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Fostroxacitabine bralpamide

CAT: 0804-HY-132815Size: 1 EachDry Ice: NoHazardous: No
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Description
Fostroxacitabine bralpamide (MIV-818) is an orally active Troxacitabine-based nucleotide proagent. Fostroxacitabine bralpamide has anticancer effects[1].
CAS Number
2129993-56-0
Product Name Alternative
MIV-818
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/fostroxacitabine-bralpamide.html
Solubility
10 mM in DMSO
Smiles
O=C1N([C@@]2([H])O[C@H](OC2)COP(OC3=CC=C(C=C3)Br)(N[C@@H](C)C(O[C@@H](C)CCC)=O)=O)C=CC(N)=N1
Molecular Formula
C22H30BrN4O8P
Molecular Weight
589.37
References & Citations
[1]T.R. Jeffry Evans, et al. Phase I study of the novel pro-drug MIV-818 in patients with hepatocellular carcinoma, intra-hepatic cholangiocarcinoma or liver metastases.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
Phase 2

Chemical Information

Fostroxacitabine Bralpamide

Fostroxacitabine Bralpamide is a liver-targeting nucleotide phosphoramidate prodrug of troxacitabine monophosphate (TRX-MP), a dioxolane derivative and L-configuration deoxycytidine analogue, with potential antineoplastic activity. Upon oral administration, fostroxacitabine bralpamide is rapidly and specifically hydrolyzed in hepatocytes by liver carboxylesterase 1 (carboxylesterase 1, CE-1), generating high levels of the chain-terminating nucleotide, troxacitabine triphosphate (TRX-TP) in the liver. TRX-TP is then incorporated into tumor cell DNA, leading to termination of DNA synthesis and inhibition of tumor cell proliferation.

CAS Number2129993-56-0
PubChem CID141649565
IUPAC Name[(2S)-pentan-2-yl] (2S)-2-[[[(2S,4S)-4-(4-amino-2-oxopyrimidin-1-yl)-1,3-dioxolan-2-yl]methoxy-(4-bromophenoxy)phosphoryl]amino]propanoate
Molecular FormulaC22H30BrN4O8P
Molecular Weight589.4
XLogP2.2
Topological Polar Surface Area151
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count13
Heavy Atom Count36
Formal Charge0
Complexity882
SMILES
CCC[C@H](C)OC(=O)[C@H](C)N[P@](=O)(OC[C@H]1OC[C@H](O1)N2C=CC(=NC2=O)N)OC3=CC=C(C=C3)Br
InChI
InChI=1S/C22H30BrN4O8P/c1-4-5-14(2)33-21(28)15(3)26-36(30,35-17-8-6-16(23)7-9-17)32-13-20-31-12-19(34-20)27-11-10-18(24)25-22(27)29/h6-11,14-15,19-20H,4-5,12-13H2,1-3H3,(H,26,30)(H2,24,25,29)/t14-,15-,19-,20-,36-/m0/s1
InChIKey
JBYKMODFCUCTGY-LLSQRQBFSA-N
Chemical Structure
2D Structure
2D structure of Fostroxacitabine Bralpamide
CAS: 2129993-56-0
CID: 141649565
Formula: C22H30BrN4O8P
MW: 589.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight589.4
XLogP32.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count13
Exact Mass588.09846
Monoisotopic Mass588.09846
Topological Polar Surface Area151 Ų
Heavy Atom Count36
Formal Charge0
Complexity882
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
GTR19189392Fostroxacitabine bralpamide

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