RABACFOSADINE

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 Search

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

Molecular Formula	C21H35N8O6P
Molecular Weight	526.5264
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.fda.gov/animalveterinary/newsevents/cvmupdates/ucm535190.htm | https://www.ncbi.nlm.nih.gov/pubmed/29778492

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

Primary Target	Pharmacology	Condition	Potency
Human herpesvirus 6 4 Target ID: CHEMBL613496 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8669893	Inhibitor 8297		1.7 µM [EC50]

PubMed

Title	Date	PubMed
Tanovea® for the treatment of lymphoma in dogs.	2018 Aug	29778492

Patents

Sample Use Guides

In Vivo Use Guide

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:25:14 UTC 2023` Edited by `admin` on `Sat Dec 16 17:25:14 UTC 2023`
Record UNII	M39BO43J9W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RABACFOSADINE

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