Rabacfosadine (succinate)

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Description

Rabacfosadine (GS-9219) succinate, a novel proagent of the nucleotide analogue PMEG, is designed as a cytotoxic agent that preferentially targets lymphoid cells[1].

CAS Number

1431856-99-3

Product Name Alternative

GS-9219 (succinate) ; VDC-1101 (succinate)

UNSPSC

12352005

Target

Nucleoside Antimetabolite/Analog

Type

Reference compound

Related Pathways

Cell Cycle/DNA Damage

Applications

Cancer-programmed cell death

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/rabacfosadine-succinate.html

Solubility

10 mM in DMSO

Smiles

OC(CCC(O)=O)=O.CCOC([C@H](C)NP(COCCN1C2=NC(N)=NC(NC3CC3)=C2N=C1)(N[C@@H](C)C(OCC)=O)=O)=O

Molecular Formula

C25H41N8O10P

Molecular Weight

644.61

References & Citations

[1]Reiser H, et al. GS-9219--a novel acyclic nucleotide analogue with potent antineoplastic activity in dogs with spontaneous non-Hodgkin's lymphoma. Clin Cancer Res. 2008 May 1;14 (9) :2824-32.|[2]De Clercq E. Tanovea® for the treatment of lymphoma in dogs. Biochem Pharmacol. 2018 Aug;154:265-269.

Shipping Conditions

Room temperature

Scientific Category

Reference compound1

Clinical Information

Phase 2

Chemical Information

Rabacfosadine Succinate

Rabacfosadine Succinate is the succinate form of rabacfosadine, an acyclic nucleotide phosphonate prodrug and polymerase inhibitor that can potentially be used for its antineoplastic activity in the treatment of lymphoma in dogs. Upon administration, rabacfosadine is hydrolyzed intracellularly to 9-(2-phosphonylmethoxyethyl)-N6-cyclopropyl-2, 6-diaminopurine (cPrPMEDAP) and subsequently deaminated to 9-(2-phosphonylmethoxyethyl) guanine (PMEG) and phosphorylated to PMEG diphosphate (PMEGpp). PMEGpp binds to and inhibits DNA polymerases. This inhibits DNA synthesis, resulting in S phase arrest and induction of apoptosis.

CAS Number	1431856-99-3
PubChem CID	73425536
IUPAC Name	butanedioic acid;ethyl (2S)-2-[[2-[2-amino-6-(cyclopropylamino)purin-9-yl]ethoxymethyl-[[(2S)-1-ethoxy-1-oxopropan-2-yl]amino]phosphoryl]amino]propanoate
Molecular Formula	C25H41N8O10P
Molecular Weight	644.6
Topological Polar Surface Area	259
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	20
Heavy Atom Count	44
Formal Charge	0
Complexity	852

SMILES

CCOC(=O)[C@H](C)NP(=O)(COCCN1C=NC2=C(N=C(N=C21)N)NC3CC3)N[C@@H](C)C(=O)OCC.C(CC(=O)O)C(=O)O

InChI

InChI=1S/C21H35N8O6P.C4H6O4/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;5-3(6)1-2-4(7)8/h11,13-15H,5-10,12H2,1-4H3,(H2,27,28,32)(H3,22,24,25,26);1-2H2,(H,5,6)(H,7,8)/t13-,14-;/m0./s1

InChIKey

XLBDQSJWTNREFA-IODNYQNNSA-N

Chemical Structure

2D Structure

CAS: 1431856-99-3

CID: 73425536

Formula: C25H41N8O10P

MW: 644.6

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	644.6
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	20
Exact Mass	644.26832653
Monoisotopic Mass	644.26832653
Topological Polar Surface Area	259 Å²
Heavy Atom Count	44
Formal Charge	0
Complexity	852
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	2
Compound Is Canonicalized	Yes

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Alternative Products

Catalog	Name
GTR19199734-01	Rabacfosadine succinate
T16716-01	Rabacfosadine
A21217-50	Rabacfosadine 50mg
A21217-1	Rabacfosadine 1mg
A21217-200	Rabacfosadine 200mg
A21217-10	Rabacfosadine 10mg
A21217-100	Rabacfosadine 100mg
A21217-25	Rabacfosadine 25mg
A21217-5	Rabacfosadine 5mg
MA-0134	Succinate

Rabacfosadine (succinate)

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