FINASTERIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H36N2O2
Molecular Weight	372.5441
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@H](C(=O)NC(C)(C)C)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])NC(=O)C=C[C@]34C

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

Molecular Formula	C23H36N2O2
Molecular Weight	372.5441
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB01216
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Steroid 5-alpha-reductase 1 5 Target ID: CHEMBL1787 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12139451	Inhibitor 8297		41.0 nM [IC50]
Steroid 5-alpha-reductase 2 3 Target ID: CHEMBL1856 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9873639	Inhibitor 8297		1.2 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Androgenic alopecia 8 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020788s018lbl.pdf	Primary		Approved 8429	PROPECIA Approved Use PROPECIA is indicated for the treatment of male pattern hair loss (androgenetic alopecia) in MEN ONLY. Launch Date 1997
Benign prostatic hyperplasia 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/020180s037lbl.pdf	Primary		Approved 8429	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 1992

C_max

Value	Dose	Co-administered	Analyte	Population
9.2 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020788s020s021s023lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
53 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020788s020s021s023lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020788s020s021s023lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020788s020s021s023lbl.pdf	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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT1A1 204 UGT1A3 84 UGT1A4 77 UGT1A6 108 UGT1A9 116 UGT2B7 146 UGT2B15 64	CYP1A1 349 CYP2B6 664 CYP2C8 693 CYP2E1 667

Drug as perpetrator

Target	Modality	Activity
UGT1A1 254	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A3 93	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A6 141	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A9 121	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT2B15 64	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT2B7 157	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	no
UGT1A4 80	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/25448279/	yes [IC50 11.5 uM]
P-gp 1650	activator 214 Sources: https://journals.eco-vector.com/pavlovj/article/view/4677	yes

Drug as victim

Target	Modality	Activity
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/8654202/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:5062	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:5062
ChemicalBook	CB9433852	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9433852
MolPort	MolPort-002-500-272	https://www.molport.com/shop/molecule-link/MolPort-002-500-272
Selleck Chemicals	Finasteride	http://www.selleckchem.com/products/Finasteride.html
ZINC	ZINC000003782599	http://zinc15.docking.org/substances/ZINC000003782599
eMolecules	27520086	https://www.emolecules.com/cgi-bin/more?vid=27520086
eMolecules	538270	https://www.emolecules.com/cgi-bin/more?vid=538270

PubMed

Title	Date	PubMed
Quality-of-life assessment in patients with benign prostatic hyperplasia: effects of various interventions.	2001	11735675
Efficacy and tolerability of drugs for treatment of benign prostatic hyperplasia.	2001	11583366
Hirsutism: diagnosis and management.	2001	11480095
Lower urinary tract symptoms suggestive of benign prostatic obstruction: how can clinical expertise contribute to rational management?	2001	11275737
Treatments for androgenetic alopecia and alopecia areata: current options and future prospects.	2001	11217871
The Prostate Cancer Prevention Trial: Current status and lessons learned.	2001 Apr	11295634
Prostate cancer prevention agent development: Criteria and pipeline for candidate chemoprevention agents.	2001 Apr	11295596
Executive Summary of the National Cancer Institute Workshop: Highlights and recommendations.	2001 Apr	11295590
Evaluation of the male pubertal onset assay to detect testosterone and steroid biosynthesis inhibitors in CD rats.	2001 Apr	11248141
The impact of participation in a study of medical treatment of lower urinary tract symptoms on the incidence of prostate surgery.	2001 Aug	11550784
Effect of androgen deprivation therapy on prostatic intraepithelial neoplasia.	2001 Aug	11502458
Neurosteroids mediate habituation and tonic inhibition in the auditory midbrain.	2001 Aug	11495974
Management of lower urinary tract symptoms of elderly men in Austria.	2001 Feb	11223673
Effects of the anti-androgen finasteride on the modulatory actions of oestradiol on androgen metabolism by human gingival fibroblasts.	2001 Feb	11163318
Suppression of spermatogenesis with desogestrel and testosterone pellets is not enhanced by addition of finasteride.	2001 Jan-Feb	11191092
The "Dorian Gray Syndrome": psychodynamic need for hair growth restorers and other "fountains of youth.".	2001 Jul	11471770
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	11446841
LC determination of finasteride and its application to storage stability studies.	2001 Jul	11377087
[Prostate problems. More clarity regarding prognosis].	2001 Jul 26	11524988
Advances in the treatment of male androgenetic alopecia: a brief review of finasteride studies.	2001 Jul-Aug	11399540
Prevention of prostate cancer.	2001 Jun	11525290
[Wellbeing or happiness medications?].	2001 Jun 30	11440653
Enhanced anticonvulsant activity of neuroactive steroids in a rat model of catamenial epilepsy.	2001 Mar	11442150
Clinical application of 5alpha-reductase inhibitors.	2001 Mar	11314752
[Gynecomastia and finasteride].	2001 May	11427816
Replacement of surgical castration by GnRH-inhibition or Leydig cell ablation in the male rat Hershberger antiandrogen assay.	2001 Oct	11603962
Progesterone and 3alpha,5alpha-THP enhance sexual receptivity in mice.	2001 Oct	11584925
Co-administration of finasteride and the pure anti-oestrogen ICI 182,780 act synergistically in modulating the IGF system in rat prostate.	2001 Oct	11572795
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	11543729
New progesterone esters as 5alpha-reductase inhibitors.	2001 Sep	11558590
Molecular epidemiologic studies within the Selenium and Vitamin E Cancer Prevention Trial (SELECT).	2001 Sep	11552710

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

In Vitro Use Guide

Finasteride (0.5 uM - 1 uM) down-regulated the expression of AR target genes in LNCaP cells

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:54 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:54 GMT 2023`
Record UNII	57GNO57U7G
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FINASTERIDE

Official Name

English

FINASTERIDE [JAN]

Common Name

English

NSC-759318

Code

English

finasteride [INN]

Common Name

English

ENTADFI COMPONENT FINASTERIDE

Brand Name

English

N-tert-Butyl-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide

Common Name

English

MK-906

Code

English

FINASTERIDE [USAN]

Common Name

English

FINASTERIDE COMPONENT OF ENTADFI

Brand Name

English

FINASTERIDE [EP IMPURITY]

Common Name

English

FINASTERIDE [EP MONOGRAPH]

Common Name

English

FINASTERIDE [USP MONOGRAPH]

Common Name

English

FINASTERIDE [USP IMPURITY]

Common Name

English

Finasteride [WHO-DD]

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

NSC-741485

Code

English

FINASTERIDE [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QG04CB01