Compound: ketorolac
SMILES: O=C(c1ccccc1)c2n3c(C(C(=O)O)CC3)cc2
InChIKey: OZWKMVRBQXNZKK-UHFFFAOYSA-N
Synonyms: ketorolac, 74103-06-3, Ketorolaco, Ketorolacum, (+-)-Ketorolac, rac-ketorolac, CHEBI:6129, YZI5105V0L, (+-)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, DTXSID8023189, 1H-Pyrrolizine-1-carboxylic acid, 2,3-dihydro-5-benzoyl-, (+-)-, 5-(benzoyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, 1H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro, RefChem:55433, DTXCID503189, M01AB15, S01BC05, 5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, Ketorolacum [Latin], 66635-83-4, Ketorolaco [Spanish], Ketoralac, MFCD00864281, RS 37619, Ketorolac (INN), Toradol (TN), (1RS)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, RS37619, KETOROLAC [INN], Macril, 5-(phenylcarbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, Ketorolac [INN:BAN], RS-37619, rac Ketorolac, NCGC00185990-01, UNII-YZI5105V0L, Toraldar, 1H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro-, Ketorolac (NSAID), Ketorolac (Standard), KETOROLAC [MI], KETOROLAC [VANDF], CHEMBL469, Epitope ID:613435, KETOROLAC [WHO-DD], SCHEMBL14891, MLS006011844, GTPL6661, orb1306372, BDBM85511, CHEBI:76223, HY-B0580R, MSK8003, GLXC-08186, HMS3604J05, HMS3884M04, HMS5079H06, HY-B0580, QYB76766, RYB45153, AC-545, EBC-03780, MSK8003-100A, s1646, STL018674, AKOS005657203, AC-1121, CCG-204762, DB00465, FK35139, IB58062, KS-5175, SDCCGSBI-0050655.P004, NCGC00185990-02, NCGC00185990-05, NCGC00185990-15, SMR001550090, SY107530, SBI-0050655.P003, CAS_74103-07-4, DB-011403, AB00053682, NS00009482, Ketorolac Solution in Acetonitrile, 100ug/mL, C07062, D08104, EN300-170843, F16555, AB00053682-12, AB00053682-14, AB00053682_15, AB00053682_16, F242512, Q2014797, BRD-A40639672-001-01-9, BRD-A40639672-234-05-7, BRD-A40639672-234-09-9, BRD-A40639672-234-17-2, BRD-A40639672-234-18-0, 5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylicacid, KETOROLAC, ketorolactromethamine, Ketorolac Tromethamine, Z2429420872, 5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid #, rac-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, (+/-)-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic acid, (.+/-.)-2,3-Dihydro-5-benzoyl-1H-pyrrolizine-1-carboxylic acid, (.+/-.)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid, 5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid - Racemic, 1H-Pyrrolizine-1-carboxylic acid, 2,3-dihydro-5-benzoyl-, (.+/-.)-, 1H-PYRROLIZINE-1-CARBOXYLIC ACID, 5-BENZOYL-2,3-DIHYDRO, (+/-)-, 5-BENZOYL-2,3-DIHYDRO-1H-PYRROLO[1,2-A]PYRROLE-1-CARBOXYLIC ACID
Theoretical properties:
molecular_formula: C15H13NO3
molecular_weight: 255.27 g/mol
exact_mass: 255.08954328 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 3
heavy_atom_count: 19
topological_polar_surface_area: 59.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 162-165 °C (tromethamine salt)
Descriptions:
{"pubchem": "Ketorolac is a racemate comprising equimolar amounts of (R)-(+)- and (S)-()-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-() enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure. It has a role as a non-steroidal anti-inflammatory drug, an analgesic, a cyclooxygenase 2 inhibitor and a cyclooxygenase 1 inhibitor. It contains a (R)-ketorolac and a (S)-ketorolac. It is a conjugate acid of a ketorolac(1-).", "chebi": "A racemate comprising equimolar amounts of (<i>R</i>)-(+)- and (<i>S</i>)-(\u2212)-5-benzoyl-2,3-dihydro-1<em>H</em>-pyrrolizine-1-carboxylic acid. While only the (<i>S</i>)-(\u2212) enantiomer is a COX1 and COX2 inhibitor, the (<i>R</i>)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.", "chembl": "KETOROLAC is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Ketorolac, sold under the brand name Toradol, Acular and Sprix, among others, is a nonsteroidal anti-inflammatory drug (NSAID) used to treat pain. Specifically it is recommended for moderate to severe pain. Recommended duration of treatment is less than six days, and in Switzerland not more than seven days (parenterally two days). It is used by mouth, by nose, by injection into a vein or muscle, and as eye drops. Effects begin within an hour and last for up to eight hours. Ketorolac also has antipyretic (fever-reducing) properties.\nCommon side effects include sleepiness, dizziness, abdominal pain, swelling, and nausea. Serious side effects may include stomach bleeding, kidney failure, heart attacks, bronchospasm, heart failure, and anaphylaxis. Use is not recommended during the last part of pregnancy or during breastfeeding. Ketorolac works by blocking cyclooxygenase 1 and 2 (COX1 and COX2), thereby decreasing production of prostaglandins.\nKetorolac was patented in 1976 and approved for medical use in 1989. It is available as a generic medication. In 2023, it was the 228th most commonly prescribed medication in the United States, with more than one million prescriptions.\nDue to a series of deaths due to gastrointestinal bleeding and kidney failure, ketorolac as a pain medication was removed from the German market in 1993. When ketorolac was introduced into Germany, it was often used as an opioid replacement in pain therapy because its side effects were perceived as much less severe, it did not produce any dependence, and a dose was effective for 7\u20138 hours compared to morphine with 3\u20134 hours. As a very potent prostaglandin inhibitor, ketorolac diminishes the kidney's own defenses against vasoconstriction-related effects, e.g. during blood loss or high endogenous catecholamine levels."}