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Entecavir Hydrate

PubChem CID
135526609
Structure
Entecavir Hydrate_small.png
Entecavir Hydrate_3D_Structure.png
Entecavir Hydrate__Crystal_Structure.png
Molecular Formula
Synonyms
  • Entecavir hydrate
  • entecavir monohydrate
  • 209216-23-9
  • Entecavir (monohydrate)
  • Entecavir hydrate (JAN)
Molecular Weight
295.29 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2019-01-15
  • Modify:
    2025-01-18
Description
Entecavir hydrate is the monohydrate form of entecavir. A synthetic analogue of 2'-deoxyguanosine, entecavir is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. It is phosphorylated intracellularly to the active triphosphate form, which competes with deoxyguanosine triphosphate, the natural substrate of hepatitis B virus reverse transcriptase, inhibiting every stage of the enzyme's activity, although it has no activity against HIV. Enteclavir is used for the treatment of chronic hepatitis B. It has a role as an EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor and an antiviral drug. It contains an entecavir (anhydrous).
ENTECAVIR is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 2005 and has 4 approved and 8 investigational indications. This drug has a black box warning from the FDA.
See also: Entecavir (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Entecavir Hydrate.png

1.2 3D Conformer

3D Conformer of Parent

1.3 Crystal Structures

COD Number
Associated Article
Jiang, Bin; Liu, Zhilu. 2-Amino-9-[(1S,3R,4S)-4-hydroxy-3-hydroxymethyl-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one monohydrate. Acta Crystallographica Section E 2009;65(9):o2232-. DOI: 10.1107/S1600536809032966
Crystal Structure Depiction
Crystal Structure Depiction
Hermann-Mauguin space group symbol
C 2 2 21
Hall space group symbol
C 2c 2
Space group number
20
a
6.9986 Å
b
11.6229 Å
c
33.932 Å
α
90.00 °
β
90.00 °
γ
90.00 °
Z
8
Z'
1
Residual factor
0.0336
Component
1 x O (Water)
Component
1 x OC[C@@H]1[C@@H](O)C[C@@H](C1=C)n1cnc2c1nc(N)[nH]c2=O (Entecavir)

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one;hydrate
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C12H15N5O3.H2O/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);1H2/t6-,7-,8-;/m0./s1
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

YXPVEXCTPGULBZ-WQYNNSOESA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

C=C1[C@H](C[C@@H]([C@H]1CO)O)N2C=NC3=C2N=C(NC3=O)N.O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C12H17N5O4
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 KEGG ID

2.3.7 Metabolomics Workbench ID

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 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 monohydrate
  • anhydrous entecavir
  • Baraclude
  • BMS 200475
  • BMS-200475
  • BMS-200475-01
  • BMS-20047501
  • BMS20047501
  • entecavir
  • entecavir hydrate
  • entecavir monohydrate
  • SQ-34676
  • SQ34676

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
295.29 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
295.12805404 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
295.12805404 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
127 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
21
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
480
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
2
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Chemical Classes

3.2.1 Drugs

3.2.1.1 Human Drugs
Human drugs -> Antivirals for systemic use -> Human pharmacotherapeutic group -> EMA Drug Category

4 Spectral Information

4.1 IR Spectra

4.1.1 FTIR Spectra

Instrument Name
Bio-Rad FTS
Technique
KBr0
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/13831>13831</a>
Lot Number
0445069-19
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/13831>13831</a>
Lot Number
0445069-19
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/13831>13831</a>
Lot Number
0445069-19
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Entecavir Mylan is indicated for the treatment of chronic hepatitis B virus (HBV) infection in adults with: compensated liver disease and evidence of active viral replication, persistently elevated serum alanine aminotransferase (ALT) levels and histological evidence of active inflammation and/or fibrosis. decompensated liver disease. For both compensated and decompensated liver disease, this indication is based on clinical trial data in nucleoside naive patients with HBeAg positive and HBeAg negative HBV infection. With respect to patients with lamivudine-refractory hepatitis B. Entecavir Mylan is also indicated for the treatment of chronic HBV infection in nucleoside naive paediatric patients from 2 to

7.2 Clinical Trials

7.2.1 EU Clinical Trials Register

7.2.2 NIPH Clinical Trials Search of Japan

7.3 EMA Drug Information

Category
Human drugs
Therapeutic area
Hepatitis B
Active Substance
entecavir monohydrate
INN/Common name
entecavir
Pharmacotherapeutic Classes
Antivirals for systemic use
Status
This medicine is authorized for use in the European Union
Company
Mylan Pharmaceuticals Limited
Market Date
2017-09-18

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Antiviral Agents
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

8.2 ATC Code

J05AF10

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Human drugs -> Antivirals for systemic use -> Human pharmacotherapeutic group -> EMA Drug Category

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Note
Pictograms displayed are for 71.4% (5 of 7) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 28.6% (2 of 7) of reports.
Pictogram(s)
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H302 (71.4%): Harmful if swallowed [Warning Acute toxicity, oral]

H351 (57.1%): Suspected of causing cancer [Warning Carcinogenicity]

H360 (28.6%): May damage fertility or the unborn child [Danger Reproductive toxicity]

H361 (28.6%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

H362 (28.6%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]

H372 (57.1%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

Precautionary Statement Codes

P203, P260, P263, P264, P270, P280, P301+P317, P318, P319, P330, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 7 reports by 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 per 2 of 7 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 4 notifications provided by 5 of 7 reports by companies with hazard statement code(s).

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.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (71.4%)

Carc. 2 (57.1%)

Repr. 1B (28.6%)

Repr. 2 (28.6%)

Lact. (28.6%)

STOT RE 1 (57.1%)

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Chemical Co-Occurrences in Literature

12.5 Chemical-Gene Co-Occurrences in Literature

12.6 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Biological Test Results

14.1 BioAssay Results

15 Classification

15.1 MeSH Tree

15.2 NCI Thesaurus Tree

15.3 ChEBI Ontology

15.4 KEGG: Drug

15.5 KEGG: USP

15.6 KEGG: ATC

15.7 KEGG: Drug Groups

15.8 KEGG : Antimicrobials

15.9 ChemIDplus

15.10 ChEMBL Target Tree

15.11 UN GHS Classification

15.12 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one, monohydrate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.116.642
    2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one, monohydrate (EC: 606-668-5)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/51349
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. ChEBI
  6. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  7. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  8. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  9. EU Clinical Trials Register
  10. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  11. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Therapeutic category of drugs in Japan
    http://www.genome.jp/kegg-bin/get_htext?br08301.keg
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  12. Metabolomics Workbench
  13. NIPH Clinical Trials Search of Japan
  14. SpectraBase
  15. Springer Nature
  16. Wikidata
  17. PubChem
  18. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  19. GHS Classification (UNECE)
  20. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
CONTENTS