Record Information
Version1.0
Creation date2011-09-21 00:19:33 UTC
Update date2015-07-21 06:57:21 UTC
Primary IDFDB022782
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameFinasteride
DescriptionFinasteride is an androgen antagonist. Finasteride is one of the currently available pharmacologic treatment modalities with proven efficacy for treatment of androgenetic alopecia. Androgenetic alopecia (AGA), or male pattern hair loss, affects approximately 50% of the male population. AGA is an androgen-related condition in genetically predisposed individuals. There is no treatment to completely reverse AGA in advanced stages, but with medical treatment (e.g., finasteride), the progression can be arrested and partly reversed in the majority of patients who have mild to moderate AGA. Finasteride may increase the sensitivity of prostate specific antigen to detect prostate cancer. At present, finasteride remains the only intervention shown in long-term prospective phase III clinical trials to reduce the incidence of prostate cancer. (PMID: 18044109, 17543725, 17414641, 17415094, 17394699) [HMDB]
CAS Number98319-26-7
Structure
Thumb
Synonyms
SynonymSource
(5a,17b)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamideGenerator
(5alpha,17beta)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamideChEBI
(5α,17β)-(1,1-dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamideGenerator
Chibro-proscarhmdb
Finasteridahmdb
Finasteridumhmdb
Finastidhmdb
Finpeciahmdb
Propeciahmdb
Proscarhmdb
Prostidehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.00095 g/LALOGPS
logP4.98ALOGPS
logP3.97ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)4.86ChemAxon
pKa (Strongest Basic)6.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.18 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity109.24 m³·mol⁻¹ChemAxon
Polarizability44.03 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC23H36N2O2
IUPAC name(1S,2R,10S,11S,14S,15S)-N-tert-butyl-5-hydroxy-2,15-dimethyl-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,5-diene-14-carboximidic acid
InChI IdentifierInChI=1S/C23H36N2O2/c1-21(2,3)25-20(27)17-8-7-15-14-6-9-18-23(5,13-11-19(26)24-18)16(14)10-12-22(15,17)4/h11,13-18H,6-10,12H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18?,22-,23+/m0/s1
InChI KeyDBEPLOCGEIEOCV-SKTQUGAYSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4NC(=O)C=C[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)NC(C)(C)C
Average Molecular Weight372.5441
Monoisotopic Molecular Weight372.277678406
Classification
Description Belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 3-oxo-4-azasteroid
  • Oxosteroid
  • 3-oxosteroid
  • Azasteroid
  • 4-azasteroid
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
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
SpectraNot Available
ChemSpider ID51714
ChEMBL IDCHEMBL710
KEGG Compound IDNot Available
Pubchem Compound ID57363
Pubchem Substance IDNot Available
ChEBI ID5062
Phenol-Explorer IDNot Available
DrugBank IDDB01216
HMDB IDHMDB01984
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 IDFinasteride
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
3-oxo-5-alpha-steroid 4-dehydrogenase 1SRD5A1P18405
Androgen receptorARP10275
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference