Identification
NameAciclovir
Accession NumberDB00787  (APRD00567, EXPT00406, DB05347)
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
Synonyms
Aciclovirum
Acycloguanosine
Acyclovir
External IDs NSC-645011
Product Ingredients
IngredientUNIICASInChI KeyDetails
Aciclovir Sodium927L42J563 69657-51-8RMLUKZWYIKEASN-UHFFFAOYSA-MDetails
Product Images
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcyclovirTablet400 mgOralSanis Health Inc2010-04-05Not applicableCanada
AcyclovirTablet200 mgOralSanis Health Inc2010-04-052014-08-01Canada
AcyclovirOintment50 mg/gTopicalActavis Pharma Company2014-04-11Not applicableUs
AcyclovirOintment50 mg/gTopicalOceanside Pharmaceuticals2012-10-032016-06-30Us
AcyclovirSuspension200 mg/5mLOralRenaissance Pharma, Inc.2014-09-03Not applicableUs
AcyclovirTablet800 mgOralSanis Health Inc2010-04-052014-08-01Canada
AcyclovirTablet800 mg/1OralRebel Distributors1998-10-30Not applicableUs
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 solution1 gIntravenousAbbott1998-02-112007-07-31Canada
Acyclovir Sodium for InjectionPowder, for solution500 mgIntravenousNovopharm Limited1998-02-04Not applicableCanada
Acyclovir Sodium InjectionSolution25 mgIntravenousIvax Pharmaceuticals IncorporatedNot applicableNot applicableCanada
Acyclovir Sodium InjectionSolution50 mgIntravenousSterimax IncNot applicableNot applicableCanada
Acyclovir Sodium InjectionSolution50 mgIntravenousFresenius Kabi1998-05-08Not applicableCanada
Acyclovir Sodium InjectionSolution50 mgIntravenousFresenius Kabi1998-05-08Not applicableCanada
Acyclovir Sodium InjectionSolution25 mgIntravenousHospira, Inc.1998-03-18Not applicableCanada
Acyclovir-200Tablet200 mgOralPro Doc Limitee1998-06-022010-07-13Canada
Acyclovir-400Tablet400 mgOralPro Doc Limitee1998-06-022010-07-13Canada
Acyclovir-800Tablet800 mgOralPro Doc Limitee1998-06-022010-07-13Canada
Alti-acyclovir - 400mgTablet400 mgOralAltimed Pharma Inc.1997-01-022001-09-05Canada
Alti-acyclovir - 800mgTablet800 mgOralAltimed Pharma Inc.1997-01-072005-05-27Canada
Alti-acyclovir - Tab 200mgTablet200 mgOralAltimed Pharma Inc.1997-01-022001-09-05Canada
Mylan-acyclovirTablet200 mgOralMylan Pharmaceuticals2000-09-14Not applicableCanada
Mylan-acyclovirTablet400 mgOralMylan Pharmaceuticals2000-06-30Not applicableCanada
Mylan-acyclovirTablet800 mgOralMylan Pharmaceuticals2000-06-30Not applicableCanada
Ntp-acyclovirTablet800 mgOralTevaNot applicableNot applicableCanada
Ntp-acyclovirTablet200 mgOralTevaNot applicableNot applicableCanada
Ntp-acyclovirTablet400 mgOralTevaNot applicableNot applicableCanada
Nu-acyclovir - Tab 200mgTablet200 mgOralNu Pharm Inc1996-12-312012-09-04Canada
Nu-acyclovir - Tab 400mgTablet400 mgOralNu Pharm Inc1996-12-312012-09-04Canada
Nu-acyclovir - Tab 800mgTablet800 mgOralNu Pharm Inc1996-12-312012-09-04Canada
Ratio-acyclovirTablet800 mgOralTeva1994-12-31Not applicableCanada
Ratio-acyclovirTablet400 mgOralTeva1994-12-31Not applicableCanada
Ratio-acyclovirTablet200 mgOralTeva1994-12-31Not applicableCanada
SitavigTablet, delayed release50 mg/1BuccalCipher Pharmaceuticals Inc.2014-03-20Not applicableUs
Teva-acyclovirTablet800 mgOralTeva2006-10-23Not applicableCanada
Teva-acyclovirTablet200 mgOralTeva2006-10-23Not applicableCanada
Teva-acyclovirTablet400 mgOralTeva2006-10-23Not applicableCanada
ZoviraxTablet800 mg/1OralGlaxosmithkline Inc1991-05-07Not applicableUs00173 0945 55 nlmimage10 ea18f547
ZoviraxCapsule200 mg/1OralRemedy Repack2014-11-102016-04-05Us00173 0991 55 nlmimage10 d7196bcb
ZoviraxCream50 mg/gTopicalValeant Pharmaceuticals North America2002-12-30Not applicableUs
ZoviraxTablet800 mg/1OralPrestium Pharma, Inc.2014-02-07Not applicableUs
ZoviraxOintment5 %TopicalValeant Canada Lp Valeant Canada S.E.C.1982-12-31Not applicableCanada
ZoviraxCream5 %TopicalValeant Canada Lp Valeant Canada S.E.C.1993-12-31Not applicableCanada
ZoviraxCapsule200 mg/1OralPrestium Pharma, Inc.2014-02-07Not applicableUs
ZoviraxOintment50 mg/gTopicalValeant Pharmaceuticals North America1982-03-29Not applicableUs
ZoviraxPowder, for solution1 gIntravenousGlaxosmithkline Inc1992-12-312002-10-08Canada
ZoviraxTablet400 mg/1OralPrestium Pharma, Inc.2014-02-07Not applicableUs
ZoviraxCream50 mg/gTopicalRebel Distributors2004-10-29Not applicableUs
ZoviraxPowder, for solution500 mgIntravenousGlaxosmithkline Inc1983-12-312002-10-08Canada
ZoviraxSuspension200 mgOralGlaxosmithkline Inc1991-12-31Not applicableCanada
ZoviraxSuspension200 mg/5mLOralPrestium Pharma, Inc.2014-02-07Not applicableUs
ZoviraxCapsule200 mg/1OralRemedy Repack2015-02-13Not applicableUs
Zovirax 400Tablet400 mgOralGlaxosmithkline Inc1991-12-312014-02-20Canada
Zovirax 800Tablet800 mgOralGlaxosmithkline Inc1991-12-312011-08-03Canada
Zovirax Cap 200mgCapsule200 mgOralGlaxo Wellcome1990-12-311997-08-13Canada
Zovirax Tab 200mgTablet200 mgOralGlaxosmithkline Inc1986-12-312016-01-11Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AcyclovirTablet800 mg/1OralRemedy Repack2011-08-012016-11-02Us
AcyclovirTablet400 mg/1Oralbryant ranch prepack1997-04-23Not applicableUs
AcyclovirTablet800 mg/1OralHeritage2013-08-08Not applicableUs23155 0228 01 nlmimage10 7039b81d
AcyclovirCapsule200 mg/1OralTeva1997-04-23Not applicableUs
AcyclovirCapsule200 mg/1OralBlenheim Pharmacal, Inc.2013-11-112017-04-14Us
AcyclovirCapsule200 mg/1OralAmerincan Health Packaging2014-01-29Not applicableUs60505 0042 06 nlmimage10 d2386903
AcyclovirTablet400 mg/1OralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
AcyclovirTablet400 mg/1OralPd Rx Pharmaceuticals, Inc.2009-10-22Not applicableUs
AcyclovirTablet800 mg/1OralPd Rx Pharmaceuticals, Inc.2011-12-07Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2011-07-132017-01-06Us63304 0504 01 nlmimage10 9f12cf96
AcyclovirCapsule200 mg/1OralRemedy Repack2017-06-27Not applicableUs
AcyclovirTablet400 mg/1OralDirectrx2015-01-01Not applicableUs
AcyclovirTablet400 mg/1OralCadila Pharnmaceuticals2012-03-072017-05-25Us
AcyclovirTablet800 mg/1OralNorthwind Pharmaceuticals2014-05-14Not applicableUs
AcyclovirTablet400 mg/1OralAidarex Pharmaceuticals LLC1997-04-23Not applicableUs
AcyclovirCapsule200 mg/1OralBlenheim Pharmacal, Inc.2012-10-24Not applicableUs
AcyclovirCapsule200 mg/1OralRebel Distributors1998-10-30Not applicableUs
AcyclovirTablet400 mg/1OralMajor2007-02-09Not applicableUs
AcyclovirCapsule200 mg/1OralRemedy Repack2010-09-242017-04-14Us
AcyclovirTablet800 mg/1OralCarlsbad Technology, Inc.2009-10-22Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2016-08-302017-03-08Us
AcyclovirInjection, powder, lyophilized, for solution50 mg/mLIntravenousAPP Pharmaceuticals, Inc.2000-10-17Not applicableUs
AcyclovirTablet400 mg/1OralPd Rx Pharmaceuticals, Inc.1997-04-23Not applicableUs00093 8943 01 nlmimage10 dd35ee9f
AcyclovirTablet400 mg/1OralRed Pharm Drug, Inc.2009-04-01Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2016-12-14Not applicableUs
AcyclovirTablet800 mg/1OralUnit Dose Services2009-10-22Not applicableUs
AcyclovirOintment50 mg/gTopicalMylan Institutional2013-11-27Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2009-07-012017-01-14Us
AcyclovirTablet800 mg/1OralPreferreed Pharmaceuticals Inc.2016-02-01Not applicableUs
AcyclovirTablet800 mg/1OralUnit Dose Services2014-09-10Not applicableUs
AcyclovirCapsule200 mg/1OralAv Kare, Inc.2013-07-08Not applicableUs
AcyclovirTablet800 mg/1OralCadila Pharnmaceuticals2017-03-23Not applicableUs
AcyclovirTablet400 mg/1OralNivagen Pharmaceuticals, Inc.2016-10-15Not applicableUs
AcyclovirTablet400 mg/1OralA S Medication Solutions2009-10-222017-06-20Us
AcyclovirCapsule200 mg/1OralCardinal Health2007-04-19Not applicableUs
AcyclovirTablet800 mg/1OralA S Medication Solutions2009-10-222017-06-20Us
AcyclovirTablet800 mg/1OralDirectrx2015-01-01Not applicableUs31722 0778 01 nlmimage10 474423e1
AcyclovirCapsule200 mg/1OralZydus Pharmaceuticals Usa, Inc.2016-05-03Not applicableUs
AcyclovirTablet400 mg/1OralMc Kesson Packaging Services A Buisness Unit Of Mc Kesson Corporation2009-10-22Not applicableUs
AcyclovirTablet800 mg/1OralA S Medication Solutions2009-10-222017-06-20Us
AcyclovirSuspension200 mg/5mLOralPreferreed Pharmaceuticals Inc.2011-03-18Not applicableUs
AcyclovirTablet400 mg/1OralNorthwind Pharmaceuticals2015-03-03Not applicableUs
AcyclovirCapsule200 mg/1OralMajor2007-04-19Not applicableUs
AcyclovirCapsule200 mg/1OralAvera Mc Kennan Hospital2016-10-14Not applicableUs
AcyclovirTablet400 mg/1OralApotheca, Inc.1997-04-23Not applicableUs
AcyclovirTablet400 mg/1OralRed Pharm Drug, Inc.1997-04-23Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2016-08-18Not applicableUs
AcyclovirCapsule200 mg/1OralPd Rx Pharmaceuticals, Inc.2010-03-232016-04-05Us
AcyclovirTablet800 mg/1OralNucare Pharmaceuticals, Inc.2013-11-29Not applicableUs
AcyclovirTablet400 mg/1OralDirectrx2014-01-01Not applicableUs
AcyclovirTablet800 mg/1OralClinical Solutions Wholsesale1997-04-302017-06-20Us
AcyclovirTablet400 mg/1OralRemedy Repack2013-02-212017-02-18Us
AcyclovirTablet400 mg/1OralUnit Dose Services2007-06-09Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2015-09-172016-10-13Us60505 5306 01 nlmimage10 7c38be25
AcyclovirTablet800 mg/1OralMylan Pharmaceuticals2010-06-152016-10-13Us
AcyclovirTablet400 mg/1OralBlenheim Pharmacal, Inc.2015-06-022017-05-13Us
AcyclovirTablet800 mg/1OralPreferreed Pharmaceuticals Inc.2009-10-22Not applicableUs
AcyclovirCapsule200 mg/1OralPhysicians Total Care, Inc.1998-07-27Not applicableUs
AcyclovirTablet400 mg/1OralCadila Pharnmaceuticals2017-03-23Not applicableUs
AcyclovirTablet400 mg/1OralGolden State Medical Supply1999-03-05Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2011-07-282016-10-13Us
AcyclovirTablet800 mg/1OralA S Medication Solutions2006-03-132017-06-20Us
AcyclovirTablet800 mg/1OralProficient Rx LP2006-03-13Not applicableUs
AcyclovirTablet400 mg/1OralCadila Pharnmaceuticals2014-09-10Not applicableUs
AcyclovirTablet800 mg/1OralState of Florida DOH Central Pharmacy2013-01-01Not applicableUs
AcyclovirInjection, powder, lyophilized, for solution1 g/1IntravenousWest Ward Pharmaceutical2016-02-29Not applicableUs
AcyclovirOintment50 mg/gTopicalAv Kare, Inc.2015-02-05Not applicableUs
AcyclovirTablet800 mg/1OralBlenheim Pharmacal, Inc.2010-07-20Not applicableUs
AcyclovirTablet400 mg/1OralHeritage2013-08-08Not applicableUs23155 0227 01 nlmimage10 f4397a0b
AcyclovirCapsule200 mg/1OralCardinal Health2013-05-02Not applicableUs
AcyclovirCapsule200 mg/1OralPd Rx Pharmaceuticals, Inc.1997-04-23Not applicableUs00093 8940 01 nlmimage10 fb267df3
AcyclovirTablet800 mg/1OralAv Pak2014-07-18Not applicableUs
AcyclovirTablet800 mg/1OralAidarex Pharmaceuticals LLC1997-04-30Not applicableUs
AcyclovirTablet400 mg/1OralMajor2010-06-14Not applicableUs
AcyclovirTablet400 mg/1OralStat Rx USA1998-09-30Not applicableUs
AcyclovirSuspension200 mg/5mLOralPhysicians Total Care, Inc.2006-10-03Not applicableUs
AcyclovirCapsule200 mg/1OralCarlsbad Technology, Inc.2009-10-22Not applicableUs
AcyclovirTablet800 mg/1OralRanbaxy Inc.1999-02-08Not applicableUs
AcyclovirCapsule200 mg/1OralDAVA Pharmaceuticals, Inc.1997-04-222016-10-13Us
AcyclovirTablet400 mg/1OralAmerincan Health Packaging2014-01-29Not applicableUs
AcyclovirTablet800 mg/1OralDAVA Pharmaceuticals, Inc.1997-11-192017-03-31Us
AcyclovirTablet800 mg/1OralA S Medication Solutions2013-11-292017-06-20Us
AcyclovirCapsule200 mg/1OralAvera Mc Kennan Hospital2015-05-20Not applicableUs
AcyclovirCapsule200 mg/1OralRed Pharm Drug, Inc.1997-04-23Not applicableUs
AcyclovirTablet800 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2006-03-13Not applicableUs
AcyclovirTablet800 mg/1OralRemedy Repack2015-07-27Not applicableUs
AcyclovirTablet800 mg/1OralRemedy Repack2011-05-092016-10-13Us60505 5307 01 nlmimage10 4d26a6d5
AcyclovirTablet400 mg/1OralBlenheim Pharmacal, Inc.2010-11-102017-08-31Us
AcyclovirTablet800 mg/1OralA S Medication Solutions2013-11-292017-06-20Us
AcyclovirTablet400 mg/1OralAv Kare, Inc.1999-03-05Not applicableUs
AcyclovirTablet400 mg/1OralApotex Corporation2007-06-09Not applicableUs
AcyclovirTablet800 mg/1OralNivagen Pharmaceuticals, Inc.2016-10-15Not applicableUs
AcyclovirTablet400 mg/1OralA S Medication Solutions2009-10-222017-06-20Us
AcyclovirTablet800 mg/1OralRemedy Repack2011-09-202016-11-11Us00093 8947 01 nlmimage10 f9357cfb
AcyclovirTablet400 mg/1OralAidarex Pharmaceuticals LLC2014-09-10Not applicableUs
AcyclovirCapsule200 mg/1OralHeritage2014-06-02Not applicableUs
AcyclovirTablet400 mg/1OralTeva1997-04-23Not applicableUs
AcyclovirTablet400 mg/1OralBlenheim Pharmacal, Inc.2013-09-302017-03-17Us
AcyclovirSuspension200 mg/5mLOralPreferreed Pharmaceuticals Inc.2012-07-27Not applicableUs
AcyclovirTablet400 mg/1OralState of Florida DOH Central Pharmacy2013-12-01Not applicableUs
AcyclovirTablet800 mg/1OralRed Pharm Drug, Inc.2013-11-29Not applicableUs
AcyclovirCapsule200 mg/1OralGolden State Medical Supply2012-09-20Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2011-07-142016-10-28Us
AcyclovirCapsule200 mg/1OralApotex Corporation2006-03-20Not applicableUs
AcyclovirCapsule200 mg/1OralProficient Rx LP1997-04-23Not applicableUs
AcyclovirTablet800 mg/1OralCadila Pharnmaceuticals2012-03-082017-05-25Us
AcyclovirTablet400 mg/1OralNorthwind Pharmaceuticals2014-10-22Not applicableUs
AcyclovirTablet400 mg/1OralRebel Distributors2009-10-22Not applicableUs
AcyclovirCapsule200 mg/1OralBlenheim Pharmacal, Inc.2011-02-15Not applicableUs
AcyclovirTablet400 mg/1OralRebel Distributors1998-10-30Not applicableUs
AcyclovirTablet800 mg/1OralPd Rx Pharmaceuticals, Inc.2013-11-29Not applicableUs
AcyclovirCapsule200 mg/1OralCardinal Health2011-12-07Not applicableUs
AcyclovirCapsule200 mg/1OralPd Rx Pharmaceuticals, Inc.2015-02-01Not applicableUs
AcyclovirCapsule200 mg/1OralRemedy Repack2015-02-162017-03-09Us
AcyclovirTablet800 mg/1OralProficient Rx LP2014-09-10Not applicableUs
AcyclovirCapsule200 mg/1Oralbryant ranch prepack1997-04-23Not applicableUs
AcyclovirCapsule200 mg/1OralA S Medication Solutions2009-10-222017-06-20Us
AcyclovirTablet400 mg/1OralZydus Pharmaceuticals Usa, Inc.2014-09-10Not applicableUs
AcyclovirTablet800 mg/1OralNucare Pharmaceuticals, Inc.2014-09-10Not applicableUs
AcyclovirTablet800 mg/1OralRemedy Repack2016-04-04Not applicableUs
AcyclovirTablet400 mg/1OralGolden State Medical Supply2012-09-21Not applicableUs
AcyclovirOintment50 mg/gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.2016-05-11Not applicableUs
AcyclovirTablet400 mg/1OralPreferreed Pharmaceuticals Inc.2016-03-14Not applicableUs
AcyclovirTablet400 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2012-09-21Not applicableUs
AcyclovirTablet400 mg/1OralCardinal Health1999-03-05Not applicableUs
AcyclovirTablet400 mg/1OralA S Medication Solutions2013-11-292017-06-20Us
AcyclovirTablet800 mg/1OralPreferreed Pharmaceuticals Inc.2016-08-25Not applicableUs
AcyclovirTablet400 mg/1OralUnit Dose Services2013-11-29Not applicableUs
AcyclovirCapsule200 mg/1OralRemedy Repack2017-01-17Not applicableUs
AcyclovirCapsule200 mg/1OralRemedy Repack2017-03-14Not applicableUs
AcyclovirTablet400 mg/1OralRed Pharm Drug, Inc.2013-11-29Not applicableUs
AcyclovirTablet800 mg/1OralAphena Pharma Solutions Tennessee, Inc.2012-09-21Not applicableUs
AcyclovirTablet400 mg/1OralRemedy Repack2017-04-17Not applicableUs
AcyclovirCapsule200 mg/1OralAv Pak2013-05-02Not applicableUs
AcyclovirTablet400 mg/1OralCamber Pharmaceuticals2013-11-29Not applicableUs31722 0777 01 nlmimage10 1e440f10
AcyclovirOintment50 mg/gTopicalMylan Pharmaceuticals2013-04-03Not applicableUs
AcyclovirTablet800 mg/1OralApotheca, Inc.2006-03-13Not applicableUs
AcyclovirTablet400 mg/1OralPhysicians Total Care, Inc.1998-11-17Not applicableUs
AcyclovirTablet800 mg/1OralGolden State Medical Supply1999-03-05Not applicableUs
AcyclovirTablet800 mg/1OralProficient Rx LP2013-11-29Not applicableUs
AcyclovirTablet800 mg/1OralCadila Pharnmaceuticals2014-09-10Not applicableUs
AcyclovirCapsule200 mg/1OralRemedy Repack2011-05-092016-10-13Us
AcyclovirTablet800 mg/1Oralbryant ranch prepack1999-03-05Not applicableUs
AcyclovirSuspension200 mg/5mLOralHi Tech Pharmacal Co., Inc.2005-06-07Not applicableUs
AcyclovirCapsule200 mg/1OralAidarex Pharmaceuticals LLC1997-04-23Not applicableUs
AcyclovirTablet400 mg/1OralBlenheim Pharmacal, Inc.2011-03-02Not applicableUs
AcyclovirSuspension200 mg/5mLOralAtlantic Biologicals Corps.2005-06-07Not applicableUs
AcyclovirTablet400 mg/1OralCarlsbad Technology, Inc.2009-10-22Not applicableUs
AcyclovirCapsule200 mg/1OralRanbaxy Inc.1999-02-08Not applicableUs
AcyclovirTablet400 mg/1OralDAVA Pharmaceuticals, Inc.1997-11-192016-10-13Us
AcyclovirTablet800 mg/1OralAmerincan Health Packaging2014-01-29Not applicableUs
AcyclovirCapsule200 mg/1OralQuinn Pharmaceuticals, Llc2015-02-01Not applicableUs
AcyclovirTablet400 mg/1OralA S Medication Solutions1997-04-232017-06-20Us
AcyclovirTablet400 mg/1OralProficient Rx LP2013-11-29Not applicableUs
AcyclovirTablet800 mg/1OralRemedy Repack2016-11-28Not applicableUs
AcyclovirTablet800 mg/1Oralbryant ranch prepack1997-04-30Not applicableUs
AcyclovirCapsule200 mg/1OralPreferreed Pharmaceuticals Inc.2013-03-26Not applicableUs
AcyclovirTablet400 mg/1OralBlenheim Pharmacal, Inc.2015-09-022017-10-31Us
AcyclovirTablet800 mg/1OralZydus Pharmaceuticals Usa, Inc.2014-09-10Not applicableUs
AcyclovirOintment50 mg/gTopicalTaro Pharmaceuticals U.S.A., Inc.2016-12-21Not applicableUs
AcyclovirTablet400 mg/1OralMylan Pharmaceuticals2010-06-15Not applicableUs
AcyclovirTablet800 mg/1OralGolden State Medical Supply2006-03-13Not applicableUs
AcyclovirTablet800 mg/1OralLiberty Pharmaceuticals, Inc.2006-03-13Not applicableUs
AcyclovirTablet800 mg/1OralRed Pharm Drug, Inc.2006-03-13Not applicableUs
AcyclovirTablet400 mg/1OralA S Medication Solutions2013-11-292017-06-20Us
AcyclovirTablet800 mg/1OralAv Kare, Inc.1999-03-05Not applicableUs
AcyclovirTablet800 mg/1OralApotex Corporation2006-03-13Not applicableUs
AcyclovirCapsule200 mg/1OralNivagen Pharmaceuticals, Inc.2016-10-15Not applicableUs
AcyclovirTablet400 mg/1OralClinical Solutions Wholsesale1997-04-23Not applicableUs
AcyclovirCapsule200 mg/1OralRemedy Repack2011-12-062016-12-13Us
AcyclovirTablet400 mg/1OralNucare Pharmaceuticals, Inc.2013-11-29Not applicableUs
AcyclovirCapsule400 mg/1OralRemedy Repack2013-02-272016-12-14Us
AcyclovirTablet800 mg/1OralTeva1997-04-30Not applicableUs
AcyclovirTablet800 mg/1OralBlenheim Pharmacal, Inc.2013-12-102017-03-17Us
AcyclovirTablet400 mg/1OralPreferreed Pharmaceuticals Inc.2009-10-22Not applicableUs
AcyclovirTablet800 mg/1OralState of Florida DOH Central Pharmacy2014-01-01Not applicableUs
AcyclovirCapsule200 mg/1OralCadila Pharnmaceuticals2015-12-29Not applicableUs
AcyclovirCapsule200 mg/1OralGolden State Medical Supply1997-04-22Not applicableUs
AcyclovirCapsule200 mg/1OralRemedy Repack2011-07-142016-10-28Us
AcyclovirCapsule200 mg/1OralA S Medication Solutions2009-10-222017-06-20Us
AcyclovirCapsule200 mg/1OralProficient Rx LP2009-10-22Not applicableUs61442 0111 01 nlmimage10 ae03d72e
AcyclovirCapsule200 mg/1OralCadila Pharnmaceuticals2014-03-112017-05-25Us
AcyclovirCapsule200 mg/1OralH.J. Harkins Company2011-05-27Not applicableUs
AcyclovirInjection, powder, lyophilized, for solution500 mg/1IntravenousWest Ward Pharmaceutical2016-02-29Not applicableUs
AcyclovirTablet800 mg/1OralRebel Distributors2009-10-22Not applicableUs
AcyclovirTablet400 mg/1OralBlenheim Pharmacal, Inc.2010-03-11Not applicableUs
AcyclovirCapsule200 mg/1OralHeritage2010-06-14Not applicableUs
AcyclovirTablet800 mg/1OralRemedy Repack2011-01-27Not applicableUs
AcyclovirTablet200 mg/1OralCardinal Health1997-04-23Not applicableUs
AcyclovirCapsule200 mg/1OralA S Medication Solutions2006-03-202017-06-20Us
AcyclovirTablet400 mg/1OralRemedy Repack2015-12-102017-04-14Us
AcyclovirCapsule200 mg/1OralCadila Pharnmaceuticals2016-05-03Not applicableUs
AcyclovirTablet400 mg/1Oralbryant ranch prepack2011-05-27Not applicableUs
AcyclovirTablet400 mg/1OralA S Medication Solutions2009-10-222017-06-20Us
AcyclovirCapsule200 mg/1OralGolden State Medical Supply1999-01-26Not applicableUs
AcyclovirTablet400 mg/1OralRanbaxy Inc.1999-02-08Not applicableUs
AcyclovirTablet400 mg/1OralMed Vantx, Inc.1997-04-23Not applicableUs
AcyclovirInjection, solution50 mg/mLIntravenousFresenius Kabi2000-10-17Not applicableUs
AcyclovirOintment50 mg/gTopicalAmneal Pharmaceuticals of New York Llc2014-01-03Not applicableUs
AcyclovirTablet400 mg/1OralA S Medication Solutions2013-11-292017-06-20Us
AcyclovirTablet400 mg/1OralPreferreed Pharmaceuticals Inc.2016-08-31Not applicableUs
AcyclovirTablet800 mg/1OralDirectrx2014-01-01Not applicableUs
AcyclovirCapsule200 mg/1OralPreferreed Pharmaceuticals Inc.2017-01-23Not applicableUs
AcyclovirTablet400 mg/1OralAvera Mc Kennan Hospital2015-03-17Not applicableUs
AcyclovirTablet800 mg/1OralRed Pharm Drug, Inc.1997-04-30Not applicableUs
AcyclovirTablet400 mg/1OralMesource Pharmaceuticals2014-09-10Not applicableUs
AcyclovirTablet800 mg/1OralBlenheim Pharmacal, Inc.2010-11-082017-08-31Us
AcyclovirTablet400 mg/1OralAv Pak1999-03-05Not applicableUs61442 0112 01 nlmimage10 bf03dffe
AcyclovirTablet800 mg/1OralCamber Pharmaceuticals2013-11-29Not applicableUs
AcyclovirSuspension200 mg/5mLOralActavis Mid Atlantic LLC,2002-09-03Not applicableUs
AcyclovirTablet800 mg/1OralStat Rx USA1998-09-30Not applicableUs
AcyclovirTablet800 mg/1OralPhysicians Total Care, Inc.1998-11-17Not applicableUs
Acyclovir SodiumInjection, solution1000 mg/20mLIntravenousAuro Medics Pharma Llc2013-10-11Not applicableUs
Acyclovir SodiumInjection, solution500 mg/10mLIntravenousAuro Medics Pharma Llc2013-10-11Not applicableUs
Apo-acyclovirTablet800 mgOralApotex Corporation1997-08-22Not applicableCanada
Apo-acyclovir - Tab 200mgTablet200 mgOralApotex Corporation1997-08-22Not applicableCanada
Apo-acyclovir - Tab 400mgTablet400 mgOralApotex Corporation1997-08-22Not applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ZovirNot Available
Brand mixtures
NameLabellerIngredients
XereseValeant Pharmaceuticals North America
Categories
UNIIX4HES1O11F
CAS number59277-89-3
WeightAverage: 225.2046
Monoisotopic: 225.086189243
Chemical FormulaC8H11N5O3
InChI KeyMKUXAQIIEYXACX-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one
SMILES
NC1=NC(=O)C2=C(N1)N(COCCO)C=N2
Pharmacology
Indication

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

Structured Indications
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.

TargetKindPharmacological actionActionsOrganismUniProt ID
DNA polymerase catalytic subunitProteinyes
inhibitor
HHV-1P04293 details
DNA polymerase catalytic subunitProteinyes
inhibitor
HHV-3P09252 details
Thymidine kinaseProteinyes
potentiator
HHV-1P03176 details
Related Articles
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 distributionNot 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.

SubstrateEnzymesProduct
Aciclovir
Not Available
9-carboxymethoxymethylguanineDetails
Route of elimination

Primarily excreted unchanged by the kidneys via active tubular secretion.

Half life

2.5-3.3 hours

ClearanceNot 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
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
TeriflunomideThe serum concentration of Aciclovir can be increased when it is combined with Teriflunomide.Approved
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Aciclovir.Approved
Food Interactions
  • Increase liquid intake.
  • Take without regard to meals.
