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

Details

Stereochemistry ACHIRAL
Molecular Formula C17H18O2S
Molecular Weight 286.389
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NAMIROTENE

SMILES

CC(C)C1=CC=C(S1)C(\C)=C\C2=CC=C(C=C2)C(O)=O

InChI

InChIKey=GDDUESKGWJTHLR-ZRDIBKRKSA-N
InChI=1S/C17H18O2S/c1-11(2)15-8-9-16(20-15)12(3)10-13-4-6-14(7-5-13)17(18)19/h4-11H,1-3H3,(H,18,19)/b12-10+

HIDE SMILES / InChI

Molecular Formula C17H18O2S
Molecular Weight 286.389
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Namirotene [CBS-211A] is a retinoic acid analogue which was undergoing phase II trials with Chauvin in France as 0.02% eye drops for corneal ulcer. It was discontinued later. Namirotene is a synthetic analogue of retinoic acid with differentiation inducing and potential antineoplastic activities. Like other retinoic acid agents, namirotene binds to and activates retinoic acid receptors (RARs), thereby altering the expression of certain genes leading to cell differentiation and decreased cell proliferation in susceptible cells. When it was associated with 1 alpha,25(OH)2D3, CBS-211A strongly potentiated the 1 alpha,25(OH)2D3-induced inhibition of U937 cell proliferation and caused a dramatic increase in their differentiation toward monocytes/macrophages. The co-inducing effect of CBS-211A was restricted to U937 cells. Our data suggest that CBS-211A may have therapeutic implications in the treatment of certain kinds of myelomonocytic leukemia. CBS-211A also provides an interesting tool to understand the mechanisms involved in the differentiation of myelomonocytic cells.

Approval Year

PubMed

PubMed

TitleDatePubMed

Sample Use Guides

0.02% eye drops
Route of Administration: Topical
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:51:52 GMT 2023
Edited
by admin
on Fri Dec 15 15:51:52 GMT 2023
Record UNII
1FG8FGL0YI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAMIROTENE
INN  
INN  
Official Name English
namirotene [INN]
Common Name English
P-((E)-2-(5-ISOPROPYL-2-THIENYL)PROPENYL)BENZOIC ACID
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C804
Created by admin on Fri Dec 15 15:51:52 GMT 2023 , Edited by admin on Fri Dec 15 15:51:52 GMT 2023
Code System Code Type Description
PUBCHEM
6436049
Created by admin on Fri Dec 15 15:51:52 GMT 2023 , Edited by admin on Fri Dec 15 15:51:52 GMT 2023
PRIMARY
SMS_ID
100000084463
Created by admin on Fri Dec 15 15:51:52 GMT 2023 , Edited by admin on Fri Dec 15 15:51:52 GMT 2023
PRIMARY
FDA UNII
1FG8FGL0YI
Created by admin on Fri Dec 15 15:51:52 GMT 2023 , Edited by admin on Fri Dec 15 15:51:52 GMT 2023
PRIMARY
EVMPD
SUB09145MIG
Created by admin on Fri Dec 15 15:51:52 GMT 2023 , Edited by admin on Fri Dec 15 15:51:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107644
Created by admin on Fri Dec 15 15:51:52 GMT 2023 , Edited by admin on Fri Dec 15 15:51:52 GMT 2023
PRIMARY
CAS
101506-83-6
Created by admin on Fri Dec 15 15:51:52 GMT 2023 , Edited by admin on Fri Dec 15 15:51:52 GMT 2023
PRIMARY
INN
6949
Created by admin on Fri Dec 15 15:51:52 GMT 2023 , Edited by admin on Fri Dec 15 15:51:52 GMT 2023
PRIMARY
NCI_THESAURUS
C83981
Created by admin on Fri Dec 15 15:51:52 GMT 2023 , Edited by admin on Fri Dec 15 15:51:52 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY