aciclovir indications/contra

Stem definitionDrug idCAS RN
antivirals bicyclic heterocycle compounds 85 59277-89-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • acyclovir
  • aciclovir
  • acyclovir sodium
A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.
  • Molecular weight: 225.21
  • Formula: C8H11N5O3
  • CLOGP: -2.42
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 3
  • TPSA: 114.76
  • ALOGS: -1.42
  • ROTB: 4

Drug dosage:

DoseUnitRoute
4 g O
4 g P

Approvals:

DateAgencyCompanyOrphan
March 29, 1982 FDA VALEANT BERMUDA

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Acute kidney injury 1151.06 35.00 397 3554 49286 3332622
Neurotoxicity 616.68 35.00 138 3813 3283 3378625
Encephalopathy 372.31 35.00 108 3843 7354 3374554
Confusional state 362.81 35.00 161 3790 37837 3344071
Blood creatinine increased 356.84 35.00 136 3815 21682 3360226
Pyrexia 332.85 35.00 194 3757 80921 3300987
Drug ineffective 283.06 35.00 200 3751 115890 3266018
Depressed level of consciousness 279.08 35.00 96 3855 11369 3370539
Altered state of consciousness 267.88 35.00 79 3872 5679 3376229
Drug resistance 257.00 35.00 73 3878 4590 3377318
Hepatotoxicity 253.41 35.00 75 3876 5456 3376452
Rash 244.83 35.00 152 3799 70669 3311239
Nephropathy toxic 233.44 35.00 62 3889 3027 3378881
Dilatation intrahepatic duct acquired 226.24 35.00 35 3916 81 3381827
Renal impairment 225.30 35.00 93 3858 18168 3363740
Hallucination, visual 215.09 35.00 63 3888 4413 3377495
Renal failure 210.35 35.00 106 3845 32834 3349074
Vomiting 191.79 35.00 143 3808 89388 3292520
Herpes zoster 190.06 35.00 72 3879 11200 3370708
Neutropenia 185.87 35.00 98 3853 33288 3348620
Toxic encephalopathy 172.54 35.00 41 3910 1263 3380645
Blood urea increased 171.01 35.00 60 3891 7500 3374408
Hallucination 167.99 35.00 69 3882 13271 3368637
Rash maculo-papular 165.70 35.00 55 3896 5812 3376096
Erythema 164.36 35.00 86 3865 28724 3353184
Delirium 164.08 35.00 62 3889 9566 3372342
Encephalitis 163.23 35.00 42 3909 1805 3380103
Multiple organ dysfunction syndrome 162.85 35.00 69 3882 14341 3367567
Alanine aminotransferase increased 159.35 35.00 79 3872 23561 3358347
Stevens-Johnson syndrome 157.97 35.00 55 3896 6717 3375191

Pharmacologic Action:

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SourceCodeDescription
ATC D06BB03 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
CHEMOTHERAPEUTICS FOR TOPICAL USE
Antivirals
ATC J05AB01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleosides and nucleotides excl. reverse transcriptase inhibitors
ATC S01AD03 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFECTIVES
Antivirals
ATC D06BB53 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
CHEMOTHERAPEUTICS FOR TOPICAL USE
Antivirals
CHEBI has role CHEBI:36044 antiviral drug
FDA MoA N0000020060 DNA Polymerase Inhibitors
FDA EPC N0000180187 Herpes Simplex Virus Nucleoside Analog DNA Polymerase Inhibitor
FDA EPC N0000180188 Herpes Zoster Virus Nucleoside Analog DNA Polymerase Inhibitor
FDA EPC N0000175468 Herpesvirus Nucleoside Analog DNA Polymerase Inhibitor
FDA Chemical/Ingredient N0000175459 Nucleoside Analog
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000998 Antiviral Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Herpes labialis indication 1475003
Herpes zoster indication 4740000 DOID:8536
Genital herpes simplex indication 33839006 DOID:8704
Varicella indication 38907003 DOID:8659
Herpes simplex indication 88594005 DOID:8566
Herpes simplex infection of skin indication 240475000
Recurrent herpes simplex labialis indication 402892009
Recurrent genital herpes simplex indication 402894005
Encephalitis due to Herpesvirus indication 428638009
Recurrent Mucocutaneous Herpes Simplex indication
Suppression of Recurrent Herpes Simplex Infection indication
Urinary tract obstruction contraindication 7163005 DOID:5200
Hypercholesterolemia contraindication 13644009
Myocardial infarction contraindication 22298006 DOID:5844
Dehydration contraindication 34095006
Hypertensive disorder contraindication 38341003 DOID:10763
Diabetes mellitus contraindication 73211009 DOID:9351
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Hyperglycemia contraindication 80394007 DOID:4195
Kidney disease contraindication 90708001 DOID:2527
Hemolytic uremic syndrome contraindication 111407006 DOID:12554
Impaired renal function disorder contraindication 197663003
Cerebrovascular accident contraindication 230690007 DOID:6713
Telangiectasia disorder contraindication 247479008 DOID:1272
Pregnancy, function contraindication 289908002
Osteopenia contraindication 312894000
Adrenal cortical hypofunction contraindication 386584007 DOID:10493
Cardiovascular event risk contraindication 395112001
Atrophoderma contraindication 399979006 DOID:2733
Peripheral vascular disease contraindication 400047006
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970
Smokes tobacco daily contraindication 449868002
Vertebral Metastases contraindication
Herpes zoster ophthalmicus off-label use 87513003
Herpes Zoster Hepatitis off-label use
Prevention of Herpes Zoster in Immunocompromised Patient off-label use
Herpes Simplex Hepatitis off-label use
Disseminated Herpes Simplex Neonatal Infection off-label use
Neonatal Herpes Meningoencephalitis off-label use
Granulomatosis Infantiseptica off-label use

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.97 acidic
pKa2 13.01 acidic
pKa3 3.83 Basic
pKa4 2.12 Basic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
5% XERESE VALEANT BERMUDA N022436 July 31, 2009 RX CREAM TOPICAL 6514980 July 24, 2018 COMBINATION PRODUCT FOR THE EARLY TREATMENT OF RECURRENT HERPES LABIALIS (COLD SORES) TO REDUCE THE LIKELIHOOD OF ULCERATIVE COLD SORES AND TO SHORTEN THE LESION HEALING TIME IN ADULTS AND CHILDREN (6 YEARS OF AGE AND OLDER)
5% XERESE VALEANT BERMUDA N022436 July 31, 2009 RX CREAM TOPICAL 6514980 July 24, 2018 NEW COMBINATION PRODUCT FOR THE EARLY TREATMENT OF RECURRENT HERPES LABIALIS (COLD SORES) TO REDUCE THE LIKELIHOOD OF ULCERATIVE COLD SORES AND TO SHORTEN THE LESION HEALING TIME IN ADULTS AND ADOLESCENTS (12 YEARS OF AGE AND OLDER)
5% XERESE VALEANT BERMUDA N022436 July 31, 2009 RX CREAM TOPICAL 7223387 Nov. 13, 2022 COMBINATION PRODUCT FOR THE EARLY TREATMENT OF RECURRENT HERPES LABIALIS (COLD SORES) TO REDUCE THE LIKELIHOOD OF ULCERATIVE COLD SORES AND TO SHORTEN THE LESION HEALING TIME IN ADULTS AND CHILDREN (6 YEARS OF AGE AND OLDER)
5% XERESE VALEANT BERMUDA N022436 July 31, 2009 RX CREAM TOPICAL 7223387 Nov. 13, 2022 NEW COMBINATION PRODUCT FOR THE EARLY TREATMENT OF RECURRENT HERPES LABIALIS (COLD SORES) TO REDUCE THE LIKELIHOOD OF ULCERATIVE COLD SORES AND TO SHORTEN THE LESION HEALING TIME IN ADULTS AND ADOLESCENTS (12 YEARS OF AGE AND OLDER)
50MG SITAVIG EPI HLTH N203791 April 12, 2013 RX TABLET BUCCAL 8791127 March 23, 2027 TREATMENT OF HERPES LABIALIS
50MG SITAVIG EPI HLTH N203791 April 12, 2013 RX TABLET BUCCAL 8747896 June 3, 2027 TREATMENT OF HERPES LABIALIS
50MG SITAVIG EPI HLTH N203791 April 12, 2013 RX TABLET BUCCAL 8592434 June 16, 2030 TREATMENT OF HERPES LABIALIS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA polymerase catalytic subunit Enzyme INHIBITOR WOMBAT-PK CHEMBL
Thymidine kinase Kinase WOMBAT-PK
Thymidine kinase Kinase WOMBAT-PK
Thymidine kinase Kinase WOMBAT-PK
DNA polymerase catalytic subunit Enzyme WOMBAT-PK
Purine nucleoside phosphorylase Unclassified Kd 4.90 CHEMBL

External reference:

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IDSource
4829 IUPHAR_LIGAND_ID
4018781 VUID
N0000147084 NUI
C0001367 UMLSCUI
D00222 KEGG_DRUG
DB00787 DRUGBANK_ID
2022 PUBCHEM_CID
4018781 VANDF
372729009 SNOMEDCT_US
N0000007269 NDFRT
N0000147084 NDFRT
003016 NDDF
981 MMSL
281 RXNORM
41193000 SNOMEDCT_US
4132 MMSL
d00001 MMSL
425884003 SNOMEDCT_US
927L42J563 UNII
69657-51-8 SECONDARY_CAS_RN
CHEMBL184 ChEMBL_ID
CHEBI:2453 CHEBI
CHEMBL1200380 ChEMBL_ID
4435 INN_ID
D000212 MESH_DESCRIPTOR_UI
AC2 PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0093-8940 CAPSULE 200 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0093-8943 TABLET 400 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0093-8947 TABLET 800 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0143-9657 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 500 mg INTRAVENOUS ANDA 13 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0143-9658 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 g INTRAVENOUS ANDA 13 sections
acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0168-0825 OINTMENT 50 mg TOPICAL ANDA 13 sections
Zovirax HUMAN PRESCRIPTION DRUG LABEL 1 0187-0993 OINTMENT 50 mg TOPICAL NDA 13 sections
Zovirax HUMAN PRESCRIPTION DRUG LABEL 1 0187-0994 CREAM 50 mg TOPICAL NDA 18 sections
Xerese HUMAN PRESCRIPTION DRUG LABEL 2 0187-5104 CREAM 50 mg TOPICAL NDA 18 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0378-8700 OINTMENT 50 mg TOPICAL ANDA 12 sections
acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0440-7033 TABLET 800 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0472-0082 SUSPENSION 200 mg ORAL ANDA 11 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0591-1159 OINTMENT 50 mg TOPICAL NDA authorized generic 13 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0713-0630 OINTMENT 50 mg TOPICAL ANDA 19 sections
ACYCLOVIR HUMAN PRESCRIPTION DRUG LABEL 1 0904-5789 CAPSULE 200 mg ORAL ANDA 12 sections
acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 0904-5790 TABLET 400 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 10544-039 TABLET 400 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 10544-089 CAPSULE 200 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 10544-101 CAPSULE 200 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 10544-102 TABLET 400 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 10544-103 TABLET 800 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 12634-520 TABLET 400 mg ORAL ANDA 12 sections
acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 12634-697 TABLET 800 mg ORAL ANDA 12 sections
ACYCLOVIR HUMAN PRESCRIPTION DRUG LABEL 1 16590-003 TABLET 800 mg ORAL ANDA 12 sections
ACYCLOVIR HUMAN PRESCRIPTION DRUG LABEL 1 16590-370 TABLET 400 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 16714-668 OINTMENT 50 mg TOPICAL ANDA 11 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 17856-0082 SUSPENSION 200 mg ORAL ANDA 11 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 21695-009 CAPSULE 200 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 21695-010 TABLET 400 mg ORAL ANDA 12 sections
Acyclovir HUMAN PRESCRIPTION DRUG LABEL 1 21695-011 TABLET 800 mg ORAL NDA authorized generic 12 sections