abacavir indications/contra

Stem definitionDrug idCAS RN
antivirals carbocyclic nucleosides 34 136470-78-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • 1592U89
  • abacavir
  • abacavir sulfate
  • ziagen
  • abacavir succinate
a carbocyclic nucleoside with potent selective anti-HIV activity; structure given in first source
  • Molecular weight: 286.34
  • Formula: C14H18N6O
  • CLOGP: 0.81
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 3
  • TPSA: 101.88
  • ALOGS: -2.37
  • ROTB: 4

Drug dosage:

DoseUnitRoute
0.60 g O

Approvals:

DateAgencyCompanyOrphan
July 8, 1999 EMA
Dec. 17, 1998 FDA VIIV HLTHCARE

FDA Adverse Event Reporting System

scroll-->
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
Exposure during pregnancy 1094.56 38.82 327 3371 27236 3354925
Virologic failure 695.54 38.82 129 3569 1225 3380936
Immune reconstitution inflammatory syndrome 667.91 38.82 136 3562 2177 3379984
Foetal exposure during pregnancy 642.28 38.82 191 3507 15360 3366801
Pyrexia 598.40 38.82 280 3418 80835 3301326
Lipodystrophy acquired 537.92 38.82 90 3608 433 3381728
Drug resistance 419.86 38.82 106 3592 4557 3377604
Abortion spontaneous 390.67 38.82 120 3578 10665 3371496
Rash 352.71 38.82 188 3510 70633 3311528
Nausea 263.94 38.82 195 3503 129450 3252711
Mitochondrial toxicity 257.87 38.82 42 3656 164 3381997
Treatment failure 254.72 38.82 77 3621 6447 3375714
Hypersensitivity 253.14 38.82 112 3586 27788 3354373
Premature baby 250.88 38.82 78 3620 7175 3374986
Vomiting 240.89 38.82 160 3538 89371 3292790
Live birth 227.75 38.82 48 3650 905 3381256
Viral mutation identified 224.29 38.82 44 3654 569 3381592
Diarrhoea 216.42 38.82 159 3539 104189 3277972
Malaise 216.01 38.82 133 3565 65044 3317117
Progressive external ophthalmoplegia 212.63 38.82 28 3670 4 3382157
Renal impairment 210.72 38.82 87 3611 18174 3363987
Anaemia 208.80 38.82 122 3576 54211 3327950
Hyperlipidaemia 208.31 38.82 61 3637 4567 3377594
Abdominal pain 177.96 38.82 104 3594 46121 3336040
Drug reaction with eosinophilia and systemic symptoms 164.70 38.82 58 3640 7837 3374324
Myocardial infarction 161.17 38.82 96 3602 44037 3338124
Abortion induced 158.81 38.82 47 3651 3644 3378517
Myalgia 158.26 38.82 85 3613 31990 3350171
Liver disorder 153.66 38.82 59 3639 10164 3371997
Maternal exposure during pregnancy 149.82 38.82 58 3640 10213 3371948

Pharmacologic Action:

scroll-->
SourceCodeDescription
ATC J05AF06 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleoside and nucleotide reverse transcriptase inhibitors
ATC J05AR02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HIV infections, combinations
ATC J05AR04 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HIV infections, combinations
ATC J05AR13 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HIV infections, combinations
FDA EPC N0000175462 Human Immunodeficiency Virus Nucleoside Analog Reverse Transcriptase Inhibitor
FDA Chemical/Ingredient N0000175459 Nucleoside Analog
FDA MoA N0000009947 Nucleoside Reverse Transcriptase Inhibitors
CHEBI has role CHEBI:88188 drug allergen
CHEBI has role CHEBI:36044 antiviral drug
MeSH PA D019380 Anti-HIV Agents
MeSH PA D000890 Anti-Infective Agents
MeSH PA D044966 Anti-Retroviral Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D019384 Nucleic Acid Synthesis Inhibitors
MeSH PA D018894 Reverse Transcriptase Inhibitors

Drug Use (View source of the data)

scroll-->
DiseaseRelationSNOMED_IDDOID
Human immunodeficiency virus infection indication 86406008 DOID:526
Toxic amblyopia contraindication 965003
Myositis contraindication 26889001 DOID:633
Hepatic failure contraindication 59927004
Pancreatitis contraindication 75694006 DOID:4989
Large liver contraindication 80515008
Kidney disease contraindication 90708001 DOID:2527
Lactic acidosis contraindication 91273001 DOID:3650
Disorder of muscle contraindication 129565002 DOID:423
Steatosis of liver contraindication 197321007 DOID:9452
Acute pancreatitis contraindication 197456007 DOID:2913
Chronic pancreatitis contraindication 235494005
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Hypertriglyceridemia contraindication 302870006
Neutropenic disorder contraindication 303011007 DOID:1227
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Obesity contraindication 414916001 DOID:9970
HLA-B 5701 Positive Status contraindication
Drug Resistance to Anti-retroviral Therapy contraindication

Acid dissociation constants calculated using MoKa v3.0.0

scroll-->
Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.09 acidic
pKa2 5.64 Basic
pKa3 0.88 Basic
pKa4 0.28 Basic

Orange Book patent data (new drug applications)

scroll-->
Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 300MG BASE ZIAGEN VIIV HLTHCARE N020977 Dec. 17, 1998 RX TABLET ORAL 6294540 May 14, 2018 METHOD OF TREATMENT OF A PATIENT INFECTED WITH HIV
EQ 20MG BASE/ML ZIAGEN VIIV HLTHCARE N020978 Dec. 17, 1998 RX SOLUTION ORAL 6294540 May 14, 2018 METHOD OF TREATMENT OF A PATIENT INFECTED WITH HIV
EQ 300MG BASE TRIZIVIR VIIV HLTHCARE N021205 Nov. 14, 2000 RX TABLET ORAL 6294540 May 14, 2018 METHOD OF TREATMENT OF A PATIENT INFECTED WITH HIV
EQ 600MG BASE EPZICOM VIIV HLTHCARE N021652 Aug. 2, 2004 RX TABLET ORAL 6294540 May 14, 2018 TREATMENT OF HIV INFECTION
EQ 600MG BASE TRIUMEQ VIIV HLTHCARE N205551 Aug. 22, 2014 RX TABLET ORAL 6294540 May 14, 2018 TREATMENT OF HUMAN IMMUNODEFICIENCY VIRUS (HIV) INFECTION.

Orange Book exclusivity data (new drug applications)

scroll-->
Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 20MG BASE/ML ABACAVIR SULFATE HETERO LABS LTD III A201107 Sept. 26, 2016 RX SOLUTION ORAL March 14, 2018 PATENT CHALLENGE
EQ 600MG BASE TRIUMEQ VIIV HLTHCARE N205551 Aug. 22, 2014 RX TABLET ORAL Aug. 12, 2018 NEW CHEMICAL ENTITY

Bioactivity Summary:

scroll-->
TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Reverse transcriptase/RNaseH Enzyme INHIBITOR EC50 5.28 CHEMBL CHEMBL
Gag-Pol polyprotein Polyprotein EC50 5.28 WOMBAT-PK

External reference:

scroll-->
IDSource
4029879 VUID
N0000180961 NUI
C0663655 UMLSCUI
D00891 KEGG_DRUG
40FH6D8CHK UNII
168146-84-7 SECONDARY_CAS_RN
DB01048 DRUGBANK_ID
441300 PUBCHEM_CID
d04376 MMSL
190521 RXNORM
116084008 SNOMEDCT_US
387005008 SNOMEDCT_US
4024130 VANDF
N0000022135 NDFRT
N0000004254 NDFRT
4029879 VANDF
N0000180961 NDFRT
007687 NDDF
CHEMBL1380 ChEMBL_ID
CHEBI:421707 CHEBI
CHEMBL1200619 ChEMBL_ID
C106538 MESH_SUPPLEMENTAL_RECORD_UI
CHEMBL2106686 ChEMBL_ID
7544 INN_ID
1KX PDB_CHEM_ID

Pharmaceutical products:

scroll-->
ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Abacavir and Lamivudine HUMAN PRESCRIPTION DRUG LABEL 2 0093-5382 TABLET, FILM COATED 600 mg ORAL ANDA 19 sections
Abacavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0378-4105 TABLET, FILM COATED 300 mg ORAL ANDA 19 sections
Abacavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0904-6523 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 31722-557 TABLET 300 mg ORAL ANDA 19 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 31722-562 SOLUTION 20 mg ORAL ANDA 19 sections
Abacavir and Lamivudine HUMAN PRESCRIPTION DRUG LABEL 2 42291-115 TABLET, FILM COATED 600 mg ORAL ANDA 19 sections
EPZICOM HUMAN PRESCRIPTION DRUG LABEL 2 49702-206 TABLET, FILM COATED 600 mg ORAL NDA 19 sections
TRIZIVIR HUMAN PRESCRIPTION DRUG LABEL 3 49702-217 TABLET, FILM COATED 300 mg ORAL NDA 19 sections
ZIAGEN HUMAN PRESCRIPTION DRUG LABEL 1 49702-221 TABLET, FILM COATED 300 mg ORAL NDA 19 sections
ZIAGEN HUMAN PRESCRIPTION DRUG LABEL 1 49702-222 SOLUTION 20 mg ORAL NDA 19 sections
Triumeq HUMAN PRESCRIPTION DRUG LABEL 3 49702-231 TABLET, FILM COATED 600 mg ORAL NDA 19 sections
EPZICOM HUMAN PRESCRIPTION DRUG LABEL 2 50090-0874 TABLET, FILM COATED 600 mg ORAL NDA 19 sections
Triumeq HUMAN PRESCRIPTION DRUG LABEL 3 50090-1606 TABLET, FILM COATED 600 mg ORAL NDA 19 sections
Abacavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 51079-204 TABLET, FILM COATED 300 mg ORAL ANDA 19 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 52125-956 TABLET 300 mg ORAL ANDA 19 sections
Abacavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 53808-0627 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
EPZICOM HUMAN PRESCRIPTION DRUG LABEL 2 53808-0767 TABLET, FILM COATED 600 mg ORAL NDA 16 sections
ZIAGEN HUMAN PRESCRIPTION DRUG LABEL 1 53808-0811 TABLET, FILM COATED 300 mg ORAL NDA 20 sections
TRIZIVIR HUMAN PRESCRIPTION DRUG LABEL 3 53808-0990 TABLET, FILM COATED 300 mg ORAL NDA 19 sections
ZIAGEN HUMAN PRESCRIPTION DRUG LABEL 1 53873-034 SOLUTION 20 mg ORAL Approved Drug Product Manufactured Under Contract 1 sections
EPZICOM HUMAN PRESCRIPTION DRUG LABEL 2 54868-5600 TABLET, FILM COATED 600 mg ORAL NDA 16 sections
ABACAVIR SULFATE, LAMIVUDINE AND ZIDOVUDINE HUMAN PRESCRIPTION DRUG LABEL 3 57297-286 TABLET 300 mg ORAL ANDA 19 sections
Abacavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 60505-3583 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
ZIAGEN HUMAN PRESCRIPTION DRUG LABEL 1 63379-041 TABLET, FILM COATED 300 mg ORAL Approved Drug Product Manufactured Under Contract 1 sections
Triumeq HUMAN PRESCRIPTION DRUG LABEL 3 63379-053 TABLET, FILM COATED 600 mg ORAL Approved Drug Product Manufactured Under Contract 1 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 64380-717 TABLET 300 1 ORAL ANDA 19 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 65862-073 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
Abacavir and Lamivudine HUMAN PRESCRIPTION DRUG LABEL 2 65862-900 TABLET, FILM COATED 600 mg ORAL ANDA 20 sections
Abacavir and Lamivudine HUMAN PRESCRIPTION DRUG LABEL 2 66993-482 TABLET, FILM COATED 600 mg ORAL NDA authorized generic 19 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 68084-021 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections