Human Metabolome Database Version 3.5

Showing metabocard for Danazol (HMDB02835)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:13 -0600
Update Date 2013-05-29 13:37:01 -0600
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 Link_out, 1640693 Link_out, 16288903 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 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
  • 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
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
Property Value Source
Water Solubility 0.018 g/L ALOGPS
LogP 3.62 ALOGPS
LogP 3.46 ChemAxon
LogS -4.28 ALOGPS
pKa (strongest acidic) 17.59 ChemAxon
pKa (strongest basic) 0.25 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 46.26 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 98.54 ChemAxon
Polarizability 38.55 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
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
DrugBank ID Not Available
DrugBank Metabolite 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 Link_out
KEGG Compound ID C06938 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Danazol Link_out
NuGOwiki Link HMDB02835 Link_out
Metagene Link HMDB02835 Link_out
METLIN ID Not Available
PubChem Compound 28417 Link_out
PDB ID Not Available
ChEBI ID 4315 Link_out
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
  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 Link_out
  2. 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 Link_out
  3. 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 Link_out

Enzymes
Name: Cytochrome P450 19A1
Reactions: Not Available
Gene Name: CYP19A1
Uniprot ID: P11511 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sex hormone-binding globulin
Reactions: Not Available
Gene Name: SHBG
Uniprot ID: P04278 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: C-C motif chemokine 2
Reactions: Not Available
Gene Name: CCL2
Uniprot ID: P13500 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Estrogen receptor
Reactions: Not Available
Gene Name: ESR1
Uniprot ID: P03372 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gonadotropin-releasing hormone receptor
Reactions: Not Available
Gene Name: GNRHR
Uniprot ID: P30968 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative gonadotropin-releasing hormone II receptor
Reactions: Not Available
Gene Name: GNRHR2
Uniprot ID: Q96P88 Link_out
Protein Sequence: FASTA
Name: N-acetylated-alpha-linked acidic dipeptidase-like protein
Reactions: Not Available
Gene Name: NAALADL1
Uniprot ID: Q9UQQ1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA