FComEx: Danazol (PC000874)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:11 UTC

Update date

2017-01-19 02:36:39 UTC

FoodComEx ID

PC000874

FoodDB Record

FDB023073

Chemical Information

Name

Danazol

Description

Danazol is a synthetic steroid with anti-oestrogenic and anti progestogenic activity, and weak androgenic properties. Danazol suppresses oestrogen and progesterone receptors in the endometrium, leading to endometrial atrophy (thinning of the lining of the uterus) and reduced menstrual loss and to amenorrhoea in some women. Danazol significantly lowers the duration of menses when compared with NSAIDs and a progesterone releasing IUD; however, caused more adverse events than NSAIDs and progestogens. The use of Danazol may be limited by its side effect profile, its acceptability to women and the need for continuing treatment. Because danazol is structurally related to the anabolic steroid stanozolol, its use should be questioned. Derivatization methods and GC/MS data are used to implement danazol detection in routine screening and confirmation procedures in doping analysis. Danazol main metabolite ethisterone is excreted relatively fast in urine. (PMID: 17636649, 1640693, 16288903) [HMDB]

CAS Number

17230-88-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(17a)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol	hmdb
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	hmdb
17 alpha-pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-ol	hmdb
17a-Pregna-2,4-dien-20-yne-[2,3-d]isoxazole-17b-ol	hmdb
17a-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol	hmdb
1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazole- pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol deriv.	hmdb
Bonzol	hmdb
Chronogyn	hmdb
Cyclomen	hmdb
Danazolum	hmdb
Danocrine	hmdb
Danol	hmdb
Danovaol	hmdb
Danzol	hmdb
Ladogal	hmdb
Winobanin	hmdb

Chemical Formula

C22H27NO2

IUPAC name

(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

InChI Identifier

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

InChI Key

POZRVZJJTULAOH-LHZXLZLDSA-N

Isomeric SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO3

Average Molecular Weight

337.4553

Monoisotopic Molecular Weight

337.204179113

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom