Human Metabolome Database Version 3.5

Showing metabocard for Finasteride (HMDB01984)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:30 -0600
Update Date 2013-05-29 13:33:10 -0600
HMDB ID HMDB01984
Secondary Accession Numbers
  • HMDB15347
Metabolite Identification
Common Name Finasteride
Description Finasteride is only found in individuals that have used or taken this drug. Finasteride is an androgen antagonist. It is an orally active testosterone 5-alpha-reductase inhibitor. Finasteride is one of the currently available pharmacologic treatment modalities with proven efficacy for treatment of androgenetic alopecia. The mechanism of action has not been fully determined, but finasteride has shown to decrease scalp DHT concentration to the levels found in hairy scalp, reduce serum DHT, increase hair regrowth, and slow hair loss. 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 is also used as a surgical alternative for treatment of benign prostatic hyperplasia. [PubChem]The mechanism of action of Finasteride is based on its preferential inhibition of Type II 5a-reductase through the formation of a stable complex with the enzyme. Inhibition of Type II 5a-reductase blocks the peripheral conversion of testosterone to DHT, resulting in significant decreases in serum and tissue DHT concentrations, minimal to moderate increase in serum testosterone concentrations, and substantial increases in prostatic testosterone concetrations. As DHT appears to be the principal androgen responsible for stimulation of prostatic growth, a decrease in DHT concentrations will result in a decrease in prostatic volume (approximately 20-30% after 6-24 months of continued therapy). 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 Link_out, 17543725 Link_out, 17414641 Link_out, 17415094 Link_out, 17394699 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Chibro-proscar
  2. Finasterida
  3. Finasteridum
  4. Finastid
  5. Finpecia
  6. Propecia
  7. Proscar
  8. Prostide
Chemical Formula C23H36N2O2
Average Molecular Weight 372.5441
Monoisotopic Molecular Weight 372.277678406
IUPAC Name (1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-3-ene-14-carboxamide
Traditional IUPAC Name finasteride
CAS Registry Number 98319-26-7
SMILES [H][C@@]12CC[C@H](C(=O)NC(C)(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])NC(=O)C=C[C@]12C
InChI Identifier InChI=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 Key DBEPLOCGEIEOCV-WSBQPABSSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Prenol Lipids
Sub Class Diterpenes
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • Benzoquinoline
  • Carboxamide Group
  • Cyclohexane
  • Decaline
  • Lactam
  • Quinoline
  • Secondary Carboxylic Acid Amide
Direct Parent Diterpenes
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Anti-baldness Agents
  • Antihyperplasia Agents
  • Cell signalling
  • Enzyme Inhibitors
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
  • Skin and Mucous Membrane Agents
Application
  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 252 - 254 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1.98e-03 g/L Not Available
LogP 3.03 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.002 g/L ALOGPS
LogP 3.53 ALOGPS
LogP 3.07 ChemAxon
LogS -5.27 ALOGPS
pKa (strongest acidic) 14.53 ChemAxon
pKa (strongest basic) 2.22 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 58.2 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 108.2 ChemAxon
Polarizability 43.96 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 DB01216 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022782
KNApSAcK ID Not Available
Chemspider ID 51714 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Finasteride Link_out
NuGOwiki Link HMDB01984 Link_out
Metagene Link HMDB01984 Link_out
METLIN ID Not Available
PubChem Compound 57363 Link_out
PDB ID Not Available
ChEBI ID 5062 Link_out
References
Synthesis Reference Peng, Dongming; Huang, Kelong; Liu, Yanfei. Improved synthesis of finasteride. Zhongguo Yaowu Huaxue Zazhi (2005), 15(5), 288-290.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Trueb RM: Pharmacologic interventions in aging hair. Clin Interv Aging. 2006;1(2):121-9. Pubmed: 18044109 Link_out
  2. Otberg N, Finner AM, Shapiro J: Androgenetic alopecia. Endocrinol Metab Clin North Am. 2007 Jun;36(2):379-98. Pubmed: 17543725 Link_out
  3. Lin AM, Small EJ: Prostate cancer update: 2006. Curr Opin Oncol. 2007 May;19(3):229-33. Pubmed: 17414641 Link_out
  4. Dunn BK, Ford LG: Hormonal interventions to prevent hormonal cancers: breast and prostate cancers. Eur J Cancer Prev. 2007 Jun;16(3):232-42. Pubmed: 17415094 Link_out
  5. Thorpe JF, Jain S, Marczylo TH, Gescher AJ, Steward WP, Mellon JK: A review of phase III clinical trials of prostate cancer chemoprevention. Ann R Coll Surg Engl. 2007 Apr;89(3):207-11. Pubmed: 17394699 Link_out
  6. Smith AB, Carson CC: Finasteride in the treatment of patients with benign prostatic hyperplasia: a review. Ther Clin Risk Manag. 2009 Jun;5(3):535-45. Epub 2009 Jul 12. Pubmed: 19707263 Link_out
  7. Suzuki R, Satoh H, Ohtani H, Hori S, Sawada Y: Saturable binding of finasteride to steroid 5alpha-reductase as determinant of nonlinear pharmacokinetics. Drug Metab Pharmacokinet. 2010;25(2):208-13. Pubmed: 20460827 Link_out

Enzymes
Name: 3-oxo-5-alpha-steroid 4-dehydrogenase 1
Reactions: Not Available
Gene Name: SRD5A1
Uniprot ID: P18405 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Androgen receptor
Reactions: Not Available
Gene Name: AR
Uniprot ID: P10275 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA