Vidarabin

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Structural formula
Structure of vidarabin
General
Non-proprietary name Vidarabin
other names
  • araA (short code)
  • Arabinosyladenin
  • 9-β- D -arabinofuranosyladenine
  • 9 - [(2 R , 3 S , 4 S , 5 R ) -3,4-dihydroxy-5- (hydroxymethyl) oxolan-2-yl] -6-aminopurine
Molecular formula C 10 H 15 N 5 O 5
External identifiers / databases
CAS number
  • 5536-17-4
  • 24356-66-9 (monohydrate)
EC number 226-893-9
ECHA InfoCard 100,024,449
PubChem 21704
ChemSpider 20400
DrugBank DB00194
Wikidata Q415107
Drug information
ATC code

S01 AD06

Drug class

Antiviral

properties
Molar mass 285.26 g mol −1
Physical state

firmly

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Vidarabine (araA) is an isomer of the nucleoside adenosine and is structurally related to fludarabine . It consists of a furanose (sugar) and adenine . It contains - in contrast to most nucleosides - instead of β- D -Ribofuranose the β- D -Arabinofuranose and thus belongs to the group of arabinosyl nucleosides .

properties

After phosphorylation to vidarabine triphosphate, it inhibits DNA polymerase in the body's cells. It is therefore cytotoxic .

use

Vidarabine was originally a cytostatic and, like ganciclovir, is used as a virostatic in severe forms of the herpes simplex and the varicella zoster virus . In the meantime, however, it has lost its importance because the later developed acyclovir works more safely. It can be used intravenously but also locally in the form of an ointment (3% vidarabine).

Side effects

Local irritation symptoms can occur as side effects, with high doses nausea.

literature

  • WE Müller, HJ Rohde, R. Beyer, A. Maidhof, M. Lachmann, H. Taschner, RK Kahn: “Mode of action of 9-beta-D-arabinofuranosyladenine on the synthesis of DNA, RNA, and protein in vivo and in vitro ", Cancer Res. 1975 Aug; 35 (8): 2160-2168 ( PMID 1149031 ).
  • SS Cohen: "The mechanisms of lethal action of arabinosyl cytosine (araC) and arabinosyl adenine (araA)", Cancer 1977 Jul; 40 (1 Suppl): 509-518 ( PMID 328134 ).
  • Ernst Mutschler: drug effects, textbook of pharmacology and toxicology, Wissenschaftliche Verlagsgesellschaft, Stuttgart 1991, ISBN 3-8047-1118-9 .

Web links

  • Entry for Vidarabine in the Human Metabolome Database (HMDB) , accessed October 16, 2013.

Individual evidence

  1. ↑ External identifiers or database links for vidarabine monohydrate : CAS number: 24356-66-9, EC number: 678-339-4, ECHA InfoCard: 100.203.402 , PubChem : 32326 , Wikidata : Q54819652 .
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.