U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H36N2O2
Molecular Weight 372.545
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FINASTERIDE

SMILES

CC(C)(C)N=C([C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@]4([H])[C@](C)(C=CC(=N4)O)[C@@]3([H])CC[C@@]21C)O

InChI

InChIKey=DBEPLOCGEIEOCV-WSBQPABSSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: http://onlinelibrary.wiley.com/doi/10.1111/j.1527-3458.2006.00053.x/pdf and https://www.drugs.com/pro/finasteride.html

Finasteride is a synthetic 4-azasteroid compound. This drug is a competitive and specific inhibitor of Type II 5a-reductase, an intracellular enzyme that converts the androgen testosterone into 5α-dihydrotestosterone (DHT). Two distinct isozymes are found in mice, rats, monkeys, and humans: Type I and II. Each of these isozymes is differentially expressed in tissues and developmental stages. In humans, Type I 5a-reductase is predominant in the sebaceous glands of most regions of skin, including scalp, and liver. Type I 5a-reductase is responsible for approximately one-third of circulating DHT. The Type II 5a-reductase isozyme is primarily found in prostate, seminal vesicles, epididymides, and hair follicles as well as liver, and is responsible for two-thirds of circulating DHT. Although finasteride is 100-fold more selective for type II 5a-reductase than for the type I isoenzyme, chronic treatment with this drug may have some effect on type I 5a-reductase. Finasteride is used for 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). Finasteride is sold under the brand names Proscar and Propecia among others.

CNS Activity

Curator's Comment:: Finasteride has been found to cross the blood-brain barrier.

Originator

Curator's Comment:: # Merck & Co

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
41 nM [IC50]
1.19999999999999996 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PROPECIA

Approved Use

PROPECIA is indicated for the treatment of male pattern hair loss (androgenetic alopecia) in MEN ONLY.

Launch Date

880848000000
Primary
Proscar

Approved Use

PROSCAR is indicated for 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 (TURP) and prostatectomy.

Launch Date

708825600000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
9.2 ng/mL
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FINASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
53 ng × h/mL
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FINASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.5 h
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FINASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
10%
1 mg 1 times / day steady-state, oral
dose: 1 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
FINASTERIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim
PubMed

PubMed

TitleDatePubMed
Anaemia in men receiving combined finasteride and flutamide therapy for advanced prostate cancer.
1999 Jan
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia.
2001
Hirsutism: diagnosis and management.
2001
Finasteride: a long-term follow-up in the treatment of recurrent hematuria associated with benign prostatic hyperplasia.
2001
A risk-benefit assessment of pharmacological therapies for hirsutism.
2001
Changing therapeutic regimens in benign prostatic hyperplasia. Clinical and economic considerations.
2001
Lower urinary tract symptoms suggestive of benign prostatic obstruction--Triumph: the role of general practice databases.
2001
Lower urinary tract symptoms suggestive of benign prostatic obstruction: what are the current practice patterns?
2001
Lower urinary tract symptoms suggestive of benign prostatic obstruction--what's the long-term effectiveness of medical therapies?
2001
Lower urinary tract symptoms suggestive of benign prostatic obstruction: how can clinical expertise contribute to rational management?
2001
Lower urinary tract symptoms suggestive of benign prostatic obstruction: what is the available evidence for rational management?
2001
Cost-sharing for prescriptions of sildenafil and finasteride: a case study in veteran patients.
2001 Apr
The Prostate Cancer Prevention Trial: Current status and lessons learned.
2001 Apr
Androgen antagonists: Potential role in prostate cancer prevention.
2001 Apr
Executive Summary of the National Cancer Institute Workshop: Highlights and recommendations.
2001 Apr
As genes differ, so should interventions for cancer.
2001 Apr 11
Effects of finasteride on size of the prostate gland and semen quality in dogs with benign prostatic hypertrophy.
2001 Apr 15
Narcissus drowned.
2001 Apr 28
The impact of participation in a study of medical treatment of lower urinary tract symptoms on the incidence of prostate surgery.
2001 Aug
Bioequivalence study of finasteride. Determination in human plasma by high-pressure liquid chromatography coupled to tandem mass spectrometry.
2001 Feb
[Status of scalp hair and therapy of alopecia in men in Switzerland].
2001 Feb 15
[Hair loss].
2001 Feb 26
Stable expression of the human 5alpha-reductase isoenzymes type I and type II in HEK293 cells to identify dual and selective inhibitors.
2001 Jan
Is there a place for combination medical therapy?
2001 Jan
Combined effect of terazosin and finasteride on apoptosis, cell proliferation, and transforming growth factor-beta expression in benign prostatic hyperplasia.
2001 Jan 1
Topical finasteride therapy in hirsutism.
2001 Jan-Feb
Finasteride cream in hirsutism.
2001 Jan-Feb
Body dysmorphic disorder and life-style drugs. Overview and case report with finasteride.
2001 Jul
A double-blind, randomized, placebo-controlled pilot study to investigate the effects of finasteride combined with a biodegradable self-reinforced poly L-lactic acid spiral stent in patients with urinary retention caused by bladder outlet obstruction from benign prostatic hyperplasia.
2001 Jul
LC determination of finasteride and its application to storage stability studies.
2001 Jul
TrichoScan: combining epiluminescence microscopy with digital image analysis for the measurement of hair growth in vivo.
2001 Jul-Aug
Steroidogenic enzymes in skin.
2001 Jul-Aug
Inhibition of 5alpha-reductase enzyme or GABA(A) receptors in the VMH and the VTA attenuates progesterone-induced sexual behavior in rats and hamsters.
2001 Jun
Comparison of the efficacy and safety of finasteride in older versus younger men with benign prostatic hyperplasia.
2001 Jun
Steroid-sensitive gene-1 is an androgen-regulated gene expressed in prostatic smooth muscle cells in vivo.
2001 Jun
Linear relationships between the ligand binding energy and the activation energy of time-dependent inhibition of steroid 5alpha-reductase by delta 1-4-azasteroids.
2001 Jun 15
Effect of finasteride on behavioural arousal and somatosensory evoked potentials in fetal sheep.
2001 Jun 22
[Long-term therapy of benign prostatic hyperplasia. Our experience].
2001 Mar
Clinical application of 5alpha-reductase inhibitors.
2001 Mar
Acute pancreatitis possibly related to finasteride.
2001 Mar
Comparison of Diane 35 and Diane 35 plus finasteride in the treatment of hirsutism.
2001 Mar
Structure-function studies of human 5-alpha reductase type 2 using site directed mutagenesis.
2001 May
Tissue effects of saw palmetto and finasteride: use of biopsy cores for in situ quantification of prostatic androgens.
2001 May
Evaluating adverse cardiovascular effects of drug treatment for benign prostatic hyperplasia (BPH): methodological considerations.
2001 May
Managing benign prostatic hyperplasia.
2001 Oct
Progesterone and 3alpha,5alpha-THP enhance sexual receptivity in mice.
2001 Oct
Direct-to-consumer advertising. Finasteride for male pattern hair loss.
2001 Sep
Possible mechanisms of miniaturization during androgenetic alopecia or pattern hair loss.
2001 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Benign Prostatic Hyperplasia
Route of Administration: Oral
Finasteride (0.5 uM - 1 uM) down-regulated the expression of AR target genes in LNCaP cells
Name Type Language
FINASTERIDE
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
FINASTERIDE [JAN]
Common Name English
NSC-759318
Code English
FINASTERIDE [INN]
Common Name English
N-TERT-BUTYL-3-OXO-4-AZA-5.ALPHA.-ANDROST-1-ENE-17.BETA.-CARBOXAMIDE
Common Name English
MK-906
Code English
FINASTERIDE [USAN]
Common Name English
FINASTERIDE [EP MONOGRAPH]
Common Name English
FINASTERIDE [USP MONOGRAPH]
Common Name English
FINASTERIDE [USP]
Common Name English
FINASTERIDE [MART.]
Common Name English
PROSCAR
Brand Name English
4-AZAANDROST-1-ENE-17-CARBOXAMIDE, N-(1,1-DIMETHYLETHYL)-3-OXO-, (5.ALPHA.,17.BETA.)-
Systematic Name English
FINASTERIDE [MI]
Common Name English
PROPECIA
Brand Name English
FINASTERIDE [ORANGE BOOK]
Common Name English
FINASTERIDE [WHO-DD]
Common Name English
FINASTERIDE [EP]
Common Name English
NSC-741485
Code English
FINASTERIDE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-VATC QG04CB01
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
EPA PESTICIDE CODE 129113
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
NCI_THESAURUS C2319
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
WHO-ATC G04CA51
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
WHO-ATC G04CB01
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
WHO-VATC QD11AX10
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
NDF-RT N0000000126
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
LIVERTOX 411
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
WHO-ATC D11AX10
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
WHO-VATC QG04CA51
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
NDF-RT N0000175836
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
Code System Code Type Description
FDA UNII
57GNO57U7G
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
IUPHAR
6818
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
ChEMBL
CHEMBL710
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
PUBCHEM
57363
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
DRUG BANK
DB01216
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
NCI_THESAURUS
C1099
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
WIKIPEDIA
FINASTERIDE
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
RXCUI
25025
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY RxNorm
EPA CompTox
98319-26-7
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
MESH
D018120
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
CAS
98319-26-7
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
MERCK INDEX
M5383
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY Merck Index
HSDB
6793
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
USP_CATALOG
1270402
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY USP-RS
DRUG CENTRAL
1171
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
INN
6539
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY
EVMPD
SUB07629MIG
Created by admin on Fri Jun 25 21:01:21 UTC 2021 , Edited by admin on Fri Jun 25 21:01:21 UTC 2021
PRIMARY