Compound: ondansetron
SMILES: O=C1c2c3c(cccc3)n(c2CCC1Cn4c(ncc4)C)C
InChIKey: FELGMEQIXOGIFQ-UHFFFAOYSA-N
Synonyms: ondansetron, 99614-02-5, Zudan, Zofran ODT, Zuplenz, 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one, 4AF302ESOS, DTXSID8023393, A04AA01, EUR-1025, NSC-757870, 1,2,3,9-Tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-4H-carbazol-4-one, 9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-2,3,4,9-tetrahydro-1H-carbazol-4-one, DTXCID803393, 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one, Odansetron [common misspelling of ondansetron], 4H-Carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-, Odansetron (common misspelling of ondansetron), ondansetronum, ondasetron, Ondansetron ODT, 9-methyl-3-((2-methylimidazol-1-yl)methyl)-2,3-dihydro-1H-carbazol-4-one, 9-methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-2,3,4,9-tetrahydro-1H-carbazol-4-one, ODT, Zofran, Ondansetron Monohydrochloride Dihydrate, RefChem:6085, Hydrochloride, Ondansetron, Ondansetron, (+,-)-, Monohydrochloride, Ondansetron, SN307, Dihydrate, Ondansetron Monohydrochloride, Monohydrochloride Dihydrate, Ondansetron, 9-Methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-2,3-dihydro-1H-carbazol-4(9H)-one, 116002-70-1, MFCD00833882, Ondansetron (Hydrochloride), NCGC00179341-02, 9-methyl-3-((2-methyl-1H-imidazol-1-yl)methyl)-1,2,3,9-tetrahydro-4H-carbazol-4-one, 9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one, GR 38032 (hydrochloride);SN 307 (hydrochloride), ondansetron (Zofran), GR 38032X, CAS-99614-02-5, Ondansetron Injection, Zofran ODT (TN), GR 38032, DESMETHYLONDANSETRON, UNII-4AF302ESOS, BRN 3622981, Ondanserton, Ondansetron (JAN/USP/INN), Ondansetron [USP:INN:BAN], SR-01000763250, 9-methyl-3-[(2-methylimidazolyl)methyl]-1,2,3,9-tetrahydro-4aH-carbazol-4-one, Ondansetron (Standard), GR-38032, CHEMBL46, ONDANSETRON [MI], Prestwick0_001058, Prestwick1_001058, Prestwick2_001058, Prestwick3_001058, ONDANSETRON [INN], ONDANSETRON [JAN], ONDANSETRON [VANDF], SCHEMBL4542, TimTec1_001750, (RS)-1,2,3,9-Tetrahydro-9-methyl-3-(2-methylimidazol-1-ylmethyl)carbazol-4-one, ONDANSETRON [MART.], Ondansetron Impurity Standard, Oprea1_435466, Oprea1_852372, BSPBio_001016, CBDivE_008994, ONDANSETRON [USP-RS], ONDANSETRON [WHO-DD], MLS006011928, SPBio_002938, BPBio1_001118, CHEBI:7773, GTPL2290, HY-B0002BR, SCHEMBL29358872, BDBM85330, HSDB 8304, HY-B0002B, ONDANSETRON [ORANGE BOOK], GLXC-07759, HMS2090H16, HMS3259H08, HMS3371E18, ONDANSETRON [USP MONOGRAPH], MSK10280, Tox21_113048, CAS_68647, EBC-06052, NSC_68647, NSC791005, s1996, SBB066158, STK370548, AKOS000599484, AKOS016340526, Tox21_113048_1, DB00904, KS-5227, NC00706, NSC 757870, NSC-791005, 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H- carbazol-4-one, NCGC00179341-04, NCGC00179341-07, NCGC00179341-12, AC-28927, FO157236, NCI60_022780, SMR001307702, ST077669, GR-38032F/GR-38032, Ondansetron(base and/or unspecified salts), GR 38032F;GR-C507/75, AB00373674, NS00010141, C07325, D00456, EN300-117273, AB00373674-15, AB00373674-17, AB00373674_18, AB00373674_19, F047250, L000456, Q410011, SR-01000763250-4, BRD-A19736161-001-01-8, BRD-A19736161-001-05-9, BRD-A19736161-001-06-7, BRD-A19736161-003-03-0, BRD-A19736161-003-14-7, Z1501485364, (+/-)-2,3-DIHYDRO-9-METHYL-3-((2-METHYLIMIDAZOL-1-YL)METHYL)CARBAZOL-4(1H)-ONE, 1,2,3,4-Tetrahydro-9-methyl-3-(2-methyl-1H-imidazol-1-ylmethyl)carbazole-4-one, 1,2,3,9,-Tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one, 1,2,3,9-Tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1yl)methyl]-4H-carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazole-1 -yl)methyl]-4H-carbazol-4-one, 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazole-1-yl)methyl]-4H-carbazol-4-one, 4H-Carbazol-4-one,?1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-, 9-Methyl-3- (2-methyl-imidazol-1ylmethyl)-1,2,3,9-tetrahydro-carbazol-4-one, 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1~{H}-carbazol-4-one, 4H-CARBAZOL-4-ONE, 1,2,3,9-TETRAHYDRO-9-METHYL-3-((2-METHYL-1H-IMIDAZOL-1-YL)METHYL)- (+/-)-
Theoretical properties:
molecular_formula: C18H19N3O
molecular_weight: 293.4 g/mol
exact_mass: 293.152812238 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 2
heavy_atom_count: 22
topological_polar_surface_area: 39.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from methanol
color: Crystals from methanol
melting_point: 231-232 °C
solubility: Sparingly soluble in water
Descriptions:
pubchem: Ondansetron is a member of carbazoles.
chembl: ONDANSETRON is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Ondansetron, sold under the brand name Zofran among others, is a medication used to prevent nausea and vomiting caused by chemotherapy, radiation therapy, migraines, or surgery. It is also effective for treating gastroenteritis. It can be given orally (by mouth), intramuscularly (injection into a muscle), or intravenously (injection into a vein).
Common side effects include diarrhea, constipation, headache, sleepiness, and itchiness. Serious side effects include QT prolongation and severe allergic reaction. It appears to be safe during pregnancy but has not been well studied in this group. It is a serotonin 5-HT3 receptor antagonist. It does not have any effect on dopamine receptors or muscarinic acetylcholine receptor and therefore does not cause akathisia.
Ondansetron was patented in 1984 and approved for medical use in 1990. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication. In 2023, it was the 53rd most commonly prescribed medication in the United States, with more than 12 million prescriptions.