylcyclohexanecarboxylic acid is used to prevent excessive blood loss.
Aminomethylcyclohexanecarboxylic acid can be used in skincare products as a cosmetic active to reduce the appearance of inflammation and hyperpigmentation.

Aminomethylcyclohexanecarboxylic acid is a zwitterion amino acid, and has a low permeability coefficient in the stratum corneum.
Aminomethylcyclohexanecarboxylic acid can be combined with penetration enhancers and microneedling to overcome this limitation.
Cosmetic uses may also employ lipophilic derivatives of Aminomethylcyclohexanecarboxylic acid (ester prodrugs like Cetyl tranexamate mesylate) that are not zwitterionic and thus have improved skin permeability.

Aminomethylcyclohexanecarboxylic acid is primarily used in clinical medicine to prevent and control excessive or prolonged bleeding in a wide range of conditions, particularly where blood clot breakdown (fibrinolysis) contributes to blood loss.
Aminomethylcyclohexanecarboxylic acid is especially effective in patients who are undergoing surgical procedures with a high risk of bleeding, such as cardiac surgery, liver transplantation, orthopedic surgery (like total knee or hip replacement), and dental procedures in patients with bleeding disorders, where it helps to minimize intraoperative and postoperative blood loss and reduce the need for blood transfusions.

One of its most common uses is in gynecology, where Aminomethylcyclohexanecarboxylic acid is prescribed to manage menorrhagia, or abnormally heavy menstrual bleeding.
When taken during the menstrual period, Aminomethylcyclohexanecarboxylic acid can significantly reduce the volume of blood loss, improving quality of life and reducing the risk of anemia in affected individuals, without altering the menstrual cycle itself.
In emergency medicine and trauma care, Aminomethylcyclohexanecarboxylic acid plays a vital role in the treatment of acute, life-threatening hemorrhage, particularly in cases of severe trauma, postpartum hemorrhage, or bleeding after major accidents or injuries.

Studies like the Aminomethylcyclohexanecarboxylic acid trial have demonstrated that when administered within three hours of injury, Aminomethylcyclohexanecarboxylic acid can lower the risk of death due to bleeding, making it an essential medication in trauma protocols worldwide.
Aminomethylcyclohexanecarboxylic acid is also used in individuals with hereditary bleeding disorders, such as hemophilia or von Willebrand disease, where it can be used alongside clotting factor replacement therapy to help maintain clot stability and prevent excessive bleeding during procedures or spontaneous bleeding episodes.

In addition to its role in hemostasis, Aminomethylcyclohexanecarboxylic acid has gained popularity in the field of dermatology and cosmetic medicine, where it is used to treat various forms of skin hyperpigmentation, including melasma, post-inflammatory hyperpigmentation, and age spots.
Aminomethylcyclohexanecarboxylic acid can be administered orally, topically, or via microneedling techniques to reduce melanin production and improve the evenness of skin tone by inhibiting interactions between melanocytes (pigment-producing cells) and keratinocytes (skin cells), as well as reducing the vascular component of pigmented lesions.

Moreover, Aminomethylcyclohexanecarboxylic acid may be used in specific medical conditions associated with recurrent nosebleeds (epistaxis), bleeding after prostate surgery, or bleeding related to abnormal blood vessel growth (such as angiodysplasia), providing targeted support to prevent blood loss and promote clot stability in vulnerable tissues.
Overall, the therapeutic uses of Aminomethylcyclohexanecarboxylic acid span across multiple specialties — including surgery, gynecology, emergency medicine, hematology, and dermatology — highlighting its versatility and significance in both life-saving and quality-of-life-improving interventions.

Aminomethylcyclohexanecarboxylic acid is used to prevent or reduce excessive bleeding for a short period of time in many different conditions such as heavy menstrual bleeding (menorrhagia) or in those with certain disorders like haemophilia.
In the field of obstetrics, Aminomethylcyclohexanecarboxylic acid has become increasingly important in the management and prevention of postpartum hemorrhage, a potentially life-threatening condition that remains one of the leading causes of maternal mortality worldwide.
By helping to stabilize blood clots after childbirth, particularly in the critical minutes and hours following delivery, Aminomethylcyclohexanecarboxylic acid can significantly reduce the need for surgical interventions like hysterectomy, minimize the necessity for blood transfusions, and improve maternal outcomes, especially in low-resource settings where access to advanced medical care may be limited.

In hematology, patients with clotting deficiencies or platelet function disorders often benefit from Aminomethylcyclohexanecarboxylic acid as a supportive therapy during minor surgical procedures, dental work, or periods of increased bleeding risk.
For individuals with hemophilia A or B, Aminomethylcyclohexanecarboxylic acid is used as an adjunct to factor replacement therapy to enhance the clotting process and prevent premature clot breakdown, especially in mucosal tissues like the mouth, gums, and nasal passages, where bleeding can be particularly difficult to control.

In urology, Aminomethylcyclohexanecarboxylic acid is sometimes prescribed after prostate surgery, bladder tumor resections, or other urological procedures to control hematuria (the presence of blood in the urine).
Aminomethylcyclohexanecarboxylic acid reduces the frequency and severity of bleeding episodes and can help avoid catheter blockages and complications due to clot formation within the urinary tract.
In otorhinolaryngology (ENT), Aminomethylcyclohexanecarboxylic acid is used in the treatment of epistaxis (nosebleeds), particularly in individuals with frequent or idiopathic episodes.

Aminomethylcyclohexanecarboxylic acid can be administered orally or applied topically using soaked gauze or nasal sprays to help arrest bleeding quickly and reduce recurrence, offering a non-invasive and well-tolerated alternative to cauterization or nasal packing.
Another emerging area of interest is in cardiology and vascular medicine, where Aminomethylcyclohexanecarboxylic acid is sometimes used to manage bleeding complications from anticoagulant therapy or to reduce perioperative blood loss during cardiopulmonary bypass surgery, which carries a significant risk of fibrinolysis due to contact with artificial surfaces in the bypass machine.

In cosmetic dermatology and aesthetic medicine, Aminomethylcyclohexanecarboxylic acid is gaining popularity not only as a treatment for hyperpigmentation but also as a skin-brightening agent used in serums, creams, chemical peels, and injectable mesotherapy solutions.
Aminomethylcyclohexanecarboxylic acid is particularly effective when combined with other depigmenting agents such as vitamin C, niacinamide, kojic acid, or retinoids, helping to fade stubborn discoloration without the harsh side effects associated with agents like hydroquinone.

Additionally, Aminomethylcyclohexanecarboxylic acid is sometimes used in ophthalmic surgeries, such as during retinal procedures, where there is a high risk of intraocular bleeding, as well as in dental surgery in patients with bleeding disorders or those taking anticoagulants, where mouthwashes containing Aminomethylcyclohexanecarboxylic acid can be used post-operatively to control local bleeding without altering systemic coagulation status.
Because of its diverse and expanding list of indications, Aminomethylcyclohexanecarboxylic acid is often stocked in hospital crash carts, surgical suites, trauma kits, and emergency rooms, and is recommended by numerous clinical guidelines, including those from the World Health Organization, as a first-line or adjunctive treatment for bleeding management.

Benefits of Aminomethylcyclohexanecarboxylic Acid:
Aminomethylcyclohexanecarboxylic acid provides significant clinical benefits by stabilizing blood clots and reducing abnormal bleeding, making it an essential drug in both emergency and routine medical care.
In surgery and trauma, Aminomethylcyclohexanecarboxylic acid lowers the need for blood transfusions, shortens recovery time, and reduces mortality from severe hemorrhage.

For women with heavy menstrual bleeding (menorrhagia), Aminomethylcyclohexanecarboxylic acid offers an effective, non-hormonal treatment option that preserves fertility and improves quality of life.
In postpartum hemorrhage, early administration of Aminomethylcyclohexanecarboxylic acid has been shown to save lives by preventing excessive maternal blood loss.

Aminomethylcyclohexanecarboxylic acid's role extends to dermatology, where it provides benefits in treating melasma and hyperpigmentation, improving skin tone and appearance by reducing excess melanin production.
Additionally, in patients with hereditary angioedema, Aminomethylcyclohexanecarboxylic acid helps reduce swelling episodes by limiting bradykinin production.
With a generally favorable safety profile and cost-effectiveness compared to alternatives, the drug delivers broad benefits across surgical medicine, gynecology, emergency care, and dermatology, making it a versatile therapeutic agent.

Production of Aminomethylcyclohexanecarboxylic Acid:
Aminomethylcyclohexanecarboxylic acid is produced industrially through synthetic organic chemistry methods, most commonly starting from lysine, its natural amino acid analogue.
The production process generally involves chemical modifications of lysine, such as selective protection of functional groups followed by transformation of the ε-amino group into a trans-4-aminomethylcyclohexane carboxylic acid derivative, which yields Aminomethylcyclohexanecarboxylic acid after deprotection and purification.

Alternative synthetic pathways use cyclohexanone derivatives that undergo reductive amination and subsequent carboxylation to obtain the final compound.
Once synthesized, the crude product is subjected to crystallization, filtration, and drying to achieve pharmaceutical-grade purity, ensuring compliance with Good Manufacturing Practices (GMP).

Industrial processes emphasize high yield, stereochemical control, and cost-effectiveness, as Aminomethylcyclohexanecarboxylic acid is widely used in both hospital medicine and dermatology.
With rising demand for bulk production, manufacturers are also exploring more eco-friendly synthetic routes and biocatalytic methods, which aim to reduce the use of harsh reagents and improve overall sustainability in large-scale production.

Synthesis of Aminomethylcyclohexanecarboxylic Acid:
Aminomethylcyclohexanecarboxylic acid is synthesized via several well-established routes that build a trans-1,4-disubstituted cyclohexane bearing a carboxyl group and an aminomethyl side chain.
Industrially, a common approach starts from cyclohexanone: (i) formation of a 4-substituted intermediate (e.g., via cyanomethylation or related C–C bond-forming steps to give a 4-cyanomethyl/cyano intermediate), (ii) conversion of the nitrile to the carboxylic acid and/or aminomethyl functions by sequential hydrogenation/hydrolysis or reductive amination, and (iii) stereochemical control (hydrogenation/isomerization) to favor the trans relationship of substituents on the ring.

Alternative routes start from 4-substituted cyclohexanecarboxylates (e.g., 4-cyanocyclohexane-1-carboxylate), with nitrile reduction → aminomethyl installation and subsequent salt-free acid workup.
A biomimetic/semisynthetic route from L-lysine is also described, using functional-group protection, side-chain transformation to a saturated ring, and deprotection to deliver Aminomethylcyclohexanecarboxylic acid.
Across processes, protecting groups on amine/acid functions enable chemo-selective transformations; final steps typically include crystallization (often as the free acid), polishing via charcoal/filtration, and GMP-grade quality control (identity, stereochemistry, residual solvents, metals) to meet pharmacopeial specs.

History of Aminomethylcyclohexanecarboxylic Acid:
Aminomethylcyclohexanecarboxylic acid was first synthesized in the early 1960s in Japan by Drs. Utako Okamoto and Shosuke Okamoto at Kobe University.
The Okamotos were searching for a safe and effective antifibrinolytic agent to help reduce maternal deaths from postpartum hemorrhage (PPH), which at the time was a leading cause of mortality among women after childbirth.

They identified Aminomethylcyclohexanecarboxylic acid as a synthetic derivative of lysine that could strongly inhibit fibrinolysis by blocking the binding of plasminogen to fibrin.
Their pioneering work was published in 1962, and by the late 1960s Aminomethylcyclohexanecarboxylic acid began clinical use in Japan.

Over the following decades, Aminomethylcyclohexanecarboxylic acid spread internationally as a treatment for heavy menstrual bleeding, surgical blood loss, trauma, and hereditary angioedema.
A major turning point came with the CRASH-2 trial (2010), one of the largest studies in trauma medicine, which demonstrated that early administration of Aminomethylcyclohexanecarboxylic acid significantly reduced mortality in bleeding trauma patients.
Since then, Aminomethylcyclohexanecarboxylic acid has been recognized by the World Health Organization (WHO) as an essential medicine, and today it is a standard of care worldwide in surgery, emergency medicine, obstetrics, and even dermatology, where it is used to treat melasma and hyperpigmentation.

Handling and Storage of Aminomethylcyclohexanecarboxylic Acid:
Handle in accordance with good laboratory and industrial hygiene practices.
Avoid generating dust or aerosols; use only with adequate ventilation.

Prevent contact with eyes, skin, and clothing.
Store in a tightly closed container, in a cool, dry, and well-ventilated area.
Keep away from strong oxidizing agents and sources of ignition.

Stability and Reactivity of Aminomethylcyclohexanecarboxylic Acid:

Stability:
Stable under normal conditions of temperature and pressure.

Conditions to avoid:
Excessive heat, moisture, and dust formation.

Incompatible materials:
Strong oxidizers, strong acids, and bases.

Hazardous decomposition products:
Carbon oxides (CO, CO₂) and nitrogen oxides (NOx) may be released during combustion or decomposition.

First Aid Measures of Aminomethylcyclohexanecarboxylic Acid:

Inhalation:
Move person to fresh air.
If symptoms occur (cough, dizziness), seek medical attention.

Skin contact:
Wash with plenty of soap and water.
Remove contaminated clothing.
Get medical help if irritation persists.

Eye contact:
Rinse immediately with water for at least 15 minutes, keeping eyelids open.
Seek medical advice if irritation continues.

Ingestion:
Rinse mouth with water.
Do not induce vomiting unless directed by medical personnel.
Seek medical attention if large quantities are ingested.

Firefighting Measures of Aminomethylcyclohexanecarboxylic Acid:

Suitable extinguishing media:
Water spray, dry chemical, CO₂, or alcohol-resistant foam.

