Substance Name: Danazol [USAN:USP:INN:BAN:JAN]
RN: 17230-88-5
InChIKey: POZRVZJJTULAOH-LHZXLZLDSA-N

Note

  • 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.

Molecular Formula

  • C22-H27-N-O2

Molecular Weight

  • 337.4603
2D chemical structure of 17230-88-5
 

Classification Codes

  • Anterior pituitary suppressant
  • Drug / Therapeutic Agent
  • Estrogen antagonists
  • Estrogen Receptor Modulators
  • Hormone
  • Hormone Antagonists
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Human Data
  • Mutation data
  • Reproductive Effect
  • Tumor data

Links to Resources


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Names and Synonyms

Name of Substance

  • Danazol
  • Danazol [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Danazol

Synonyms

  • 17-alpha-2,4-Pregnadien-20-yno(2,3-d)isoxazol-17-ol
  • 17-alpha-Pregn-4-en-20-yno(2,3-d)isoxazol-17-ol
  • 17alpha-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol
  • CCRIS 6747
  • Chronogyn
  • Danazol
  • Danazole
  • Danazolum
  • Danazolum [INN-Latin]
  • Danocrine
  • Danogen
  • Danokrin
  • Danol
  • EINECS 241-270-1
  • Ladogal
  • NSC 270916
  • Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol,(17alpha)-
  • UNII-N29QWW3BUO
  • Win 17,757
  • WIN 17757
  • Winobanin

Systematic Names

  • 17alpha-Pregna-2,4-dien-20-yno(2,3-d)isoxazol-17-ol
  • Danazol
  • 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)-

Superlist Name

  • Danazol

Registry Numbers

CAS Registry Number

  • 17230-88-5

System Generated Number

  • 0017230885

Structure Descriptors

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

Smiles

C1[C@H]2[C@H]([C@H]3[C@@]([C@@](C#C)(O)CC3)(C)C1)CCC=1[C@@]2(Cc2cnoc2C1)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 5gm/kg (5000mg/kg)   Journal of International Medical Research. Vol. 5(Suppl,
man TDLo oral 274mg/kg/32D- (274mg/kg) LIVER: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

LIVER: "JAUNDICE, CHOLESTATIC"
Postgraduate Medical Journal. Vol. 69, Pg. 237, 1993.
Link to PubMed
man TDLo oral 1029mg/kg/17W (1029mg/kg) LIVER: "JAUNDICE, CHOLESTATIC" Postgraduate Medical Journal. Vol. 68, Pg. 984, 1992.
mouse LD50 intraperitoneal 6770mg/kg (6770mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 484, 1983.
mouse LD50 oral 4830mg/kg (4830mg/kg)   Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 25, Pg. 55, 1990.
mouse LD50 subcutaneous > 10gm/kg (10000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 691, 1983.
rabbit LD50 oral > 5gm/kg (5000mg/kg)   Journal of International Medical Research. Vol. 5(Suppl,
rat LD50 intraperitoneal > 10gm/kg (10000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 691, 1983.
rat LD50 oral > 17gm/kg (17000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 691, 1983.
rat LD50 subcutaneous > 10gm/kg (10000mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 25, Pg. 691, 1983.
women TDLo oral 120mg/kg/10D- (120mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" Archives of Internal Medicine. Vol. 145, Pg. 2251, 1985.
Link to PubMed
women TDLo oral 974mg/kg/23W- (974mg/kg) BEHAVIORAL: HEADACHE

SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE

PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE
Therapie. Vol. 43, Pg. 501, 1988.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 225.6 deg C   EXP
log P (octanol-water) 4.210 (none)   EST
Atmospheric OH Rate Constant 1.35E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by Syracuse Research Corporation.
See all available property data for this compound, including references.