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entecavir (anhydrous)

CHEBI:CHEBI_473990

Definition

Guanine substituted at the 9 position by a 4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl group. A synthetic analogue of 2'-deoxyguanosine, it is a nucleoside reverse transcriptase inhibitor with selective antiviral activity against hepatitis B virus. Entecavir 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. It is used for the treatment of chronic hepatitis B.

Chemical Information

Molecular Formula
C12H15N5O3
Molecular Mass
277.27920
Charge
0
SMILES
Nc1nc2n(cnc2c(=O)[nH]1)[C@H]1C[C@H](O)[C@@H](CO)C1=C
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

Alternative Names

  • 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one
  • entecavir

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

core#notation
CHEBI:473990
DRON_00010000
306266
oboInOwl#hasDbXref
LINCS:LSM-5258

Additional References

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

core#notation
CHEBI:473990
has_treatment
http://purl.obolibrary.org/obo/DOID_5497
owl#annotatedSource
t227962
owl#someValuesFrom
t952284
listing_expiration_date
20241231
route
ORAL
marketing_start_date
20150222
spl_id
1a905283-0058-a7dd-e063-6394a90a1909
package_ndc
70771-1020-9
labeler_name
Cipla Ltd.
package_description
90 TABLET, FILM COATED in 1 BOTTLE (70771-1020-9)
oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
306266
oboInOwl#hasDbXref
LINCS:LSM-5258
oboInOwl#id
CHEBI:473990
generic_name
Entecavir Monohydrate
product_type
BULK INGREDIENT
marketing_category
BULK INGREDIENT
dosage_form
GRANULE
brand_name
BARACLUDE
brand_name_base
BARACLUDE
product_ndc
70771-1020
application_number
NDA021797
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_59897
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
rxcui
607579
active_ingredient_strength
50 kg/50kg
nui
N0000175656
pharm_class
Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]
package_marketing_start_date
03-SEP-24
pharm_class_moa
Nucleoside Reverse Transcriptase Inhibitors [MoA]
pharm_class_epc
Hepatitis B Virus Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]
manufacturer_name
Carlsbad Technology, Inc.
active_ingredient_name
ENTECAVIR ANHYDROUS
unii
NNU2O4609D
spl_set_id
1a905283-0057-a7dd-e063-6394a90a1909
upc
0369097426057
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class