References
Synthesis ReferenceUS4294831
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
ATC CodesS01AD03 — AciclovirD06BB03 — AciclovirJ05AB01 — AciclovirD06BB53 — Aciclovir, combinations
AHFS Codes
  • 08:18.32
  • 84:04.06
PDB Entries
FDA labelNot Available
MSDSDownload (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 / Sjogren's Syndrome1
1CompletedTreatmentHerpes Simplex Virus / Neonatal Sepsis1
1CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentProgressive Multiple Sclerosis1
1RecruitingTreatmentProgressive Multiple Sclerosis1
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 RecruitingTreatmentMetastatic Castration Resistant Prostate Cancer1
2Active Not RecruitingTreatmentNon-Small-Cell Lung Carcinoma (NSCLC)1
2CompletedPreventionCritical Illness1
2CompletedPreventionHerpes simplex of the genitals / Ulcers1
2CompletedTreatmentChickenpox / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHerpes simplex of the genitals / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHerpesvirus 2, Human / Human Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
2RecruitingSupportive CareStem Cell Transplant Complications1
2RecruitingTreatmentHerpes Labialis1
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
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 CareCancers1
3CompletedSupportive CareHerpes Simplex1
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
3RecruitingTreatmentHerpes Zoster1
3Unknown StatusTreatmentHerpes Simplex1
3Unknown StatusTreatmentKeratitis, Herpetic / Ocular Herpes Simplex1
4Active Not RecruitingNot AvailableGenital Herpes1
4CompletedPreventionHerpes / HIV Disease1
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 AvailableMeningitis, Aseptic1
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
Dosage forms
FormRouteStrength
CapsuleOral200 mg/1
CapsuleOral400 mg/1
Injection, powder, lyophilized, for solutionIntravenous1 g/1
Injection, powder, lyophilized, for solutionIntravenous50 mg/mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/1
Injection, solutionIntravenous50 mg/mL
OintmentTopical50 mg/g
SuspensionOral200 mg/5mL
TabletOral200 mg/1
TabletOral400 mg/1
TabletOral800 mg/1
Injection, solutionIntravenous1000 mg/20mL
Injection, solutionIntravenous500 mg/10mL
Powder, for solutionIntravenous500 mg
SolutionIntravenous25 mg
SolutionIntravenous50 mg
TabletOral200 mg
TabletOral400 mg
TabletOral800 mg
Tablet, delayed releaseBuccal50 mg/1
CreamTopical
CreamTopical5 %
CreamTopical50 mg/g
OintmentTopical5 %
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)
CA2098108 No2001-07-032012-01-29Canada
US6514980 No1999-01-242019-01-24Us
US7223387 No2001-07-242021-07-24Us
US8592434 No2010-06-162030-06-16Us
US8747896 No2007-06-032027-06-03Us
US8791127 No2007-03-232027-03-23Us
USRE39264 No1996-08-022016-08-02Us
Properties
StateSolid
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
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0090000000-59599385810ae2952ce5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0290000000-9410504409e66bcd08f9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0uyi-1900000000-0930eb38cecf2a197001View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05nf-4900000000-10d8c1e33c5d46d6ff80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-05mo-9600000000-e25ed55283d7d66d80c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-004i-0390000000-079dc309c9ffbbde3375View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-201a17a51960fdc3bcefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-6c63ec4268a52381191cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f79-1900000000-20fdfa17569c6b2f479fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-2900000000-4f7a822e6652ec471aeeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-69b23ed6f334f4571eccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udr-2910100000-2b1624536b0084ca299cView in MoNA
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
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 Parents6-oxopurines / Pyrimidones / Aminopyrimidines and derivatives / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Primary alcohols / Organopnictogen compounds
Substituents6-oxopurine / Hypoxanthine / Aminopyrimidine / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound / Vinylogous amide
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsoxopurine, 2-aminopurines (CHEBI:2453 )

Targets

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 protein. Additionally, the polymerase contains an intrinsic ribonuclease H (RNase H) activity that specifically degrades RNA/DNA heteroduplexes or duplex DNA substrates in the 5' to 3' direction. Therefo...
Gene Name:
Not Available
Uniprot ID:
P04293
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 protein. Additionally, the polymerase contains an intrinsic ribonuclease H (RNase H) activity that specifically degrades RNA/DNA heteroduplexes or duplex DNA substrates in the 5' to 3' direction. Therefo...
Gene Name:
Not Available
Uniprot ID:
P09252
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 ]
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 their genome.
Gene Name:
TK
Uniprot ID:
P03176
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 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da

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-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
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
substrateinhibitor
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
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
substrateinhibitor
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, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
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
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 sulfate, acyclovir, ganciclovir and also the zwitterionic cephalosporin, cephalexin and cephradin. Seems to also play a role in the uptake of oxaliplatin (a new platinum anticancer agent). Able to transport...
Gene Name:
SLC47A1
Uniprot ID:
Q96FL8
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 ]
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, acyclovir, and ganciclovir. Responsible for the secretion of cationic drugs across the brush border membranes.
Gene Name:
SLC47A2
Uniprot ID:
Q86VL8
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 ]
Drug created on June 13, 2005 07:24 / Updated on July 20, 2017 12:23