U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17ClN6O2
Molecular Weight 396.83
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KETO-DAROLUTAMIDE

SMILES

C[C@@H](CN1C=CC(=N1)C2=CC=C(C#N)C(Cl)=C2)NC(=O)C3=NNC(=C3)C(C)=O

InChI

InChIKey=GMBPVBVTPBWIKC-NSHDSACASA-N
InChI=1S/C19H17ClN6O2/c1-11(22-19(28)18-8-17(12(2)27)23-24-18)10-26-6-5-16(25-26)13-3-4-14(9-21)15(20)7-13/h3-8,11H,10H2,1-2H3,(H,22,28)(H,23,24)/t11-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H17ClN6O2
Molecular Weight 396.83
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

ORM-15341 is an active main metabolite of ODM-201, which is structurally distinct from any known antiandrogens including the second-generation antiandrogens enzalutamide. ORM-15341 is a potent and full antagonist for human androgen receptor. It was shown, that in VCaP prostate cancer cells containing endogenous AR gene amplification and overexpressing AR, ORM-15341 inhibited cell proliferation more efficiently than enzalutamide or ARN-509.

CNS Activity

Curator's Comment: Known to be CNS non-penetrant in mouse. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
38.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
HepaRG cells were treated with 10 μM of ORM-15341
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:21:25 GMT 2023
Edited
by admin
on Sat Dec 16 11:21:25 GMT 2023
Record UNII
9EPS75QMTL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
KETO-DAROLUTAMIDE
Common Name English
ORM-15341
Common Name English
1H-PYRAZOLE-3-CARBOXAMIDE, 5-ACETYL-N-((1S)-2-(3-(3-CHLORO-4-CYANOPHENYL)-1H-PYRAZOL-1-YL)-1-METHYLETHYL)-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID101111196
Created by admin on Sat Dec 16 11:21:25 GMT 2023 , Edited by admin on Sat Dec 16 11:21:25 GMT 2023
PRIMARY
FDA UNII
9EPS75QMTL
Created by admin on Sat Dec 16 11:21:25 GMT 2023 , Edited by admin on Sat Dec 16 11:21:25 GMT 2023
PRIMARY
PUBCHEM
52919826
Created by admin on Sat Dec 16 11:21:25 GMT 2023 , Edited by admin on Sat Dec 16 11:21:25 GMT 2023
PRIMARY
CAS
1297537-33-7
Created by admin on Sat Dec 16 11:21:25 GMT 2023 , Edited by admin on Sat Dec 16 11:21:25 GMT 2023
PRIMARY
DRUG BANK
DB15647
Created by admin on Sat Dec 16 11:21:25 GMT 2023 , Edited by admin on Sat Dec 16 11:21:25 GMT 2023
PRIMARY
WIKIPEDIA
Ketodarolutamide
Created by admin on Sat Dec 16 11:21:25 GMT 2023 , Edited by admin on Sat Dec 16 11:21:25 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Ki
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY