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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
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