ENTECAVIR

Search structure
Trade Names:
Synonyms:
Status: Approved (2005)
Entry Type: Small molecule
Molecule Category: UNKNOWN Prodrug
ATC: J05AF10
UNII: NNU2O4609D

Structure
InChI Key QDGZDCVAUDNJFG-FXQIFTODSA-N
Smile C=C1[C@@H](n2cnc3c(=O)[nH]c(N)nc32)C[C@H](O)[C@H]1CO
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H15N5O3
Molecular Weight 277.28
AlogP -0.83
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 4.0
Number of Rotational Bond 2.0
Polar Surface Area 130.05
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 20.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR DNA polymerase/reverse transcriptase inhibitor DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Structural protein
0 - - - 23-98

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Hepatitis D 2 D003699 ClinicalTrials
Liver Failure 2 D017093 ClinicalTrials
Hepatitis C, Chronic 2 D019698 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Liver Neoplasms 2 D008113 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Cardiac disorders Oedema peripheral 16.0
Cardiac disorders Ascites 15.0
Investigations Body temperature increased 14.0
Renal and urinary disorders Haematuria 10.0
Hepatobiliary disorders Hepatic encephalopathy 10.0
Infections and infestations Upper respiratory tract infection 10.0
Renal and urinary disorders Haematuria 9.0
Nervous system disorders Headache 9.0
Nervous system disorders Headache 8.0
Nervous system disorders Headache 7.0
General disorders and administration site conditions Asthenia 6.0
General disorders and administration site conditions Fatigue 6.0
Renal and urinary disorders Glycosuria 6.0
Renal and urinary disorders Haematuria 6.0
Gastrointestinal disorders Abdominal pain upper 5.0
General disorders and administration site conditions Asthenia 5.0
General disorders and administration site conditions Fatigue 5.0
Cardiac disorders Dizziness 4.0
Renal and urinary disorders Glycosuria 4.0
Gastrointestinal disorders Abdominal pain upper 3.0
General disorders and administration site conditions Asthenia 3.0
Cardiac disorders Dizziness 3.0
General disorders and administration site conditions Fatigue 3.0
Renal and urinary disorders Glycosuria 3.0
Gastrointestinal disorders Nausea 3.0
Gastrointestinal disorders Abdominal pain upper 2.0
Investigations Blood bicarbonate decreased 2.0
Cardiac disorders Dizziness 2.0
Gastrointestinal disorders Dyspepsia 2.0
Nervous system disorders Headache 2.0
Endocrine disorders Hyperglycaemia 2.0
Nervous system disorders Insomnia 2.0
Gastrointestinal disorders Nausea 2.0
General disorders and administration site conditions Asthenia 1.0
Gastrointestinal disorders Diarrhoea 1.0
Cardiac disorders Dizziness 1.0
Gastrointestinal disorders Dyspepsia 1.0
General disorders and administration site conditions Fatigue 1.0
Nervous system disorders Headache 1.0
Endocrine disorders Hyperglycaemia 1.0
Nervous system disorders Insomnia 1.0
Gastrointestinal disorders Nausea 1.0
Renal and urinary disorders Renal failure 1.0
Nervous system disorders Somnolence 1.0
Gastrointestinal disorders Vomiting 1.0

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
10.24
Hepatobiliary disorders
9.14
Injury, poisoning and procedural complications
8.06
Pregnancy, puerperium and perinatal conditions
7.28
Gastrointestinal disorders
6.69
Nervous system disorders
6.33
Vascular disorders
5.05
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
4.98
Surgical and medical procedures
4.78
Investigations
4.76
Infections and infestations
4.66
Renal and urinary disorders
3.49
Cardiac disorders
3.37
Respiratory, thoracic and mediastinal disorders
2.94
Skin and subcutaneous tissue disorders
2.82
Blood and lymphatic system disorders
2.61
Metabolism and nutrition disorders
2.45
Psychiatric disorders
2.3
Musculoskeletal and connective tissue disorders
2.24
Immune system disorders
2.12

Cross References

Resources Reference
CAS NUMBER 142217-69-4
ChEBI 473990
ChEMBL CHEMBL713
DrugBank DB00442
DrugCentral 1019
EPA CompTox DTXSID4046446
FDA SRS NNU2O4609D
Human Metabolome Database HMDB0014585
PharmGKB PA164784025
PubChem 135526609
SureChEMBL SCHEMBL28648
ZINC ZINC000003802690
CONTENTS