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Details

Stereochemistry RACEMIC
Molecular Formula C13H11F6N3O5
Molecular Weight 403.234
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TOPILUTAMIDE

SMILES

CC(O)(CNC(=O)C(F)(F)F)C(=O)NC1=CC(=C(C=C1)[N+]([O-])=O)C(F)(F)F

InChI

InChIKey=YCNCRLKXSLARFT-UHFFFAOYSA-N
InChI=1S/C13H11F6N3O5/c1-11(25,5-20-10(24)13(17,18)19)9(23)21-6-2-3-8(22(26)27)7(4-6)12(14,15)16/h2-4,25H,5H2,1H3,(H,20,24)(H,21,23)

HIDE SMILES / InChI

Molecular Formula C13H11F6N3O5
Molecular Weight 403.234
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Topilutamide is a non-steroidal anti-androgen. Topilutamide downregulated androgen receptor expression by 40% at 3 uM and up to 95% at 10 uM in LNCaP Cells After 48-h drug incubation. While highly hydrophobic and hydrolytically degradable, it is systemically nonresorbable. In animals, fluridil demonstrated high local and general tolerance. After 3 months of topical application of topilutamide, the average anagen percentage did not change in placebo subjects but increased in topilutamide subjects (male with androgenetic alopecia) from 76% to 85%, and at 9 months to 87%. In former placebo subjects, topilutamide increased the anagen percentage after 6 months from 76% to 85%. Sexual functions, libido, hematology, and blood chemistry values were normal.

Approval Year

PubMed

PubMed

TitleDatePubMed
Fluridil, a rationally designed topical agent for androgenetic alopecia: first clinical experience.
2002 Aug
Review of HPLC and LC-MS/MS assays for the determination of various nonsteroidal anti-androgens used in the treatment of prostate cancer.
2018 Jan
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:49:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:49:14 GMT 2023
Record UNII
A8EU2FXY13
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TOPILUTAMIDE
INN   WHO-DD  
INN  
Official Name English
topilutamide [INN]
Common Name English
FLURIDIL
INCI  
INCI  
Official Name English
Topilutamide [WHO-DD]
Common Name English
(2RS)-2-HYDROXY-2-METHYL-N-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)-3-((TRIFLUOROACETYL)AMINO)PROPANAMIDE
Systematic Name English
PROPANAMIDE, 2-HYDROXY-2-METHYL-N-(4-NITRO-3-(TRIFLUOROMETHYL)PHENYL)-3-((2,2,2-TRIFLUOROACETYL)AMINO)-
Systematic Name English
FLURIDIL [INCI]
Common Name English
BP-766
Code English
Classification Tree Code System Code
NCI_THESAURUS C242
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
Code System Code Type Description
INN
8293
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
PUBCHEM
9930988
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
WIKIPEDIA
Topilutamide
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID30870298
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
SMS_ID
100000175724
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
CAS
260980-89-0
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
NCI_THESAURUS
C66612
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
FDA UNII
A8EU2FXY13
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107790
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY