Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
antivirals carbocyclic nucleosides	1019	142217-69-4

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: entecavir monohydrate anhydrous entecavir BMS-200475-01 entecavir baraclude entecavir hydrate	Entecavir, a guanosine nucleoside analogue with activity against HBV reverse transcriptase, is efficiently phosphorylated to the active triphosphate form, which has an intracellular half-life of 15 hours. By competing with the natural substrate deoxyguanosine triphosphate, entecavir triphosphate functionally inhibits all three activities of the HBV reverse transcriptase: (1) base priming, (2) reverse transcription of the negative strand from the pregenomic messenger RNA, and (3) synthesis of the positive strand of HBV DNA. Entecavir triphosphate is a weak inhibitor of cellular DNA polymerases alpha, beta, and delta and mitochondrial DNA polymerase gamma with Ki values ranging from 18 to > 160 microM. Molecular weight: 277.28 Formula: C12H15N5O3 CLOGP: -1.78 LIPINSKI: 0 HAC: 8 HDO: 4 TPSA: 125.76 ALOGS: -1.63 ROTB: 2 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

entecavir monohydrate
anhydrous entecavir
BMS-200475-01
entecavir
baraclude
entecavir hydrate

Entecavir, a guanosine nucleoside analogue with activity against HBV reverse transcriptase, is efficiently phosphorylated to the active triphosphate form, which has an intracellular half-life of 15 hours. By competing with the natural substrate deoxyguanosine triphosphate, entecavir triphosphate functionally inhibits all three activities of the HBV reverse transcriptase: (1) base priming, (2) reverse transcription of the negative strand from the pregenomic messenger RNA, and (3) synthesis of the positive strand of HBV DNA. Entecavir triphosphate is a weak inhibitor of cellular DNA polymerases alpha, beta, and delta and mitochondrial DNA polymerase gamma with Ki values ranging from 18 to > 160 microM.

Molecular weight: 277.28
Formula: C12H15N5O3
CLOGP: -1.78
LIPINSKI: 0
HAC: 8
HDO: 4
TPSA: 125.76
ALOGS: -1.63
ROTB: 2

Status: OFP

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

Drug dosage:

Dose	Unit	Route
0.50	mg	O

ADMET properties:

Property	Value	Reference
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
S (Water solubility)	2.40 mg/mL	Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine)	70 %	Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose)	0.05 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability)	99 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
fu (Fraction unbound in plasma)	1 %	Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K

Predicted pharmacokinetic/toxicological properties (PK-AZ):

Property	Description	Value	Unit	Confidence	Similarity
pfas-class	PFAS structural alert (1 = True, 0 = False)	0

Approvals:

Date	Agency	Company	Orphan
March 29, 2005	FDA	BRISTOL MYERS SQUIBB
June 26, 2006	EMA	BRISTOL-MYERS SQUIBB PHARMA EEIG

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
Hepatitis B	161.00	19.83	42	6737	4477	90617191
Hepatitis B reactivation	137.07	19.83	36	6743	3938	90617730
Drug resistance	129.04	19.83	57	6722	30392	90591276
Hepatocellular carcinoma	103.29	19.83	26	6753	2402	90619266
Hepatitis B DNA increased	103.03	19.83	18	6761	272	90621396
Viral load increased	98.74	19.83	23	6756	1533	90620135
Platelet count decreased	90.92	19.83	78	6701	136891	90484777
Neutrophil count decreased	83.40	19.83	57	6722	71475	90550193
Hypophosphataemia	80.10	19.83	33	6746	14821	90606847
Exposure via body fluid	77.46	19.83	16	6763	608	90621060
Neutropenia	73.14	19.83	87	6692	224817	90396851
Viral mutation identified	63.42	19.83	17	6762	2008	90619660
White blood cell count decreased	63.34	19.83	70	6709	167039	90454629
Febrile neutropenia	61.17	19.83	67	6712	158282	90463386
Fanconi syndrome acquired	55.97	19.83	14	6765	1260	90620408
Hepatic failure	54.37	19.83	35	6744	39693	90581975
Abortion induced	52.74	19.83	23	6756	11865	90609803
Hepatic cancer	52.55	19.83	18	6761	4863	90616805
Hepatic function abnormal	47.20	19.83	34	6745	46254	90575414
Pathogen resistance	47.06	19.83	19	6760	8096	90613572
Lymphocyte count decreased	45.80	19.83	30	6749	35020	90586648
Liver transplant	43.31	19.83	13	6766	2304	90619364
Pulmonary microemboli	42.51	19.83	5	6774	0	90621668
Mixed liver injury	41.31	19.83	17	6762	7606	90614062
Osteomalacia	40.14	19.83	10	6769	885	90620783
Leukopenia	39.53	19.83	43	6736	100667	90521001
Thrombocytopenia	39.27	19.83	62	6717	208663	90413005
Anaemia	37.59	19.83	82	6697	352720	90268948
Blood creatinine increased	37.56	19.83	42	6737	101344	90520324
Hepatic encephalopathy	37.43	19.83	19	6760	13753	90607915
Alanine aminotransferase increased	37.12	19.83	45	6734	118293	90503375
Renal impairment	32.92	19.83	40	6739	105381	90516287
Agranulocytosis	31.83	19.83	24	6755	34978	90586690
Cardiac failure	31.70	19.83	40	6739	109456	90512212
Hypoproteinaemia	31.55	19.83	11	6768	3131	90618537
Abortion spontaneous	30.27	19.83	28	6751	54028	90567640
Hypokalaemia	27.53	19.83	41	6738	131075	90490593
Pregnancy on contraceptive	27.41	19.83	8	6771	1287	90620381
Excessive dynamic airway collapse	26.52	19.83	4	6775	22	90621646
Hepatitis C	25.26	19.83	11	6768	5649	90616019
Hypoalbuminaemia	24.23	19.83	15	6764	15882	90605786
Acute hepatic failure	23.97	19.83	17	6762	22544	90599124
Hepatitis D	23.83	19.83	4	6775	47	90621621
Systemic infection	23.69	19.83	10	6769	4765	90616903
Urinary tract stoma complication	23.38	19.83	4	6775	53	90621615
Blood bilirubin increased	23.34	19.83	22	6757	43448	90578220
Death	23.27	19.83	81	6698	456470	90165198
Cytokine release syndrome	22.85	19.83	18	6761	27955	90593713
Gastroenteritis staphylococcal	21.74	19.83	4	6775	82	90621586
Cryoglobulinaemia	21.64	19.83	6	6773	804	90620864
Septic shock	21.63	19.83	29	6750	84131	90537537
Swelling	21.37	19.83	3	6776	419055	90202613
Maternal exposure during pregnancy	21.11	19.83	67	6712	359996	90261672
Immune-mediated lung disease	20.50	19.83	7	6772	1873	90619795
Hyperuricaemia	20.42	19.83	10	6769	6709	90614959
Fanconi syndrome	20.27	19.83	7	6772	1936	90619732
Electrocardiogram P pulmonale	20.13	19.83	3	6776	15	90621653
Genotype drug resistance test positive	20.05	19.83	5	6774	444	90621224

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
Hepatocellular carcinoma	334.70	16.60	117	13032	8077	42600109
Drug resistance	333.50	16.60	177	12972	34071	42574115
Viral mutation identified	269.65	16.60	80	13069	3251	42604935
Hepatic cancer	242.02	16.60	93	13056	8387	42599799
Hepatic failure	206.88	16.60	135	13014	37965	42570221
Hepatitis B DNA increased	203.30	16.60	45	13104	544	42607642
Genotype drug resistance test	178.32	16.60	29	13120	45	42608141
Hepatitis B reactivation	170.25	16.60	61	13088	4517	42603669
Hepatitis B	157.81	16.60	64	13085	6647	42601539
Pathogen resistance	148.77	16.60	72	13077	11378	42596808
Hepatic encephalopathy	116.34	16.60	69	13080	16373	42591813
Viral load increased	115.46	16.60	41	13108	2956	42605230
Osteomalacia	111.32	16.60	30	13119	854	42607332
Fanconi syndrome acquired	109.84	16.60	36	13113	2034	42606152
Ascites	104.62	16.60	107	13042	56571	42551615
Hepatic cirrhosis	95.24	16.60	65	13084	19637	42588549
Hepatic function abnormal	85.58	16.60	92	13057	51475	42556711
Blood HIV RNA decreased	85.01	16.60	12	13137	0	42608186
Multiple-drug resistance	83.08	16.60	42	13107	7280	42600906
Genotype drug resistance test positive	80.63	16.60	25	13124	1179	42607007
Hypophosphataemia	71.49	16.60	56	13093	20889	42587297
Hepatitis B surface antigen positive	61.15	16.60	13	13136	128	42608058
Blood phosphorus decreased	54.03	16.60	25	13124	3568	42604618
Alanine aminotransferase increased	49.76	16.60	94	13055	88312	42519874
Blood bilirubin increased	49.39	16.60	63	13086	42189	42565997
Portal vein thrombosis	48.42	16.60	25	13124	4524	42603662
Oesophageal varices haemorrhage	44.78	16.60	22	13127	3585	42604601
Platelet count decreased	42.74	16.60	116	13033	138465	42469721
Fanconi syndrome	41.79	16.60	17	13132	1777	42606409
Osteoporosis	40.67	16.60	35	13114	14871	42593315
Autoimmune haemolytic anaemia	40.62	16.60	24	13125	5647	42602539
Palmar-plantar erythrodysaesthesia syndrome	38.18	16.60	39	13110	20543	42587643
Viral infection	37.06	16.60	40	13109	22443	42585743
Renal impairment	35.72	16.60	94	13055	110134	42498052
Hypoalbuminaemia	35.36	16.60	33	13116	15577	42592609
White blood cell count decreased	34.61	16.60	93	13056	110303	42497883
Proteinuria	32.92	16.60	38	13111	22945	42585241
Aspartate aminotransferase increased	30.48	16.60	71	13078	77092	42531094
Lymphocyte count decreased	30.20	16.60	40	13109	27769	42580417
Mycoplasma infection	29.37	16.60	10	13139	635	42607551
Hypokalaemia	28.33	16.60	66	13083	71655	42536531
Portal vein occlusion	27.29	16.60	6	13143	70	42608116
Meningitis cryptococcal	26.45	16.60	15	13134	3268	42604918
Asymptomatic viral hepatitis	26.00	16.60	5	13144	28	42608158
Neutrophil count decreased	25.75	16.60	59	13090	63356	42544830
Parotid gland haemorrhage	25.70	16.60	5	13144	30	42608156
Hepatorenal syndrome	25.62	16.60	14	13135	2840	42605346
Optic disc hyperaemia	24.67	16.60	4	13145	6	42608180
Malignant anorectal neoplasm	24.34	16.60	5	13144	41	42608145
Hypocalciuria	23.63	16.60	4	13145	9	42608177
Liver transplant	23.60	16.60	13	13136	2678	42605508
Hepatitis B e antigen positive	23.54	16.60	5	13144	49	42608137
Retinal toxicity	23.33	16.60	8	13141	519	42607667
Retinopathy hypertensive	22.93	16.60	7	13142	313	42607873
Renal tubular injury	22.53	16.60	11	13138	1768	42606418
Hepatitis B virus test positive	22.31	16.60	7	13142	343	42607843
Jaundice	22.25	16.60	39	13110	34550	42573636
Drug abuse	22.22	16.60	3	13146	104768	42503418
Renal glycosuria	22.11	16.60	4	13145	15	42608171
Retinal depigmentation	21.77	16.60	5	13144	72	42608114
Liver transplant rejection	21.65	16.60	12	13137	2501	42605685
Foetal hypokinesia	21.57	16.60	7	13142	383	42607803
Mitochondrial myopathy	21.38	16.60	6	13143	199	42607987
Foetal heart rate abnormal	21.27	16.60	6	13143	203	42607983
Monkeypox	21.16	16.60	7	13142	407	42607779
Renal tubular acidosis	20.65	16.60	12	13137	2738	42605448
Blood alkaline phosphatase increased	20.47	16.60	37	13112	33560	42574626
Varices oesophageal	20.13	16.60	14	13135	4351	42603835
Venoocclusive liver disease	19.98	16.60	20	13129	10282	42597904
Completed suicide	19.90	16.60	3	13146	96462	42511724
Nephropathy toxic	19.49	16.60	25	13124	16813	42591373
Starvation	19.39	16.60	7	13142	529	42607657
Antiviral drug level below therapeutic	19.17	16.60	3	13146	3	42608183
Blood uric acid	19.17	16.60	3	13146	3	42608183
Cancer surgery	19.17	16.60	7	13142	546	42607640
Chronic hepatitis B	19.02	16.60	5	13144	129	42608057
Immunosuppressant drug level increased	18.78	16.60	17	13132	7714	42600472
Dyspnoea	18.63	16.60	72	13077	442549	42165637
Schistosomiasis	18.41	16.60	4	13145	44	42608142
HIV associated nephropathy	18.15	16.60	6	13143	348	42607838
Alkalosis hypokalaemic	17.96	16.60	3	13146	6	42608180
Laryngeal erythema	17.96	16.60	3	13146	6	42608180
Hypoproteinaemia	17.81	16.60	11	13138	2801	42605385
COVID-19 pneumonia	17.44	16.60	27	13122	21586	42586600
Febrile neutropenia	17.23	16.60	107	13042	185596	42422590
Toxicity to various agents	16.83	16.60	28	13121	229108	42379078
Amylase increased	16.75	16.60	15	13134	6714	42601472
Malaria	16.61	16.60	5	13144	213	42607973

FDA Adverse Event Reporting System (Geriatric)

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
Hepatocellular carcinoma	428.39	15.25	127	18094	9753	110561325
Viral mutation identified	354.16	15.25	92	18129	4327	110566751
Hepatic cancer	317.83	15.25	104	18117	11052	110560026
Hepatitis B reactivation	310.51	15.25	93	18128	7391	110563687
Drug resistance	288.33	15.25	154	18067	56220	110514858
Hepatic failure	278.29	15.25	161	18060	68578	110502500
Hepatitis B DNA increased	249.69	15.25	51	18170	804	110570274
Pathogen resistance	194.80	15.25	82	18139	17590	110553488
Hepatitis B	174.43	15.25	64	18157	9548	110561530
Hepatic encephalopathy	158.05	15.25	82	18139	28174	110542904
Viral load increased	157.52	15.25	46	18175	3344	110567734
Fanconi syndrome acquired	153.56	15.25	44	18177	2990	110568088
Platelet count decreased	149.73	15.25	187	18034	230256	110340822
Hypophosphataemia	148.40	15.25	83	18138	33099	110537979
Hepatic function abnormal	140.60	15.25	117	18104	89178	110481900
Osteomalacia	131.80	15.25	34	18187	1553	110569525
Ascites	124.57	15.25	111	18110	92697	110478381
Genotype drug resistance test positive	101.73	15.25	27	18194	1379	110569699
White blood cell count decreased	96.30	15.25	151	18070	229239	110341839
Neutrophil count decreased	94.67	15.25	108	18113	120833	110450245
Renal impairment	90.37	15.25	132	18089	188313	110382765
Alanine aminotransferase increased	88.52	15.25	129	18092	183644	110387434
Multiple-drug resistance	87.44	15.25	43	18178	13192	110557886
Blood bilirubin increased	84.78	15.25	82	18139	75890	110495188
Lymphocyte count decreased	81.86	15.25	71	18150	57172	110513906
Blood HIV RNA decreased	77.11	15.25	10	18211	0	110571078
Febrile neutropenia	75.16	15.25	163	18058	316604	110254474
Hepatic cirrhosis	68.05	15.25	69	18152	67557	110503521
Hypoalbuminaemia	67.61	15.25	48	18173	28926	110542152
Portal vein thrombosis	65.46	15.25	29	18192	7029	110564049
Oesophageal varices haemorrhage	64.87	15.25	26	18195	4919	110566159
Hypokalaemia	64.24	15.25	111	18110	182337	110388741
Neutropenia	62.25	15.25	168	18053	374452	110196626
Hepatitis B surface antigen positive	59.36	15.25	12	18209	179	110570899
Liver transplant	56.32	15.25	23	18198	4566	110566512
Hypoproteinaemia	53.76	15.25	24	18197	5921	110565157
Blood creatinine increased	51.43	15.25	101	18120	182788	110388290
Thrombocytopenia	50.63	15.25	149	18072	348736	110222342
Proteinuria	49.99	15.25	46	18175	39972	110531106
Jaundice	48.19	15.25	54	18167	59182	110511896
Fanconi syndrome	47.89	15.25	19	18202	3500	110567578
Palmar-plantar erythrodysaesthesia syndrome	47.11	15.25	45	18176	40980	110530098
Aspartate aminotransferase increased	47.01	15.25	90	18131	159846	110411232
Joint swelling	45.24	15.25	9	18212	442836	110128242
Septic shock	44.29	15.25	87	18134	157441	110413637
Blood phosphorus decreased	42.14	15.25	22	18199	7643	110563435
Autoimmune haemolytic anaemia	40.72	15.25	24	18197	10543	110560535
Blood alkaline phosphatase increased	38.86	15.25	53	18168	70882	110500196
Death	38.54	15.25	221	18000	698648	109872430
Rheumatoid arthritis	38.02	15.25	3	18218	299610	110271468
Nasopharyngitis	36.35	15.25	10	18211	394351	110176727
Drug intolerance	36.19	15.25	11	18210	406501	110164577
Drug hypersensitivity	35.81	15.25	15	18206	454075	110117003
Leukopenia	35.72	15.25	77	18144	148714	110422364
Anaemia	35.55	15.25	181	18040	546905	110024173
Portal vein occlusion	35.38	15.25	7	18214	93	110570985
Pyrexia	34.85	15.25	260	17961	898005	109673073
Hypocalcaemia	34.54	15.25	48	18173	65318	110505760
Pain	34.23	15.25	66	18155	954889	109616189
Liver transplant rejection	32.84	15.25	15	18206	3903	110567175
Acute hepatic failure	32.71	15.25	35	18186	36433	110534645
Swelling	32.16	15.25	9	18212	351032	110220046
Cytokine release syndrome	31.86	15.25	48	18173	70258	110500820
Anxiety	31.33	15.25	9	18212	345069	110226009
Transaminases increased	31.20	15.25	45	18176	63345	110507733
Systemic lupus erythematosus	31.04	15.25	3	18218	254335	110316743
Hepatorenal syndrome	30.55	15.25	15	18206	4582	110566496
Blood creatine phosphokinase increased	30.46	15.25	48	18173	73029	110498049
Meningitis cryptococcal	30.05	15.25	15	18206	4747	110566331
Arthralgia	29.59	15.25	52	18169	779580	109791498
Therapeutic product effect decreased	29.50	15.25	3	18218	244313	110326765
Arthropathy	29.02	15.25	6	18215	287516	110283562
Pulmonary microemboli	28.98	15.25	5	18216	29	110571049
Parotid gland haemorrhage	28.69	15.25	5	18216	31	110571047
Plasma cell myeloma	28.56	15.25	43	18178	62893	110508185
Sinusitis	28.33	15.25	7	18214	296681	110274397
Musculoskeletal stiffness	27.91	15.25	6	18215	279816	110291262
Abortion induced	27.76	15.25	17	18204	8002	110563076
Hyperuricaemia	27.01	15.25	21	18200	14510	110556568
Varices oesophageal	26.79	15.25	16	18205	7199	110563879
Wheezing	26.44	15.25	5	18216	255225	110315853
Monkeypox	26.21	15.25	7	18214	366	110570712
Antiviral drug level below therapeutic	26.06	15.25	5	18216	56	110571022
Mixed liver injury	25.87	15.25	19	18202	12060	110559018
Liver abscess	25.75	15.25	16	18205	7723	110563355
Interstitial lung disease	25.66	15.25	65	18156	139269	110431809
COVID-19 pneumonia	25.43	15.25	31	18190	37112	110533966
Confusional state	25.25	15.25	24	18197	468656	110102422
Malignant anorectal neoplasm	24.64	15.25	5	18216	76	110571002
Renal tubular acidosis	24.41	15.25	13	18208	4702	110566376
Immunosuppressant drug level increased	24.11	15.25	18	18203	11706	110559372
Product substitution issue	24.05	15.25	24	18197	23037	110548041
Optic disc hyperaemia	24.03	15.25	4	18217	18	110571060
Nephropathy toxic	23.99	15.25	26	18195	27452	110543626
Infusion related reaction	23.64	15.25	17	18204	381145	110189933
Pregnancy on contraceptive	23.17	15.25	8	18213	1000	110570078
Hepatitis B e antibody positive	23.13	15.25	3	18218	0	110571078
Retinopathy hypertensive	23.06	15.25	7	18214	581	110570497
Cytomegalovirus infection reactivation	22.75	15.25	21	18200	18312	110552766
Lower respiratory tract infection	22.70	15.25	6	18215	243100	110327978
Renal glycosuria	22.53	15.25	4	18217	28	110571050
Gamma-glutamyltransferase increased	22.47	15.25	38	18183	61271	110509807
Agranulocytosis	22.27	15.25	38	18183	61722	110509356
Venoocclusive liver disease	22.01	15.25	19	18202	15188	110555890
Excessive dynamic airway collapse	21.85	15.25	4	18217	34	110571044
Cryptococcosis	21.83	15.25	12	18209	4619	110566459
HIV associated nephropathy	21.73	15.25	6	18215	356	110570722
Hypocalciuria	21.64	15.25	4	18217	36	110571042
Blood uric acid	21.06	15.25	3	18218	3	110571075
Amylase increased	20.93	15.25	17	18204	12502	110558576
Renal failure	20.71	15.25	83	18138	226491	110344587
Mycoplasma infection	20.61	15.25	8	18213	1390	110569688
Myelosuppression	20.58	15.25	47	18174	94293	110476785
Blood cholesterol increased	20.51	15.25	3	18218	184782	110386296
Acute kidney injury	20.26	15.25	176	18045	635254	109935824
Abdominal discomfort	20.25	15.25	21	18200	393837	110177241
Renal tubular injury	20.23	15.25	10	18211	3098	110567980
Schistosomiasis	20.16	15.25	4	18217	54	110571024
Asthma	20.15	15.25	8	18213	250283	110320795
Immune-mediated hepatitis	20.15	15.25	13	18208	6698	110564380
Cancer surgery	19.50	15.25	7	18214	980	110570098
Hepatitis B virus test positive	19.42	15.25	6	18215	528	110570550
Retinal toxicity	19.29	15.25	8	18213	1651	110569427
Starvation	19.26	15.25	7	18214	1016	110570062
Peripheral swelling	19.18	15.25	23	18198	404011	110167067
Therapeutic embolisation	18.83	15.25	6	18215	584	110570494
Metastases to lung	18.71	15.25	21	18200	23042	110548036
Vomiting	18.63	15.25	82	18139	910593	109660485
Depression	18.59	15.25	15	18206	317320	110253758
Multiple organ dysfunction syndrome	18.45	15.25	61	18160	151649	110419429
Hypersensitivity	18.13	15.25	24	18197	403974	110167104
Pneumonia bacterial	18.11	15.25	22	18199	26239	110544839
Cytomegalovirus infection	17.68	15.25	32	18189	54412	110516666
Hepatectomy	17.54	15.25	5	18216	333	110570745
Urinary tract stoma complication	17.46	15.25	4	18217	110	110570968
Cardiac failure	17.35	15.25	69	18152	187557	110383521
Retinal depigmentation	17.15	15.25	5	18216	361	110570717
Bone pain	17.12	15.25	35	18186	65098	110505980
Hyperbilirubinaemia	16.92	15.25	23	18198	30648	110540430
Haemolytic anaemia	16.89	15.25	19	18202	20901	110550177
Weight increased	16.80	15.25	27	18194	419617	110151461
Lactic acidosis	16.77	15.25	43	18178	92768	110478310
Renal tubular disorder	16.62	15.25	12	18209	7417	110563661
Hyperphosphaturia	16.62	15.25	4	18217	137	110570941
Sleep disorder	16.57	15.25	6	18215	198638	110372440
Toxicity to various agents	16.49	15.25	34	18187	480521	110090557
Dyspnoea	16.40	15.25	111	18110	1106761	109464317
Malaria	16.39	15.25	5	18216	422	110570656
Urine protein/creatinine ratio increased	16.33	15.25	7	18214	1566	110569512
Pneumonia	16.32	15.25	218	18003	876496	109694582
Hypophosphataemic osteomalacia	16.28	15.25	5	18216	432	110570646
Alkalosis hypokalaemic	16.23	15.25	3	18218	27	110571051
Mitochondrial myopathy	16.09	15.25	5	18216	449	110570629
Haemorrhagic cholecystitis	15.90	15.25	4	18217	165	110570913
Blister	15.65	15.25	9	18212	227367	110343711
Injection site pain	15.49	15.25	5	18216	177917	110393161
Contraindicated product administered	15.48	15.25	11	18210	248256	110322822
Drug abuse	15.42	15.25	5	18216	177406	110393672
Loss of personal independence in daily activities	15.40	15.25	3	18218	150017	110421061
Ileal ulcer	15.36	15.25	7	18214	1810	110569268
Immune-mediated lung disease	15.25	15.25	10	18211	5293	110565785

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

Source	Code	Description
ATC	J05AF10	ANTIINFECTIVES FOR SYSTEMIC USE ANTIVIRALS FOR SYSTEMIC USE DIRECT ACTING ANTIVIRALS Nucleoside and nucleotide reverse transcriptase inhibitors
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000998	Antiviral Agents
CHEBI has role	CHEBI:22587	antiviral agent
CHEBI has role	CHEBI:35441	antiinfective agent
CHEBI has role	CHEBI:35610	antineoplastic agent
CHEBI has role	CHEBI:36044	antiviral drug
CHEBI has role	CHEBI:59897	EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
CHEBI has role	CHEBI:64951	anti-HBV agent

Related Drugs by ATC class:

J05AF Nucleoside and nucleotide reverse transcriptase inhibitors 12 drugs

abacavir adefovir dipivoxil clevudine didanosine emtricitabine lamivudine stavudine telbivudine tenofovir alafenamide tenofovir disoproxil zalcitabine zidovudine

Drug Use | Suggest Off label Use Form| |View source of the data|

Disease	Relation	SNOMED_ID	DOID
Chronic type B viral hepatitis	indication	61977001
Lamivudine-Refractory Chronic Hepatitis B	indication
Lactic acidosis	contraindication	91273001	DOID:3650
Liver function tests abnormal	contraindication	166603001
Steatosis of liver	contraindication	197321007
Impaired renal function disorder	contraindication	197663003
Drug Resistance to Anti-retroviral Therapy	contraindication

🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation level	Dissociation constant	Type (acidic/basic)
pKa1	9.56	acidic
pKa2	12.33	acidic
pKa3	13.37	acidic
pKa4	4.58	Basic
pKa5	3.37	Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

Target	Class	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Protein P	Polyprotein	Q9IF40_HBV	INHIBITOR			CHEMBL	CHEMBL
Protein P	Polyprotein	DPOL_HBVB1				WOMBAT-PK
Capsid protein	Structural	Q03732_HBV		EC50	9.62	CHEMBL

External reference:

