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24356-66-9 molecular structure
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(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

ChemBase ID: 79
Molecular Formular: C10H13N5O4
Molecular Mass: 267.24132
Monoisotopic Mass: 267.09675392
SMILES and InChIs

SMILES:
O1[C@@H](n2c3ncnc(N)c3nc2)[C@@H](O)[C@H](O)[C@H]1CO
Canonical SMILES:
OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1cnc2c1ncnc2N
InChI:
InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1
InChIKey:
OIRDTQYFTABQOQ-UHTZMRCNSA-N

Cite this record

CBID:79 http://www.chembase.cn/molecule-79.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
IUPAC Traditional name
armes
Brand Name
Arasena-A
Spongoadenosine
Vira-A
Vidarabin
Synonyms
Adenine Arabinoside
Arabinofuranosyladenine Triphosphate
Arabinoside Adenine
Arabinosyl Adenine
Arabinosyladenine
Arabinosyladenine Triphosphate
Vidarabine Triphosphate
Ara Atp
Ara-A
Ara-a Triphosphate
Ara-Atp
Araadenosine
Arabinosyl-Atp
9-beta-D-arabinofuranosyl-adenine
Vidarabine
9-β-D-Arabinofuranosyladenine
Vidarabine
Vira-A
Adenine 9-β-D-arabinofuranoside
6-Amino-9-b-D-arabinofuranosylpurine
CAS Number
24356-66-9
5536-17-4
EC Number
226-893-9
MDL Number
MFCD00065471
Beilstein Number
624881
PubChem SID
46506630
160963542
24891019
PubChem CID
21704
32326

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 12.454003  H Acceptors
H Donor LogD (pH = 5.5) -2.2061195 
LogD (pH = 7.4) -2.09263  Log P -2.0909638 
Molar Refractivity 63.1956 cm3 Polarizability 24.545797 Å3
Polar Surface Area 139.54 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Hydrophobicity(logP)
-2.115 expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
AU6200000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
63 expand Show data source
Safety Statements
36/37 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H361 expand Show data source
GHS Precautionary statements
P281 expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
mouse ... Ahcy(269378) expand Show data source
Purity
≥99% expand Show data source
≥99.0% (HPLC) expand Show data source
98% expand Show data source
Salt Data
Free Base expand Show data source
Empirical Formula (Hill Notation)
C10H13N5O4 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
DrugBank - DB00194 external link
Item Information
Drug Groups approved
Description A nucleoside antibiotic isolated from Streptomyces antibioticus. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the vaccinia VIRUS and varicella zoster virus. [PubChem]
Indication For treatment of chickenpox - varicella, herpes zoster and herpes simplex
Pharmacology Vidarabine is a synthetic purine nucleoside analogue with in vitro and in vivo inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), and varicella-zoster virus (VZV). The inhibitory activity of Vidarabine is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts Vidarabine into Vidarabine monophosphate, a nucleotide analogue. The monophosphate is further converted into diphosphate by cellular guanylate kinase and into triphosphate by a number of cellular enzymes. in vitro, Vidarabine triphosphate stops replication of herpes viral DNA. When used as a substrate for viral DNA polymerase, Vidarabine triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where Vidarabine triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand.
Toxicity Acute massive overdosage by oral ingestion of the ophthalmic ointment has not occurred. However, the rapid deamination to arabinosylhypoxanthine should preclude any difficulty. The oral LD50 for vidarabine is greater than 5020 mg/kg in mice and rats. No untoward effects should result from ingestion of the entire contents of the tube. Overdosage by ocular instillation is unlikely because any excess should be quickly expelled from the conjunctival sac.
Affected Organisms
Human Herpes Virus
Biotransformation In laboratory animals, vidarabine is rapidly deaminated in the gastrointestinal tract to Ara-Hx.
Absorption Systemetic absorption of vidarabine should not be expected to occur following ocular administration and swallowing lacrimal secretions.
Protein Binding 24-38%
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1784 external link
Research Area: Infection
Biological Activity:
Vidarabine(Vira-A) is an antiviral drug which is active against herpes simplex and varicella zoster viruses. Vidarabine works by interfering with the synthesis of viral DNA. It is a nucleoside analog, therefore it has to be phosphorylated and to be active. Vidarabine stops replication of herpes viral DNA in 3 ways: 1) competitive inhibition of viral DNA polymerase, 2) incorporation into and termination of the growing viral DNA chain, 3) inactivation of the viral DNA polymerase. [1]
Sigma Aldrich - 01832 external link
Biochem/physiol Actions
Cell-permeable adenylate cyclase inhibitor; in detergent-dispersed rat brain preparation, IC50 = 30 μM. Clinically significant antiviral agent, especially against herpes simplex (HSV),1 by inhibition of DNA polymerase.
Sigma Aldrich - A5762 external link
Application
Used to study the roles of AMP-activated protein kinase (AMPK) in cell signaling.
Biochem/physiol Actions
Cell-permeable adenylate cyclase inhibitor; in detergent-dispersed rat brain preparation, IC50 = 30 μM. Clinically significant antiviral agent, especially against herpes simplex (HSV),1 by inhibition of DNA polymerase.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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