Sporanox is a synthetic triazole antifungal agent that works by inhibiting the cytochrome P450–dependent enzyme lanosterol 14-α-demethylase, disrupting ergosterol synthesis and impairing fungal cell membrane integrity.
With a broad antifungal spectrum, Sporanox is effective against dermatophytes, Candida species, and systemic pathogens such as Histoplasma, Blastomyces, and Aspergillus, making it useful for both superficial and systemic mycoses, including onychomycosis and esophageal candidiasis.
First patented in 1978 and approved for medical use in the United States in 1992, Sporanox is included on the World Health Organization’s List of Essential Medicines and remains an important treatment option despite newer azoles entering the market.
CAS Number: 84625‑61‑6
EC Number: 100.123.596
Molecular Formula: C35H38Cl2N8O4
Molecular Weight: ~705.6 g/mol
Synonyms: Itraconazole, ITZ, itraconazole, Sporanox, 84625-61-6, Oriconazole, Itraconazol, Sporonox, Fungitraxx, Itraconazolo, Itraconazolum, Candistat, Canditral, Itralek, Sempera, Sporamelt, Traconal, Triasporin, Sporal, Itrac, Cladosal 100, Spherazole CR, Spherazole IR, 2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one, DTXSID3023180, R-51211, NSC-759239, 304NUG5GF4, CHEBI:6076, DTXCID903180, R51211, R 51211, 3H-1,2,4-Triazol-3-one, 4-(4-(4-(4-((2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-2,4-dihydro-2-(1-methylpropyl)-, Onmel, Sporanos, 1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one, R 51,211, Itrafungol, Lozanoc, Sporanox-pulse, Itraconazole Oral, Sporanox i.v., (+-)-1-sec-Butyl-4-(p-(4-(p-(((2R*,4S*)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-delta(sup 2)-1,2,4-triazolin-5-one, 1-(butan-2-yl)-4-(4-(4-(4-(((2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-4,5-dihydro-1H-1,2,4-triazol-5-one, 2-butan-2-yl-4-(4-(4-(4-(((2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)phenyl)-1,2,4-triazol-3-one, TOLSURA, J02AC02, 617-596-9, Itrizole (TN), 873066-43-4, Sporanox (TN), ITCZ, Itrizole, Itraconazole (Sporanox), Itraconazol [Spanish], Itraconazolum [Latin], cis-Itraconazole, ITZ, 2-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-2,4-dihydro-3H-1,2,4-triazol-3-one, 3H-1,2,4-Triazol-3-one,4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-, 4-[4-[4-[4-[[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-sec-butyl-1,2,4-triazol-3-one, CAS-84625-61-6, 84604-65-9, Intraconazole, MFCD00941396, Sporanox(TM), NCGC00018268-03, 4-(4-{4-[4-({[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl}oxy)phenyl]piperazin-1-yl}phenyl)-2-(1-methylpropyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, Itraconazole & Nyotran, Itraconazole (Standard), ITRACONAZOLE [MI], ITRACONAZOLE [INN], ITRACONAZOLE [JAN], ITRACONAZOLE [USAN], Itraconazole (JP18/USP), ITRACONAZOLE [VANDF], SCHEMBL23934, ITRACONAZOLE [MART.], MLS006011958, CHEMBL22587, ITRACONAZOLE [USP-RS], ITRACONAZOLE [WHO-DD], orb1310057, SCHEMBL27256172, GTPL11426, ITRACONAZOLE [GREEN BOOK], Itraconazole & Bovine Lactoferrin, ITRACONAZOLE [EP IMPURITY], ITRACONAZOLE [ORANGE BOOK], Pharmakon1600-01505756, ITRACONAZOLE [EP MONOGRAPH], MSK14876, ITRACONAZOLE [USP MONOGRAPH], Tox21_110854, AC-542, BDBM50127138, HY-17514R, NSC759239, s2476, AKOS015842738, AKOS015961385, Tox21_110854_1, CCG-270391, DB01167, KS-1268, NCGC00274068-01, NCGC00274068-02, NCGC00274068-07, HY-17514, SMR001827898, Itraconazole & Nyotran(Liposomal Nystatin), SBI-0206914.P001, ITRACONAZOLE (EMA EPAR: VETERINARY), NS00003507, SW219756-1, Itraconazole 2.0 mg/ml in Dimethyl Sulfoxide, D00350, EN300-122640, SUBA-ITRACONAZOLE COMPONENT ITRACONAZOLE, AB01274818-01, AB01274818_02, AB01274818_03, Q411229, BRD-A23067620-001-01-7, BRD-A23067620-001-03-3, BRD-A23067620-001-04-1, BRD-A23067620-300-01-3, Z1544404944, (+/-)-1-SEC-BUTYL-4-(P-(4-(P-(((2R*,4S*)-2-(2,4-DICHLOROPHENYL)-2-(1H-1,2,4-TRIAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)-1-PIPERAZINYL)PHENYL)-.DELTA.(SUP 2)-1,2,4-TRIAZOLIN-5-ONE, 1-(butan-2-yl)-4-{4-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1,2,4-triazol-5-one, 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-pipera-zinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl), 4-[4-[4-[4-[[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one;, 4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1h-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3h-1,2,4-triazol-3-one
Sporanox is a synthetic triazole antifungal agent widely used in the treatment of systemic and superficial fungal infections.
Sporanox acts by inhibiting the cytochrome P450–dependent enzyme lanosterol 14-α-demethylase, a key catalyst in the biosynthesis of ergosterol, an essential component of fungal cell membranes.
By disrupting ergosterol production, Sporanox alters membrane permeability, leading to impaired growth and eventual death of susceptible fungi.
The drug is typically supplied as capsules, oral solution, or intravenous formulations, and appears as a white to slightly yellow crystalline powder, practically insoluble in water but soluble in organic solvents.
With a broad antifungal spectrum, Sporanox is effective against dermatophytes, yeasts (including Candida spp.), and systemic pathogens such as Histoplasma, Blastomyces, and Aspergillus, making it an essential therapeutic agent in both dermatological and systemic mycoses.
Sporanox's relatively high lipophilicity and affinity for keratinized tissues contribute to its prolonged activity in skin and nails, which underlies its use in onychomycosis and chronic superficial infections.
Sporanox works by killing or stopping the growth of the fungus that causes the infection.
Sporanox is a synthetic triazole antifungal drug used to treat various fungal infections.
Sporanox belongs to a class of drugs known as the azoles.
Sporanox may be administered orally as a capsule or as a solution formulation.
Sporanox may be given intravenously (directly into a vein) as well.
Bioavailability varies based on the type of formulation given.
Absorption of Sporanox is erratic and requires gastric acid, so it is recommended that it be taken with a meal.
Drugs that decrease gastric acid should not be administered concurrently.
Sporanox is an N-arylpiperazine that is cis-ketoconazole in which the imidazol-1-yl group is replaced by a 1,2,4-triazol-1-yl group and in which the actyl group attached to the piperazine moiety is replaced by a p-[(+-)1-sec-butyl-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]phenyl group.
Certain types of mucocutaneouscandidiasis, including esophageal candidiasis (infection of the esophagus) and oropharyngeal candidiasis (infection of part of the throat)
Histoplasmosis and mucocutaneous candidiasis can be opportunistic infections (OIs) of HIV.
First synthesized in the early 1980s, Sporanox is a broad-spectrum triazole antifungal agent used to treat a variety of infections.
Sporanox is a 1:1:1:1 racemic mixture of four diastereomers, made up of two enantiomeric pairs, each possessing three chiral centers.
Sporanox was first approved in the US in 1992 and is available orally.
While the intravenous formulation of the drug was formerly available, Sporanox was discontinued in the US in 2007.
Sporanox is an Azole Antifungal.
The mechanism of action of Sporanox is as a Cytochrome P450 3A4 Inhibitor, and P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor.
Sporanox is a orally administered, triazole antifungal agent used in the treatment of systemic and superficial fungal infections.
Sporanox therapy is associated with transient, mild-to-moderate serum elevations and can lead to clinically apparent acute drug induced liver injury.
Sporanox is a synthetic triazole agent with antimycotic properties.
Formulated for both topical and systemic use, Sporanox preferentially inhibits fungal cytochrome P450 enzymes, resulting in a decrease in fungal ergosterol synthesis.
Because of Sporanox's low toxicity profile, this agent can be used for long-term maintenance treatment of chronic fungal infections.
Sporanox is only found in individuals that have used or taken this drug.
Sporanox is one of the triazole antifungal agents that inhibits cytochrome P-450-dependent enzymes resulting in impairment of ergosterol synthesis.
Sporanox is an antifungal medication that is used in adults to treat infections caused by fungus.
This includes infections in any part of the body including the lungs, mouth or throat, toenails, or fingernails.
Sporanox should be taken an hour before food, or two hours after food (and likewise if a combination of capsules and oral solution are used).
Sporanox may be taken with orange juice or cola, as absorption is also improved by acid.
Absorption of Sporanox is impaired when taken with an antacid, H2 blocker or proton pump inhibitor.
Sporanox is in the triazole family of medications.
Sporanox stops fungal growth by affecting the cell membrane or affecting their metabolism.
Sporanox was patented in 1978 and approved for medical use in the United States in 1992.
Sporanox is on the World Health Organization's List of Essential Medicines.
Recent research works suggest Sporanox (ITZ) could also be used in the treatment of cancer by inhibiting the hedgehog pathway in a similar way to sonidegib.
Market Overview of Sporanox:
The global Sporanox market was valued at around USD 639-640 million in 2023 and is projected to grow to approximately USD 866 million by 2034, with a compound annual growth rate (CAGR) of about 2.8% over that period.
Growth is driven by rising incidence of fungal infections worldwide, increasing demand for improved drug formulations (such as more bioavailable and once-daily dosage forms), and expanded use in both systemic and superficial mycoses.
North America currently holds a large share of revenue, supported by strong healthcare infrastructure and awareness, while Asia-Pacific is expected to grow faster due to increasing fungal disease burden, aging populations, and improved access to healthcare.
Despite moderate growth, challenges such as generic competition, safety concerns, and formulation complexity (e.g., poor solubility, drug interactions) may restrain faster expansion.
Uses of Sporanox:
Sporanox is a systemic antifungal medication used to treat fungal infections such as ringworm and blastomycosis.
Sporanox's use in dogs, small mammals, and some exotics to treat fungal infections is “off label” or “extra label”.
Sporanox has a role as a P450 inhibitor, an EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor and a Hedgehog signaling pathway inhibitor.
Sporanox is a member of triazoles, a dioxolane, a N-arylpiperazine, a dichlorobenzene, a cyclic ketal, a conazole antifungal drug, a triazole antifungal drug and an aromatic ether.
Sporanox is an antifungal prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of certain fungal infections, such as: Histoplasmosis
Sporanox has been used against histoplasmosis, blastomycosis, cryptococcal meningitis & aspergillosis.
Sporanox interacts with 14-alpha demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol.
As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents.
Sporanox may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial
Sporanox is used to treat or prevent fungal infections.
Sporanox is an antifungal medicine.
Sporanox is used to treat certain kinds of fungal or yeast infections.
Sporanox may be used for other purposes; ask your health care provider or pharmacist if you have questions.
Sporanox is an triazole medicine used to treat fungal infections.
Sporanox may also be used for purposes not listed in this medication guide.
Sporanox capsules and oral solution are absorbed into the body in different ways and work to treat different conditions.
Sporanox oral solution is only used to treat oropharyngeal or esophageal candidiasis (thrush, oral thrush).
Sporanox capsule is used to treat fungal infections, such as aspergillosis (fungal infection in the lungs), blastomycosis (Gilchrist’s disease), or histoplasmosis (Darling’s disease).
Sporanox is also used to treat onychomycosis (fungal infection in the fingernails or toenails).
Sporanox tablet is only used to treat onychomycosis of the toenails.
Sporanox works by killing the fungus or yeast and preventing its growth.
Sporanox is available only with your doctor's prescription.
Sporanox, sometimes abbreviated ITZ, is an antifungal medication used to treat a number of fungal infections.
Sporanox includes aspergillosis, blastomycosis, coccidioidomycosis, histoplasmosis, and paracoccidioidomycosis.
Sporanox may be given by mouth or intravenously.
Medical uses:
Sporanox has a broader spectrum of activity than fluconazole (but not as broad as voriconazole or posaconazole).
In particular, Sporanox is active against Aspergillus, which fluconazole is not.
Sporanox is also licensed for use in blastomycosis, sporotrichosis, histoplasmosis, and onychomycosis.
Sporanox is over 99% protein-bound and has virtually no penetration into cerebrospinal fluid.
Therefore, Sporanox should not be used to treat meningitis or other central nervous system infections.
Sporanox has "negligible CSF penetration, however treatment has been successful for cryptococcal and coccidioidal meningitis.
Sporanox is also prescribed for systemic infections, such as aspergillosis, candidiasis, and cryptococcosis, where other antifungal drugs are inappropriate or ineffective.
Sporanox has been explored as an anticancer agent for patients with basal cell carcinoma, non-small cell lung cancer, glioblastoma and prostate cancer.
For example, in a phase II study involving men with advanced prostate cancer, high-dose Sporanox (600 mg/day) was associated with significant PSA responses and a delay in tumor progression.
Sporanox also showed activity in a phase II trial in men with non-small cell lung cancer when it was combined with the chemotherapy agent, pemetrexed.
A recent review also highlights Sporanox's use topically and orally in conjunction with other chemotherapeutic agents for advanced and metastatic basal cell carcinomas that cannot be treated surgically.
Benefits of Sporanox:
Sporanox offers several clinical and therapeutic benefits that make it a valuable antifungal agent in modern medicine.
Sporanox's broad-spectrum activity allows it to target a wide range of fungal pathogens, including dermatophytes, Candida species, Aspergillus, Histoplasma, and Blastomyces, covering both superficial and systemic mycoses with a single drug.
Unlike many older antifungals, Sporanox exhibits high tissue affinity and lipophilicity, enabling it to accumulate in keratin-rich tissues such as skin and nails, which provides prolonged protection and makes it particularly effective in treating onychomycosis and chronic cutaneous infections.
Another key benefit is Sporanox's oral availability in multiple formulations (capsules, oral solution, and newer nanocrystal suspensions), which improve patient compliance and therapeutic outcomes.
Sporanox is also considered a safer alternative to amphotericin B in certain systemic infections, offering efficacy with fewer severe toxicities such as nephrotoxicity.
Beyond Sporanox's antifungal action, research has explored its potential repurposing in oncology and antiviral therapy, highlighting its pharmacological versatility.
Overall, Sporanox combines broad efficacy, favorable tissue penetration, and flexible formulations, making it a cornerstone therapy for many fungal infections.
Production of Sporanox:
Sporanox is manufactured synthetically through a multi-step organic process involving the assembly of its triazole ring system and lipophilic side chains.
The synthesis typically begins with substituted dioxolane or piperazine intermediates, which are coupled with triazole derivatives via alkylation and condensation reactions.
Key steps include introduction of the 1,2,4-triazole moiety, construction of the dioxolane ring system, and formation of the dichlorophenyl side chain, which together provide the drug’s antifungal activity by targeting fungal cytochrome P450 enzymes.
After core assembly, the crude product undergoes purification through recrystallization, chromatography, and solvent extraction to remove isomers and by-products.
The final product is obtained as a white to slightly yellow crystalline powder, practically insoluble in water, and is processed into various dosage forms including capsules, oral solution (using cyclodextrin complexes for solubility enhancement), and newer nanocrystal formulations that improve bioavailability.
Industrial-scale production is carried out under Good Manufacturing Practice (GMP) conditions with strict quality control, including identity confirmation, purity assays, residual solvent testing, particle size analysis, and stability studies to ensure compliance with pharmacopoeial standards (e.g., USP, EP).
History of Sporanox:
Sporanox was developed in the late 1970s and early 1980s as part of efforts to create safer and more effective systemic antifungal agents than the then-standard therapies, particularly ketoconazole and amphotericin B.
Sporanox was first synthesized and patented by Janssen Pharmaceutica (Belgium), led by the pioneering antifungal researcher Dr. Paul Janssen, who sought triazole derivatives with improved potency, reduced toxicity, and better oral absorption.
Clinical trials through the early 1980s demonstrated Sporanox’s broad spectrum of activity, covering dermatophytes, Candida, Aspergillus, and endemic mycoses such as histoplasmosis and blastomycosis, while offering a safer alternative to amphotericin B for long-term therapy.
The drug received Sporanox's first regulatory approval in Europe in 1984, followed by approval in the United States in 1992.
Over the 1990s, Sporanox became widely prescribed for onychomycosis, systemic mycoses, and chronic fungal infections, benefiting from its high tissue penetration and relatively mild side effect profile.
In the 2000s, newer azoles such as voriconazole and posaconazole entered the market, but Sporanox retained an important role due to its cost-effectiveness and oral formulations.
Sporanox has also drawn attention for drug repurposing research, including studies on its potential anticancer and antiviral properties.
Today, Sporanox remains a cornerstone triazole antifungal, valued for its clinical track record, broad utility, and continuing relevance in global health, especially in regions where newer azoles are less accessible.
Handling and Storage of Sporanox:
Handling:
Avoid dust formation, inhalation, and contact with eyes/skin.
Use in well-ventilated areas with appropriate PPE.
Wash hands after handling.
Storage:
Keep in tightly closed containers, in a cool, dry, well-ventilated place, protected from light and moisture.
Separate from strong oxidizers and acids.
Stability and Reactivity of Sporanox:
Stability:
Stable under normal storage and handling conditions.
Reactivity:
Incompatible with strong oxidizing agents, strong acids, and alkalis.
Decomposition Products:
HCl, NOx, CO, CO₂, and irritating organic vapors when heated or burned.
First Aid Measures of Sporanox:
Inhalation:
Move to fresh air; seek medical attention if respiratory symptoms persist.
Skin Contact:
Wash thoroughly with soap and water; remove contaminated clothing.
Eye Contact:
Rinse with water for at least 15 minutes; seek medical advice if irritation persists.
Ingestion:
Rinse mouth, do not induce vomiting, give water if conscious; obtain medical attention.
Firefighting Measures of Sporanox:
Extinguishing Media:
Water spray, CO₂, dry chemical, or foam.
Hazards:
Combustible dust; thermal decomposition releases toxic fumes.
Protective Equipment:
Firefighters wear SCBA and protective gear.
Accidental Release Measures of Sporanox:
Personal Precautions:
Avoid dust, provide ventilation, wear gloves/goggles/respiratory protection.
Spill Cleanup:
Collect with HEPA vacuum or damp absorbent; place in labeled container for disposal.
Environmental Precautions:
Prevent release into drains and waterways.
Exposure Controls / Personal Protective Equipment of Sporanox:
Engineering Controls:
Local exhaust or containment for dust; eyewash and safety shower available.
Respiratory Protection:
Not required with adequate ventilation; use particulate respirator if dust levels are significant.
Hand Protection:
Nitrile or neoprene gloves.
Eye/Face Protection:
Safety goggles; face shield if large amounts handled.
Skin/Body Protection:
Lab coat or protective clothing; chemical-resistant apron for bulk handling.
Identifiers of Sporanox:
Formula: C35H38Cl2N8O4
Molar Mass: 705.64 g·mol−1
Chirality: Racemic mixture
Melting Point: 165°C (329 °F)
Solubility in Water: 7.8 ± 0.4 × 10−6 mol/L (pH 1.6) mg/mL (20 °C)
CAS Number: 84625-61-6
EC / EINECS Number: Listed by ECHA (substance ID 100.123.596)
IUPAC Name: (±)‑1‑[(RS)‑sec‑butyl]‑4‑[...]‑triazolin-5‑one (complex)
PubChem CID: 55283
ChemSpider ID: 49927
Molecular Formula: C₃₅H₃₈Cl₂N₈O₄ (~705.6g/mol)
Appearance: White or off‑white crystalline powder
Substance Name: Sporanox
IUPAC Name: 4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2,4-dihydro-1,2,4-triazol-3-one
CAS Number: 84625-61-6
EC (EINECS) Number: 283-934-3
PubChem CID: 55283
ChemSpider ID: 49943
DrugBank ID: DB01167
ChEBI ID: CHEBI:6076
ChEMBL ID: CHEMBL1640
KEGG Drug ID: D01718
UNII (FDA): 0E6V27QA56
Molecular Formula: C₃₅H₃₈Cl₂N₈O₄
Molecular Weight: 705.64 g/mol
SMILES: C1CN(CCN1CC2=CC=C(C=C2)OC3CC(N(C3)CN4C=NC=N4)C5=CC(=C(C=C5)Cl)Cl)CC6=CC=C(C=C6)N7C=NC=N7
InChI: InChI=1S/C35H38Cl2N8O4/c36-28-20-26(21-29(37)27(28)22-43-34-33(41-40-25-43)32(47)42-45-34)35(46)44-24-14-38-13-23-7-9-30(10-8-23)39-15-25-17-31(18-39)49-19-29(48-25)16-38/h7-10,20-21,33H,13-19,22,24H2,1-6H3,(H,42,45)(H,41,40)
InChI Key: GDXLRPFZZUTUJX-UHFFFAOYSA-N
Pharmacological Class: Triazole antifungal
ATC Code: J02AC02 (Systemic antifungal for systemic use)
Regulatory Status: FDA- and EMA-approved; listed in pharmacopeias (USP, EP, JP)
UN Number (Transport): Not classified as a dangerous good
CAS Number: 84625-61-6
EC Number: 283-934-3
RTECS Number: Not assigned
UNII: 0E6V27QA56
Database Cross-References
PubChem CID: 55283
ChemSpider ID: 49943
DrugBank ID: DB01167
ChEBI ID: CHEBI:6076
ChEMBL ID: CHEMBL1640
KEGG Drug ID: D01718
WHO INN: Sporanox
Properties of Sporanox:
Appearance: White to slightly yellow crystalline powder
Molecular Weight: 705.64 g/mol
Melting Point: ~166–170 °C (decomposes)
Boiling Point: Not applicable (decomposes before boiling)
Solubility: Practically insoluble in water; soluble in methanol, ethanol, acetone, dichloromethane; soluble in cyclodextrins (oral solution)
Log P (octanol/water): ~5.6 (lipophilic)
pKa: ~3.7 and ~11 (basic nitrogens)
Vapor Pressure: Negligible at room temperature
Protein Binding: >99%
Half-Life: ~24–42 hours (longer with repeated dosing)
Molecular Weight: 705.6 g/mol
XLogP3: 5.7
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 9
Rotatable Bond Count: 11
Exact Mass: 704.2393071 Da
Monoisotopic Mass: 704.2393071 Da
Topological Polar Surface Area: 101 Ų
Heavy Atom Count: 49
Complexity: 1120
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Appearance: White to slightly yellow crystalline powder
Odor: Odorless to faint characteristic odor
Molecular Formula: C₃₅H₃₈Cl₂N₈O₄
Molecular Weight: 705.64 g/mol
Density: ~1.3 g/cm³ (estimated solid density)
Melting Point: 166–170 °C (decomposes)
Boiling Point: Not applicable (decomposes before boiling)
Flash Point: Not determined (solid, low volatility)
Autoignition Temperature: >400 °C (estimated)
Solubility in Water: Practically insoluble (<1 µg/mL at 25 °C)
Solubility in Solvents: Freely soluble in dichloromethane, methanol, ethanol, acetone; soluble in PEGs and cyclodextrins (used in oral solutions)
Log P (octanol/water): ~5.6 (highly lipophilic)
pKa values: ~3.7 (basic nitrogen), ~11 (weakly basic nitrogen)
Vapor Pressure: Negligible at ambient temperature
Refractive Index (solid crystal): ~1.62 (estimated)
Stability: Stable under normal dry storage; sensitive to strong oxidizers and acids
Shelf Life (formulated product): 2–3 years depending on dosage form
Protein Binding: >99% (plasma)
Elimination Half-Life: 24–42 h (may extend with repeated dosing)
Metabolism: Hepatic, mainly via CYP3A4
Excretion: Predominantly fecal (metabolites), <1% renal unchanged