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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H38N2O2
Molecular Weight 374.56
Optical Activity ( + )
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROFINASTERIDE

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)CC[C@]34C

InChI

InChIKey=ZOIUUCNFVDJSJK-WSBQPABSSA-N
InChI=1S/C23H38N2O2/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/h14-18H,6-13H2,1-5H3,(H,24,26)(H,25,27)/t14-,15-,16-,17+,18+,22-,23+/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H38N2O2
Molecular Weight 374.56
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/7488021 | https://www.ncbi.nlm.nih.gov/pubmed/9749833

3-Oxo-4-aza-5α-androstane-17β-(N-t-butylcarboxamide) (or dihydrofinasteride) is the reduced product of Finasteride. Finasteride acts as an alternate substrate for steroid 5α-reductase and is initially bound in an extremely stable enzyme-bound NADP-dihydrofinasteride adduct which is ultimately processed to dihydrofinasteride. Dihydrofinasteride acts as a selective inhibitor of steroid 5α-reductase type 1.

Originator

Curator's Comment: # Merck Sharp & Dohme Research Laboratories

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
560.0 nM [IC50]
3.4 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Inhibition of rat alpha-reductases by finasteride: evidence for isozyme differences in the mechanism of inhibition.
1997 Apr
Cloning, expression and characterization of rhesus macaque types 1 and 2 5alpha-reductase: evidence for mechanism-based inhibition by finasteride.
1998 Sep
Sebocytes are the key regulators of androgen homeostasis in human skin.
2001 May
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Sources: doi: 10.1111/1523-1747.ep12286950
Curator's Comment: https://www.infona.pl/resource/bwmeta1.element.elsevier-c6d7d1ca-411f-3d04-ab96-327b88497833
The metabolism of 3H-testosterone in cultured human sebocytes and keratinocytes was assessed in the presence of the specific type II inhibitor dihydrofinasteride. In both cell types dihydrofinasteride, being ineffective at 2^10 - 8 M, exhibited a complete inhibitory effect at 2^10 - 6 M.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:13:25 GMT 2023
Edited
by admin
on Sat Dec 16 11:13:25 GMT 2023
Record UNII
YXO6UEY0UP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDROFINASTERIDE
Common Name English
1H-INDENO(5,4-F)QUINOLINE-7-CARBOXAMIDE, N-(1,1-DIMETHYLETHYL)HEXADECAHYDRO-4A,6A-DIMETHYL-2-OXO-, (4AR,4BS,6AS,7S,9AS,9BS,11AR)
Systematic Name English
N-(1,1-DIMETHYLETHYL)-3-OXO-4-AZA-5.ALPHA.-ANDROSTANE-17.BETA.-CARBOXAMIDE
Systematic Name English
1,2-DIHYDROFINASTERIDE
Common Name English
FINASTERIDE IMPURITY A [EP IMPURITY]
Common Name English
Code System Code Type Description
PUBCHEM
9864387
Created by admin on Sat Dec 16 11:13:25 GMT 2023 , Edited by admin on Sat Dec 16 11:13:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID40432068
Created by admin on Sat Dec 16 11:13:25 GMT 2023 , Edited by admin on Sat Dec 16 11:13:25 GMT 2023
PRIMARY
CAS
98319-24-5
Created by admin on Sat Dec 16 11:13:25 GMT 2023 , Edited by admin on Sat Dec 16 11:13:25 GMT 2023
PRIMARY
FDA UNII
YXO6UEY0UP
Created by admin on Sat Dec 16 11:13:25 GMT 2023 , Edited by admin on Sat Dec 16 11:13:25 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP