Drug Information

General Information
Drug ID
DR01277
Drug Name
Entecavir
Synonyms
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-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-water (1/1); 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one; 6-H-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 monohydrate; BMS-200475; Baraclude; Baraclude (TN); ETV; Entecavir (INN); Entecavir (USAN); Entecavir hydrate; Entecavir hydrate (JAN); Entecavir monohydrate; SQ-34676
Drug Type
Small molecular drug
Indication Chronic hepatitis B infection [ICD11:1E51.0] Approved [1]
Therapeutic Class
Antiviral Agents
Structure
3D MOL 2D MOL
Formula
C12H15N5O3
Canonical SMILES
C=C1C(CC(C1CO)O)N2C=NC3=C2N=C(NC3=O)N
InChI
InChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1
InChIKey
QDGZDCVAUDNJFG-FXQIFTODSA-N
CAS Number
CAS 142217-69-4
Pharmaceutical Properties Molecular Weight 277.28 Topological Polar Surface Area 126
Heavy Atom Count 20 Rotatable Bond Count 2
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 5
XLogP
-1.3
PubChem CID
135398508
PubChem SID
17398002 ,37101953 ,49830936 ,56391942 ,57379683 ,91749140 ,99319526 ,104253461 ,118313779 ,124757591 ,125001900 ,125164395 ,126651626 ,134222146 ,136920321 ,137129051 ,137179356 ,152034465 ,162011500 ,162183301 ,163370951 ,163908003 ,164825059 ,164833113 ,172087090 ,172440023 ,174531851 ,175265673 ,180672743 ,186013131 ,196106268 ,198991663 ,210274904 ,210280539 ,223379249 ,223398838 ,226415922 ,249739265 ,251893489 ,252110220 ,252162333 ,252316076
ChEBI ID
CHEBI:473990
TTD Drug ID
D0KR2J
DT(s) Transporting This Drug 3-Oct Transporter Info Organic cation transporter 3 Substrate [2]
BCRP Transporter Info Breast cancer resistance protein Substrate [2]
CNT2 Transporter Info Concentrative nucleoside transporter 2 Substrate [2]
CNT3 Transporter Info Concentrative Na(+)-nucleoside cotransporter 3 Substrate [2]
ENT1 Transporter Info Equilibrative nucleoside transporter 1 Substrate [2]
ENT2 Transporter Info Equilibrative nucleoside transporter 2 Substrate [2]
OAT2 Transporter Info Organic anion transporter 2 Substrate [3]
OCTN2 Transporter Info Organic cation/carnitine transporter 2 Substrate [2]
PEPT2 Transporter Info Peptide transporter 2 Substrate [4]
Drug-Transporter Activity Data
Drug-Transporter Activity Data CNT2 Transporter Info Km =53.2 microM Madin-Darby canine kidney (MDCK) cells-hCNT2 [2]
CNT3 Transporter Info Km =23.1 microM Madin-Darby canine kidney (MDCK) cells-hCNT3 [2]
References
1 Entecavir was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Multiple SLC and ABC Transporters Contribute to the Placental Transfer of Entecavir. Drug Metab Dispos. 2017 Mar;45(3):269-278.
3 Human organic anion transporter 2 is an entecavir, but not tenofovir, transporter. Drug Metab Pharmacokinet. 2017 Feb;32(1):116-119.
4 The oligopeptide transporter 2-mediated reabsorption of entecavir in rat kidney. Eur J Pharm Sci. 2014 Feb 14;52:41-7.

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