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Showing Compound Danazol (FDB023073)

Record Information
Version1.0
Creation date2011-09-21 00:24:16 UTC
Update date2015-10-09 22:33:11 UTC
Primary IDFDB023073
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDanazol
DescriptionDanazol 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 Number17230-88-5
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
CyclomenChEBI
DanazolumChEBI
DanocrineChEBI
(17a)-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-olHMDB
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-olHMDB
17 alpha-Pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-olHMDB
17a-Pregna-2,4-dien-20-yne-[2,3-D]isoxazole-17b-olHMDB
17a-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-olHMDB
1H-Cyclopenta[7,8]phenanthro[3,2-D]isoxazole- pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol deriv.HMDB
BonzolHMDB
ChronogynHMDB
DanolHMDB
DanovaolHMDB
DanzolHMDB
LadogalHMDB
WinobaninHMDB
Alphapharm brand OF danazolHMDB
Kendrick brand OF danazolHMDB
Sanofi brand OF danazolHMDB
DanatrolHMDB
DanazantHMDB
Danazol-ratiopharmHMDB
DanovalHMDB
Ratiopharm brand OF danazolHMDB
Antigen brand OF danazolHMDB
AzolHMDB
NorcidenHMDB
PanacrineHMDB
Sanofi synthelabo brand OF danazolHMDB
Sanofi winthrop brand OF danazolHMDB
Danazol ratiopharmHMDB
(17a)-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-olhmdb
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-olhmdb
17 alpha-pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-olhmdb
17a-Pregna-2,4-dien-20-yne-[2,3-d]isoxazole-17b-olhmdb
17a-Pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-olhmdb
1H-Cyclopenta[7,8]phenanthro[3,2-d]isoxazole- pregna-2,4-dien-20-yno[2,3-d]isoxazol-17-ol deriv.hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP3.62ALOGPS
logP3.46ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)17.59ChemAxon
pKa (Strongest Basic)0.25ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.26 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity98.54 m³·mol⁻¹ChemAxon
Polarizability38.44 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H27NO2
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 IdentifierInChI=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 KeyPOZRVZJJTULAOH-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 Weight337.4553
Monoisotopic Molecular Weight337.204179113
Classification
Description Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane steroids
Alternative Parents
Substituents
  • Estrane-skeleton
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Ynone
  • Heteroaromatic compound
  • Azole
  • Cyclic alcohol
  • Tertiary alcohol
  • Isoxazole
  • Acetylide
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDanazol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-0669000000-7afc135d5b1e92134191Spectrum
Predicted GC-MSDanazol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000x-2479000000-d5f94bb7e7215a30f820Spectrum
Predicted GC-MSDanazol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-9e745b8feecd354f66182012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01b9-6902000000-854476472755ef5419e52012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-0d62c0c1b53c1cea5a252012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0329000000-56adc37fd83dfa3c686f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-05ia-3931000000-1490f6c4984a840160762017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-002f-6900000000-529d2d24864b26fdd6112021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-002f-6900000000-01f21f6ea357e6649d152021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-000i-1309000000-271d4ce8113e1bf160162021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00dj-2910000000-3af637f5ddbf8cfd6b842021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-00dj-2920000000-ba6bb4b948be2171d8642021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-05tg-3900000000-29df3c1f08b04956955d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-000i-0009000000-5fc69729a45a40e940732021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-002f-4900000000-7ba349192301fd4e50132021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-05tg-3900000000-a692616aee182eeb12702021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0119000000-d7acb78e38c02e285d4f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01wr-0289000000-2db311b410937e72f25a2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-3690000000-5eb98df42b0016f9967a2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-d1a89ea3e6c72ff1ab882017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-71fbd4000b06296a83862017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-2089000000-24b6d7f3ec074a6c2b592017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-2626c30d979a970252f02021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007y-0982000000-4cf29ec44560862d68c72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1001-1890000000-24565065bfdf6e8edf392021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-8413c28ca2b1374741c72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-3424fea43411af8361042021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID26436
ChEMBL IDCHEMBL1479
KEGG Compound IDC06938
Pubchem Compound ID28417
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB01406
HMDB IDHMDB02835
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDanazol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Sex hormone-binding globulinSHBGP04278
Estrogen receptorESR1P03372
C-C motif chemokine 2CCL2P13500
N-acetylated-alpha-linked acidic dipeptidase-like proteinNAALADL1Q9UQQ1
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference