Basic information
- CAS
29984-33-6- Standard SMILES
Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@@H]1O- InChIKey
UDMBCSSLTHHNCD-UHTZMRCNSA-N- Molecular formula
- C10H14N5O7P
- Average molar mass
- 347.22 g/mol
- Monoisotopic mass
- 347.0630848
Overview
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.
Names & identifiers
- Preferred name
- ara-AMP
- IUPAC
- [(2R,3S,4S,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
- English name
- Vidarabine monophosphate
- Molecular formula
- C10H14N5O7P
- Molecular weight
- 347.22
Names & synonyms
29984-33-6VIDARABINE PHOSPHATEVidarabine monophosphateAra-AMPAdenine arabinoside monophosphateCL-8089-(5-O-Phosphono-beta-D-arabinofuranosyl)-9H-purin-6-amine9H-Purin-6-amine, 9-(5-O-phosphono-beta-D-arabinofuranosyl)-106XV160TZDTXSID401009318NSC-1272239-beta-D-Arabinofuranosyladenine 5'-(dihydrogen phosphate)
Show more names
Vidarabine MonophasphateAra-AVidarabine Impurity 1ara-A 5'-monophosphateVidarabine Impurity 02vidarabinemonophosphatevidarabine-5’-monophosphate
Arabinofuranosyladenine MonophosphateAra AMPPhosphate, VidarabineMonophosphate, VidarabineMonophosphate, Adenine ArabinosideMonophosphate, ArabinofuranosyladenineRefChem:194229DTXCID901436144
Database identifiers
- CAS
29984-33-6
Properties
Computed structural properties
- XLogP
- -3.5
- Topological polar surface area
- 186 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 4
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 481
Physicochemical properties
- Melting point
- 213 °C · 213 °C
- Boiling point
- 798.5 · 798.5±70.0 °C(Predicted)
- Density
- 2.32 · 2.32±0.1 g/cm3(Predicted)
- storage temp.
- 0 °C · Store at 0°C
- form
- Powder
- pka
- 1.86 · 1.86±0.10(Predicted)
- color
- White to Off-white
- Water Solubility
- 4 mg/ml · Soluble in water at 4mg/ml
- 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-/s3
- InChIKey
- UDMBCSSLTHHNCD-GCTRTDOSNA-N
- SMILES
- O[C@H]1[C@@H]([C@@H](COP(O)(O)=O)O[C@H]1N1C=NC2C(=NC=NC1=2)N)O |&1:1,2,3,11,r|
- FDA UNII
- 106 XV160TZ · 106XV160TZ
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- rtecs
- AU6204000
- ridadr
- 2811
- hs_code
- 29400090
- Toxicity
- LD50 ipr-rat: 1700 mg/kg DRFUD4 4,547,79
- risk_code
- 20/22-40-23/24/25-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,T,Xi
- safety_code
- 37/39-24/25-45-36/37/39-22-36-26
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
Applications
DescriptionVidarabine 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.
UsesAntiviral.
UsesDisrupts viral DNA synthesis. Competitive viral DNA polymerase inhibitor. Active against herpes simplex and varicella zoster viruses in vivo.
Suppliers100 total
常州帝通化工有限公司+86-0519-88298848 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
上海康朗生物科技有限公司
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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