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9 Drugs in Development

9 Drugs in Development

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Chemistry

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Also known as: Miv818, Miv-818, Unii-q1i6yz0ngf, Q1i6yz0ngf, Troxacitabine nucleotide prodrug miv-818, 1-((2s,4s)-2-((((s)-(4-bromophenoxy)(((s)-1-oxo-1-(((s)-pentan-2-yl)oxy)propan-2-yl)amino)phosphoryl)oxy)methyl)-1,3-dioxolan-4-yl)-2-oxo-1,2-dihydropyrimidin-4-amine

Molecular Formula

C₂₂H₃₀BrN₄O₈P

Molecular Weight

589.4 g/mol

InChI Key

JBYKMODFCUCTGY-LLSQRQBFSA-N

FDA UNII

Q1I6YZ0NGF

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.

1 2D Structure

MIV-818

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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

2.1.3 InChI Key

JBYKMODFCUCTGY-LLSQRQBFSA-N

2.1.4 Canonical SMILES

CCCC(C)OC(=O)C(C)NP(=O)(OCC1OCC(O1)N2C=CC(=NC2=O)N)OC3=CC=C(C=C3)Br

2.1.5 Isomeric 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

2.2 Other Identifiers

2.2.1 UNII

Q1I6YZ0NGF

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Miv818

2. Miv-818

3. Unii-q1i6yz0ngf

4. Q1i6yz0ngf

5. Troxacitabine Nucleotide Prodrug Miv-818

6. 1-((2s,4s)-2-((((s)-(4-bromophenoxy)(((s)-1-oxo-1-(((s)-pentan-2-yl)oxy)propan-2-yl)amino)phosphoryl)oxy)methyl)-1,3-dioxolan-4-yl)-2-oxo-1,2-dihydropyrimidin-4-amine

7. 2129993-56-0

8. L-alanine, N-((((2s,4s)-4-(4-amino-2-oxo-1(2h)-pyrimidinyl)-1,3-dioxolan-2-yl)methoxy)(4-bromophenoxy)phosphinyl)-, (1s)-1-methylbutyl Ester

9. Chembl4594349

10. Fostroxacitabine Bralpamide [usan]

11. Who 11760

12. Fostroxacitabine Bralpamide [inn]

13. [(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

14. 1884205-97-3

2.4 Create Date

2019-12-06

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₃₀BrN₄O₈P
Molecular Weight	589.4 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	13
Exact Mass	588.09846 g/mol
Monoisotopic Mass	588.09846 g/mol
Topological Polar Surface Area	151 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	882
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1