Compound: oxymorphone
SMILES: O=C1[C@@H]2Oc3c(O)ccc4c3[C@]25[C@](O)([C@H](N(C)CC5)C4)CC1
InChIKey: UQCNKQCJZOAFTQ-ISWURRPUSA-N
Synonyms: oxymorphone, 76-41-5, Oximorphonum, 14-Hydroxydihydromorphinone, Dihydrohydroxymorphinone, Dihydroxymorphinone, Oximorfona, (-)-Oxymorphone, 7,8-Dihydro-14-hydroxymorphinone, Oxymorphonum, Oxymorphone cii, Dihydro-14-hydroxymorphinone, (14S)-14-Hydroxydihydromorphinone, Morphinone, dihydro-14-hydroxy-, NSC-19045, 9VXA968E0C, IDS-NO-003, NIH 10323, DTXSID5023409, NSC19045, Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-methyl-, (5alpha)-, MORPHINAN-6-ONE, 4,5-EPOXY-3,14-DIHYDROXY-17-METHYL-, Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-methyl-, (5-alpha)-, oximorfone, (1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7(18),8,10-trien-14-one, (1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one, (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7-one, (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one, RefChem:55796, DTXCID703409, 4,5alpha-Epoxy-3,14-dihydroxy-17-methylmorphinan-6-one, (1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.01,13.05,17.07,18)octadeca-7(18),8,10-trien-14-one, (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-one, 200-959-7, Numorphan, Oxymorphine, Opana, Numorphone, CHEMBL963, CHEBI:7865, NIH10323, Oxymorphone (INN), 3,14-Dihydroxy-4,5-alpha-epoxy-17-methylmorphinan-6-one, OXYMORPHONE [INN], Ossimorfone, Morphinan-6-one, 3,14-dihydroxy-4,5-alpha-epoxy-17-methyl-, NSC 19045, Oxymorphone (1.0 mg/mL in Methanol), Ossimorfone [DCIT], Oxymorphone [INN:BAN], Oximorfona [INN-Spanish], Oxymorphonum [INN-Latin], UNII-9VXA968E0C, HSDB 8060, EINECS 200-959-7, EN3202, BRN 0041588, OXYMORPHONE [MI], OXYMORPHONE [VANDF], SCHEMBL3571, 4,5.alpha.-Epoxy-3,14-dihydroxy-17-methylmorphinan-6-one, Epitope ID:2270540, OXYMORPHONE [WHO-DD], GTPL7094, DEA No. 9652, SCHEMBL29633247, Oxymorphone, 1mg/ml in Methanol, OXYMORPHONE CII [USP-RS], HY-B0618, Oxymorphone 0.1 mg/ml in Methanol, Oxymorphone 1.0 mg/ml in Methanol, BDBM50001707, Oxycodone Hydrochloride EP Impurity A, AKOS015962232, DB01192, Oxycodone hydrochloride impurity, oxymorphone-, C08019, D08323, Q423380, 4,5-Epoxy-3,14-dihydroxy-N-methyl-6-oxomorphinan, Morphinone, 7,8-dihydro-14-hydroxy- (6CI,7CI), OXYCODONE HYDROCHLORIDE IMPURITY A [EP IMPURITY], 3,14-Dihydroxy-17-methyl-5alpha-4,5-epoxymorphinan-6-one, 4,5alpha-Epoxy-3,14-dihydroxy-17-methyl morphinan-6-one, Morphinan-6-one,5.alpha.-epoxy-3,14-dihydroxy-17-methyl-, (5alpha)-3,14-dihydroxy-17-methyl-4,5-epoxymorphinan-6-one, (5alpha)-4,5-Epoxy-3,14-dihydroxyl-17-methylmorphinan-6-one, Morphinan-6-one, 4,5alpha-epoxy-3,14-dihydroxy-17-methyl-, Morphinan-6-one, 4,5alpha-epoxy-3,14-dihydroxy-17-methyl- (8CI), Morphinan-6-one,5-epoxy-3,14-dihydroxy-17-methyl-, (5.alpha.)-, OXYCODONE HYDROCHLORIDE IMPURITY, OXYMORPHONE- [USP IMPURITY], Morphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-methyl-, (5alpha)- (9CI), (4R,4aS,7aR,12bS)-4a,9-dihydroxy-3-methyl-2,3,4,4a,5,6-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one, 10,17-dihydroxy-4-methyl-(13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one, 10,17-dihydroxy-4-methyl-(13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one(oxymorphone), 10,17-dihydroxy-4-methyl-(13R,17S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one(xymorphone), 10,17-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18)-trien-14-one
Theoretical properties:
molecular_formula: C17H19NO4
molecular_weight: 301.34 g/mol
exact_mass: 301.13140809 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 0
heavy_atom_count: 22
topological_polar_surface_area: 70 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from boiling ethanol, ethyl acetate, or benzene
color: Crystals from boiling ethanol, ethyl acetate, or benzene
melting_point: 248-249 °C
Descriptions:
pubchem: Oxymorphone is a morphinane alkaloid.
chembl: OXYMORPHONE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Oxymorphone (sold under the brand names Numorphan and Opana among others) is a highly potent opioid analgesic indicated for treatment of severe pain. Pain relief after injection begins after about 5–10 minutes; after oral administration it begins after about 30 minutes and lasts about 3–4 hours for immediate-release tablets and 12 hours for extended-release tablets. The elimination half-life of oxymorphone is much faster intravenously, and as such, the drug is most commonly used orally. Like oxycodone, which metabolizes to oxymorphone, oxymorphone has a high abuse potential.
Oxymorphone was developed in Germany in 1914. It was patented in 1955 and approved for medical use in 1959. In June 2017 the FDA asked Endo Pharmaceuticals to remove its product from the US market. This was in part due to the opioid epidemic in the US, and the fact that a 2012 reformulation failed to stop illicit injection of the drug. Endo responded by voluntarily removing Opana ER from the market a month later. Generic versions of extended-release oxymorphone, such as those manufactured by Amneal Pharmaceuticals, are still available in the US.