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Ketorolac

Synopsis, Chemistry

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Also known as: 74103-07-4, Ketorolac tris salt, Toradol, Acular, Ketorolac (tromethamine salt), Ketorolac tromethamine salt

Molecular Formula

C₁₉H₂₄N₂O₆

Molecular Weight

376.4 g/mol

InChI Key

BWHLPLXXIDYSNW-UHFFFAOYSA-N

FDA UNII

4EVE5946BQ

A pyrrolizine carboxylic acid derivative structurally related to INDOMETHACIN. It is a non-steroidal anti-inflammatory agent used for analgesia for postoperative pain and inhibits cyclooxygenase activity.

1 2D Structure

Ketorolac

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-amino-2-(hydroxymethyl)propane-1,3-diol;5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid

2.1.2 InChI

InChI=1S/C15H13NO3.C4H11NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13;5-4(1-6,2-7)3-8/h1-7,11H,8-9H2,(H,18,19);6-8H,1-3,5H2

2.1.3 InChI Key

BWHLPLXXIDYSNW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN2C(=CC=C2C(=O)C3=CC=CC=C3)C1C(=O)O.C(C(CO)(CO)N)O

2.2 Other Identifiers

2.2.1 UNII

4EVE5946BQ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acular

2. Toradol

2.3.2 Depositor-Supplied Synonyms

1. 74103-07-4

2. Ketorolac Tris Salt

3. Toradol

4. Acular

5. Ketorolac (tromethamine Salt)

6. Ketorolac Tromethamine Salt

7. Ketorolac Trometamol

8. Acular Ls

9. Acuvail

10. Lixidol

11. Acular Pf

12. Sprix

13. Dolac

14. Tarasyn

15. Ketorolac (toradol)

16. 2-amino-2-(hydroxymethyl)propane-1,3-diol 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate

17. Nsc-758637

18. 4eve5946bq

19. Syntex

20. Toradol (tn)

21. (+/-)-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid Tris Salt

22. 2-amino-2-(hydroxymethyl)propane-1,3-diol;5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

23. Godek

24. Acular Preservative Free

25. Ketorolac Tromethamine;ketorolac Tris Salt;rs37619 Tromethamine Salt

26. Chebi:6130

27. Smr000058461

28. Ketorolac Tromethamine [usan]

29. Tromethamine Ketorolac

30. Sr-01000075948

31. Rs-37619

32. Unii-4eve5946bq

33. Toratex

34. Droal

35. Ketorolactrissalt

36. Tora-dol

37. Ketorolac Tromethamine [usan:usp]

38. Acular (tn)

39. Mfcd00887595

40. Bppc

41. Spectrum_001578

42. Cpd000058461

43. Ketorolac Tromethamine Ophthalmic Solution

44. Prestwick0_000929

45. Prestwick1_000929

46. Prestwick2_000929

47. Prestwick3_000929

48. Spectrum2_001598

49. Spectrum3_001975

50. Spectrum4_000215

51. Spectrum5_001273

52. Ketrolac.tromethamine Salt

53. Schembl5036

54. Lopac0_000676

55. Bspbio_000838

56. Bspbio_003575

57. Kbiogr_000849

58. Kbioss_002058

59. (+-)-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid, Compound With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

60. 2-amino-2-(hydroxymethyl)propane-1,3-diol; 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid

61. Ketorolac Tromethamine (usp)

62. Mls000069689

63. Mls001401455

64. Mls002222310

65. Divk1c_000836

66. Spectrum1503925

67. Spbio_001596

68. Spbio_003017

69. Bpbio1_000922

70. Chembl1201124

71. Dtxsid0045597

72. Hms502j18

73. Kbio1_000836

74. Kbio2_002058

75. Kbio2_004626

76. Kbio2_007194

77. Kbio3_002953

78. Rox-828

79. Rox-888

80. Ninds_000836

81. Hms1570j20

82. Hms1922k22

83. Hms2051p06

84. Hms2093m05

85. Hms2097j20

86. Hms2235n13

87. Hms3262g13

88. Hms3373m06

89. Hms3393p06

90. Hms3655e15

91. Hms3714j20

92. Ketorolac Trometamol [jan]

93. Pharmakon1600-01503925

94. Bcp02917

95. Hy-b0138

96. (+/-)-ketorolac Tromethamine Salt

97. Tox21_500676

98. Ccg-39376

99. Ketorolac Trometamol [mart.]

100. Nsc758637

101. S5698

102. Ketorolac Tromethamine [vandf]

103. Akos024386301

104. Bcp9000811

105. Ccg-101006

106. Cs-1933

107. Ketorolac Tromethamine [usp-rs]

108. Ketorolac Tromethamine [who-dd]

109. Lp00676

110. Nc00256

111. Nsc 758637

112. Idi1_000836

113. Ncgc00016159-02

114. Ncgc00016159-03

115. Ncgc00016159-04

116. Ncgc00094036-01

117. Ncgc00094036-02

118. Ncgc00094036-03

119. Ncgc00261361-01

120. 1h-pyrrolizine-1-carboxylic Acid, 5-benzoyl-2,3-dihydro, (+-)-, Compound With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

121. As-15193

122. Ketorolac Tris Salt;ketorolac Tromethamine

123. Bcp0726000301

124. Ketorolac Tris Salt, >=99%, Crystalline

125. Ketorolac Trometamol [ep Monograph]

126. Db-055837

127. Ketorolac Trometamol For Peak Identification

128. Ketorolac Tromethamine [orange Book]

129. Eu-0100676

130. Ft-0630829

131. K0053

132. Sw197293-4

133. Ketorolac Tromethamine [usp Monograph]

134. D00813

135. K 1136

136. M02042

137. Omidria Component Ketorolac Tromethamine

138. 103k074

139. A838011

140. Ketorolac Tromethamine Component Of Omidria

141. Sr-01000946595

142. Q-201269

143. Sr-01000075948-1

144. Sr-01000075948-6

145. Sr-01000075948-8

146. Sr-01000946595-1

147. Ketorolac (+/-)-form Tromethamine Salt [mi]

148. Q27107089

149. F0001-2390

150. Ketorolac Trometamol 1.0 Mg/ml In Methanol (as Free Acid)

151. Ketorolac Trometamol, European Pharmacopoeia (ep) Reference Standard

152. Ketorolac Tromethamine, United States Pharmacopeia (usp) Reference Standard

153. Ketorolac Trometamol For Peak Identification, European Pharmacopoeia (ep) Reference Standard

154. Ketorolac Tromethamine, Pharmaceutical Secondary Standard; Certified Reference Material

155. (+/-)-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylic Acid, Compound With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

156. 1h-pyrrolizine-1-1h-pyrrolizine-1-carboxylic Acid, 5-benzoyl-2,3-dihydro, (+/-)-, Compound With 2-amino-2-(hydroxymethyl)-1,3-propanediol (1:1)

157. 2-amino-2-(hydroxymethyl)propane-1,3-diol (1rs)-5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate

158. 5-benzoyl-2,3-dihydro-1h-pyrrolizine-1-carboxylate; 2-hydroxyethyl-bis(hydroxymethyl)ammonium;ketorolac Tromethamine

2.3.3 Other Synonyms

1. Trometamol Ketorolac

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₄N₂O₆
Molecular Weight	376.4 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	6
Exact Mass	376.16343649 g/mol
Monoisotopic Mass	376.16343649 g/mol
Topological Polar Surface Area	146 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	430
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 10
Drug Name	Acular
PubMed Health	Ketorolac
Drug Classes	Analgesic, Central Nervous System Agent, Ophthalmologic Agent
Drug Label	ACULAR (ketorolac tromethamine ophthalmic solution) is a member of the pyrrolo-pyrrole group of nonsteroidal anti-inflammatory drugs (NSAIDs) for ophthalmic use. Its chemical name is ()-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, comp...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%
Market Status	Prescription
Company	Allergan

2 of 10
Drug Name	Acular ls
PubMed Health	Ketorolac (Into the eye)
Drug Classes	Ophthalmologic Agent
Drug Label	ACULAR LS (ketorolac tromethamine ophthalmic solution) 0.4% is a member of the pyrrolo-pyrrole group of nonsteroidal anti-inflammatory drugs (NSAIDs) for ophthalmic use. Structural and Molecular Formula: C19H24N2O6Mol Wt 376.40Chemical Name...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.4%
Market Status	Prescription
Company	Allergan

3 of 10
Drug Name	Acuvail
PubMed Health	Ketorolac
Drug Classes	Analgesic, Central Nervous System Agent, Ophthalmologic Agent
Drug Label	ACUVAIL (ketorolac tromethamine ophthalmic solution) 0.45% is a member of the pyrrolo-pyrrole group of nonsteroidal anti-inflammatory drugs (NSAIDs) for ophthalmic use. Its chemical name is ()-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic aci...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.45%
Market Status	Prescription
Company	Allergan

4 of 10
Drug Name	Ketorolac tromethamine
Drug Label	Ketorolac tromethamine is a member of the pyrrolo-pyrrole group of non-steroidal anti-inflammatory drugs (NSAIDs). The chemical name for ketorolac tromethamine is (acid, compound with 2-amino-2-(hydroxymethyl)-1,3-propanediol, and the structural form...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Solution/drops; Tablet; Injectable
Route	injection; Ophthalmic; Injection; Oral
Strength	0.5%; 0.4%; 30mg/ml; 60mg/2ml; 10mg; 15mg/ml
Market Status	Prescription
Company	Wockhardt; Hospira; Gland Pharma; Teva; Apotex; Sandoz; Sun Pharma Global; Fresenius Kabi Usa; Hikma Maple; Alcon Pharms; Amphastar Pharm; Sagent Pharms; Pliva; Agila Speclts; Mylan; Akorn

5 of 10
Drug Name	Sprix
Drug Label	Ketorolac tromethamine is a member of the pyrrolo-pyrrole group of nonsteroidal anti-inflammatory drugs (NSAIDs). The chemical name for ketorolac tromethamine is ()-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, compound with 2-amino-2-(hy...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Spray, metered
Route	Nasal
Strength	15.75mg/spray
Market Status	Prescription
Company	Luitpold

6 of 10
Drug Name	Acular
PubMed Health	Ketorolac
Drug Classes	Analgesic, Central Nervous System Agent, Ophthalmologic Agent
Drug Label	ACULAR (ketorolac tromethamine ophthalmic solution) is a member of the pyrrolo-pyrrole group of nonsteroidal anti-inflammatory drugs (NSAIDs) for ophthalmic use. Its chemical name is ()-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, comp...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.5%
Market Status	Prescription
Company	Allergan

7 of 10
Drug Name	Acular ls
PubMed Health	Ketorolac (Into the eye)
Drug Classes	Ophthalmologic Agent
Drug Label	ACULAR LS (ketorolac tromethamine ophthalmic solution) 0.4% is a member of the pyrrolo-pyrrole group of nonsteroidal anti-inflammatory drugs (NSAIDs) for ophthalmic use. Structural and Molecular Formula: C19H24N2O6Mol Wt 376.40Chemical Name...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.4%
Market Status	Prescription
Company	Allergan

8 of 10
Drug Name	Acuvail
PubMed Health	Ketorolac
Drug Classes	Analgesic, Central Nervous System Agent, Ophthalmologic Agent
Drug Label	ACUVAIL (ketorolac tromethamine ophthalmic solution) 0.45% is a member of the pyrrolo-pyrrole group of nonsteroidal anti-inflammatory drugs (NSAIDs) for ophthalmic use. Its chemical name is ()-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic aci...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.45%
Market Status	Prescription
Company	Allergan

9 of 10
Drug Name	Ketorolac tromethamine
Drug Label	Ketorolac tromethamine is a member of the pyrrolo-pyrrole group of non-steroidal anti-inflammatory drugs (NSAIDs). The chemical name for ketorolac tromethamine is (acid, compound with 2-amino-2-(hydroxymethyl)-1,3-propanediol, and the structural form...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Solution/drops; Tablet; Injectable
Route	injection; Ophthalmic; Injection; Oral
Strength	0.5%; 0.4%; 30mg/ml; 60mg/2ml; 10mg; 15mg/ml
Market Status	Prescription
Company	Wockhardt; Hospira; Gland Pharma; Teva; Apotex; Sandoz; Sun Pharma Global; Fresenius Kabi Usa; Hikma Maple; Alcon Pharms; Amphastar Pharm; Sagent Pharms; Pliva; Agila Speclts; Mylan; Akorn

10 of 10
Drug Name	Sprix
Drug Label	Ketorolac tromethamine is a member of the pyrrolo-pyrrole group of nonsteroidal anti-inflammatory drugs (NSAIDs). The chemical name for ketorolac tromethamine is ()-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid, compound with 2-amino-2-(hy...
Active Ingredient	Ketorolac tromethamine
Dosage Form	Spray, metered
Route	Nasal
Strength	15.75mg/spray
Market Status	Prescription
Company	Luitpold

4.2 Drug Indication

Investigated for use/treatment in pain (acute or chronic).

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

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.)

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Cyclooxygenase Inhibitor [EPC]; Cyclooxygenase Inhibitors [MoA]; Nonsteroidal Anti-inflammatory Drug [EPC]; Anti-Inflammatory Agents, Non-Steroidal [CS]

5.3 Mechanism of Action

ROX-888 is a intranasal formulation of the broadly used injectible analgesic, ketorolac. It has ability to provide effective analgesia in acute medical conditions resulting in moderate-severe pain, without the disabling side effects of opioid analgesics

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