Compound: Entecavir
SMILES: O=c1nc([nH]c2c1ncn2[C@@H]3C(=C)[C@H](CO)[C@H](C3)O)N
InChIKey: QDGZDCVAUDNJFG-FXQIFTODSA-N
Synonyms: Entecavir, 142217-69-4, Baraclude, anhydrous entecavir, Entecavir anhydrous, BMS 200475, BMS-200475, entecavir (anhydrous), NNU2O4609D, DTXSID4046446, CHEBI:473990, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-, DTXCID2026446, SQ-34676, 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one, 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl)-, Entecavirum, 2-amino-9-((1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl)-6,9-dihydro-3H-purin-6-one, RefChem:5792, J05AF10, BMS20047501, BMS-20047501, 604-279-5, 6H-Purin-6-One, 2-Amino-1,9-Dihydro-9-((1S,3R,4S)-4-Hydroxy-3-(Hydroxymethyl)-2-Methylenecyclopentyl)-Monohydrate, 5968Y6H45M, 9-((1S,3R,4S)-4-Hydroxy-3-(Hydroxymethyl)-2-Methylenecyclopentyl)Guanine Monohydrate, BMS-200475-01, SQ34676, 2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one, MFCD00907887, Entecavir [USAN:INN], 2-AMINO-9-((1S,3R,4S)-4-HYDROXY-3-(HYDROXYMETHYL)-2-METHYLENECYCLOPENTYL)-1H-PURIN-6(9H)-ONE, 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one, Entecavir (INN), Entecavir [INN], 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-1H-purin-6-one, 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-3H-purin-6-one, 1333204-94-6, 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-methylidenecyclopentyl]-1,9-dihydro-6H-purin-6-one, UNII-NNU2O4609D, Entecavir sodium, HSDB 7334, NCGC00164563-01, 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylene-cyclopentyl]-1H-purin-6-one, 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-[4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-, [1S-(1a,3a,4ss)]-; BMS 200475; Baraclude; Entecavir; SQ 34676, ENTECAVIR [MI], ENTECAVIR [HSDB], CHEMBL713, ENTECAVIR [WHO-DD], SCHEMBL28648, Baraclude, BMS 200475, SCHEMBL367156, orb1310954, Entecavir, >=98% (HPLC), SCHEMBL15198001, 2-amino-9-[4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-1,9-dihydro-6H-purin-6-one, QDGZDCVAUDNJFG-FXQIFTODSA-N, GLXC-07996, MSK10442, Tox21_112192, BDBM50248008, EBC-26411, MFCD11046562, AKOS015854916, AKOS015920226, AKOS025312554, AC-1593, CCG-267218, CS-3160, DB00442, GS-6386, 2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylene-cyclopentyl]-3H-purin-6-one, NCGC00164563-04, NCGC00164563-06, NCGC00164563-09, NCGC00164563-11, NCGC00164563-13, HY-13623, SY028610, SQ 34,676, CAS-142217-69-4, E0899, S5246, D07896, AR-270/43507901, EN300-37158607, F093332, Q418586, BRD-K08206212-001-01-2, BRD-K08206212-002-01-0, 9-[(1S,3R,4S)-4-Hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]guanine, 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, 6-H-Purin-6-one-,2-amino-1,9-dihydro-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]
Theoretical properties:
molecular_formula: C12H15N5O3
molecular_weight: 277.28 g/mol
exact_mass: 277.11748936 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 2
heavy_atom_count: 20
topological_polar_surface_area: 126 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off white powder
color: White to off white powder
solubility: Slightly soluble (2.4 mg/mL at pH 7.9, 25 °C)
Descriptions:
{"pubchem": "Entecavir (anhydrous) is 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. It has a role as an antiviral drug and an EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor. It is a primary alcohol, a member of 2-aminopurines, an oxopurine and a secondary alcohol.", "chebi": "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.", "chembl": "ENTECAVIR ANHYDROUS is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Entecavir, sold under the brand name Baraclude, is an antiviral medication used in the treatment of hepatitis B virus infection. In those with both HIV/AIDS and hepatitis B virus antiretroviral medication should also be used. Entecavir is taken by mouth as a tablet or solution.\nCommon side effects include headache, nausea, high blood sugar, and decreased kidney function. Severe side effects include enlargement of the liver, high blood lactate levels, and liver inflammation if the medication is stopped. While there appears to be no harm from use during pregnancy, this use has not been well studied. Entecavir is in the nucleoside reverse transcriptase inhibitors (NRTIs) family of medications. It prevents the hepatitis B virus from multiplying by blocking reverse transcriptase.\nEntecavir was approved for medical use in 2005. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication."}