Identification

Name
Acyclovir
Accession Number
DB00787  (APRD00567, EXPT00406, DB05347)
Type
Small Molecule
Groups
Approved
Description

A guanosine analog antiviral drug that acts as an antimetabolite. Aciclovir is used for the treatment of herpes simplex virus infections, varicella zoster (chickenpox) and herpes zoster (shingles).

Aciclovir has also been investigated for the treatment of herpes labialis applied using an iontophoretic device. Currently approved drugs for the treatment of herpes labialis (cold sores) exhibit low levels of efficacy due to the limited ability of the drugs to penetrate the skin to the site where the herpes virus is replicating. Iontophoresis uses electric current to enhance the delivery of drugs through the skin.

Synonyms
  • Aciclovir
  • Aciclovirum
  • Acycloguanosine
External IDs
NSC-645011
Product Ingredients
IngredientUNIICASInChI Key
Acyclovir sodium927L42J56369657-51-8RMLUKZWYIKEASN-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcyclovirTablet400 mgOralSanis Health Inc2010-04-05Not applicableCanada
AcyclovirTablet800 mgOralSanis Health Inc2010-04-052014-08-01Canada
AcyclovirTablet200 mgOralSanis Health Inc2010-04-052014-08-01Canada
Acyclovir Sodium for InjectionPowder, for solution1 gIntravenousAbbott1998-02-112007-07-31Canada
Acyclovir Sodium for InjectionPowder, for solution500 mgIntravenousAbbott1998-02-112007-07-31Canada
Acyclovir Sodium for InjectionPowder, for solution1 gIntravenousNovopharm Limited1998-02-042005-08-10Canada
Acyclovir Sodium for InjectionPowder, for solution500 mgIntravenousNovopharm Limited1998-02-04Not applicableCanada
Acyclovir Sodium InjectionSolution25 mgIntravenousIvax Pharmaceuticals IncorporatedNot applicableNot applicableCanada
Acyclovir Sodium InjectionSolution50 mgIntravenousFresenius Kabi1998-05-08Not applicableCanada
Acyclovir Sodium InjectionSolution25 mgIntravenousPfizer1998-03-18Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcyclovirTablet400 mg/1OralMylan Institutional2010-07-232012-04-30Us
AcyclovirTablet400 mg/1Oralbryant ranch prepack1997-04-23Not applicableUs63629 167720180907 15195 1d7brrg
AcyclovirTablet800 mg/1OralA-S Medication Solutions2013-11-29Not applicableUs54569 472420180907 15195 3e6yrn
AcyclovirTablet800 mg/1Oralbryant ranch prepack2014-09-10Not applicableUs
AcyclovirTablet800 mg/1OralStat Rx USA1998-09-30Not applicableUs
AcyclovirTablet400 mg/1OralAmerincan Health Packaging2014-01-29Not applicableUs
AcyclovirTablet800 mg/1OralZydus Pharmaceuticals Usa, Inc.2014-09-10Not applicableUs
AcyclovirTablet400 mg/1OralBlenheim Pharmacal, Inc.2015-09-022017-10-31Us
AcyclovirSuspension200 mg/5mLOralPreferreed Pharmaceuticals Inc.2011-03-18Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2018-08-09Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
XereseAcyclovir (5 %) + Hydrocortisone (1 %)CreamTopicalValeant Canada Lp Valeant Canada S.E.C.2013-07-26Not applicableCanada
XereseAcyclovir (50 mg/1g) + Hydrocortisone (10 mg/1g)CreamTopicalValeant Pharmaceuticals North America2009-07-31Not applicableUs
XereseAcyclovir (50 mg/1g) + Hydrocortisone (10 mg/1g)CreamTopicalMeda Pharmaceuticals Ltd2010-07-152013-02-28Us
International/Other Brands
Zovir
Categories
UNII
X4HES1O11F
CAS number
59277-89-3
Weight
Not Available
Chemical Formula
C8H11N5O3
InChI Key
MKUXAQIIEYXACX-UHFFFAOYSA-N
InChI
Not Available
IUPAC Name
Not Available
SMILES
Not Available

Pharmacology

Indication

For the treatment and management of herpes zoster (shingles), genital herpes, and chickenpox.

Associated Conditions
Pharmacodynamics

Aciclovir (INN) or acyclovir (USAN, former BAN) is a synthetic deoxyguanosine analog and it is the prototype antiviral agent that is activated by viral thymidine kinase. The selective activity of aciclovir is due to its affinity for the thymidine kinase enzyme encoded by HSV and VZV. EC50 value of acyclovir against clinical herpes virus isolates was 1.3 μM (range: < 0.56 to 3.3 μM).

Mechanism of action

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. One may consider aciclovir to be a prodrug as it is metabolized to more active compounds. Aciclovir is selective and low in cytotoxicity as the cellular thymidine kinase of normal, uninfected cells does not use aciclovir effectively as a substrate.

TargetActionsOrganism
AThymidine kinase
potentiator
HHV-1
ADNA polymerase catalytic subunit
inhibitor
HHV-1
ADNA polymerase catalytic subunit
inhibitor
HHV-3
Absorption

The oral bioavailability is 10% to 20%, and decreases with increasing dose. Food does not affect the absorption of acyclovir. The following are the pharmacokinetic parameters for 50 mg buccal tablet, Sitavig, in the saliva: AUC 0 - 24 hours = 2900±2400 mcg.h/mL; Cmax = 440±241 mcg/mL; Tmax = 7.95 ± 4.08 hours.

Volume of distribution
Not Available
Protein binding

9%-33%

Metabolism

Hepatic, Acyclovir is metabolized to 9-[(carboxymethoxy)methyl]guanine (CMMG) and 8­ hydroxy-acyclovir (8-OH-ACV) by oxidation and hydroxylation. It is suggested in studies that acyclovir is first metabolized to acyclovir aldehyde by alcohol dehydrogenase and then converted to CMMG. The build up of acyclovir aldehyde may be the cause of acyclovir-induced nephrotoxicity in the absence of crystalluria.

Route of elimination

Primarily excreted unchanged by the kidneys via active tubular secretion.

Half life

2.5-3.3 hours

Clearance
Not Available
Toxicity

Aciclovir may cause nephrotoxicity (crystallization of aciclovir within renal tubules, elevation of serum creatinine, transient), and neurotoxicity (coma, hallucinations, lethargy, seizures, tremors). Nephrotoxicity and neurotoxicity usually resolve after cessation of aciclovir therapy. However, there is no well-defined relationship between aciclovir concentrations in the blood and these adverse effects.

Affected organisms
  • Human Herpes Virus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Acyclovir.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Acyclovir.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Acyclovir.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Acyclovir.
7,9-DimethylguanineThe serum concentration of 7,9-Dimethylguanine can be increased when it is combined with Acyclovir.
8-azaguanineThe serum concentration of 8-azaguanine can be increased when it is combined with Acyclovir.
8-chlorotheophyllineThe serum concentration of 8-chlorotheophylline can be increased when it is combined with Acyclovir.
9-DeazaguanineThe serum concentration of 9-Deazaguanine can be increased when it is combined with Acyclovir.
9-MethylguanineThe serum concentration of 9-Methylguanine can be increased when it is combined with Acyclovir.
AbacavirAcyclovir may decrease the excretion rate of Abacavir which could result in a higher serum level.
Food Interactions
  • Increase liquid intake.
  • Take without regard to meals.

References

Synthesis Reference
US4294831
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]
  3. Morrel EM, Spruance SL, Goldberg DI: Topical iontophoretic administration of acyclovir for the episodic treatment of herpes labialis: a randomized, double-blind, placebo-controlled, clinic-initiated trial. Clin Infect Dis. 2006 Aug 15;43(4):460-7. Epub 2006 Jul 3. [PubMed:16838235]
External Links
Human Metabolome Database
HMDB0014925
KEGG Drug
D00222
KEGG Compound
C06810
PubChem Compound
2022
PubChem Substance
46506002
ChemSpider
1945
BindingDB
50021776
ChEBI
2453
ChEMBL
CHEMBL184
Therapeutic Targets Database
DNC000157
PharmGKB
PA448045
HET
AC2
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Aciclovir
ATC Codes
D06BB03 — AciclovirS01AD03 — AciclovirD06BB53 — Aciclovir, combinationsJ05AB01 — Aciclovir
AHFS Codes
  • 84:04.06 — Antivirals
  • 08:18.32 — Nucleosides and Nucleotides
PDB Entries
1pwy / 2ki5 / 3mjr / 4da7 / 5i3c
MSDS
Download (37 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingTreatmentProgressive Multiple Sclerosis1
1CompletedNot AvailableInfection NOS1
1CompletedTreatmentAcute and Chronic Inflammation / Autoimmune Diseases / Disorder of Pleura and Pleural Cavity / Disorder of Synovium / Felty's Syndrome / Rheumatoid Arthritis / Rheumatoid Nodules / Sjögren's Syndrome1
1CompletedTreatmentHerpes Simplex Virus / Neonatal Sepsis1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentProgressive Multiple Sclerosis2
1, 2CompletedTreatmentAcute Undifferentiated Leukemia (AUL) / B-cell Adult Acute Lymphoblastic Leukemia / B-cell Childhood Acute Lymphoblastic Leukemia / L1 Adult Acute Lymphoblastic Leukemia / L1 Childhood Acute Lymphoblastic Leukemia / L2 Adult Acute Lymphoblastic Leukemia / L2 Childhood Acute Lymphoblastic Leukemia / Philadelphia Chromosome Negative Adult Precursor Acute Lymphoblastic Leukemia / Philadelphia Chromosome Positive Adult Precursor Acute Lymphoblastic Leukemia / Philadelphia Chromosome Positive Childhood Precursor Acute Lymphoblastic Leukemia / T-cell Adult Acute Lymphoblastic Leukemia / T-cell Childhood Acute Lymphoblastic Leukemia / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
1, 2CompletedTreatmentHerpes Simplex1
1, 2CompletedTreatmentKidney Diseases / Transplantation, Kidney1
2Active Not RecruitingTreatmentHerpes Labialis1
2Active Not RecruitingTreatmentLung Cancer Non-Small Cell Cancer (NSCLC)1
2CompletedPreventionCritical Illness1
2CompletedPreventionHerpes simplex of the genitals / Ulcers1
2CompletedTreatmentChickenpox / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHerpes Labialis1
2CompletedTreatmentHerpes simplex of the genitals / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHerpesvirus 2, Human / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentMetastatic Castration Resistant Prostate Cancer1
2RecruitingSupportive CareStem Cell Transplant Complications1
2, 3CompletedPreventionHIV-1 and HSV-2 Coinfection / Human Immunodeficiency Virus (HIV) Infections1
2, 3CompletedTreatmentHerpes Simplex / Human Immunodeficiency Virus (HIV) Infections / Ulcers1
2, 3Unknown StatusTreatmentMenière's Disease1
2, 3WithdrawnTreatmentHerpes Simplex1
3Active Not RecruitingTreatmentDrug Use for Unapproved Schedule1
3CompletedNot AvailableVZV Infection After Bone Marrow Transplantation1
3CompletedPreventionCytomegalovirus / Transplantation, Bone Marrow1
3CompletedPreventionHerpes simplex of the genitals / HIV Seronegativity / Human Immunodeficiency Virus (HIV) Infections1
3CompletedPreventionHerpes Simplex, Genital / Human Immunodeficiency Virus (HIV) Infections / Sexually Transmitted Disease (STD)1
3CompletedSupportive CareHerpes Simplex1
3CompletedSupportive CareMalignancies1
3CompletedTreatmentChickenpox / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentGenital Herpes1
3CompletedTreatmentHerpes Labialis3
3CompletedTreatmentHerpes Simplex4
3CompletedTreatmentHerpes Simplex / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHerpes Simplex / Keratitis, Herpetic / Ocular Herpes Simplex1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infections, Cytomegalovirus1
3RecruitingPreventionCMV Disease1
3RecruitingTreatmentDisseminated Sclerosis1
3RecruitingTreatmentHerpes Zoster1
3Unknown StatusTreatmentHerpes Simplex1
3Unknown StatusTreatmentKeratitis, Herpetic / Ocular Herpes Simplex1
4Active Not RecruitingNot AvailableGenital Herpes1
4CompletedPreventionHerpes / Human Immunodeficiency Virus (HIV)1
4CompletedTreatmentGenital Herpes2
4CompletedTreatmentGenital Herpes / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentHerpes Simplex Infection / Human Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentRelapsing Remitting Multiple Sclerosis (RRMS)1
4RecruitingTreatmentViral Pneumonia1
4Unknown StatusTreatmentHerpes Zoster1
4Unknown StatusTreatmentReccurent Herpes Labialis1
Not AvailableCompletedNot AvailableGenital Herpes1
Not AvailableCompletedBasic ScienceDermatologic Disorders1
Not AvailableCompletedTreatmentCytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentFacial Paralysis1
Not AvailableCompletedTreatmentGenital Herpes1
Not AvailableCompletedTreatmentHerpes Simplex / Human Immunodeficiency Virus (HIV) Infections4
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral hairy leukoplakia1
Not AvailableCompletedTreatmentUlcers of Female Genital Organs1
Not AvailableRecruitingNot AvailableChildren; Infection / Newborn; Infection1
Not AvailableRecruitingNot AvailableMeningitis, Aseptic1
Not AvailableRecruitingTreatmentUveitis1

Pharmacoeconomics

Manufacturers
  • Actavis elizabeth llc
  • Apotex inc etobicoke site
  • Belcher pharmaceuticals inc
  • Dava pharmaceuticals inc
  • Genpharm inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lek pharmaceutical and chemical co dd
  • Mylan pharmaceuticals inc
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Stason industrial corp
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • Watson laboratories inc
  • Glaxosmithkline
  • Actavis mid atlantic llc
  • Hi tech pharmacal co inc
  • Carlsbad technology inc
  • Mylan laboratories inc
  • Abbott laboratories
  • Baxter healthcare corp anesthesia and critical care
  • Apothecon inc div bristol myers squibb
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Hospira inc
  • Teva parenteral medicines inc
Packagers
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotex Inc.
  • Apotheca Inc.
  • Apothecary Shop Wholesale
  • APP Pharmaceuticals
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bryant Ranch Prepack
  • BTA Pharmaceuticals
  • Cardinal Health
  • Carlsbad Technology Inc.
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • DAVA Pharmaceuticals
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • DSM Corp.
  • East Coast Medical Network Inc.
  • Eczacibasi Health Products Co.
  • GlaxoSmithKline Inc.
  • Goldline Laboratories Inc.
  • H.J. Harkins Co. Inc.
  • Heritage Pharmaceuticals
  • Hi Tech Pharmacal Co. Inc.
  • Hospira Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medvantx Inc.
  • Meridian Medical Technologies Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Neuman Distributors Inc.
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Patheon Inc.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Pharmpak Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stason Pharmaceuticals Inc.
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • Watson Pharmaceuticals
  • Xactdose Inc.
  • Yung Shin Pharmaceutical Industry Ltd.
Dosage forms
FormRouteStrength
CapsuleOral200 mg/1
CapsuleOral400 mg/1
Injection, powder, lyophilized, for solutionIntravenous1 g/1
Injection, powder, lyophilized, for solutionIntravenous1000 mg/1
Injection, powder, lyophilized, for solutionIntravenous1000 mg/20mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/1
Injection, solutionIntravenous25 mg/1mL
Injection, solutionIntravenous50 mg/1mL
OintmentCutaneous50 mg/1g
SuspensionOral200 mg/5mL
TabletOral200 mg/1
TabletOral400 mg/1
TabletOral400.00 mg/1
TabletOral800 mg/1
TabletOral800.00 mg/1
Injection, solutionIntravenous1000 mg/20mL
Injection, solutionIntravenous500 mg/10mL
Powder, for solutionIntravenous500 mg
SolutionIntravenous25 mg
SolutionIntravenous50 mg
TabletOral800 mg
TabletOral200 mg
TabletOral400 mg
TabletBuccal50 mg
Tablet, delayed releaseBuccal50 mg/1
CreamTopical
CreamTopical5 %
CreamTopical50 mg/1g
Injection, powder, lyophilized, for solutionIntravenous50 mg/1mL
OintmentTopical5 %
OintmentTopical50 mg/1g
Powder, for solutionIntravenous1 g
SuspensionOral200 mg
CapsuleOral200 mg
Prices
Unit descriptionCostUnit
Zovirax 200 mg/5ml Suspension 473ml Bottle264.95USD bottle
Zovirax 5% Ointment 15 gm Tube191.56USD tube
Zovirax 5% Cream 5 gm Tube165.07USD tube
Zovirax 5% Cream 2 gm Tube69.44USD tube
Zovirax 5% cream30.22USD g
Zovirax 800 mg tablet11.83USD tablet
Zovirax 400 mg tablet6.09USD tablet
Zovirax 800 mg Tablet5.71USD tablet
Acyclovir 800 mg tablet3.81USD tablet
Zovirax 200 mg capsule3.08USD capsule
Acyclovir 800 mg Tablet2.99USD tablet
Apo-Acyclovir 800 mg Tablet2.99USD tablet
Mylan-Acyclovir 800 mg Tablet2.99USD tablet
Novo-Acyclovir 800 mg Tablet2.99USD tablet
Nu-Acyclovir 800 mg Tablet2.99USD tablet
Ratio-Acyclovir 800 mg Tablet2.99USD tablet
Zovirax 400 mg Tablet2.9USD tablet
Acyclovir 400 mg tablet2.26USD tablet
Acyclovir 400 mg Tablet1.63USD tablet
Apo-Acyclovir 400 mg Tablet1.63USD tablet
Mylan-Acyclovir 400 mg Tablet1.63USD tablet
Novo-Acyclovir 400 mg Tablet1.63USD tablet
Nu-Acyclovir 400 mg Tablet1.63USD tablet
Ratio-Acyclovir 400 mg Tablet1.63USD tablet
Zovirax 200 mg Tablet1.44USD tablet
Acyclovir 200 mg capsule1.01USD capsule
Acyclovir 200 mg Tablet0.81USD tablet
Apo-Acyclovir 200 mg Tablet0.81USD tablet
Mylan-Acyclovir 200 mg Tablet0.81USD tablet
Novo-Acyclovir 200 mg Tablet0.81USD tablet
Ratio-Acyclovir 200 mg Tablet0.81USD tablet
Acyclovir 200 mg/5ml Suspension0.3USD ml
Zovirax 40 mg/ml Suspension0.28USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2098108No2001-07-032012-01-29Canada
USRE39264No2006-09-052016-08-02Us
US6514980No2003-02-042019-01-24Us
US7223387No2007-05-292021-07-24Us
US8747896No2014-06-102027-06-03Us
US8791127No2014-07-292027-03-23Us
US8592434No2013-11-262030-06-16Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)255 °CPhysProp
water solubility2.5 mg/mL at 37°CFDA label
logP-1.56KRISTL,A ET AL. (1993)
Caco2 permeability-6.15ADME Research, USCD
pKa2.27 and 9.25 FDA label
Predicted Properties
Not Available
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Hypoxanthines
Alternative Parents
6-oxopurines / Pyrimidones / Aminopyrimidines and derivatives / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Primary alcohols / Organopnictogen compounds
show 2 more
Substituents
6-oxopurine / Hypoxanthine / Aminopyrimidine / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound / Vinylogous amide
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
oxopurine, 2-aminopurines (CHEBI:2453)

Targets

Kind
Protein
Organism
HHV-1
Pharmacological action
Yes
Actions
Potentiator
General Function
Thymidine kinase activity
Specific Function
In latent infection, may allow the virus to be reactivated and to grow in cells lacking a high concentration of phosphorylated nucleic acid precursors, such as nerve cells that do not replicate the...
Gene Name
TK
Uniprot ID
P03176
Uniprot Name
Thymidine kinase
Molecular Weight
40971.555 Da
References
  1. Bennett MS, Wien F, Champness JN, Batuwangala T, Rutherford T, Summers WC, Sun H, Wright G, Sanderson MR: Structure to 1.9 A resolution of a complex with herpes simplex virus type-1 thymidine kinase of a novel, non-substrate inhibitor: X-ray crystallographic comparison with binding of aciclovir. FEBS Lett. 1999 Jan 25;443(2):121-5. [PubMed:9989588]
Kind
Protein
Organism
HHV-1
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Replicates viral genomic DNA. The replication complex is composed of six viral proteins: the DNA polymerase, processivity factor, primase, primase-associated factor, helicase, and ssDNA-binding pro...
Gene Name
Not Available
Uniprot ID
P04293
Uniprot Name
DNA polymerase catalytic subunit
Molecular Weight
136419.66 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Sergerie Y, Boivin G: Hydroxyurea enhances the activity of acyclovir and cidofovir against herpes simplex virus type 1 resistant strains harboring mutations in the thymidine kinase and/or the DNA polymerase genes. Antiviral Res. 2008 Jan;77(1):77-80. Epub 2007 Sep 17. [PubMed:17913252]
  4. Suzuki M, Okuda T, Shiraki K: Synergistic antiviral activity of acyclovir and vidarabine against herpes simplex virus types 1 and 2 and varicella-zoster virus. Antiviral Res. 2006 Nov;72(2):157-61. Epub 2006 May 30. [PubMed:16797734]
  5. Liu S, Knafels JD, Chang JS, Waszak GA, Baldwin ET, Deibel MR Jr, Thomsen DR, Homa FL, Wells PA, Tory MC, Poorman RA, Gao H, Qiu X, Seddon AP: Crystal structure of the herpes simplex virus 1 DNA polymerase. J Biol Chem. 2006 Jun 30;281(26):18193-200. Epub 2006 Apr 24. [PubMed:16638752]
Kind
Protein
Organism
HHV-3
Pharmacological action
Yes
Actions
Inhibitor
General Function
Rna-dna hybrid ribonuclease activity
Specific Function
Replicates viral genomic DNA. The replication complex is composed of six viral proteins: the DNA polymerase, processivity factor, primase, primase-associated factor, helicase, and ssDNA-binding pro...
Gene Name
Not Available
Uniprot ID
P09252
Uniprot Name
DNA polymerase catalytic subunit
Molecular Weight
134046.615 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Sergerie Y, Boivin G: Hydroxyurea enhances the activity of acyclovir and cidofovir against herpes simplex virus type 1 resistant strains harboring mutations in the thymidine kinase and/or the DNA polymerase genes. Antiviral Res. 2008 Jan;77(1):77-80. Epub 2007 Sep 17. [PubMed:17913252]
  4. Suzuki M, Okuda T, Shiraki K: Synergistic antiviral activity of acyclovir and vidarabine against herpes simplex virus types 1 and 2 and varicella-zoster virus. Antiviral Res. 2006 Nov;72(2):157-61. Epub 2006 May 30. [PubMed:16797734]
  5. Liu S, Knafels JD, Chang JS, Waszak GA, Baldwin ET, Deibel MR Jr, Thomsen DR, Homa FL, Wells PA, Tory MC, Poorman RA, Gao H, Qiu X, Seddon AP: Crystal structure of the herpes simplex virus 1 DNA polymerase. J Biol Chem. 2006 Jun 30;281(26):18193-200. Epub 2006 Apr 24. [PubMed:16638752]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation 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-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion 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 ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
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. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. [PubMed:12358729]
  3. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [PubMed:11306713]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Bile acid:sodium symporter activity
Specific Function
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism.
Gene Name
SLC10A2
Uniprot ID
Q12908
Uniprot Name
Ileal sodium/bile acid cotransporter
Molecular Weight
37713.405 Da
References
  1. Tolle-Sander S, Lentz KA, Maeda DY, Coop A, Polli JE: Increased acyclovir oral bioavailability via a bile acid conjugate. Mol Pharm. 2004 Jan 12;1(1):40-8. [PubMed:15832499]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. Nies AT, Damme K, Schaeffeler E, Schwab M: Multidrug and toxin extrusion proteins as transporters of antimicrobial drugs. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1565-77. doi: 10.1517/17425255.2012.722996. Epub 2012 Sep 13. [PubMed:22970772]
  2. Xu Y, Liu X, Wang Y, Zhou N, Peng J, Gong L, Ren J, Luo C, Luo X, Jiang H, Chen K, Zheng M: Combinatorial Pharmacophore Modeling of Multidrug and Toxin Extrusion Transporter 1 Inhibitors: a Theoretical Perspective for Understanding Multiple Inhibitory Mechanisms. Sci Rep. 2015 Sep 2;5:13684. doi: 10.1038/srep13684. [PubMed:26330298]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Drug transmembrane transporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
Gene Name
SLC47A2
Uniprot ID
Q86VL8
Uniprot Name
Multidrug and toxin extrusion protein 2
Molecular Weight
65083.915 Da
References
  1. Nies AT, Damme K, Schaeffeler E, Schwab M: Multidrug and toxin extrusion proteins as transporters of antimicrobial drugs. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1565-77. doi: 10.1517/17425255.2012.722996. Epub 2012 Sep 13. [PubMed:22970772]
  2. Yonezawa A, Inui K: Importance of the multidrug and toxin extrusion MATE/SLC47A family to pharmacokinetics, pharmacodynamics/toxicodynamics and pharmacogenomics. Br J Pharmacol. 2011 Dec;164(7):1817-25. doi: 10.1111/j.1476-5381.2011.01394.x. [PubMed:21457222]

Drug created on June 13, 2005 07:24 / Updated on November 17, 2018 04:48