MITOTOX

Drug

D0048 | Entecavir

Properties

Molecular Formula	C12H15N5O3
Molecular Weight	277.28
Structure
State	solid
Clearance	* renal cl=383.2 +/- 101.8 mL/min [Unimpaired renal function] * renal cl=197.9 +/- 78.1 mL/min [Mild impaired renal function] * renal cl=135.6 +/- 31.6 mL/min [Moderate impaired renal function] * renal cl=40.3 +/- 10.1 mL/min [severe impaired renal function] * apparent oral cl=588.1 +/- 153.7 mL/min [Unimpaired renal function] * apparent oral cl=309.2 +/- 62.6 mL/min [Mild impaired renal function] * apparent oral cl=226.3 +/- 60.1 mL/min [Moderate impaired renal function] * apparent oral cl=100.6 +/- 29.1 mL/min [severe impaired renal function] * apparent oral cl=50.6 +/- 16.5 mL/min [severe impaired renal function amnaged with Hemodialysis] * apparent oral cl=35.7 +/- 19.6 mL/min [severe impaired renal function amnaged with CAPD]
Protein binding	Binding of entecavir to human serum proteins in vitro is approximately 13%.
Half life	After reaching peak concentration, entecavir plasma concentrations decreased in a bi-exponential manner with a terminal elimination half-life of approximately 128-149 hours. The phosphorylated metabolite has a half-life of 15 hours.
Absorption	Absorption Following oral administration in healthy subjects, entecavir peak plasma concentrations occurred between 0.5 and 1.5 hours. In healthy subjects, the bioavailability of the tablet is 100% relative to the oral solution.
Trade names	Baraclude
Description	a guanine analogue; antiviral

Therapeutic Classification Source: DrugBank

J05AF10 Entecavir

[J05AF] Nucleoside and nucleotide reverse transcriptase inhibitors

[J05A] DIRECT ACTING ANTIVIRALS

[J05] ANTIVIRALS FOR SYSTEMIC USE

[J] Antiinfectives for systemic use

GHS Hazard Tables Source: PubChem

Pictogram	Signal	Statements	Precautionary Statement Codes
	Danger	Aggregated GHS information provided by 7 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. Reported as not meeting GHS hazard criteria by 2 of 7 companies. For more detailed information, please visit ECHA C&L website Of the 4 notification(s) provided by 5 of 7 companies with hazard statement code(s): H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] H351 (80%): Suspected of causing cancer [Warning Carcinogenicity] H360 (40%): May damage fertility or the unborn child [Danger Reproductive toxicity] H361 (40%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity] H362 (40%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation] H372 (80%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure] Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.	P201, P202, P260, P263, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Pictogram

Signal

Statements

Precautionary Statement Codes

Danger

Aggregated GHS information provided by 7 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 2 of 7 companies. For more detailed information, please visit ECHA C&L website

Of the 4 notification(s) provided by 5 of 7 companies with hazard statement code(s):

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H351 (80%): Suspected of causing cancer [Warning Carcinogenicity]

H360 (40%): May damage fertility or the unborn child [Danger Reproductive toxicity]

H361 (40%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H362 (40%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

H372 (80%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

P201, P202, P260, P263, P264, P270, P281, P301+P312, P308+P313, P314, P330, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Indications Source: SIDER

Alanine aminotransferase increased

Chronic hepatitis B

Fibrosis

Foetor hepaticus

Hepatic cirrhosis

Hepatitis B e antigen positive

Hepatocellular injury

Infection

Inflammation

Liver disorder

Viral infection

Side effects Source: SIDER

Ascites (0.15)

Upper respiratory tract infection (0.1)

Abdominal pain upper

Asthenia

Diarrhoea

Dizziness

Dyspepsia

Fatigue

Glycosuria

Haematuria

Headache

Hyperglycaemia

Insomnia

Nausea

Somnolence

Vomiting

Synonyms Source: PubChem

1333204-94-6	142217-69-4	2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylene-cyclopentyl]-3,9-dihydro-purin-6-one
2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one	2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one	2-amino-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-1,9-dihydro-6H-purin-6-one
2-amino-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-3,9-dihydro-6H-purin-6-one	2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-	2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylene-cyclopentyl]-1H-purin-6-one
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one	2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one hydrate (1:1)	2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one
2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one	2-amino-9-[4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one	2-amino-9-[4-hydroxy-3-(hydroxymethyl)-2-methylidene-cyclopentyl]-3H-purin-6-one
209216-23-9	217E694	6-H-Purin-6-one-,2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]
6H-Purin-6-one, 2-amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-	6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-	9-[(1S,3R,4S)-4-Hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]guanine
AB0071164	AB1004838	ABP001043
AC-1593	AKOS015854916	AKOS015920226
AKOS025312554	AM20080880	AR-270/43507901
BDBM50248008	BMS 200475	BMS-200475
BMS-200475-01	BMS200475	BR-77289
BRD-K08206212-001-01-2	Baraclude	CAS-142217-69-4
CHEBI:473990	CHEMBL713	CS-3160
D07896	DB00442	DSSTox_CID_26446
DSSTox_GSID_46446	DSSTox_RID_81621	DTXSID4046446
E0899	Entecavir	Entecavir (INN)
Entecavir anhydrous	Entecavir, >=98% (HPLC)	Entecavirum
FT-0083013	GS-6386	HSDB 7334
HY-13623	J90027	KS-00000G4U
LS41110	MFCD00907887	NCGC00164563-01
NCGC00164563-09	NCGC00164563-13	NNU2O4609D
PB30663	Q418586	QDGZDCVAUDNJFG-FXQIFTODSA-N
S-7388	SC-20106	SCHEMBL15198001
SCHEMBL28648	SQ 34,676	SQ 34676
SQ-34676	SQ34676	Tox21_112192
UNII-NNU2O4609D	ZINC3802690	anhydrous entecavir
entecavir (anhydrous)	methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one

External IDs

DrugBank Name	Entecavir
DrugBank	DB00442
CAS Number	1333204-94-6, 142217-69-4, 188399-46-4, 209216-23-9
PubChem Compound	135398508
KEGG Drug	D04008(hydrate)/D07896(pure)
PubChem.Substance	46504864
ChEBI	473990
PharmGKB	PA164784025
ChemSpider	135679
TTD	DAP000697
Wikipedia	Entecavir
DPD	13030

References

1. Dykens et al. (2007)