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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 of LAPISTERIDE

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
The novel drug CS-891 inhibits 5alpha-reductase activity in freshly isolated dermal papilla of human hair follicles.
2000 Dec
Solid phase transition of CS-891 enantiotropes during grinding.
2003 Apr 14
Patents
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:40:40 UTC 2023
Edited
by admin
on Fri Dec 15 16:40:40 UTC 2023
Record UNII
T50SJ23G82
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LAPISTERIDE
INN  
INN  
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
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
Code System Code Type Description
INN
8104
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
PRIMARY
CAS
142139-60-4
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
PRIMARY
EPA CompTox
DTXSID801029879
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
PRIMARY
SMS_ID
300000036969
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
PRIMARY
NCI_THESAURUS
C83863
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
PRIMARY
FDA UNII
T50SJ23G82
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
PRIMARY
PUBCHEM
9847295
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
PRIMARY
WIKIPEDIA
LAPISTERIDE
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
PRIMARY
ChEMBL
CHEMBL2104358
Created by admin on Fri Dec 15 16:40:40 UTC 2023 , Edited by admin on Fri Dec 15 16:40:40 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY