| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2006-05-22 09:12:13 -0600 |
| Update Date |
2013-02-08 17:12:08 -0700 |
| HMDB ID |
HMDB02835 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common 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 ). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- (17a)-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol
- 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
- 17 alpha-Pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-ol
- 17a-Pregna-2,4-dien-20-yne-[2,3-D]isoxazole-17b-ol
- 17a-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol
- 1H-Cyclopenta[7,8]phenanthro[3,2-D]isoxazole- pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol deriv.
- Bonzol
- Chronogyn
- Cyclomen
- Danazolum
- Danocrine
- Danol
- Danovaol
- Danzol
- Ladogal
- Winobanin
|
| Chemical Formula |
C22H27NO2 |
| Average Molecular Weight |
337.4553 |
| Monoisotopic Molecular Weight |
337.204179113 |
| 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 |
| Traditional IUPAC Name |
danazol |
| CAS Registry Number |
17230-88-5 |
| 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 |
| 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 |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Steroids and Steroid Derivatives |
| Sub Class |
Gluco/mineralocorticoids, Progestogins and Derivatives |
| Other Descriptors |
- 17beta-hydroxy steroid(ChEBI)
- Aromatic Heteropolycyclic Compounds
|
| Substituents |
- 17 Hydroxy Steroid
- Alkyne
- Cyclic Alcohol
- Cyclohexane
- Decaline
- Isoxazole
- Oxazole
- Tertiary Alcohol
- Ynone
|
| Direct Parent |
Gluco/mineralocorticoids, Progestogins and Derivatives |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
- Extracellular
- Membrane (predicted from logP)
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
225.6 °C |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
4.081 |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Extracellular
- Membrane (predicted from logP)
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
Not Available
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB023073 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
26436 |
| KEGG Compound ID |
C06938 |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Danazol |
| NuGOwiki Link |
HMDB02835 |
| Metagene Link |
HMDB02835 |
| METLIN ID |
Not Available |
| PubChem Compound |
28417 |
| PDB ID |
Not Available |
| ChEBI ID |
4315 |
| References |
|---|
| Synthesis Reference |
Raczkowska, Sabina; Lypacewicz, Maria K.; Chojecka-Koryn, Ewa; Jaworska, Romana; Wasiak, Teresa; Mozolowski, Felicjan; Wajcht, Jozef. Method of obtaining highly pure danazol. Pol. (1991), 3 pp. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
Not Available |
