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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22FN3O8
Molecular Weight 439.3917
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALOCITABINE

SMILES

COC1=CC(=CC(OC)=C1OC)C(=O)NC2=NC(=O)N(C=C2F)[C@@H]3O[C@H](C)[C@@H](O)[C@H]3O

InChI

InChIKey=TVYPSLDUBVTDIS-FUOMVGGVSA-N
InChI=1S/C19H22FN3O8/c1-8-13(24)14(25)18(31-8)23-7-10(20)16(22-19(23)27)21-17(26)9-5-11(28-2)15(30-4)12(6-9)29-3/h5-8,13-14,18,24-25H,1-4H3,(H,21,22,26,27)/t8-,13-,14-,18-/m1/s1

HIDE SMILES / InChI
Galocitabine is an orally available 5-fluorouracil (5-FU) prodrug with potential antineoplastic activity. Upon administration, galocitabine is converted to 5’-deoxy-fluorocytidine (5’-DFCR) by acylamidase in the liver and is then converted to 5’-DFUR by cytidine deaminase. Efficient conversion of galocitabine to 5-FU is necessary for galocitabine to have a therapeutic effect. 5-FU is further metabolized into other cytotoxic metabolites that interfere with RNA and DNA synthesis via inhibition of thymidylate synthase. As a result, this agent eventually inhibits tumor cell growth.

Approval Year

Patents

Patents

Name Type Language
GALOCITABINE
INN   WHO-DD  
INN  
Official Name English
N-(1-(5-DEOXY-.BETA.-D-RIBOFURANOSYL)-5-FLUORO-1,2-DIHYDRO-2-OXO-4-PYRIMIDINYL)-3,4,5-TRIMETHOXYBENZAMIDE
Common Name English
Galocitabine [WHO-DD]
Common Name English
galocitabine [INN]
Common Name English
RO 09-1390
Code English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
Code System Code Type Description
SMS_ID
100000084513
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
PRIMARY
FDA UNII
X9788XI79O
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
PRIMARY
INN
6806
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
PRIMARY
PUBCHEM
65950
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID10154189
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
PRIMARY
NCI_THESAURUS
C73254
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106813
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
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CAS
124012-42-6
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
PRIMARY
EVMPD
SUB07875MIG
Created by admin on Fri Dec 15 15:37:05 GMT 2023 , Edited by admin on Fri Dec 15 15:37:05 GMT 2023
PRIMARY