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CHEMISTRY
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11 Drugs in Development

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Chemistry

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Also known as: Aspacytarabine, Aspacytarabine [inn], Bst-236, Aspacytarabine [usan], Jl7v54z2br, 2098942-53-9

Molecular Formula

C₁₃H₁₈N₄O₈

Molecular Weight

358.30 g/mol

InChI Key

PVPJTBAEAQVTPN-HRAQMCAYSA-N

FDA UNII

JL7V54Z2BR

Aspacytarabine is a small molecule pro-drug consisting of cytarabine, an antimetabolite analog of cytidine with a modified arabinose sugar moiety, covalently bonded to asparagine, with potential antineoplastic activity. Upon intravenous administration, aspacytarabine targets cancer cells, which often lack asparagine synthetase and are dependent on an external source of amino acids due to their high metabolic rate. Once the prodrug is inside target cells, the cytarabine component is cleaved and competes with cytidine for incorporation into DNA. The arabinose sugar moiety of cytarabine sterically hinders the rotation of the molecule within DNA, resulting in cell cycle arrest, specifically during the S phase of replication. Cytarabine also inhibits DNA polymerase, resulting in a decrease in DNA replication and repair. Because BST-236 specifically targets cancer cells, it may spare normal tissues from cytarabine-related toxicities.

1 2D Structure

Aspacytarabine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-amino-4-[[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]-4-oxobutanoic acid

2.1.2 InChI

InChI=1S/C13H18N4O8/c14-5(12(22)23)3-8(19)15-7-1-2-17(13(24)16-7)11-10(21)9(20)6(4-18)25-11/h1-2,5-6,9-11,18,20-21H,3-4,14H2,(H,22,23)(H,15,16,19,24)/t5-,6+,9+,10-,11+/m0/s1

2.1.3 InChI Key

PVPJTBAEAQVTPN-HRAQMCAYSA-N

2.1.4 Canonical SMILES

C1=CN(C(=O)N=C1NC(=O)CC(C(=O)O)N)C2C(C(C(O2)CO)O)O

2.1.5 Isomeric SMILES

C1=CN(C(=O)N=C1NC(=O)C[C@@H](C(=O)O)N)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O

2.2 Other Identifiers

2.2.1 UNII

JL7V54Z2BR

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Aspacytarabine

2. Aspacytarabine [inn]

3. Bst-236

4. Aspacytarabine [usan]

5. Jl7v54z2br

6. 2098942-53-9

7. Unii-jl7v54z2br

8. Aspacytarabine [who-dd]

9. Chembl4297599

10. Who 10941

11. L-asparagine, N-(1-.beta.-d-arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-

12. L-asparagine, N-(1-beta-d-arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)-

13. N4-(1-.beta.-d-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin-4-yl)-l-asparagine

14. N4-(1-n2-d-arabinofuranosyl-2-oxo-1,2-dihydropyrimidin-4-yl)- L-asparagine

2.4 Create Date

2018-12-16

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₈N₄O₈
Molecular Weight	358.30 g/mol
XLogP3	-4.5
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	6
Exact Mass	358.11246355 g/mol
Monoisotopic Mass	358.11246355 g/mol
Topological Polar Surface Area	195 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	621
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