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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:13 UTC
Update Date2021-09-14 15:40:11 UTC
HMDB IDHMDB0002835
Secondary Accession Numbers
  • HMDB02835
Metabolite Identification
Common 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 ).
Structure
Data?1582752257
Synonyms
ValueSource
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
Chemical FormulaC22H27NO2
Average Molecular Weight337.4553
Monoisotopic Molecular Weight337.204179113
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 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
CAS Registry Number17230-88-5
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 KeyPOZRVZJJTULAOH-LHZXLZLDSA-N
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.
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

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point225.6 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.081Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP10(3.62) g/LALOGPS
logP10(3.46) g/LChemAxon
logS10(-4.3) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.08631661259
DarkChem[M-H]-174.9231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Danazol[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO34044.9Standard polar33892256
Danazol[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO32871.3Standard non polar33892256
Danazol[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC3=C(C[C@]12C)C=NO32971.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Danazol,1TMS,isomer #1C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC5=C(C=NO5)C[C@]4(C)[C@H]3CC[C@@]21C3060.0Semi standard non polar33892256
Danazol,1TBDMS,isomer #1C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC5=C(C=NO5)C[C@]4(C)[C@H]3CC[C@@]21C3326.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Danazol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-0669000000-7afc135d5b1e921341912017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Danazol GC-MS (1 TMS) - 70eV, Positivesplash10-000x-2479000000-d5f94bb7e7215a30f8202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Danazol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0009000000-9e745b8feecd354f66182012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-01b9-6902000000-854476472755ef5419e52012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9100000000-0d62c0c1b53c1cea5a252012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol , positive-QTOFsplash10-000i-0329000000-56adc37fd83dfa3c686f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol , positive-QTOFsplash10-05ia-3931000000-1490f6c4984a840160762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol 90V, Positive-QTOFsplash10-002f-6900000000-529d2d24864b26fdd6112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol 90V, Positive-QTOFsplash10-002f-6900000000-01f21f6ea357e6649d152021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol 30V, Positive-QTOFsplash10-000i-1309000000-271d4ce8113e1bf160162021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol 45V, Positive-QTOFsplash10-00dj-2910000000-3af637f5ddbf8cfd6b842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol 45V, Positive-QTOFsplash10-00dj-2920000000-ba6bb4b948be2171d8642021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol 60V, Positive-QTOFsplash10-05tg-3900000000-29df3c1f08b04956955d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol 15V, Positive-QTOFsplash10-000i-0009000000-5fc69729a45a40e940732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol 75V, Positive-QTOFsplash10-002f-4900000000-7ba349192301fd4e50132021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Danazol 60V, Positive-QTOFsplash10-05tg-3900000000-a692616aee182eeb12702021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 10V, Positive-QTOFsplash10-000i-0119000000-d7acb78e38c02e285d4f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 20V, Positive-QTOFsplash10-01wr-0289000000-2db311b410937e72f25a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 40V, Positive-QTOFsplash10-000j-3690000000-5eb98df42b0016f9967a2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 10V, Negative-QTOFsplash10-000i-0009000000-d1a89ea3e6c72ff1ab882017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 20V, Negative-QTOFsplash10-000i-0009000000-71fbd4000b06296a83862017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 40V, Negative-QTOFsplash10-00e9-2089000000-24b6d7f3ec074a6c2b592017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 10V, Positive-QTOFsplash10-000i-0019000000-2626c30d979a970252f02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 20V, Positive-QTOFsplash10-007y-0982000000-4cf29ec44560862d68c72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 40V, Positive-QTOFsplash10-1001-1890000000-24565065bfdf6e8edf392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 10V, Negative-QTOFsplash10-000i-0009000000-8413c28ca2b1374741c72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Danazol 20V, Negative-QTOFsplash10-000i-0009000000-3424fea43411af8361042021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01406
Phenol Explorer Compound IDNot Available
FooDB IDFDB023073
KNApSAcK IDNot Available
Chemspider ID26436
KEGG Compound IDC06938
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDanazol
METLIN IDNot Available
PubChem Compound28417
PDB IDNot Available
ChEBI ID4315
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRaczkowska, 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
  1. Beaumont H, Augood C, Duckitt K, Lethaby A: Danazol for heavy menstrual bleeding. Cochrane Database Syst Rev. 2007 Jul 18;(3):CD001017. [PubMed:17636649 ]
  2. de Oca Porto RM, Fernandez AR, Brito DM, Vidal TC, Diaz AL: Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Jan 2;830(1):178-83. Epub 2005 Nov 8. [PubMed:16288903 ]
  3. de Boer D, de Jong EG, Maes RA: The detection of danazol and its significance in doping analysis. J Anal Toxicol. 1992 Jan-Feb;16(1):14-8. [PubMed:1640693 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:
CYP19A1
Uniprot ID:
P11511
Molecular weight:
57882.48
General function:
Involved in androgen binding
Specific function:
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration
Gene Name:
SHBG
Uniprot ID:
P04278
Molecular weight:
43778.8
General function:
Involved in chemokine activity
Specific function:
Chemotactic factor that attracts monocytes and basophils but not neutrophils or eosinophils. Augments monocyte anti-tumor activity. Has been implicated in the pathogenesis of diseases characterized by monocytic infiltrates, like psoriasis, rheumatoid arthritis or atherosclerosis. May be involved in the recruitment of monocytes into the arterial wall during the disease process of atherosclerosis
Gene Name:
CCL2
Uniprot ID:
P13500
Molecular weight:
11024.9
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular weight:
66215.4
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle- stimulating hormone (FSH). This receptor mediates its action by association with G-proteins that activate a phosphatidylinositol- calcium second messenger system. Isoform 2 may act as an inhibitor of GnRH-R signaling
Gene Name:
GNRHR
Uniprot ID:
P30968
Molecular weight:
37730.4
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for gonadotropin releasing hormone II (GnRH II). This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system (Potential)
Gene Name:
GNRHR2
Uniprot ID:
Q96P88
Molecular weight:
19031.1
General function:
Involved in peptidase activity
Specific function:
NAALADase-like activity unknown. Has no NAAG hydrolyzing activity. Exhibits a dipeptidyl-peptidase IV type activity. In vitro, cleaves Gly-Pro-AMC
Gene Name:
NAALADL1
Uniprot ID:
Q9UQQ1
Molecular weight:
80566.9