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
Finasteride: a long-term follow-up in the treatment of recurrent hematuria associated with benign prostatic hyperplasia.	2001	11464120
The value of hair cosmetics and pharmaceuticals.	2001	11455137
Inhibition of 5alpha-reductase in rat prostate reveals differential regulation of androgen-response gene expression by testosterone and dihydrotestosterone.	2001	11444528
Treatment of localized prostate cancer with intermittent triple androgen blockade: preliminary results in 110 consecutive patients.	2001	11306729
Changing therapeutic regimens in benign prostatic hyperplasia. Clinical and economic considerations.	2001	11284380
The Prostate Cancer Prevention Trial: Current status and lessons learned.	2001 Apr	11295634
Enlarged prostate gland. Many treatment options.	2001 Apr	11284232
Evaluation of the male pubertal onset assay to detect testosterone and steroid biosynthesis inhibitors in CD rats.	2001 Apr	11248141
Docetaxel followed by hormone therapy after failure of definitive treatments for clinically localized/locally advanced prostate cancer: preliminary results.	2001 Aug	11685725
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
Androgen deprivation therapy for prostate cancer chemoprevention: current status and future directions for agent development.	2001 Aug	11502457
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	11502450
Neurosteroids mediate habituation and tonic inhibition in the auditory midbrain.	2001 Aug	11495974
Discontinuation of alpha-blockade after initial treatment with finasteride and doxazosin in men with lower urinary tract symptoms and clinical evidence of benign prostatic hyperplasia.	2001 Aug	11489700
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	11722704
Stable expression of the human 5alpha-reductase isoenzymes type I and type II in HEK293 cells to identify dual and selective inhibitors.	2001 Jan	11496834
Topical finasteride therapy in hirsutism.	2001 Jan-Feb	11250772
Finasteride cream in hirsutism.	2001 Jan-Feb	11250761
Online prescriptions of pharmaceuticals: where is the evidence for harm or for benefit? A call for papers--and for reflection.	2001 Jan-Mar	11720943
Management of male pattern hair loss.	2001 Jul	11480145
Body dysmorphic disorder and life-style drugs. Overview and case report with finasteride.	2001 Jul	11471771
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
The appropriateness of treatment of benign prostatic hyperplasia: a comparison of Dutch and multinational criteria.	2001 Jul	11348693
[Prostate problems. More clarity regarding prognosis].	2001 Jul 26	11524988
Prevention of prostate cancer.	2001 Jun	11525290
Comparison of the efficacy and safety of finasteride in older versus younger men with benign prostatic hyperplasia.	2001 Jun	11377309
Steroid-sensitive gene-1 is an androgen-regulated gene expressed in prostatic smooth muscle cells in vivo.	2001 Jun	11357054
Questions whether clients were properly informed about treatment protocol.	2001 Jun 1	11394816
Evaluation of new pregnane derivatives as 5alpha-reductase inhibitor.	2001 May	11383600
Structure-function studies of human 5-alpha reductase type 2 using site directed mutagenesis.	2001 May	11377983
[Finasteride in prolonged therapy of patients with benign prostatic hyperplasia].	2001 May-Jun	11505535
Influence of estrogens on the androgen metabolism in different subunits of human hair follicles.	2001 May-Jun	11358723
Contribution of androgens to chronic allograft nephropathy is mediated by dihydrotestosterone.	2001 Nov	11703615
Baldness. Medical solutions for men and women.	2001 Nov	11692629
Managing benign prostatic hyperplasia.	2001 Oct	11677898
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	11677270
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
Direct-to-consumer advertising. Finasteride for male pattern hair loss.	2001 Sep	11570300
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
Possible mechanisms of miniaturization during androgenetic alopecia or pattern hair loss.	2001 Sep	11511857

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