LAPISTERIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C29H40N2O3
Molecular Weight	464.6395
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])NC(=O)C=C[C@]4(C)[C@@]3([H])CC[C@]12C)C(=O)NC(C)(C)C5=CC=C(OC)C=C5

InChI

InChIKey=NAGKTIAFDQEFJI-DPMIIFTQSA-N

InChI=1S/C29H40N2O3/c1-27(2,18-6-8-19(34-5)9-7-18)31-26(33)23-12-11-21-20-10-13-24-29(4,17-15-25(32)30-24)22(20)14-16-28(21,23)3/h6-9,15,17,20-24H,10-14,16H2,1-5H3,(H,30,32)(H,31,33)/t20-,21-,22-,23+,24+,28-,29+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C29H40N2O3
Molecular Weight	464.6395
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67477151 | https://www.ncbi.nlm.nih.gov/pubmed/11125319 | https://adisinsight.springer.com/drugs/800013642

LAPISTERIDE is an inhibitor of 5alpha-reductase (5aR), converting testosterone to the more potent androgen dihydrotestosterone. It has dual inhibitory activity on both 5aR isoenzymes. It was under investigation for the treatment of benign prostatic hyperplasia and androgenic alopecia, but its development was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
The novel drug CS-891 inhibits 5alpha-reductase activity in freshly isolated dermal papilla of human hair follicles.	2000 Dec	11125319
Solid phase transition of CS-891 enantiotropes during grinding.	2003 Apr 14	12672603

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:40:40 GMT 2023` Edited by `admin` on `Fri Dec 15 16:40:40 GMT 2023`
Record UNII	T50SJ23G82
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAPISTERIDE

Official Name

English

N-(1-(4-METHOXYPHENYL)-1-METHYLETHYL)-3-OXO-4-AZA-5.ALPHA.-ANDROST-1-ENE-17.BETA.-CARBOXAMIDE

Common Name

English

lapisteride [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471