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Record Information
Version1.0
Creation Date2014-09-11 05:18:00 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003777
Identification
Common NameFinasteride
ClassSmall Molecule
DescriptionAn orally active testosterone 5-alpha-reductase inhibitor. It is used as a surgical alternative for treatment of benign prostatic hyperplasia.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • 5-alpha Reductase Inhibitor
  • Amide
  • Amine
  • Drug
  • Ester
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Skin and Mucous Membrane Agent
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
ValueSource
(5alpha,17beta)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamideChEBI
FinasteridaChEBI
FinasteridumChEBI
PropeciaKegg
ProscarKegg
(5a,17b)-(1,1-Dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamideGenerator
(5Α,17β)-(1,1-dimethylethyl)-3-oxo-4-azaandrost-1-ene-17-carboxamideGenerator
Chibro-proscarHMDB
FinastidHMDB
FinpeciaHMDB
ProstideHMDB
Chibro proscarHMDB
EucoprostHMDB
Merck brand 1 OF finasterideHMDB
Merck brand 2 OF finasterideHMDB
Cahill may roberts brand OF finasterideHMDB
Lipha brand OF finasterideHMDB
Merck frosst brand 1 OF finasterideHMDB
Frosst iberica brand OF finasterideHMDB
MSD Chibropharm brand OF finasterideHMDB
Merck sharp and dohme brand 1 OF finasterideHMDB
PropeshiaHMDB
MSD Brand OF finasterideHMDB
Merck frosst brand 2 OF finasterideHMDB
Merck sharp and dhome brand 2 OF finasterideHMDB
Chemical FormulaC23H36N2O2
Average Molecular Mass372.544 g/mol
Monoisotopic Mass372.278 g/mol
CAS Registry Number98319-26-7
IUPAC Name(1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide
Traditional Name(1S,2R,7R,10S,11S,14S,15S)-N-tert-butyl-2,15-dimethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxamide
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 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-WSBQPABSSA-N
Chemical Taxonomy
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
  • 20-hydroxysteroid
  • Androgen-skeleton
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 4-azasteroid
  • Azasteroid
  • Cyclic carboximidic acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point252-254°C
Boiling PointNot Available
Solubility11.7 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP3.53ALOGPS
logP3.07ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)14.53ChemAxon
pKa (Strongest Basic)0.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.2 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity108.2 m³·mol⁻¹ChemAxon
Polarizability43.96 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0a4i-1579000000-3a73a92e1d34b87c3e4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-5910000000-7dd7b7fbb29b6ae08f4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0ab9-1319000000-9f18f09bea4e9168f1dfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-5900000000-3ad6a0d10c51f9892144View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0119000000-f683db304300c01e907aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0129000000-a097bfd2187d4d4c97c6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00xr-0119000000-43c6646bf19d62255966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01b9-2539000000-c47506144391db372c4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-0900000000-a55cf309ee5a976c5e45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-a6be7718311b4f11aad5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zmi-0439000000-e0a2fad4c18c6da72e1cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uej-3790000000-df2f90aa3664e0df8776View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-be3980c97e5b8f8767a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-3029000000-5489b391a47dec8eb0f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9131000000-a1b8897126899f67f5fbView in MoNA
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityThe 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). In men with androgenic 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.
MetabolismDrug is extensively metabolized, primarily in the liver via CYP3A4. Two metabolites have been identified with дЉ_20% of the activity of finasteride. Route of Elimination: Following an oral dose of 14C-finasteride in man (n = 6), a mean of 39% (range, 32 to 46%) of the dose was excreted in the urine in the form of metabolites; 57% (range, 51 to 64%) was excreted in the feces. Urinary excretion of metabolites was decreased in patients with renal impairment. This decrease was associated with an increase in fecal excretion of metabolites. Half Life: 4.5 hours (range 3.3-13.4 hours)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of symptomatic benign prostatic hyperplasia (BPH) in men with an enlarged prostate to: Improve symptoms, reduce the risk of acute urinary retention, reduce the risk of the need for surgery including transurethral resection of the prostate. Also used for the stimulation of regrowth of hair in men with mild to moderate androgenetic alopecia (male pattern alopecia, hereditary alopecia, common male baldness).
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01216
HMDB IDHMDB0001984
FooDB IDFDB022782
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFinasteride
Chemspider ID51714
ChEBI ID5062
PubChem Compound ID57363
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Roman Davis, Alan Millar, “Method for preparing finasteride.” U.S. Patent US5670643, issued October, 1992.

MSDSLink
General References
1. Peng, Dongming; Huang, Kelong; Liu, Yanfei. Improved synthesis of finasteride. Zhongguo Yaowu Huaxue Zazhi (2005), 15(5), 288-290.
2. Trueb RM: Pharmacologic interventions in aging hair. Clin Interv Aging. 2006;1(2):121-9.
3. Otberg N, Finner AM, Shapiro J: Androgenetic alopecia. Endocrinol Metab Clin North Am. 2007 Jun;36(2):379-98.
4. Lin AM, Small EJ: Prostate cancer update: 2006. Curr Opin Oncol. 2007 May;19(3):229-33.
5. Dunn BK, Ford LG: Hormonal interventions to prevent hormonal cancers: breast and prostate cancers. Eur J Cancer Prev. 2007 Jun;16(3):232-42.
6. 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.
7. 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.
8. 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.
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=15956333
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23552442