ID	Source
4024911	VUID
N0000171606	NUI
D04008	KEGG_DRUG
4024911	VANDF
C0971023	UMLSCUI
CHEBI:59902	CHEBI
CHEMBL5314362	ChEMBL_ID
CHEMBL713	ChEMBL_ID
DB00442	DRUGBANK_ID
C413685	MESH_SUPPLEMENTAL_RECORD_UI
135398508	PUBCHEM_CID
5968Y6H45M	UNII
1546027	RXNORM
19722	MMSL
228280	MMSL
67562	MMSL
d05525	MMSL
010730	NDDF
1269008001	SNOMEDCT_US
416248007	SNOMEDCT_US
416644000	SNOMEDCT_US
725853008	SNOMEDCT_US
209216-23-9	SECONDARY_CAS_RN

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
BARACLUDE	HUMAN PRESCRIPTION DRUG LABEL	1	0003-1611	TABLET, FILM COATED	0.50 mg	ORAL	NDA	27 sections
BARACLUDE	HUMAN PRESCRIPTION DRUG LABEL	1	0003-1612	TABLET, FILM COATED	1 mg	ORAL	NDA	27 sections
BARACLUDE	HUMAN PRESCRIPTION DRUG LABEL	1	0003-1614	SOLUTION	0.05 mg	ORAL	NDA	27 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	10135-615	TABLET, FILM COATED	0.50 mg	ORAL	ANDA	29 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	10135-616	TABLET, FILM COATED	1 mg	ORAL	ANDA	29 sections
ENTECAVIR	HUMAN PRESCRIPTION DRUG LABEL	1	16714-717	TABLET, FILM COATED	0.50 mg	ORAL	ANDA	26 sections
ENTECAVIR	HUMAN PRESCRIPTION DRUG LABEL	1	16714-718	TABLET, FILM COATED	1 mg	ORAL	ANDA	26 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	42291-261	TABLET, FILM COATED	0.50 mg	ORAL	ANDA	28 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	42291-262	TABLET, FILM COATED	1 mg	ORAL	ANDA	28 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	42806-658	TABLET	0.50 mg	ORAL	ANDA	28 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	42806-659	TABLET	1 mg	ORAL	ANDA	28 sections
ENTECAVIR	HUMAN PRESCRIPTION DRUG LABEL	1	50771-013	TABLET, FILM COATED	0.50 mg	ORAL	ANDA	28 sections
ENTECAVIR	HUMAN PRESCRIPTION DRUG LABEL	1	50771-014	TABLET, FILM COATED	1 mg	ORAL	ANDA	28 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	51407-589	TABLET	0.50 mg	ORAL	ANDA	19 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	60687-216	TABLET	0.50 mg	ORAL	ANDA	26 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	61442-311	TABLET	0.50 mg	ORAL	ANDA	19 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	65162-446	TABLET, FILM COATED	0.50 mg	ORAL	ANDA	26 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	65162-449	TABLET, FILM COATED	1 mg	ORAL	ANDA	26 sections
Entecavir	Human Prescription Drug Label	1	65862-841	TABLET	0.50 mg	ORAL	ANDA	26 sections
Entecavir	Human Prescription Drug Label	1	65862-842	TABLET	1 mg	ORAL	ANDA	26 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	68382-920	TABLET, FILM COATED	0.50 mg	ORAL	ANDA	24 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	68382-921	TABLET, FILM COATED	1 mg	ORAL	ANDA	24 sections
ENTECAVIR	HUMAN PRESCRIPTION DRUG LABEL	1	69097-425	TABLET, FILM COATED	1 mg	ORAL	ANDA	25 sections
ENTECAVIR	HUMAN PRESCRIPTION DRUG LABEL	1	69097-426	TABLET, FILM COATED	0.50 mg	ORAL	ANDA	25 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	70771-1019	TABLET, FILM COATED	0.50 mg	ORAL	ANDA	1 sections
Entecavir	HUMAN PRESCRIPTION DRUG LABEL	1	70771-1020	TABLET, FILM COATED	1 mg	ORAL	ANDA	1 sections