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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:13 UTC
Update Date2017-10-23 19:04:01 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
Thumb
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 danazolMeSH
Kendrick brand OF danazolMeSH
Sanofi brand OF danazolMeSH
DanatrolMeSH
DanazantMeSH
Danazol-ratiopharmMeSH
DanovalMeSH
Ratiopharm brand OF danazolMeSH
Antigen brand OF danazolMeSH
AzolMeSH
NorcidenMeSH
PanacrineMeSH
Sanofi synthelabo brand OF danazolMeSH
Sanofi winthrop brand OF danazolMeSH
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[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁸]icosa-4(8),5,9-trien-17-ol
Traditional Namedanazol
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
DescriptionThis compound 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:

  Subcellular:

  Biofluid and excreta:

  Tissue and substructures:

  Cell and elements:

Source:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

  Molecular messenger:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    System process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225.6 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.081Not Available
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
Polarizability38.56 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-0669000000-7afc135d5b1e92134191View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000x-2479000000-d5f94bb7e7215a30f820View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0009000000-9e745b8feecd354f6618View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01b9-6902000000-854476472755ef5419e5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9100000000-0d62c0c1b53c1cea5a25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0329000000-56adc37fd83dfa3c686fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-05ia-3931000000-1490f6c4984a84016076View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0119000000-d7acb78e38c02e285d4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01wr-0289000000-2db311b410937e72f25aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000j-3690000000-5eb98df42b0016f9967aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-d1a89ea3e6c72ff1ab88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-71fbd4000b06296a8386View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00e9-2089000000-24b6d7f3ec074a6c2b59View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB 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
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