Compound: danazol
SMILES: o1ncc2c1C=C3CC[C@@H]4[C@@H]([C@]3(C2)C)CC[C@]5([C@H]4CC[C@@]5(O)C#C)C
InChIKey: POZRVZJJTULAOH-LHZXLZLDSA-N
Synonyms: danazol, 17230-88-5, Danocrine, Chronogyn, Danol, Winobanin, Danazolum, Cyclomen, Ladogal, Bonzol, Danatrol, WIN 17757, WIN-17757, WIN 17,757, N29QWW3BUO, DTXSID2022880, 17alpha-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol, NSC-270916, CHEBI:4315, DTXCID202880, NSC270916, Danoval, Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol,(17alpha)-, (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^{2,10}.0^{4,8}.0^{14,18}]icosa-4(8),5,9-trien-17-ol, Danazol Ratiopharm, (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo(11.7.0.0^(2,10).0^(4,8).0^(14,18))icosa-4(8),5,9-trien-17-ol, RefChem:388912, (17alpha)-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol, (17Alpha)-pregna-2,4-dien-20-yno(2,3-d)-isoxazol-17-ol, 17Alpha-ethynyl-17beta-hydroxy-4-androsteno(2,3-d)isoxazole, 1-Ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-1H-cyclopental(7,8)phenanthro(3,2-d)isoxazol-1-ol, 241-270-1, Danazol, USP, (1R,3aS,3bR,10aR,10bS,12aS)-1-ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol, Danazole, MFCD00056838, Danzol, Danovaol, Danokrin, (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.02,10.04,8.014,18]icosa-4(8),5,9-trien-17-ol, NCGC00164400-01, Danogen, Danazolum [INN-Latin], NSC 270916, Danazol (1.0 mg/mL in acetonitrile), Danocrine (TN), (1R,3aS,3bR,10aR,10bS,12aS)-1-Ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-cyclopenta[7,8]phenanthro[3,2-d][1,2]oxazol-1-ol, SMR000058321, CCRIS 6747, EINECS 241-270-1, UNII-N29QWW3BUO, Vasaloc, 17-alpha-Pregn-4-en-20-yno(2,3-d)isoxazol-17-ol, Optina, 17-alpha-2,4-Pregnadien-20-yno(2,3-d)isoxazol-17-ol, Danazol?, s9506, Win 17, 757, Prestwick_150, Danazol (Standard), CAS-17230-88-5, Danazol [USAN:USP:INN:BAN:JAN], DANAZOL [VANDF], ethynyl(dimethyl)[?]ol, DANAZOL [USAN], DANAZOL [INN], DANAZOL [JAN], DANAZOL [MI], DANAZOL [MART.], Prestwick0_000105, Prestwick1_000105, Prestwick2_000105, Prestwick3_000105, DANAZOL [USP-RS], DANAZOL [WHO-DD], CHEMBL1479, SCHEMBL21107, BSPBio_000090, MLS001066617, MLS001306473, Danazol (JP18/USP/INN), DANAZOL [ORANGE BOOK], SPBio_002029, BPBio1_000100, GTPL6942, DANAZOL [USP MONOGRAPH], HY-B1029R, MSK2202, Win-17,757, POZRVZJJTULAOH-LHZXLZLDSA-N, GLXC-21458, HMS1568E12, HMS2090A22, HMS2095E12, HMS2231M08, HMS3259M10, HMS3712E12, [1,2]oxazolo[4',5':2,3]-17alpha-pregn-4-en-20-yn-17-ol, 17.Alpha.-Pregna-2, {4-dien-20-yno[2,3-d]isoxazol-17-ol}, Danazol (1 mg/mL in acetonitrile), HY-B1029, Tox21_112114, Tox21_301940, BDBM50423541, MSK2202-100A, AKOS015961192, MSK2202-1000A, Tox21_112114_1, AC-6836, CCG-220105, CS-4547, Danazol 100 microg/mL in Acetonitrile, DB01406, NC00557, NCGC00179665-01, NCGC00179665-02, NCGC00179665-04, NCGC00255335-01, 1-Ethynyl-10a,12a-dimethyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-1H-cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol, AS-13035, DA-72548, FD156781, Danazol Solution in Acetonitrile, 100ug/mL, NS00004972, Danazol Solution in Acetonitrile, 1000ug/mL, C06938, D00289, Q419652, SR-01000760722, SR-05000000445, SR-01000760722-2, SR-05000000445-2, 17a-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol, BRD-K48970916-001-03-0, (17a)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol, 17a-Pregna-2,4-dien-20-yne-[2,3-d]isoxazole-17b-ol, 17 alpha-pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-ol, 17.ALPHA.-PREGNA-2,4-DIEN-20-YNO(2,3)-DISOXAZOL-17-OL, Pregna-2, {4-dien-20-yno[2,3-d]isoxazol-17-ol,} (17.alpha.)-, PREGNA-2,4-DIEN-20-YNO(2,3-D)ISOXAZOL-17-OL,(17.ALPHA.)-, 1-ethynyl-2,3,3a,3b,4,5,10,10a,10b,11,12,12a-dodecahydro-10a,12a-dimethyl-1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazol-1-ol, 1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazole- pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol deriv.
Theoretical properties:
molecular_formula: C22H27NO2
molecular_weight: 337.5 g/mol
exact_mass: 337.204179104 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 25
topological_polar_surface_area: 46.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 224.2-226.8
Descriptions:
pubchem: Danazol can cause developmental toxicity according to state or federal government labeling requirements.
chembl: DANAZOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Danazol, sold as Danocrine and other brand names, is an oral medication used in the treatment of endometriosis, fibrocystic breast disease, hereditary angioedema and other conditions.
The use of danazol is limited by masculinizing side effects such as acne, excessive hair growth, and voice deepening. Danazol has a complex mechanism of action, and is characterized as a weak androgen and anabolic steroid, a weak progestogen, a weak antigonadotropin, a weak steroidogenesis inhibitor, and a functional antiestrogen.
Danazol was discovered in 1963 and was introduced for medical use in 1971. Due to their improved side-effect profiles, particularly their lack of masculinizing side effects, danazol has largely been replaced by gonadotropin-releasing hormone analogues (GnRH analogues) in the treatment of endometriosis.