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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:36 UTC
HMDB IDHMDB0014925
Secondary Accession Numbers
  • HMDB14925
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
Data?1582753236
Synonyms
ValueSource
AciclovirumChEBI
AcycloguanosineChEBI
ZovirChEBI
AcyclovirKegg
SitavigKegg
ZoviraxKegg
9-HyroxyethoxymethylguanineHMDB
AC2HMDB
AciclovierHMDB
Wellcome-248uHMDB
9-((2-Hydroxyethoxy)methyl)guanineHMDB
Abello brand OF aciclovirHMDB
Aciclovir betapharm brandHMDB
Aciclovir fabrigen brandHMDB
Aciclovir grin brandHMDB
Aciclovir liomont brandHMDB
Aciclovir novartis brandHMDB
Aciclovir zyma brandHMDB
Aciclovir CT-arzneimittel brandHMDB
Acyclo VHMDB
Britisfarma brand OF aciclovir sodium saltHMDB
Bull brand OF aciclovirHMDB
Fustery brand OF aciclovirHMDB
Hexal brand OF aciclovir sodium saltHMDB
Isis brand OF aciclovirHMDB
Novag brand OF aciclovirHMDB
OpthavirHMDB
Pensa brand OF aciclovirHMDB
Rentschler brand OF aciclovirHMDB
Sanorania brand OF aciclovir sodium saltHMDB
Warner-lambert brand OF aciclovirHMDB
Wellcome brand OF aciclovirHMDB
Wellcome brand OF aciclovir sodium saltHMDB
ZoliparinHMDB
Zovirax for injectionHMDB
Curasan brand OF aciclovir sodium saltHMDB
AciclobetaHMDB
Aciclovir amrad brandHMDB
Aciclovir fustery brandHMDB
Aciclovir mann brandHMDB
Aciclovir niddapharm brandHMDB
Aciclovir sanorania brandHMDB
Aciclovir ursapharm brandHMDB
Aciclovir-sanoraniaHMDB
ActivirHMDB
Acyclo-VHMDB
Alcon brand OF aciclovirHMDB
Alonga brand OF aciclovirHMDB
AviraxHMDB
Azupharma brand OF aciclovirHMDB
CicloferonHMDB
Clonmel brand OF aciclovirHMDB
CusiviralHMDB
Dermapharm brand OF aciclovirHMDB
Fabrigen brand OF aciclovirHMDB
Grünenthal brand OF aciclovir sodium saltHMDB
HerpofugHMDB
HerpoviricHMDB
Hexal brand OF aciclovirHMDB
IsavirHMDB
MilavirHMDB
Parke davis brand OF aciclovirHMDB
Pharma investi brand OF aciclovirHMDB
ViraxPurenHMDB
VirherpesHMDB
VirolexHMDB
VirzinHMDB
Warner wellcome brand OF aciclovirHMDB
Wolff brand OF aciclovirHMDB
ZyclirHMDB
Zyma brand OF aciclovirHMDB
CT Arzneimittel brand OF aciclovirHMDB
Aci sanoraniaHMDB
AcicHMDB
Aciclovir alongaHMDB
Aciclovir britisfarma brandHMDB
Aciclovir grünenthal brandHMDB
Aciclovir isis brandHMDB
Aciclovir kendrick brandHMDB
Aciclovir lichtenstein brandHMDB
Aciclovir menarini brandHMDB
Aciclovir sanoraniaHMDB
Aciclovir stada brandHMDB
Aciclovir tad brandHMDB
Aciclovir warner-lambert brandHMDB
Aciclovir wellcome brandHMDB
Aciclovir wolff brandHMDB
AcifurHMDB
Amrad brand OF aciclovirHMDB
Antiherpes cremeHMDB
Britisfarma brand OF aciclovirHMDB
GenvirHMDB
Glaxo wellcome brand OF aciclovirHMDB
Grünenthal brand OF aciclovirHMDB
HerpetadHMDB
LacikenHMDB
Lichtenstein brand OF aciclovirHMDB
MapoxHMDB
MaynarHMDB
Menarini brand OF aciclovirHMDB
Pisa brand OF aciclovirHMDB
Rentschler brand OF aciclovir sodium saltHMDB
Stada brand OF aciclovirHMDB
TAD brand OF aciclovirHMDB
Ursapharm brand OF aciclovirHMDB
ViclovirHMDB
Virax purenHMDB
Virax-purenHMDB
VirmenHMDB
ViruposHMDB
Warner lambert brand OF aciclovirHMDB
Wellcome 248uHMDB
Wellcome248uHMDB
Yamanouchi brand OF aciclovirHMDB
Aciclovir von CTHMDB
Aci-sanoraniaHMDB
AciclostadHMDB
Aciclovir abello brandHMDB
Aciclovir alcon brandHMDB
Aciclovir alphapharm brandHMDB
Aciclovir azupharma brandHMDB
Aciclovir clonmel brandHMDB
Aciclovir dermapharm brandHMDB
Aciclovir hexal brandHMDB
Aciclovir novag brandHMDB
Aciclovir pensa brandHMDB
Aciclovir pisa brandHMDB
Aciclovir rentschler brandHMDB
Aciclovir yamanouchi brandHMDB
Acipen solutabHMDB
AcivirHMDB
Acyclovir sodiumHMDB
Alonga brand OF aciclovir sodium saltHMDB
Alphapharm brand OF aciclovirHMDB
Betapharm brand OF aciclovirHMDB
ClonoraxHMDB
Glaxo wellcome brand OF aciclovir sodium saltHMDB
Grin brand OF aciclovirHMDB
HerpoternHMDB
Kendrick brand OF aciclovirHMDB
Liomont brand OF aciclovirHMDB
Mann brand OF aciclovirHMDB
Menarini brand OF aciclovir sodium saltHMDB
Niddapharm brand OF aciclovirHMDB
Novartis brand OF aciclovirHMDB
Pensa brand OF aciclovir sodium saltHMDB
Sanorania brand OF aciclovirHMDB
Sodium, acyclovirHMDB
Solutab, acipenHMDB
SupraviranHMDB
VipralHMDB
CT-Arzneimittel brand OF aciclovirHMDB
AciclovirChEBI
Aciclovir granulesKEGG
Aciclovir ophthalmic oinmentKEGG
Aciclovir tabletsKEGG
Alonga, 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 KeyMKUXAQIIEYXACX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hypoxanthines. Hypoxanthines 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
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point256.5 - 257 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility9.08 g/LNot Available
LogP-1.56KRISTL,A ET AL. (1993)
Predicted Properties
PropertyValueSource
Water Solubility9.08 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.63 m³·mol⁻¹ChemAxon
Polarizability21.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0il4-4900000000-e7f4be9e9211bcd07ea1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-008a-9580000000-295761ea9247315168aaSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-001i-4952000000-c2782962b5849c9d5395Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0090000000-59599385810ae2952ce5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0290000000-9410504409e66bcd08f9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0uyi-1900000000-0930eb38cecf2a197001Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05nf-4900000000-10d8c1e33c5d46d6ff80Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05mo-9600000000-e25ed55283d7d66d80c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0390000000-079dc309c9ffbbde3375Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-201a17a51960fdc3bcefSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-6c63ec4268a52381191cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f79-1900000000-20fdfa17569c6b2f479fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-2900000000-4f7a822e6652ec471aeeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0udi-0900000000-69b23ed6f334f4571eccSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udr-2910100000-2b1624536b0084ca299cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ufr-0940000000-0b6cdb1810607b80dcf0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-f414bb6c66d7d6a9e87fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0lz0-0900000000-965fbda32a0fe68f4c8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3590000000-ca962b44ebac1bef4412Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kmi-2930000000-1b8b208aa827ae1f11e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-5900000000-c41b0d5e328742b24c7eSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00787 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00787 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00787
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1945
KEGG Compound IDC06810
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcyclovir
METLIN IDNot Available
PubChem Compound2022
PDB IDAC2
ChEBI ID2453
Food Biomarker OntologyNot Available
VMH IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:10945832 ]