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

Stem definition	Drug id	CAS RN
antivirals carbocyclic nucleosides	34	136470-78-5

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
0.60	g	O

ADMET properties:

Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	29.93 µM/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:

Date	Agency	Company	Orphan
July 8, 1999	EMA
Dec. 17, 1998	FDA	VIIV HLTHCARE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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)

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Mechanism action	Bioact source	MoA source
Reverse transcriptase/RNaseH	Enzyme		Q72547_9HIV1	INHIBITOR	EC50	5.28		CHEMBL	CHEMBL
Gag-Pol polyprotein	Polyprotein		POL_HV1A2		EC50	5.28		WOMBAT-PK

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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