3D Mol Similar

Vidarabine monophosphate

Iupac Name：[(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate

CAS No.: 29984-33-6

Molecular Weight：347.224

Modify Date.: 2023-02-19 05:43

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1. Names and Identifiers

1.1 Name: Vidarabine monophosphate
1.2 Synonyms: 9-(5-O-Phosphonato-β-D-arabinofuranosyl)-9H-purin-6-amine 9-(5-O-PHOSPHONO-BETA-D-ARABINOFURANOSYL)-9H-PURIN-6-AMINE 9-BETA-D-ARABINOFURANOSYLADENINE MONOPHOSPHATE 9-BETA-D-ARABINOFURANOSYLADENINE-5'-MONOPHOSPHATE 9-BETA-D-ARABINOFURANOSYL-ADENINE-5'-MONOPHOSPHORIC ACID 9H-Purin-6-amine, 9-(5-O-phosphono-β-D-arabinofuranosyl)-, ion(2-) 9H-Purin-6-amine,9-(5-O-phosphono-b-D-arabinofuranosyl)- ADENINE-9-BETA-D-ARABINOFURANOSIDE-5'-MONOPHOSPHATE ADENINE-BETA-D-ARABINOFURANOSIDE-5'-PHOSPHATE ARA-AMP

1.3 CAS No.: 29984-33-6

1.4 CID: 34768

1.5 EINECS(EC#): 249-990-8

1.6 Molecular Formula: C10H14N5O7P (isomer)

1.7 Inchi: InChI=1/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7+,10-/s2

1.8 InChkey: UDMBCSSLTHHNCD-XIOLPSNYNA-N

1.9 Canonical Smiles: NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O

1.10 Isomers Smiles: C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N

2. Properties

2.1 Density: 2.32±0.1 g/cm3(Predicted)

2.1 Melting point: 213 °C

2.1 Boiling point: 798.5±70.0 °C(Predicted)

2.1 Flash Point: 436.7±35.7 °C (Predicted)

2.1 logP: -0.22 (Predicted)

2.1 pKa: 1.86±0.10(Predicted)

2.2 StorageTemp: Store at 0°C

3. Safety and Handling

3.1 Hazard Codes: Xn,T,Xi

3.1 Risk Statements: 20/22-40-23/24/25-36/37/38

3.1 Safety Statements: 37/39-24/25-45-36/37/39-22-36-26

3.1 RIDADR: 2811

3.1 RTECS: AU6204000

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

6. Synthesis Route

29984-33-6Total: 2 Synthesis Route

5536-17-4 158 Suppliers

29984-33-6 83 Suppliers

Literatures:
Journal of Pharmaceutical Sciences, , vol. 73, # 2 p. 278 - 280
Yield: ~76%

78-40-0 314 Suppliers

5536-17-4 158 Suppliers

29984-33-6 83 Suppliers

Literatures:
US4123609 A1, ;
Yield: null

7. Precursor and Product

precursor:

78-40-0

5536-17-4

8. Other Information

8.0 Description: Vidarabine monophosphate, chemical name: 9-(5-O-Phosphono-beta-D-arabinofuranosyl)adenine is an anti deoxyribonucleic acid virus drug. IVidarabine triphosphate directly inhibits DNA polymerase and also acts as a chain terminator in DNA replication. An adenosine monophosphate analog in which ribose is replaced by an arabinose moiety. It is the monophosphate ester of VIDARABINE with antiviral and possibly antineoplastic properties.

8.1 Chemical Properties: Crystalline

8.2 Uses: Antiviral.

8.3 Uses: Disrupts viral DNA synthesis. Competitive viral DNA polymerase inhibitor. Active against herpes simplex and varicella zoster viruses in vivo.

8.4 Application: Vidarabine monophosphate has broad-spectrum anti-virus effect and can inhibit a variety of DNA viruses. It is mainly used to treat chronic hepatitis B and other viral infections, such as herpes zoster, herpes simplex and genital herpes. It has quick effect and clear curative effect. It is a common drug for clinical anti-virus treatment.

8.5 Safety Profile: Moderately toxic byintraperitoneal route. When heated to decomposition itemits very toxic fumes of POx and NOx.

9. Computational chemical data

Molecular Weight: 347.224g/mol
Molecular Formula: C₁₀H₁₄N₅O₇P
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 347.06308480
Monoisotopic Mass: 347.06308480
Complexity: 481
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 11
Topological Polar Surface Area: 186
Heavy Atom Count: 23
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzuAIAAAAAAAAAAAAAAAAAAWJAAAAsAAAAAAAAAFgB+AAAHgAQCCAACBzhlwYF8L9MFxCgQQZhZICAgC0REKABUCAoVBCDWAJAyEAeRAgPAALTACDwMAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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White crystal powder Vidarabine phosphate Ara-A CAS 29984-33-6 with high quality