abacavir Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.60 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 29.93 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 77 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1.20 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 83 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.84 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 13 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.50 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1 hours Lombardo F, Berellini G, Obach RS

Approvals:

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

FDA Adverse Event Reporting System (Female)

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 927.94 52.90 227 844 24992 2332022
Abortion spontaneous 417.69 52.90 107 964 13338 2343676
Foetal exposure during pregnancy 302.46 52.90 69 1002 5183 2351831
Live birth 285.62 52.90 52 1019 1239 2355775
Viral mutation identified 242.57 52.90 36 1035 219 2356795
Drug resistance 220.04 52.90 47 1024 2577 2354437
Immune reconstitution inflammatory syndrome 204.21 52.90 39 1032 1205 2355809
Maternal exposure during pregnancy 192.56 52.90 60 1011 14803 2342211
Premature baby 188.87 52.90 43 1028 3161 2353853
Pregnancy 163.68 52.90 46 1025 7903 2349111
Pyrexia 163.66 52.90 75 996 53633 2303381
Abortion induced 159.50 52.90 38 1033 3398 2353616
Foetal growth restriction 157.80 52.90 31 1040 1109 2355905
Premature labour 144.34 52.90 32 1039 2074 2354940
Lipodystrophy acquired 133.76 52.90 22 1049 277 2356737
Stillbirth 133.11 52.90 28 1043 1413 2355601
Pathogen resistance 129.35 52.90 25 1046 818 2356196
Rash 129.22 52.90 66 1005 59492 2297522
Caesarean section 113.64 52.90 30 1041 4051 2352963
Hypersensitivity 111.11 52.90 45 1026 23548 2333466
Anaemia 109.93 52.90 50 1021 34742 2322272
Virologic failure 106.60 52.90 18 1053 268 2356746
Supernumerary nipple 99.34 52.90 12 1059 6 2357008
Premature delivery 96.15 52.90 25 1046 3175 2353839
Foetal death 93.04 52.90 22 1049 1890 2355124
Low set ears 90.29 52.90 13 1058 61 2356953
Congenital naevus 89.76 52.90 12 1059 28 2356986
Acoustic stimulation tests abnormal 89.47 52.90 12 1059 29 2356985
Pre-eclampsia 82.09 52.90 19 1052 1485 2355529
Oligohydramnios 79.15 52.90 17 1054 943 2356071
Rash maculo-papular 75.60 52.90 22 1049 4230 2352784
Renal failure 74.39 52.90 31 1040 17318 2339696
Placental insufficiency 60.83 52.90 11 1060 247 2356767
Trisomy 21 60.52 52.90 10 1061 129 2356885
Vomiting 59.40 52.90 43 1028 71559 2285455
Drug reaction with eosinophilia and systemic symptoms 57.64 52.90 19 1052 5499 2351515
Treatment failure 56.37 52.90 20 1051 7219 2349795
Generalised anxiety disorder 55.49 52.90 10 1061 220 2356794
Lactic acidosis 54.26 52.90 18 1053 5312 2351702
Abdominal pain 54.23 52.90 31 1040 34343 2322671
Hepatotoxicity 53.07 52.90 16 1055 3465 2353549

FDA Adverse Event Reporting System (Male)

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
Immune reconstitution inflammatory syndrome 622.09 40.54 123 1865 1426 1743367
Lipodystrophy acquired 554.31 40.54 90 1898 283 1744510
Pyrexia 418.16 40.54 193 1795 46207 1698586
Mitochondrial toxicity 381.54 40.54 60 1928 142 1744651
Progressive external ophthalmoplegia 319.36 40.54 44 1944 16 1744777
Foetal exposure during pregnancy 244.71 40.54 77 1911 6282 1738511
Eyelid ptosis 244.09 40.54 50 1938 687 1744106
Rash 224.43 40.54 120 1868 38573 1706220
Nausea 219.11 40.54 130 1858 51066 1693727
Diarrhoea 213.01 40.54 130 1858 53722 1691071
Renal impairment 198.45 40.54 78 1910 12236 1732557
Hyperlipidaemia 193.83 40.54 51 1937 2178 1742615
Diplopia 186.64 40.54 51 1937 2519 1742274
Drug resistance 184.01 40.54 53 1935 3177 1741616
Vomiting 183.83 40.54 105 1883 38210 1706583
Exposure during pregnancy 159.41 40.54 46 1942 2771 1742022
Malaise 146.77 40.54 83 1905 29482 1715311
Myocardial infarction 139.46 40.54 78 1910 27096 1717697
Liver disorder 139.45 40.54 49 1939 5587 1739206
Osteonecrosis 127.62 40.54 42 1946 3920 1740873
Abdominal pain 122.01 40.54 66 1922 21424 1723369
Hepatic function abnormal 121.41 40.54 47 1941 7027 1737766
Hypersensitivity 119.87 40.54 52 1936 10392 1734401
Drug hypersensitivity 110.27 40.54 55 1933 15080 1729713
Anaemia 102.68 40.54 66 1922 29391 1715402
Premature baby 102.03 40.54 33 1955 2909 1741884
Myalgia 99.79 40.54 52 1936 15606 1729187
Drug interaction 98.30 40.54 63 1925 27895 1716898
Virologic failure 96.69 40.54 21 1967 385 1744408
Viral mutation identified 92.53 40.54 20 1968 358 1744435
Jaundice 92.44 40.54 37 1951 6025 1738768
Hypertriglyceridaemia 92.35 40.54 25 1963 1184 1743609
Mycobacterium avium complex infection 89.04 40.54 19 1969 319 1744474
Asthenia 88.28 40.54 64 1924 34606 1710187
Acute kidney injury 87.83 40.54 64 1924 34880 1709913
Lactic acidosis 87.64 40.54 34 1954 5095 1739698
Cytomegalovirus chorioretinitis 86.19 40.54 19 1969 374 1744419
Pathogen resistance 85.43 40.54 23 1965 1066 1743727
Coronary artery disease 84.30 40.54 40 1948 9806 1734987
Cough 81.94 40.54 49 1939 19148 1725645
Dyslipidaemia 81.88 40.54 21 1967 804 1743989
Diabetes mellitus 81.13 40.54 35 1953 6873 1737920
Fatigue 80.61 40.54 71 1917 50710 1694083
Headache 79.71 40.54 60 1928 34316 1710477
Weight decreased 79.20 40.54 51 1937 22702 1722091
Pancytopenia 78.88 40.54 40 1948 11317 1733476
Hepatitis 78.15 40.54 31 1957 4924 1739869
Mitochondrial cytopathy 77.99 40.54 13 1975 49 1744744
Aspartate aminotransferase increased 77.97 40.54 39 1949 10717 1734076
Cachexia 77.54 40.54 21 1967 995 1743798
Alanine aminotransferase increased 75.93 40.54 40 1948 12238 1732555
Blood alkaline phosphatase increased 73.29 40.54 30 1958 5165 1739628
Mitochondrial myopathy 72.46 40.54 12 1976 43 1744750
Portal hypertension 70.71 40.54 18 1970 668 1744125
Liver function test abnormal 70.47 40.54 30 1958 5696 1739097
Lipoatrophy 70.08 40.54 13 1975 101 1744692
Hyperlactacidaemia 69.71 40.54 16 1972 380 1744413
Lymphadenopathy 69.29 40.54 27 1961 4087 1740706
Hepatotoxicity 69.29 40.54 25 1963 3059 1741734
HIV-associated neurocognitive disorder 68.90 40.54 12 1976 62 1744731
Small for dates baby 68.04 40.54 17 1971 584 1744209
HIV associated nephropathy 67.71 40.54 10 1978 12 1744781
Progressive multifocal leukoencephalopathy 67.62 40.54 21 1967 1618 1743175
Renal failure 67.48 40.54 44 1944 19973 1724820
Drug reaction with eosinophilia and systemic symptoms 67.19 40.54 28 1960 5042 1739751
Blood triglycerides increased 65.70 40.54 23 1965 2577 1742216
HIV infection 64.78 40.54 14 1974 250 1744543
Pancreatitis 63.93 40.54 30 1958 7157 1737636
Pruritus 63.87 40.54 45 1943 23177 1721616
Gamma-glutamyltransferase increased 63.69 40.54 27 1961 5071 1739722
Oral candidiasis 63.50 40.54 19 1969 1290 1743503
Nephrolithiasis 63.01 40.54 25 1963 3967 1740826
Dyspnoea 61.78 40.54 62 1926 51997 1692796
Rash maculo-papular 61.28 40.54 24 1964 3679 1741114
Blood lactic acid increased 61.26 40.54 17 1971 882 1743911
Ophthalmoplegia 60.53 40.54 13 1975 225 1744568
Hypertension 58.89 40.54 40 1948 19408 1725385
Hepatomegaly 58.78 40.54 19 1969 1666 1743127
Transplant rejection 58.60 40.54 18 1970 1336 1743457
Chills 58.17 40.54 33 1955 11654 1733139
Blood creatinine increased 57.87 40.54 35 1953 13911 1730882
Hepatic fibrosis 57.56 40.54 15 1973 611 1744182
C-reactive protein increased 56.80 40.54 26 1962 5859 1738934
Blood bilirubin increased 55.46 40.54 26 1962 6184 1738609
Hyperuricaemia 55.31 40.54 16 1972 965 1743828
Hypokalaemia 54.81 40.54 26 1962 6348 1738445
Pneumonia 54.74 40.54 55 1933 46127 1698666
Oesophageal candidiasis 54.11 40.54 14 1974 554 1744239
Viral load increased 53.73 40.54 14 1974 570 1744223
Chest pain 53.35 40.54 38 1950 19876 1724917
Acute myocardial infarction 53.10 40.54 28 1960 8559 1736234
Pharyngitis 52.82 40.54 16 1972 1132 1743661
Kaposi's sarcoma 52.72 40.54 15 1973 852 1743941
Varices oesophageal 52.67 40.54 14 1974 616 1744177
Proteinuria 52.64 40.54 20 1968 2824 1741969
Pancreatitis acute 52.21 40.54 22 1966 4065 1740728
Nervous system disorder 51.78 40.54 19 1969 2435 1742358
Thrombocytopenia 51.14 40.54 38 1950 21211 1723582
Oesophageal atresia 47.95 40.54 9 1979 75 1744718
Neuropathy peripheral 45.67 40.54 26 1962 9227 1735566
Tachycardia 45.54 40.54 29 1959 12599 1732194
Meningitis cryptococcal 45.26 40.54 11 1977 336 1744457
Decreased appetite 45.09 40.54 37 1951 23834 1720959
Encephalitis 44.49 40.54 14 1974 1124 1743669
Blood creatine phosphokinase increased 44.01 40.54 25 1963 8831 1735962
Splenomegaly 43.20 40.54 16 1972 2104 1742689
Hepatic cirrhosis 43.19 40.54 17 1971 2636 1742157
Nephropathy toxic 42.51 40.54 15 1973 1717 1743076
Renal disorder 42.41 40.54 19 1969 4067 1740726
Hepatitis B 41.61 40.54 14 1974 1389 1743404
Arthralgia 41.49 40.54 35 1953 23409 1721384
Chronic kidney disease 41.40 40.54 19 1969 4298 1740495
Cerebral toxoplasmosis 41.31 40.54 9 1979 167 1744626
Cholestasis 41.11 40.54 18 1970 3647 1741146
Treatment failure 41.05 40.54 19 1969 4382 1740411

Pharmacologic Action:

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)

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:557
Lactic acidosis contraindication 91273001 DOID:3650
Disorder of muscle contraindication 129565002 DOID:423
Steatosis of liver contraindication 197321007
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

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)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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:

IDSource
4029879 VUID
N0000180961 NUI
C0663655 UMLSCUI
D00891 KEGG_DRUG
40FH6D8CHK UNII
168146-84-7 SECONDARY_CAS_RN
d04376 MMSL
190521 RXNORM
387005008 SNOMEDCT_US
116084008 SNOMEDCT_US
66957 MMSL
4024130 VANDF
4029879 VANDF
007687 NDDF
CHEBI:421707 CHEBI
CHEMBL1380 ChEMBL_ID
DB01048 DRUGBANK_ID
CHEMBL1200619 ChEMBL_ID
1KX PDB_CHEM_ID
7544 INN_ID
441300 PUBCHEM_CID
CHEMBL2106686 ChEMBL_ID
C106538 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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 0904-6874 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 35573-402 TABLET, FILM COATED 600 mg ORAL ANDA 20 sections
Abacavir and Lamivudine HUMAN PRESCRIPTION DRUG LABEL 2 35573-430 TABLET, FILM COATED 600 mg ORAL ANDA 20 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 18 sections
ZIAGEN HUMAN PRESCRIPTION DRUG LABEL 1 49702-221 TABLET, FILM COATED 300 mg ORAL NDA 18 sections
ZIAGEN HUMAN PRESCRIPTION DRUG LABEL 1 49702-222 SOLUTION 20 mg ORAL NDA 18 sections
Triumeq HUMAN PRESCRIPTION DRUG LABEL 3 49702-231 TABLET, FILM COATED 600 mg ORAL NDA 19 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 50268-049 TABLET 300 mg ORAL ANDA 19 sections
Abacavir Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 51079-204 TABLET, FILM COATED 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
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
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 64380-717 TABLET 300 1 ORAL ANDA 19 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 64980-405 SOLUTION 20 mg ORAL ANDA 20 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 65862-073 TABLET, FILM COATED 300 mg ORAL ANDA 20 sections
Abacavir HUMAN PRESCRIPTION DRUG LABEL 1 65862-089 SOLUTION 20 mg ORAL ANDA 20 sections
Abacavir and Lamivudine HUMAN PRESCRIPTION DRUG LABEL 2 65862-335 TABLET, FILM COATED 600 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 18 sections