SUMATRIPTAN SUCCINATE

Sumatriptan Succinate is a synthetic drug belonging to a class of medications known as 5-hydroxytryptamine agonists (also called "triptans"), which is commonly used to treat cluster and migraine headaches with or without aura (warning signs occurring prior to the onset of a migraine). 
Sumatriptan Succinate is effective to relieve or eliminate the intensity of migraine and cluster headaches and accompanying symptoms including sensitivity to light or sound, nausea, and vomiting.
Sumatriptan Succinate cannot help prevent future migraines/headaches or decrease the frequency of getting migraine and it is not recommended for other types of headache or for headache prevention.

CAS Number: 103628-48-4
Molecular Formula: C18H27N3O6S
Molecular Weight: 413.48848
EINECS Number: 600-463-4

Synonyms:SUMATRIPTAN SUCCINATE, 103628-48-4, Sumavel DosePro, Alsuma, Onzetra Xsail, Imitrex Statdose, GR 43175C, Zembrace SymTouch, Sumatriptan Galpharm, Sumatriptan (as succinate), GR-43175C, NSC-760362, CHEBI:64359, J8BDZ68989, DTXSID60145966, Zecuity, Migraitan, Imigran subject, Migraleve ultra, Migraine Pack, Imigran 50, RefChem:56077, sumatriptan succinate tablet, DTXCID9068457, Sumatriptan Succinate, MENTHOLUM, BELLADONNA, IRIS VERSICOLOR, SANGUINARIA CANADENSIS, Micralgin, Migratan, Suminat, 1-(3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide succinate, MFCD00902856, Sumatriptan succinate [USAN], Sumatriptan (succinate), C18H27N3O6S, GR 43175, sumatriptan hydrogen succinate, 103628-48-4 (succinate), mitrex, Migratriptan, Antibet, Arcoiran, Diletan, Imijekt, Novelian, Permicran, Sumadol, Sumatrin, Sumigrene, Sumitrex, Migmax, Imitrex (TN), 1-{3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}-n-methylmethanesulfonamide succinate, 1H-Indole-5-methanesulfonamide, 3-(2-(dimethylamino)ethyl)-N-methyl-, butanedioate (1:1), 3-[2-(DIMETHYLAMINO)ETHYL]-N-METHYL-1H-INDOLE-5-METHANESULFONAMIDE SUCCINATE, 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide, butanedioate(1:1), Zelrix, butanedioic acid;1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methylmethanesulfonamide, SMR000469158, Imigrane, UNII-J8BDZ68989, Sumatriptan SDI, Zecutity (TN), 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide succinate; Imigran; Imitrex, Sumatriptan Succinate; GR 43175C; Sumatriptan succinate (GR 43175C); Ph Eur Sumatriptan Impurity Mixture; GR 43175X; Sumatriptan Test Mix for Impurity Identification Solution 2, Alsuma (TN), Sumave dosepro (TN), 3-(2-(Dimethylamino)ethyl)-N-methylindole-5-methanesulfonamide succinate (1:1), SCHEMBL41674, MLS001401405, MLS006011969, orb1310839, CHEMBL1201150, SCHEMBL29360288, HY-B0121R, Sumatriptan succinate (JAN/USP), TO-303S, HMS2051H04, HMS2090G21, HMS2231K14, HMS3370G19, HMS3393H04, HMS3414A11, HMS3651E11, HMS3678A11, HMS3714G05, HMS3747O17, HMS3884K15, HMS5079K04, Pharmakon1600-01505372, SUMATRIPTAN SUCCINATE [MI], SUMATRIPTAN SUCCINATE [JAN], BCP05168, HY-B0121, Sumatriptan (succinate) (Standard), AC-751, GW 102, HB1769, NSC760362, SN 308, SN-308, SUMATRIPTAN SUCCINATE [VANDF], SUMATRIPTAN SUCCINATE [MART.], 3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl-N-methylmethanesulfonamide Succinate, AKOS015900409, SUMATRIPTAN SUCCINATE [USP-RS], SUMATRIPTAN SUCCINATE [WHO-DD], AB07670, CCG-100994, CS-1884, FD27976, KS-1116, NC00244, NSC 760362, BS164422, DA-78115, Sumatriptan succinate - Bio-X trade mark, SY067033, SUMATRIPTAN SUCCINATE [ORANGE BOOK], SUMATRIPTAN SUCCINATE [EP MONOGRAPH], S0851, SUMATRIPTAN SUCCINATE [USP MONOGRAPH], SW197624-3, D00676, EN300-122643, Sumatriptan succinate, >=98% (HPLC), solid, T71542, TREXIMET COMPONENT SUMATRIPTAN SUCCINATE, 628S484, A800771, SR-01000763688, SR-01000763688-4, Q10374626, F0001-2411, Z1544404947, 3-(2-(Dimethylamino)ethyl)-N-methylindole-5-methanesulfonamide succinate, Sumatriptan succinate, European Pharmacopoeia (EP) Reference Standard, Sumatriptan succinate, United States Pharmacopeia (USP) Reference Standard, 1-(3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide succinate, 1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methyl-methanesulfonamide; succinic acid, 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide butanedioate, 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide; butanedioic acid, butanedioic acid; 1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methyl-methanesulfonamide, butanedioic acid; 1-[3-[2-(dimethylamino)ethyl]-1H-indol-5-yl]-N-methyl-methanesulfonamide, N,N-dimethyl-2-{5-[(methylsulfamoyl)methyl]-1H-indol-3-yl}ethanaminium 3-carboxypropanoate, Sumatriptan for system suitability, European Pharmacopoeia (EP) Reference Standard, 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide, Succinate, Imigran, Imitrex,;Butanedioic acid, compd. with 3-2-(dimethylamino)ethyl-N-methyl-1H-indole-5-methanesulfonamide (1:1);SUMATRIPTANSUCCINATE(1:1);1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide succinate;Sumatriptan succinate;SuMatriptan Succinate, EP;Sumatriptan Succinate (200 mg);SuMitrex

Sumatriptan Succinate is believed that the pain of migraine headaches is induced by dilated blood vessels inside the head. 
Sumatriptan succinate relieves migraine headaches by affecting the serotonin in the brain, which results in constriction of blood vessels. Subcutaneous injection of this drug is more effective than other formulations.
Sumatriptan Succinate is a synthetic pharmaceutical compound that belongs to the triptan class of medications, which are specifically designed to treat migraine headaches and cluster headaches. 

Chemically, it is the succinate salt form of sumatriptan, which enhances its solubility and stability for oral, subcutaneous, or nasal administration. 
Sumatriptan Succinate works by selectively stimulating serotonin (5-HT1) receptors in the brain, causing the constriction of dilated cranial blood vessels and inhibiting the release of pro-inflammatory neuropeptides that contribute to migraine pain. 
This dual action helps relieve the intense headache, nausea, and sensitivity to light and sound that are characteristic of migraines. 

Sumatriptan Succinate is available in various dosage forms, including tablets, nasal sprays, and injection solutions, allowing flexibility depending on the severity of symptoms and patient preference. 
Its onset of action is relatively rapid, which is essential for managing acute migraine attacks, and it is generally prescribed only for acute treatment rather than for the prevention of migraine episodes. 
In addition to its therapeutic effects, Sumatriptan Succinate is carefully formulated to maintain chemical stability, reduce degradation, and ensure consistent dosing for patients.

Sumatriptan Succinate, sold under the brand name Imitrex among others, is a medication used to treat migraine headaches and cluster headaches.
Sumatriptan Succinate is taken orally, intranasally, or by subcutaneous injection.
Therapeutic effects generally occur within three hours.

Sumatriptan Succinate is a serotonin (5-HT1B/1D) receptor agonist (triptan).
The drug acts as a serotonin 5-HT1B, 5-HT1D, and 5-HT1F receptor agonism and its common side effects include chest pressure, fatigue, vomiting, tingling, and vertigo. 
Serious side effects may include serotonin syndrome, heart attack, stroke, and seizures. With excessive use, medication overuse headaches may occur.

Sumatriptan Succinate is unclear if use during pregnancy or breastfeeding is safe.
The mechanism of action is not entirely clear. 
Sumatriptan Succinate is in the triptan class of medications.

Sumatriptan Succinate was patented in 1982 and approved for medical use in 1992.
Sumatriptan Succinate is on the World Health Organization's List of Essential Medicines.
Sumatriptan Succinate is available as a generic medication.

In 2023, Sumatriptan Succinate was the 107th most commonly prescribed medication in the United States, with more than 6 million prescriptions.
Sumatriptan Succinate is also available as the combination product sumatriptan/naproxen.
Sumatriptan succinate is a highly selective 5HT1-like receptor agonist introduced as a new treatment for migraine. 

Sumatriptan Succinate is indicated for the acute relief of migraine and cluster headache. 
Oral administration is reported to be free of substantial side effects. 
The compound appears to be a significant advance over the use of ergotamine and other agents in the treatment of migraine.

A succinate salt obtained by reaction of sumatriptan with one equivalent of succinic acid. 
Selective agonist for a vascular 5-HT1 receptor subtype (probably a member of the 5-HT1D family). 
Sumatriptan Succinate is used for the acute treatm nt of migraine with or without aura in adults.

Sumatriptan Succinate is a prescription medicine used to treat acute migraine headaches. 
Sumatriptan Succinate works by narrowing blood vessels around the brain and reducing substances in the body that can trigger headache pain, nausea, sensitivity to light, and sound. 
Sumatriptan Succinate treats acute migraine, it will not prevent migraine or reduce the number of migraine attacks.

Sumatriptan Succinate is a serotonin receptor agonist commonly used to treat migraines and sometimes cluster headaches.
Sumatriptan Succinate is the first of the triptans and was made available in Europe in 1991 to treat migraines.
Sumatriptan Succinate was granted FDA approval on 28 December 1992.

Melting point: 165-166°C
storage temp.: -20°C
solubility: H2O: >20mg/mL
form: solid
color: white to off-white
Merck: 14,8997
BCS Class: 3
InChIKey: PORMUFZNYQJOEI-UHFFFAOYSA-N

Sumatriptan Succinate has a low abuse potential;[19] however overuse is associated with medication overuse headache.
Moreover, prolonged sumatriptan use is associated with pronociceptive effects, resulting in allodynia. 
This effect's association with medication overuse headache, however, is controversial, due to the fact that animal-model studies are not consistent with typical presentation of this disorder.

Suprofen, a nonsteroidal anti-inflammatory agent, was introduced in 1983 for use as an analgesic for the symptomatic relief of mild to moderate pain and for primary dysmenorrhoea. 
By 1986 it had become evident that its use was occasionally associated with flank pain sometimes accompanied by evidence of decreased renal function. 
The Arthritis Advisory Committee of the United States Food and Drug Administration met in December 1986 to review the situation and decided against withdrawing suprofen from the market. 

However, in May 1987 the Committee for Proprietary Medicinal Products of the European Community recommended that all marketing authorizations should be suspended. 
The manufacturer subsequently decided to suspend sale worldwide on the grounds that sales had diminished to the point where the product was no longer economically viable.
Sumatriptan Succinate is structurally similar to the neurotransmitter serotonin (5-HT) and acts as an agonist of the serotonin 5-HT1B, 5-HT1D, and 5-HT1F receptors.

Sumatriptan Succinate's primary therapeutic effect is related in its inhibition of the release of calcitonin gene-related peptide (CGRP), likely through its 5-HT1D/1B receptor agonist action.
This has been substantiated by the efficacy of more recently developed CGRP targeting drugs and antibodies developed for the preventive treatment of migraine.
How agonism of the 5-HT1D/1B receptors inhibits CGRP release is not fully understood. 

Sumatriptan Succinate is believed to cause sensitization of trigeminal nociceptive neurons, contributing to the pain experienced in migraine.
Sumatriptan Succinate is administered in several forms: tablets, subcutaneous injection, and nasal spray. 
Oral administration (as succinate salt) has low bioavailability, partly due to presystemic metabolism—some of it gets broken down in the stomach and bloodstream before it reaches the target arteries. 

There is no simple, direct relationship between Sumatriptan Succinate concentration (pharmacokinetics) per se in the blood and its anti-migraine effect (pharmacodynamics). 
This paradox has, to some extent, been resolved by comparing the rates of absorption of the various sumatriptan formulations, rather than the absolute amounts of drug that they deliver.
Sumatriptan Succinate is a relatively hydrophilic molecule, which may limit its ability to cross the blood–brain barrier and enter the central nervous system.

In accordance, early animal studies found lack of indication of central penetration by sumatriptan.
This was in contrast to more lipophilic triptans like zolmitriptan, naratriptan, rizatriptan, and eletriptan.
For these reasons, it was thought for many years that Sumatriptan Succinate could not cross the blood–brain barrier in significant amounts to exert central effects.

However, in subsequent animal studies, Sumatriptan Succinate was found to enter the brain and produce centrally mediated effects.
Besides animal research, clinical studies have found sumatriptan to produce centrally mediated side effects such as sleepiness, tiredness, thinking difficulty, and dizziness, among others.
In addition, Sumatriptan Succinate has been found to be discernibly psychoactive in human drug discrimination tests, with effects like apathy, sedation, and mild dysphoria.

Certain other clinical findings also support centrally mediated effects of sumatriptan.
A 2010 literature review concluded that Sumatriptan Succinate can enter the brain to some minor extent in both animals and humans but that this minor penetration is nonetheless sufficient to cause pharmacological effects.
Subsequent research has found Sumatriptan Succinate given during migraine attacks decreases brain serotonin 5-HT1B receptor binding in humans, with a corresponding receptor occupancy of 16%.

However, this apparent occupancy could alternatively be due to increased serotonin release during migraine attacks.
In contrast to receptor antagonists, it is notable that agonists like sumatriptan require only a low fractional receptor occupancy to produce central effects.
Sumatriptan Succinate is notable in this regard that the possible occupancy with Sumatriptan Succinate was comparable to that with centrally acting opioids.

Besides the clinical findings, further animal studies have found that sumatriptan rapidly enters the brain in spite of its poor lipophilicity and was able to do so more quickly than the benzodiazepine oxazepam.
Sumatriptan Succinate is metabolized primarily by monoamine oxidase A into indol-3-yl-acetaldehyde and then into corresponding carboxylic acid. 
Sumatriptan Succinate is further modified by UDP-glucuronosyltransferase into a conjugate with glucuronic acid. 

Other pathways are mediated by cytochrome P450 isoenzymes, which give an N-oxide derivative, and N-desmethyl and N,N-didesmethyl forms (the latter can be converted into the aldehyde by monoamine oxidase A). 
The N-desmethyl derivative can also undergo a reaction with D-cysteine.
The metabolites of sumatriptan are excreted in the urine and bile. Only about 3% of the active drug may be recovered unchanged.

Sumatriptan succinate is widely recognized for its effectiveness in rapidly alleviating the pain and associated symptoms of migraines, including nausea, vomiting, and sensitivity to light (photophobia) and sound (phonophobia). 
The succinate form, as a salt of sumatriptan, improves its solubility in water, which facilitates its absorption into the bloodstream when administered orally or via injection, ensuring predictable pharmacokinetics and therapeutic effects. 
Upon administration, sumatriptan selectively targets 5-HT1B and 5-HT1D serotonin receptors, which are predominantly located on cranial blood vessels and nerve endings in the brain, leading to vasoconstriction and inhibition of neuropeptide release that would otherwise trigger migraine pain. 

This targeted mechanism helps limit systemic side effects while providing fast relief, often within 30 minutes to two hours depending on the route of administration. 
Sumatriptan succinate is also formulated in various delivery systems, such as subcutaneous auto-injectors, nasal sprays, and orally disintegrating tablets, to accommodate patients who may experience nausea or difficulty swallowing during a migraine attack. 
Sumatriptan Succinate is typically prescribed for adults and must be used under medical supervision due to potential contraindications in patients with cardiovascular conditions, as the vasoconstrictive effect could pose risks for individuals with heart disease, uncontrolled hypertension, or a history of stroke. 

Moreover, repeated use should be monitored to avoid medication-overuse headaches, a phenomenon that can occur when triptans are taken excessively over time. 
Sumatriptan Succinate is a highly valuable drug in migraine management due to its rapid onset, targeted receptor activity, and versatility in administration forms.

Uses:
Sumatriptan Succinate is a serotonin 5-hydroxytryptamine 1 (5-HT1) receptor agonist with selective affinity for 5-HT1B and 5-HT1D receptors with IC50 values of 9.3 and 7.3 nM, respectively. 
Sumatriptan Succinate also has affinity for the 5-HT1F receptor (IC50 = 17.8 nM). 
Sumatriptan Succinate has been shown to induce vasoconstriction of human middle meningeal arteries (EC50 = 89.9 nM) and reduce vascular inflammation associated with migraines.

Sumatriptan Succinate is indicated for the acute treatment of migraine with or without aura in adults; or the acute treatment of cluster headache in adults.
Sumatriptan Succinate is effective for ending or relieving the intensity of migraine and cluster headaches.
Injected sumatriptan is more effective than other formulations.

Oral Sumatriptan Succinate can be used also in the treatment of post-dural puncture headache.
Sumatriptan Succinate is a synthetic medication belonging to the triptan class, specifically developed to treat acute migraine attacks characterized by moderate to severe head pain, often accompanied by symptoms such as nausea, vomiting, sensitivity to light (photophobia), sensitivity to sound (phonophobia), and, in some cases, visual disturbances known as aura. 

Sumatriptan Succinate works by selectively binding to serotonin (5-hydroxytryptamine, 5-HT) 1B and 1D receptors, which are predominantly located on cranial blood vessels and trigeminal nerve endings, leading to vasoconstriction of dilated intracranial arteries and inhibition of the release of vasoactive neuropeptides, thereby reducing inflammation and the neurogenic component of migraine pain. 
The drug is available in multiple forms, including oral tablets, orally disintegrating tablets, subcutaneous injections, and nasal sprays, allowing for rapid absorption and effectiveness even when patients experience gastrointestinal symptoms such as nausea or vomiting that might interfere with oral drug intake. 

Sumatriptan succinate is usually administered at the onset of migraine symptoms, and a second dose may be taken after a minimum interval if the headache recurs, but the total daily dose must not exceed recommended limits to prevent adverse effects, including cardiovascular complications in susceptible individuals
Sumatriptan Succinate is a selective 5-HT1B/1D-receptor agonist with anticonvulsant properties (1,2). 

Sumatriptan Succinate is used for migraine relief (2).
Sumatriptan succinate is primarily used for the acute treatment of migraine attacks with or without aura in adults, providing relief from the severe, throbbing headache pain as well as accompanying symptoms such as nausea, vomiting, photophobia (sensitivity to light), and phonophobia (sensitivity to sound), and it is not intended for the prevention of migraines or for use in patients under 18 years of age. 
Its therapeutic effects are achieved through selective agonism of serotonin 5-HT1B and 5-HT1D receptors, which results in cranial vasoconstriction, inhibition of pro-inflammatory neuropeptide release, and suppression of trigeminal nerve activity, all of which contribute to reducing the intensity and duration of migraine episodes. 

The drug is formulated in multiple delivery systems—including oral tablets, orally disintegrating tablets, subcutaneous injections, and intranasal sprays—allowing for rapid absorption and effectiveness even in patients who experience nausea or vomiting during migraine attacks, thereby offering flexibility and convenience in acute management. 
Sumatriptan succinate is also sometimes used in clinical practice under specialist guidance to treat cluster headaches, though this is an off-label application, and its use must be carefully monitored in patients with cardiovascular risk factors due to the vasoconstrictive mechanism. 
Additionally, the medication is not suitable for daily or preventive use, as overuse can lead to medication-overuse headaches, making careful adherence to prescribed dosing schedules essential to maintain efficacy and minimize potential adverse effects.

Safety Profile:
Sumatriptan succinate, while effective for treating acute migraine attacks, carries several potential hazards and safety concerns that must be carefully considered before and during use. 
The primary hazard is its cardiovascular risk: sumatriptan causes vasoconstriction of cranial and systemic blood vessels, which can precipitate serious cardiovascular events such as myocardial infarction (heart attack), angina, arrhythmias, and stroke, particularly in patients with a history of heart disease, uncontrolled hypertension, peripheral vascular disease, or cerebrovascular disease. 
Individuals with risk factors such as diabetes, high cholesterol, smoking, or a family history of heart disease should be evaluated prior to administration.

Another significant hazard is serotonin syndrome, which may occur if Sumatriptan Succinate is taken concomitantly with other serotonergic medications such as selective serotonin reuptake inhibitors (SSRIs), serotonin-norepinephrine reuptake inhibitors (SNRIs), monoamine oxidase inhibitors (MAOIs), or other triptans. 
Serotonin syndrome is a potentially life-threatening condition characterized by agitation, confusion, rapid heart rate, high blood pressure, dilated pupils, muscle rigidity, tremor, and in severe cases, seizures or coma.

Common but less severe hazards include nausea, dizziness, drowsiness, paresthesia (tingling sensations), flushing, and tightness or pressure in the chest, neck, or jaw. 
Although these are usually transient, chest tightness can be a warning sign of more serious cardiovascular events and requires immediate medical attention. 
Rarely, allergic reactions, including rash, itching, swelling, severe dizziness, or difficulty breathing, may occur, and such reactions necessitate urgent medical care.