Hazards:
Aminomethylcyclohexanecarboxylic acid is combustible; thermal decomposition can produce irritating/toxic fumes.

Protective equipment:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear.

Accidental Release Measures of Aminomethylcyclohexanecarboxylic Acid:

Personal precautions:
Avoid inhalation of dust; use personal protective equipment (PPE).
Ensure adequate ventilation.

Environmental precautions:
Prevent release into sewers or waterways.

Cleanup methods:
Sweep or vacuum without creating dust.
Place in a suitable container for disposal.
Wash area with water after cleanup.

Exposure Controls / Personal Protective Equipment of Aminomethylcyclohexanecarboxylic Acid:

Engineering controls:
Use in a chemical fume hood or with local exhaust ventilation to minimize exposure.

Eye protection:
Safety goggles or face shield.

Skin protection:
Nitrile or latex gloves; lab coat or protective clothing.

Respiratory protection:
If dust is present, use an appropriate dust mask or respirator (NIOSH-approved).

Hygiene measures:
Wash hands after handling.
Do not eat, drink, or smoke while working with the chemical.

Identifiers of Aminomethylcyclohexanecarboxylic Acid:
IUPAC Name: trans-4-(aminomethyl)cyclohexane-1-carboxylic acid
Common Name: Aminomethylcyclohexanecarboxylic acid

CAS Number: 1197-18-8
EC Number (EINECS): 214-818-2
PubChem CID: 5526
ChEBI ID: CHEBI:45924
DrugBank ID: DB00302
KEGG ID: D00758
UNII (FDA): 4J0ZR5D3QO
Merck Index Number: 13, 9736

InChI: InChI=1S/C8H15NO2/c9-5-7-3-1-2-4-8(7)6(10)11/h7-8H,1-5,9H2,(H,10,11)/t7-,8-/m1/s1
InChI Key: GYDWRBQDJZTJSV-LEKSSAKUSA-N
SMILES: C1CCC(CC1C@@H
C(=O)O)

IUPAC Name: trans-4-(aminomethyl)cyclohexane-1-carboxylic acid
Common Name: Aminomethylcyclohexanecarboxylic acid

Molecular Formula: C₈H₁₅NO₂
Molecular Weight: 157.21 g/mol
Monoisotopic Mass: 157.1103 g/mol
Heavy Atom Count: 11
Rotatable Bond Count: 2
Chiral Centers: 2 (typically marketed as trans-isomer)

CAS Number: 1197-18-8
EC/EINECS Number: 214-818-2
UNII (FDA): 4J0ZR5D3QO
Beilstein Registry Number: 1728040
Merck Index Number: 13, 9736

PubChem CID: 5526
ChemSpider ID: 5327
ChEBI ID: CHEBI:45924
DrugBank ID: DB00302
KEGG Drug ID: D00758
KEGG Compound ID: C07075
ZINC ID: ZINC000003874006
BindingDB ID: 50011869
HMDB ID: HMDB0015142
UNIPROT Ligand ID: TXA

InChI: InChI=1S/C8H15NO2/c9-5-7-3-1-2-4-8(7)6(10)11/h7-8H,1-5,9H2,(H,10,11)/t7-,8-/m1/s1
InChI Key: GYDWRBQDJZTJSV-LEKSSAKUSA-N
Canonical SMILES: C1CCC(CC1C@@H
C(=O)O)
Isomeric SMILES: O=C(O)C@@H
C1CCCCC1

Properties of Aminomethylcyclohexanecarboxylic Acid:
Chemical Name: Aminomethylcyclohexanecarboxylic acid (trans-4-(aminomethyl)cyclohexane-1-carboxylic acid)
Molecular Formula: C₈H₁₅NO₂
Molecular Weight: 157.21 g/mol
Appearance: White crystalline powder or colorless crystals
Odor: Odorless
Taste: Practically tasteless, slightly bitter
Melting Point: 386–392 °C (with decomposition)
Boiling Point: Decomposes before boiling
Density: ~1.2 g/cm³ (solid)
pKa: 4.3 (carboxyl group), 10.6 (amino group)
Isoelectric Point (pI): ~7.4

Solubility:
Freely soluble in water (approx. 1 g dissolves in <10 mL)
Sparingly soluble in ethanol
Insoluble in chloroform and ether

Partition coefficient (Log P): –0.7 (hydrophilic compound)
Stability: Stable under normal conditions; hygroscopic in moist air.

Melting point: 233 °C
Boiling point: 300.2±15.0 °C(Predicted)
Density: 1.095±0.06 g/cm3(Predicted)
storage temp.: Keep in dark place,Inert atmosphere,Room temperature
solubility: Water (Sparingly)
form: Solid
pka: 4.65±0.10(Predicted)
color: White to Off-White