Valganciclovir

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Structural formula
Structural formula of valganciclovir
( S , S ) -diastereomer (left) and ( S , R ) -diastereomer (right)
General
Non-proprietary name Valganciclovir
other names

( RS ) -5-amino-3- [1-hydroxymethyl-2- ( S -valyloxy) ethoxymethyl] -6,7-dihydro-3 H -imidazo [4,5- d ] pyrimidin-7-one

Molecular formula C 14 H 22 N 6 O 5
External identifiers / databases
CAS number
  • 175865-60-8
  • 175865-59-5 (hydrochloride)
PubChem 64147
ChemSpider 57721
DrugBank DB01610
Wikidata Q423384
Drug information
ATC code

J05 AB14

Drug class

Antivirals

properties
Molar mass 354.36 g · mol -1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling hydrochloride
08 - Dangerous to health

danger

H and P phrases H: 340-350-360-372
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Valganciclovir is a virostat from the group of nucleoside analogues . It is the L- valinyl ester of ganciclovir and functions as an absorption ester : while ganciclovir has to be infused, valganciclovir is well absorbed after oral administration and has a high bioavailability . After absorption, valganciclovir is converted in the body to the actually effective ganciclovir. Valganciclovir is used as the hydrochloride in the drug Valcyte ® ( Roche ) for the treatment of cytomegalovirus retinitis in AIDS patients.

As a prodrug of ganciclovir, valganciclovir has the same effects and side effects as this. There are z. T. life-threatening disorders. It is neutropenia up to agranulocytosis , anemia , thrombocytopenia , diarrhea , vomiting , abdominal pain , headache , neuropathy reported and liver cell damage associated with the use of valganciclovir. It should therefore only be used in the case of infections that threaten life or eyesight.

Stereoisomerism

Valganciclovir contains two stereocenters. In principle there are therefore four stereoisomers. The stereocenter at the valine residue is uniformly ( S ) -configured. The number of stereoisomers is thus limited to two . These two stereoisomers are diastereomers with different chemical, physical and physiological properties. The commercial products contain the drug as a mixture of diastereomers .

Trade names

Valganciclovir is commercially available in Germany, Austria and Switzerland under the name Valcyte.

Individual evidence

  1. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of 2 - [(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl) methoxy] -3-hydroxypropyl L-valinate in the classification and labeling is shown, which is derived from a self-classification by the distributor Inventory of the European Chemicals Agency (ECHA), accessed on February 3, 2019.
  2. ↑ External identifiers or database links for valganciclovir hydrochloride : CAS number: 175865-59-5, EC number: 641-360-4, ECHA InfoCard: 100.169.153 , PubChem : 135413534 , ChemSpider : 99298 , Wikidata : Q72515989 .
  3. ↑ Product information Valcyte 450 mg film-coated tablets, as of February 2008.
  4. ↑ ROTE LISTE 2017, Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-946057-10-9 , p. 225.
  5. ↑ Swiss Medicines Compendium , as of August 2009.
  6. ↑ AGES-PharmMed, as of August 2009.