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:: Description was created based on several sources, including 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
41.0 nM [IC50]
1.2 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

8.8084801E11
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

7.0882558E11
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
Quality-of-life assessment in patients with benign prostatic hyperplasia: effects of various interventions.
2001
Management of patients with LUTS suggestive of BPH.
2001
Dietary supplement use in the Prostate Cancer Prevention Trial: implications for prevention trials.
2001
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia.
2001
Finasteride: a long-term follow-up in the treatment of recurrent hematuria associated with benign prostatic hyperplasia.
2001
The value of hair cosmetics and pharmaceuticals.
2001
Inhibition of 5alpha-reductase in rat prostate reveals differential regulation of androgen-response gene expression by testosterone and dihydrotestosterone.
2001
Docetaxel followed by hormone therapy after failure of definitive treatments for clinically localized/locally advanced prostate cancer: preliminary results.
2001 Aug
Effects of different steroid-biosynthesis inhibitors on the testicular steroidogenesis of the toad Bufo arenarum.
2001 Aug
The impact of participation in a study of medical treatment of lower urinary tract symptoms on the incidence of prostate surgery.
2001 Aug
Effect of androgen deprivation therapy on prostatic intraepithelial neoplasia.
2001 Aug
Androgen deprivation therapy for prostate cancer chemoprevention: current status and future directions for agent development.
2001 Aug
Androgen deprivation therapy for patients with clinically localized (stages T1 to T3) prostate cancer and for patients with biochemical recurrence after radical prostatectomy.
2001 Aug
Neurosteroids mediate habituation and tonic inhibition in the auditory midbrain.
2001 Aug
Ventral tegmental area infusions of inhibitors of the biosynthesis and metabolism of 3alpha,5alpha-THP attenuate lordosis of hormone-primed and behavioural oestrous rats and hamsters.
2001 Dec
Stable expression of the human 5alpha-reductase isoenzymes type I and type II in HEK293 cells to identify dual and selective inhibitors.
2001 Jan
Online prescriptions of pharmaceuticals: where is the evidence for harm or for benefit? A call for papers--and for reflection.
2001 Jan-Mar
Management of male pattern hair loss.
2001 Jul
Body dysmorphic disorder and life-style drugs. Overview and case report with finasteride.
2001 Jul
The "Dorian Gray Syndrome": psychodynamic need for hair growth restorers and other "fountains of youth.".
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
[Prostate problems. More clarity regarding prognosis].
2001 Jul 26
TrichoScan: combining epiluminescence microscopy with digital image analysis for the measurement of hair growth in vivo.
2001 Jul-Aug
Advances in the treatment of male androgenetic alopecia: a brief review of finasteride studies.
2001 Jul-Aug
Androgen responsive genes as they affect hair growth.
2001 Jul-Aug
Steroidogenic enzymes in skin.
2001 Jul-Aug
Prevention of prostate cancer.
2001 Jun
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
Finasteride and tamsulosin used in benign prostatic hypertrophy: a review of the prescription-event monitoring data.
2001 Jun
Questions whether clients were properly informed about treatment protocol.
2001 Jun 1
Effect of finasteride on behavioural arousal and somatosensory evoked potentials in fetal sheep.
2001 Jun 22
[Wellbeing or happiness medications?].
2001 Jun 30
Enhanced anticonvulsant activity of neuroactive steroids in a rat model of catamenial epilepsy.
2001 Mar
Neurosteroid withdrawal model of perimenstrual catamenial epilepsy.
2001 Mar
[Gynecomastia and finasteride].
2001 May
Evaluation of new pregnane derivatives as 5alpha-reductase inhibitor.
2001 May
[Finasteride in prolonged therapy of patients with benign prostatic hyperplasia].
2001 May-Jun
Contribution of androgens to chronic allograft nephropathy is mediated by dihydrotestosterone.
2001 Nov
Baldness. Medical solutions for men and women.
2001 Nov
Managing benign prostatic hyperplasia.
2001 Oct
Increased expression of the neuropeptide Y receptor Y(1) gene in the medial amygdala of transgenic mice induced by long-term treatment with progesterone or allopregnanolone.
2001 Oct
Replacement of surgical castration by GnRH-inhibition or Leydig cell ablation in the male rat Hershberger antiandrogen assay.
2001 Oct
Progesterone and 3alpha,5alpha-THP enhance sexual receptivity in mice.
2001 Oct
Co-administration of finasteride and the pure anti-oestrogen ICI 182,780 act synergistically in modulating the IGF system in rat prostate.
2001 Oct
Pharmacokinetic parameters and mechanisms of inhibition of rat type 1 and 2 steroid 5alpha-reductases: determinants for different in vivo activities of GI198745 and finasteride in the rat.
2001 Oct 1
Direct-to-consumer advertising. Finasteride for male pattern hair loss.
2001 Sep
New progesterone esters as 5alpha-reductase inhibitors.
2001 Sep
Molecular epidemiologic studies within the Selenium and Vitamin E Cancer Prevention Trial (SELECT).
2001 Sep
Possible mechanisms of miniaturization during androgenetic alopecia or pattern hair loss.
2001 Sep
Anxiolytic effect of Kami-Shoyo-San (TJ-24) in mice: possible mediation of neurosteroid synthesis.
2001 Sep 21
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Benign Prostatic Hyperplasia 5 mg orally once a day Usual Adult Dose for Androgenetic Alopecia 1 mg orally once a day
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