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Record Information
Version3.6
Creation Date2006-05-22 15:12:13 UTC
Update Date2013-05-29 19:37:01 UTC
HMDB IDHMDB02835
Secondary Accession NumbersNone
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
  1. (17a)-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol
  2. 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
  3. 17 alpha-Pregna-2,4-dien-20-yno[2,3-D] isoxazol-17 beta-ol
  4. 17a-Pregna-2,4-dien-20-yne-[2,3-D]isoxazole-17b-ol
  5. 17a-Pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol
  6. 1H-Cyclopenta[7,8]phenanthro[3,2-D]isoxazole- pregna-2,4-dien-20-yno[2,3-D]isoxazol-17-ol deriv.
  7. Bonzol
  8. Chronogyn
  9. Cyclomen
  10. Danazolum
  11. Danocrine
  12. Danol
  13. Danovaol
  14. Danzol
  15. Ladogal
  16. Winobanin
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 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
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassGluco/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 ParentGluco/mineralocorticoids, Progestogins and Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point225.6 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP4.081Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.018ALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity98.54 m3·mol-1ChemAxon
Polarizability38.55 Å3ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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
NuGOwiki LinkHMDB02835
Metagene LinkHMDB02835
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