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29984-33-6 , Vidarabine monophosphate, CAS:29984-33-6

29984-33-6 , Vidarabine monophosphate, CAS:29984-33-6
C10H14N5O7P / 347.22
MFCD00069723

单磷酸阿糖腺苷, Vidarabine monophosphate

9-(b-D-Arabinofuranosyl)adenine 5'-monophosphate

Vidarabine Phosphate is a phosphate salt form of vidarabine, a nucleoside analog with activity against herpes simplex virus and varicella zoster virus. Vidarabine is converted to a monophosphate by viral thymidine kinase and is further modified to a triphosphate form by host enzymes. Vidarabine 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.

9-(β-D-Arabinofuranosyl)adenine 5'-monophosphate (Ara-AMP) is a prodrug that is converted to adenine arabinoside in vivo. It is used as an antiviral agent for the prevention of hepatitis B and C. Ara-AMP inhibits viral DNA synthesis by acting as a competitive inhibitor of adenosine triphosphate, which is required for viral DNA polymerase activity. Ara-AMP also has antiviral properties against some RNA viruses, such as HIV and influenza virus. Ara-AMP can be administered orally or by injection, making it suitable for use in children who are unable to take oral medication.

CAS Number

29984-33-6

Product Name

Vidarabine phosphate

IUPAC Name

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

Molecular Formula

C10H14N5O7P

Molecular Weight

347.22 g/mol

InChI

InChI=1S/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-/m1/s1

InChI Key

UDMBCSSLTHHNCD-UHTZMRCNSA-N

SMILES

C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)N

Solubility

Soluble in DMSO

Synonyms

9-(5-O-Phosphono-beta-D-arabinofuranosyl)-9H-purin-6-amine, Adenine Arabinoside Monophosphate, Ara AMP, Ara-AMP, Arabinofuranosyladenine Monophosphate, Monophosphate, Adenine Arabinoside, Monophosphate, Arabinofuranosyladenine, Monophosphate, Vidarabine, Phosphate, Vidarabine, Vidarabine Monophosphate, Vidarabine Phosphate

Canonical SMILES

C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)N

Isomeric 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


CAS No: 29984-33-6 Synonyms: Vidarabine monophosphate MDL No: MFCD00069723 Chemical Formula: C10H14N5O7P Molecular Weight: 347.22


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