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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Substance Class Chemical
Record UNII
T50SJ23G82
Record Status Validated (UNII)
Record Version