Chemical Component Summary

Name2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl L-valinate
SynonymsValacyclovir
Identifiers2-[(2-azanyl-6-oxidanylidene-1H-purin-9-yl)methoxy]ethyl (2S)-2-azanyl-3-methyl-butanoate
FormulaC13 H20 N6 O4
Molecular Weight324.336
TypeNON-POLYMER
Isomeric SMILESCC(C)[C@@H](C(=O)OCCOCn1cnc2c1N=C(NC2=O)N)N
InChIInChI=1S/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1
InChIKeyHDOVUKNUBWVHOX-QMMMGPOBSA-N

Chemical Details

Formal Charge0
Atom Count43
Chiral Atom Count1
Bond Count44
Aromatic Bond Count5

Drug Info: DrugBank

DrugBank IDDB00577 
NameValaciclovir
Groups
  • investigational
  • approved
DescriptionValaciclovir (valacyclovir), also known as _Valtrex_, is an antiviral drug that has been used to manage and treat various herpes infections for more than 2 decades. It was initially approved by the FDA in 1995 [FDA label] and marketed by GlaxoSmithKline [L5671]. Valacyclovir is the L-valine ester of aciclovir. It is a member of the purine (guanine) nucleoside analog drug class [F3949]. This class of drugs forms an important part of hepatitis, HIV, and cytomegalovirus drug regimens [A175900]. One major use of valacyclovir is the treatment of genital herpes episodes or outbreaks. Genital herpes is a frequently diagnosed sexually transmitted disease which currently affects more than 400 million individuals worldwide. It is caused by infection with the herpes simplex virus (HSV). Infection with this virus is lifelong with periodic episodes of reactivation [A175903].
Synonyms
  • Valaciclovir hydrochloride
  • Valaciclovirum
  • L-Valine ester with 9-((2-hydroxyethoxy)methyl)guanine
  • L-Valine, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl ester
  • Valacyclovir
Brand Names
  • Jamp-valacyclovir
  • Valacyclovir Hydrochloride
  • Mylan-valacyclovir
  • Dom-valacyclovir
  • Auro-valacyclovir
IndicationValacyclovir is a nucleoside analog DNA polymerase inhibitor indicated for [FDA label]: **Adults** • Cold Sores (Herpes Labialis) • Genital Herpes • Treatment of genital herpes lesions in immunocompetent patients (initial or recurrent episode) • Suppression of genital herpes lesions in immunocompetent or HIV-infected patients • Reduction of viral transmission • Herpes Zoster **Pediatric Patients** • Cold Sores (Herpes Labialis) • Chickenpox **Limitations of use** [FDA label] The efficacy and safety of valacyclovir have not been established in immunocompromised patients other than for the suppression of genital herpes in HIV-infected patients.
Categories
  • Acyclovir and prodrug
  • Amino Acids
  • Amino Acids, Branched-Chain
  • Amino Acids, Peptides, and Proteins
  • Anti-Infective Agents
ATC-CodeJ05AB11
CAS number124832-26-4

Drug Targets

NameTarget SequencePharmacological ActionActions
Thymidine kinaseMASYPCHQHASAFDQAARSRGHSNRRTALRPRRQQEATEVRLEQKMPTLL...unknownsubstrate
DNA polymerase catalytic subunitMFSGGGGPLSPGGKSAARAASGFFAPAGPRGASRGPPPCLRQNFYNPYLA...unknowninhibitor
Guanylate kinaseMSGPRPVVLSGPSGAGKSTLLKRLLQEHSGIFGFSVSHTTRNPRPGEENG...unknownsubstrate
Thymidine kinaseMASYPCHQHASAFDQAARSRGHSNRRTALRPRRQQEATEVRLEQKMPTLL...unknownsubstrate
Solute carrier family 15 member 1MGMSKSHSFFGYPLSIFFIVVNEFCERFSYYGMRAILILYFTNFISWDDN...unknownsubstrate,inhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5281019, 135398742, 60773
ChEMBL CHEMBL1349
ChEBI CHEBI:35854