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Record Information
Version3.6
Creation Date2006-05-22 14:17:30 UTC
Update Date2013-05-29 19:33:10 UTC
HMDB IDHMDB01984
Secondary Accession Numbers
  • HMDB15347
Metabolite Identification
Common NameFinasteride
DescriptionFinasteride 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 , 17543725 , 17414641 , 17415094 , 17394699 ).
Structure
Thumb
Synonyms
  1. Chibro-proscar
  2. Finasterida
  3. Finasteridum
  4. Finastid
  5. Finpecia
  6. Propecia
  7. Proscar
  8. Prostide
Chemical FormulaC23H36N2O2
Average Molecular Weight372.5441
Monoisotopic Molecular Weight372.277678406
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 Namefinasteride
CAS Registry Number98319-26-7
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 KeyDBEPLOCGEIEOCV-WSBQPABSSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassPrenol Lipids
Sub ClassDiterpenes
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • Benzoquinoline
  • Carboxamide Group
  • Cyclohexane
  • Decaline
  • Lactam
  • Quinoline
  • Secondary Carboxylic Acid Amide
Direct ParentDiterpenes
Ontology
StatusExpected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point252 - 254 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.98e-03 g/LNot Available
LogP3.03HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility0.002 g/LALOGPS
logP3.53ALOGPS
logP3.07ChemAxon
logS-5.3ALOGPS
pKa (strongest acidic)14.53ChemAxon
pKa (strongest basic)2.22ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area58.2ChemAxon
rotatable bond count2ChemAxon
refractivity108.2ChemAxon
polarizability43.96ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDDB01216
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022782
KNApSAcK IDNot Available
Chemspider ID51714
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFinasteride
NuGOwiki LinkHMDB01984
Metagene LinkHMDB01984
METLIN IDNot Available
PubChem Compound57363
PDB IDNot Available
ChEBI ID5062
References
Synthesis ReferencePeng, 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. 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
  2. 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
  3. Trueb RM: Pharmacologic interventions in aging hair. Clin Interv Aging. 2006;1(2):121-9. Pubmed: 18044109
  4. Otberg N, Finner AM, Shapiro J: Androgenetic alopecia. Endocrinol Metab Clin North Am. 2007 Jun;36(2):379-98. Pubmed: 17543725
  5. Lin AM, Small EJ: Prostate cancer update: 2006. Curr Opin Oncol. 2007 May;19(3):229-33. Pubmed: 17414641
  6. 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
  7. 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

Enzymes

General function:
Involved in 3-oxo-5-alpha-steroid 4-dehydrogenase activity
Specific function:
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and androgen physiology.
Gene Name:
SRD5A1
Uniprot ID:
P18405
Molecular weight:
29458.18
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
General function:
Involved in DNA binding
Specific function:
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3
Gene Name:
AR
Uniprot ID:
P10275
Molecular weight:
98987.9