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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H35N8O6P
Molecular Weight 526.5264
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RABACFOSADINE

SMILES

CCOC(=O)[C@H](C)NP(=O)(COCCN1C=NC2=C(NC3CC3)N=C(N)N=C12)N[C@@H](C)C(=O)OCC

InChI

InChIKey=ANSPEDQTHURSFQ-KBPBESRZSA-N
InChI=1S/C21H35N8O6P/c1-5-34-19(30)13(3)27-36(32,28-14(4)20(31)35-6-2)12-33-10-9-29-11-23-16-17(24-15-7-8-15)25-21(22)26-18(16)29/h11,13-15H,5-10,12H2,1-4H3,(H2,27,28,32)(H3,22,24,25,26)/t13-,14-/m0/s1

HIDE SMILES / InChI
Rabacfosadine was approved in 2017 under the brand name Tanovea-CA1 for the treatment of canine lymphoma. In addition, this drug has demonstrated effectiveness against non-Hodgkin's lymphoma in dogs, as well as canine cutaneous T-cell lymphoma, and relapsed canine B-cell lymphoma. Rabacfosadine a prodrug, which is hydrolyzed intracellularly to the metabolites, 9-(2-phosphonylmethoxyethyl)-N6-cyclopropyl-2,6-diaminopurine (cPrPMEDAP) and 9-(2-phosphonylmethoxyethyl) guanine (PMEG). PMEG is then converted to its active phosphorylated form, which is a chain-terminating inhibitor of the replicative deoxyribonucleic acid (DNA) polymerases.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.7 µM [EC50]
PubMed

PubMed

TitleDatePubMed
Tanovea® for the treatment of lymphoma in dogs.
2018 Aug
Patents

Patents

Sample Use Guides

Administer TANOVEA-CA1 at 1 mg/kg body weight as a 30-minute intravenous infusion, once every three weeks, for up to five doses. Stepwise dose reductions to 0.8 mg/kg and 0.66 mg/kg or dose delays may be used to manage adverse reactions.
Route of Administration: Intravenous
Name Type Language
RABACFOSADINE
INN   USAN  
INN   USAN  
Official Name English
RABACFOSADINE [MI]
Common Name English
GS-9219
Code English
VDC-1101
Code English
rabacfosadine [INN]
Common Name English
RABACFOSADINE [USAN]
Common Name English
L-ALANINE, N,N'-(((2-(2-AMINO-6-(CYCLOPROPYLAMINO)-9H-PURIN-9-YL)ETHOXY)METHYL)PHOSPHINYLIDENE)BIS-, 1,1'-ETHYL ESTER
Systematic Name English
RABACFOSADINE [GREEN BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C274
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
Code System Code Type Description
RXCUI
2003595
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
PRIMARY
PUBCHEM
16047979
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL1823518
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
PRIMARY
DRUG BANK
DB12762
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
PRIMARY
FDA UNII
M39BO43J9W
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
PRIMARY
NCI_THESAURUS
C152134
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PRIMARY
INN
9943
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PRIMARY
CAS
859209-74-8
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MERCK INDEX
m12243
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PRIMARY
DAILYMED
M39BO43J9W
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PRIMARY
SMS_ID
300000023721
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
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WIKIPEDIA
Rabacfosadine
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
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EPA CompTox
DTXSID10235245
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
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USAN
AB-137
Created by admin on Sat Dec 16 17:25:14 GMT 2023 , Edited by admin on Sat Dec 16 17:25:14 GMT 2023
PRIMARY