(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

• ChemBase ID: 1215
• Molecular Formular: C22H27NO2
• Molecular Mass: 337.45528
• Monoisotopic Mass: 337.20417911
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=Cc5oncc5C4)CC3)C)CC2)CC1)C)C#C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=Cc3c(C[C@]12C)cno3
• InChI: InChI=1S/C22H27NO2/c1-4-22(24)10-8-18-16-6-5-15-11-19-14(13-23-25-19)12-20(15,2)17(16)7-9-21(18,22)3/h1,11,13,16-18,24H,5-10,12H2,2-3H3/t16-,17+,18+,20+,21+,22+/m1/s1
• InChIKey: POZRVZJJTULAOH-LHZXLZLDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,13R,14S,17R,18S)-17-ethynyl-2,18-dimethyl-7-oxa-6-azapentacyclo[11.7.0.0^2,^1^0.0^4,^8.0^1^4,^1^8]icosa-4(8),5,9-trien-17-ol; (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
• IUPAC Traditional name: danazol
• Brand Name: Anatrol; Chronogyn; Cyclomen; Danocrine
• Synonyms: 17β-hydroxy-2,4,17α-pregnadien-20-yno[2,3-D]isoxazole; (17α)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol; 17α-Ethynyl-17β-hydroxy-4-androsteno[2,3-d]isoxazole; Win-17757; Bonzol; Cyclomen; Danatrol; Danocrine; Danol; Danazol; 17β-Hydroxy-2,4,17α-pregnadien-20-yno[2,3-d]-isoxazole; 2,4,17α-Pregnadien-20-yno[2,3-d]-isoxa-zol-17-ol

Database IDs

• CAS Number: 17230-88-5
• EC Number: 241-270-1
• PubChem SID: 46506475; 160964675
• PubChem CID: 28417
• CHEBI ID: 4315
• ATC CODE: G03XA01
• CHEMBL: 1479
• Chemspider ID: 26436
• DrugBank ID: DB01406
• KEGG ID: D00289
• Unique Ingredient Identifier: N29QWW3BUO
• Wikipedia Title: Danazol
• Medline Plus: a682599

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.594933
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.4620798
• LogD (pH = 7.4): 3.4620821
• Log P: 3.4620821
• Molar Refractivity: 98.5352 cm^3
• Polarizability: 37.660843 Å^3
• Polar Surface Area: 46.26 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.62
• LOG S: -4.28
• Solubility (Water): 1.76e-02 g/l

PROPERTIES

Physical Property

• Solubility: Acetonitrile; Chloroform; Ethanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 218-2200C; 225°C (dec.)
• Hydrophobicity(logP): 0.51 [PERRISSOUD,D & TESTA,B (1986)]

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: TU4157070
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 15 hours
• Metabolism: Hepatic
• Legal Status: Rx-only (US); S4 (Australia)
• Pregnancy Category: D (Australia); X (US)

Product Information

• Classification: Rare Derivatives of Natural Compounds

DETAILS

DrugBank - DB01406

• Drug Groups: approved
• Description: A synthetic steroid with antigonadotropic and anti-estrogenic activities that acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties. Danazol has been used in the treatment of endometriosis and some benign breast disorders. [PubChem]
• Indication: For the treatment of endometriosis and fibrocystic breast disease (in patients unresponsive to simple measures). Also used for the prophylactic treatment of all types of hereditary angioedema in males and females.
• Pharmacology: Danazol is a derivative of the synthetic steroid ethisterone, a modified testosterone. It was approved by the U.S. Food and Drug Administration (FDA) as the first drug to specifically treat endometriosis, but its role as a treatment for endometriosis has been largely replaced by the gonadotropin-releasing hormone (GnRH) agonists. Danazol has antigonadotropic and anti-estrogenic activities. Danazol acts as an anterior pituitary suppressant by inhibiting the pituitary output of gonadotropins. It possesses some androgenic properties.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, to principal metabolites, ethisterone and 17-hydroxymethylethisterone.
• Half Life: Approximately 24 hours.
• References: Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. [Pubmed] ; Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. [Pubmed] ; Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - D145000

Danazol is an anterior pituitary supressant. Danazol is an anabolic steroid derivative of ethisterone, with mild androgenic side effects (an impeded androgen). Antigonadotropin.

REFERENCES

• Dmowski WP: Danazol. A synthetic steroid with diverse biologic effects. J Reprod Med. 1990 Jan;35(1 Suppl):69-74; discussion 74-5. Pubmed
• Jenkin G: Review: The mechanism of action of danazol, a novel steroid derivative. Aust N Z J Obstet Gynaecol. 1980 May;20(2):113-8. Pubmed
• Donaldson VH: Danazol. Am J Med. 1989 Sep;87(3N):49N-55N. Pubmed
• Ahn, Y.S., et al.: N. Engl. J. Med., 308, 1396 (1983)