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Also known as: 74103-06-3, 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic acid, Ketorolaco, Ketorolacum [latin], Ketorolaco [spanish], Ketoralac
Molecular Formula
C15H13NO3
Molecular Weight
255.27  g/mol
InChI Key
OZWKMVRBQXNZKK-UHFFFAOYSA-N
FDA UNII
YZI5105V0L

CAS 74103-06-3
A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is an NSAID and is used principally for its analgesic activity. (From Martindale The Extra Pharmacopoeia, 31st ed)
Ketorolac is a Nonsteroidal Anti-inflammatory Drug and Cyclooxygenase Inhibitor. The mechanism of action of ketorolac is as a Cyclooxygenase Inhibitor.
1 2D Structure

CAS 74103-06-3

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
2.1.2 InChI
InChI=1S/C15H13NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13/h1-7,11H,8-9H2,(H,18,19)
2.1.3 InChI Key
OZWKMVRBQXNZKK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CN2C(=CC=C2C(=O)C3=CC=CC=C3)C1C(=O)O
2.2 Other Identifiers
2.2.1 UNII
YZI5105V0L
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 74103-06-3

2. 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

3. Ketorolaco

4. Ketorolacum [latin]

5. Ketorolaco [spanish]

6. Ketoralac

7. Ketorolacum

8. Macril

9. (+-)-ketorolac

10. 66635-83-4

11. Rac-ketorolac

12. Rs 37619

13. Ketorolac (inn)

14. Toradol (tn)

15. (+-)-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

16. Yzi5105v0l

17. 1h-pyrrolizine-1-carboxylic Acid, 5-benzoyl-2,3-dihydro-

18. Chebi:76223

19. Mfcd00864281

20. Rs37619

21. Ketorolac [inn]

22. 5-(phenylcarbonyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

23. Ketorolac [inn:ban]

24. Rs-37619

25. Unii-yzi5105v0l

26. Toraldar

27. Rac Ketorolac-[d4]

28. Ketorolac [mi]

29. Ketorolac [vandf]

30. Ncgc00185990-01

31. Chembl469

32. Ketorolac [who-dd]

33. Schembl14891

34. Mls006011844

35. Chebi:6129

36. Gtpl6661

37. Dtxsid8023189

38. Bdbm85511

39. Hms3604j05

40. Hms3884m04

41. Hy-b0580

42. 1h-pyrrolizine-1-carboxylic Acid, 2,3-dihydro-5-benzoyl-, (+-)-

43. Ac-545

44. S1646

45. Stl018674

46. Akos005657203

47. Ac-1121

48. Ccg-204762

49. Db00465

50. Ks-5175

51. Sdccgsbi-0050655.p004

52. Ncgc00185990-02

53. Ncgc00185990-05

54. Ncgc00185990-15

55. Smr001550090

56. Sy107530

57. Sbi-0050655.p003

58. Cas_74103-07-4

59. Db-011403

60. Ab00053682

61. Ft-0653523

62. Ft-0670664

63. Ft-0670665

64. Ft-0670666

65. C07062

66. D08104

67. F16555

68. Ab00053682-12

69. Ab00053682-14

70. Ab00053682_15

71. Ab00053682_16

72. 635k834

73. A934549

74. Q2014797

75. Brd-a40639672-234-05-7

76. Brd-a40639672-234-09-9

77. 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylicacid

78. Ketorolac, Ketorolactromethamine, Ketorolac Tromethamine

79. 5-(benzoyl)-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

80. 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid #

81. Rac-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

82. (+/-)-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

83. (1rs)-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

84. (.+/-.)-2,3-dihydro-5-benzoyl-1h-pyrrolizine-1-carboxylic Acid

85. (.+/-.)-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

86. 5-benzoyl-1,2-dihydro-3h-pyrrolo[1,2-a]pyrrole-1-carboxylic Acid

87. 1h-pyrrolizine-1-carboxylic Acid, 2,3-dihydro-5-benzoyl-, (.+/-.)-

88. 1h-pyrrolizine-1-carboxylic Acid, 5-benzoyl-2,3-dihydro, (+/-)-

89. 5-benzoyl-2,3-dihydro-1h-pyrrolo[1,2-a]pyrrole-1-carboxylic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 255.27 g/mol
Molecular Formula C15H13NO3
XLogP31.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count3
Exact Mass255.08954328 g/mol
Monoisotopic Mass255.08954328 g/mol
Topological Polar Surface Area59.3 Ų
Heavy Atom Count19
Formal Charge0
Complexity376
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Ketorolac is a Non-steroidal anti-inflammatory drug (NSAID) and has antipyretic, analgesic and anti-inflammatory properties. It is indicated for short term management of acute pain that requires the calibre of pain management offered by opioids. Clinicians may choose to initiate ketorolac to manage post-operative pain, spinal and soft tissue pain, rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, menstrual disorders and headaches among other ailments. Regardless of the etiology of pain, patients should use the lowest possible dose, and avoid using ketorolac for an extended period of time (ideally 5 days). A benefit of choosing ketorolac over other analgesics with similar potency is that that there does not appear to be a risk of dependence or tolerance with ketorolac use.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ketorolac is a non-selective NSAID and acts by inhibiting both COX-1 and COX-2 enzymes which are normally responsible for converting arachidonic acid to prostaglandins. The COX-1 enzyme is constitutively active and can be found in platelets, gastric mucosa, and vascular endothelium. On the other hand, the COX-2 enzyme is inducible and mediates inflammation, pain and fever. As a result, inhibition of the COX-1 enzyme is linked to an increased risk of bleeding and risk of gastric ulceration, while the desired anti-inflammatory and analgesic properties are linked to inhibition of the COX-2 enzyme. Therefore, despite it's effectiveness in pain management, ketorolac should not be used long-term since this increases the risk of serious adverse effects such as gastrointestinal bleeding, peptic ulcers, and perforations.


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)


Cyclooxygenase Inhibitors

Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes. (See all compounds classified as Cyclooxygenase Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
KETOROLAC
5.3.2 FDA UNII
YZI5105V0L
5.3.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Cyclooxygenase Inhibitor
5.4 ATC Code

S01BC05

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AB - Acetic acid derivatives and related substances

M01AB15 - Ketorolac


S - Sensory organs

S01 - Ophthalmologicals

S01B - Antiinflammatory agents

S01BC - Antiinflammatory agents, non-steroids

S01BC05 - Ketorolac


5.5 Absorption, Distribution and Excretion

Absorption

Ketorolac is rapidly, and completely absorbed after oral administration with a bioavailability of 80% after oral administration. Cmax is attained 20-60 minutes after administration, and after intramuscular administration, the area under the plasma concentration-time curve (AUC) is proportional to the dose administered. After intramuscular administration, ketorolac demonstrates a time to maximal plasma concentration (tmax) of approximately 45-50 minutes, and a tmax of 30-40 minutes after oral administration. The rate of absorption may be reduced by food; however, the extent of absorption remains unaffected.


Route of Elimination

Ketorolac is primarily renally eliminated and approximately 92% of the dose can be recovered in the urine with 60% of this proportion recovered unchanged, and 40% recovered as metabolites. In addition 6% of a single dose is eliminated in the feces.


Volume of Distribution

The apparent volume of distribution of ketorolac in healthy human subjects is 0.25 L/kg or less.


Clearance

The plasma clearance of ketorolac is 0.021 to 0.037 L/h/kg. Further, studies have illustrated that clearance of oral, IM and IV doses of ketorolac are comparable which suggests linear kinetics. It should also be noted that clearance in children is about double the clearance found in adults.


5.6 Metabolism/Metabolites

Ketorolac is heavily metabolized via hydroxylation or conjugation in the liver; however, it appears that the key metabolic pathway is glucuronic acid conjugation. Enzymes involved in phase I metabolism include CYP2C8 and CYP2C9, while phase II metabolism is carried out by UDP-glucuronosyltransferase (UGT) 2B7.


5.7 Biological Half-Life

Ketorolac tromethamine is administered as a racemic mixture, therefore the half-life of each enantiomer must be considered. The half life of the S-enantiomer is ~2.5 hours, while the half life of the R-enantiomer is ~5 hours. Based on this data, the S enantiomer is cleared about twice as fast as the R enantiomer.


5.8 Mechanism of Action

Ketorolac inhibits key pathways in prostaglandin synthesis which is crucial to it's mechanism of action. Although ketorolac is non-selective and inhibits both COX-1 and COX-2 enzymes, it's clinical efficacy is derived from it's COX-2 inhibition. The COX-2 enzyme is inducible and is responsible for converting arachidonic acid to prostaglandins that mediate inflammation and pain. By blocking this pathway, ketorolac achieves analgesia and reduces inflammation. Ketorolac is administered as a racemic mixture; however, the "S" enantiomer is largely responsible for it's pharmacological activity.


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