You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2016-02-11 01:30:37 UTC
HMDB IDHMDB14925
Secondary Accession NumbersNone
Metabolite Identification
Common NameAciclovir
DescriptionAciclovir is only found in individuals that have used or taken this drug. It is a guanosine analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes. [PubChem]Viral (HSV-1, HSV-2 and VZV) thymidine kinase converts aciclovir to the aciclovir monophosphate, which is then converted to the diphosphate by cellular guanylate kinase, and finally to the triphosphate by phosphoglycerate kinase, phosphoenolpyruvate carboxykinase, and pyruvate kinase. Aciclovir triphosphate competitively inhibits viral DNA polymerase and competes with the natural deoxyguanosine triphosphate, for incorporation into viral DNA. Once incorporated, aciclovir triphosphate inhibits DNA synthesis by acting as a chain terminator.
Structure
Thumb
Synonyms
ValueSource
AciclovirumChEBI
AcycloguanosineChEBI
ZovirChEBI
9-HyroxyethoxymethylguanineHMDB
AC2HMDB
AciclovierHMDB
AcyclovirHMDB
Wellcome-248uHMDB
9-((2-Hydroxyethoxy)methyl)guanineMeSH
abello Brand OF aciclovirMeSH
Aciclovir betapharm brandMeSH
Aciclovir fabrigen brandMeSH
Aciclovir grin brandMeSH
Aciclovir liomont brandMeSH
Aciclovir novartis brandMeSH
Aciclovir zyma brandMeSH
Aciclovir CT-arzneimittel brandMeSH
acyclo VMeSH
Britisfarma brand OF aciclovir sodium saltMeSH
Bull brand OF aciclovirMeSH
Fustery brand OF aciclovirMeSH
Hexal brand OF aciclovir sodium saltMeSH
Isis brand OF aciclovirMeSH
Novag brand OF aciclovirMeSH
OpthavirMeSH
Pensa brand OF aciclovirMeSH
Rentschler brand OF aciclovirMeSH
Sanorania brand OF aciclovir sodium saltMeSH
Warner-lambert brand OF aciclovirMeSH
Wellcome brand OF aciclovirMeSH
Wellcome brand OF aciclovir sodium saltMeSH
ZoliparinMeSH
Zovirax for injectionMeSH
Curasan brand OF aciclovir sodium saltMeSH
AciclobetaMeSH
Aciclovir amrad brandMeSH
Aciclovir fustery brandMeSH
Aciclovir mann brandMeSH
Aciclovir niddapharm brandMeSH
Aciclovir sanorania brandMeSH
Aciclovir ursapharm brandMeSH
Aciclovir-sanoraniaMeSH
ActivirMeSH
acyclo-VMeSH
Alcon brand OF aciclovirMeSH
Alonga brand OF aciclovirMeSH
AviraxMeSH
Azupharma brand OF aciclovirMeSH
CicloferonMeSH
Clonmel brand OF aciclovirMeSH
CusiviralMeSH
Dermapharm brand OF aciclovirMeSH
Fabrigen brand OF aciclovirMeSH
Grünenthal brand OF aciclovir sodium saltMeSH
HerpofugMeSH
HerpoviricMeSH
Hexal brand OF aciclovirMeSH
IsavirMeSH
MilavirMeSH
Parke davis brand OF aciclovirMeSH
Pharma investi brand OF aciclovirMeSH
ViraxPurenMeSH
VirherpesMeSH
VirolexMeSH
VirzinMeSH
Warner wellcome brand OF aciclovirMeSH
Wolff brand OF aciclovirMeSH
ZyclirMeSH
Zyma brand OF aciclovirMeSH
CT Arzneimittel brand OF aciclovirMeSH
Aci sanoraniaMeSH
AcicMeSH
Aciclovir alongaMeSH
Aciclovir britisfarma brandMeSH
Aciclovir grünenthal brandMeSH
Aciclovir isis brandMeSH
Aciclovir kendrick brandMeSH
Aciclovir lichtenstein brandMeSH
Aciclovir menarini brandMeSH
Aciclovir sanoraniaMeSH
Aciclovir stada brandMeSH
Aciclovir tad brandMeSH
Aciclovir warner-lambert brandMeSH
Aciclovir wellcome brandMeSH
Aciclovir wolff brandMeSH
AcifurMeSH
Amrad brand OF aciclovirMeSH
Antiherpes cremeMeSH
Britisfarma brand OF aciclovirMeSH
GenvirMeSH
glaxo Wellcome brand OF aciclovirMeSH
Grünenthal brand OF aciclovirMeSH
HerpetadMeSH
LacikenMeSH
Lichtenstein brand OF aciclovirMeSH
MapoxMeSH
MaynarMeSH
Menarini brand OF aciclovirMeSH
Pisa brand OF aciclovirMeSH
Rentschler brand OF aciclovir sodium saltMeSH
Stada brand OF aciclovirMeSH
TAD brand OF aciclovirMeSH
Ursapharm brand OF aciclovirMeSH
ViclovirMeSH
Virax purenMeSH
Virax-purenMeSH
VirmenMeSH
ViruposMeSH
Warner lambert brand OF aciclovirMeSH
Wellcome 248uMeSH
Wellcome248uMeSH
Yamanouchi brand OF aciclovirMeSH
Aciclovir von CTMeSH
Aci-sanoraniaMeSH
AciclostadMeSH
Aciclovir abello brandMeSH
Aciclovir alcon brandMeSH
Aciclovir alphapharm brandMeSH
Aciclovir azupharma brandMeSH
Aciclovir clonmel brandMeSH
Aciclovir dermapharm brandMeSH
Aciclovir hexal brandMeSH
Aciclovir novag brandMeSH
Aciclovir pensa brandMeSH
Aciclovir pisa brandMeSH
Aciclovir rentschler brandMeSH
Aciclovir yamanouchi brandMeSH
Acipen solutabMeSH
AcivirMeSH
Acyclovir sodiumMeSH
Alonga brand OF aciclovir sodium saltMeSH
Alphapharm brand OF aciclovirMeSH
Betapharm brand OF aciclovirMeSH
ClonoraxMeSH
glaxo Wellcome brand OF aciclovir sodium saltMeSH
Grin brand OF aciclovirMeSH
HerpoternMeSH
Kendrick brand OF aciclovirMeSH
Liomont brand OF aciclovirMeSH
Mann brand OF aciclovirMeSH
Menarini brand OF aciclovir sodium saltMeSH
Niddapharm brand OF aciclovirMeSH
Novartis brand OF aciclovirMeSH
Pensa brand OF aciclovir sodium saltMeSH
Sanorania brand OF aciclovirMeSH
Sodium, acyclovirMeSH
Solutab, acipenMeSH
SupraviranMeSH
VipralMeSH
ZoviraxMeSH
CT-Arzneimittel brand OF aciclovirMeSH
Chemical FormulaC8H11N5O3
Average Molecular Weight225.2046
Monoisotopic Molecular Weight225.086189243
IUPAC Name2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one
Traditional Namezovirax
CAS Registry Number59277-89-3
SMILES
NC1=NC(=O)C2=C(N1)N(COCCO)C=N2
InChI Identifier
InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)
InChI KeyInChIKey=MKUXAQIIEYXACX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentHypoxanthines
Alternative Parents
Substituents
  • 6-oxopurine
  • Hypoxanthine
  • Aminopyrimidine
  • Pyrimidone
  • N-substituted imidazole
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Azacycle
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antiviral Agents
  • Nucleosides and Nucleotides
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point256.5 - 257 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.08e+00 g/LNot Available
LogP-1.56KRISTL,A ET AL. (1993)
Predicted Properties
PropertyValueSource
Water Solubility9.08 mg/mLALOGPS
logP-0.95ALOGPS
logP-1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.99ChemAxon
pKa (Strongest Basic)2.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.76 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.63 m3·mol-1ChemAxon
Polarizability21.51 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00787
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00787
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00787
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1945
KEGG Compound IDC06810
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAciclovir
NuGOwiki LinkHMDB14925
Metagene LinkHMDB14925
METLIN IDNot Available
PubChem Compound2022
PDB IDAC2
ChEBI ID2453
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. [2653790 ]
  2. Gunness P, Aleksa K, Bend J, Koren G: Acyclovir-induced nephrotoxicity: the role of the acyclovir aldehyde metabolite. Transl Res. 2011 Nov;158(5):290-301. doi: 10.1016/j.trsl.2011.07.002. Epub 2011 Aug 3. [22005269 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [11861798 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [11861798 ]
  2. Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [10945832 ]