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Acemetacin

Synopsis, Chemistry

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Also known as: 53164-05-9, Rantudil, Emflex, Acemix, Acemetacinum, Acemetacina

Molecular Formula

C₂₁H₁₈ClNO₆

Molecular Weight

415.8 g/mol

InChI Key

FSQKKOOTNAMONP-UHFFFAOYSA-N

FDA UNII

5V141XK28X

Acemetacin is a carboxymethyl ester of indometacin. It is a potent non-steroidal anti-inflammatory drug, derived from the indol-3-acetic acid, whose activity is thought to be mainly through its active metabolite indomethacin. In clinical trials, acemetacin exhibits a better gastric tolerability compared to its active metabolite indometacin. It was developed by E. Merck and Company in Germany as an attempt to provide a safer drug but other than the amelioration on the gastrointestinal effects, the metabolism of acetamicin led to the formation of indomethacin and it kept the same side effects.

1 2D Structure

Acemetacin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyacetic acid

2.1.2 InChI

InChI=1S/C21H18ClNO6/c1-12-16(10-20(26)29-11-19(24)25)17-9-15(28-2)7-8-18(17)23(12)21(27)13-3-5-14(22)6-4-13/h3-9H,10-11H2,1-2H3,(H,24,25)

2.1.3 InChI Key

FSQKKOOTNAMONP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)OCC(=O)O

2.2 Other Identifiers

2.2.1 UNII

5V141XK28X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Acemetacin Heumann

2. Acemetacin Intermuti

3. Acemetacin Monohydrate

4. Acemetacin Sodium

5. Acemetacin Stada

6. Acemetacin Von Ct

7. Acemetadoc

8. Acephlogont

9. Azeat

10. Emflex

11. Espledol

12. Indomethacin Carboxymethyl Ester

13. Oldan

14. Rantodil

15. Rantudil

16. Tvx 1322

2.3.2 Depositor-Supplied Synonyms

1. 53164-05-9

2. Rantudil

3. Emflex

4. Acemix

5. Acemetacinum

6. Acemetacina

7. Acemetacine

8. Tvx 1322

9. Indomethacin Carboxymethyl Ester

10. Tvx 3322

11. K-708

12. 1h-indole-3-acetic Acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, Carboxymethyl Ester

13. K 708

14. Indometacin Glycolic Ester

15. Indomethacin Glycolic Ester

16. Nsc-757413

17. Indometacin Carboxymethyl Ester

18. Chembl189171

19. Chebi:31162

20. 5v141xk28x

21. 2-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyacetic Acid

22. 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole-3-acetic Acid Carboxymethyl Ester

23. Ncgc00016868-09

24. Aximeixin

25. Rheumibis

26. 2-[2-[1-(4-chloro-2,3,5,6-tetradeuteriobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyacetic Acid

27. Cas-53164-05-9

28. Dsstox_cid_2540

29. 1-[p-chlorobenzoyl]-5-methoxy-2-methylindole-3-acetic Acid Carboxymethyl Ester

30. 1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic Acid Ester With Glycolic Acid

31. Dsstox_rid_76618

32. Dsstox_gsid_22540

33. Bay F 4975

34. Solart

35. Acemetacine [inn-french]

36. Acemetacinum [inn-latin]

37. Acemetacina [inn-spanish]

38. 1-(4-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetic Acid Carboxymethyl Ester

39. 2-(2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl)acetoxy)acetic Acid

40. Smr000058409

41. Sr-01000000070

42. Einecs 258-403-4

43. Brn 0501672

44. Acemetacin [inn:ban:jan]

45. Unii-5v141xk28x

46. Rantudil (tn)

47. Prestwick_669

48. Acemetacin (emflex)

49. Mfcd00151473

50. Spectrum_000428

51. Acemetacin [mi]

52. Acemetacin [inn]

53. Acemetacin [jan]

54. Prestwick0_000296

55. Prestwick1_000296

56. Prestwick2_000296

57. Prestwick3_000296

58. Spectrum2_001162

59. Spectrum3_001868

60. Spectrum4_000803

61. Spectrum5_001385

62. ((1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl)acetoxy)acetic Acid

63. Acemetacin (jp17/inn)

64. (1-(p-chlorbenzoyl)-5-methoxy-2-methylindol-3-acetoxy)essigsaeure [german]

65. 2-(2-(1-(p-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl)acetoxy)acetic Acid

66. Acemetacin [mart.]

67. Acemetacin [who-dd]

68. Bay-f-4975

69. Schembl23843

70. Bspbio_000232

71. Bspbio_003316

72. Kbiogr_001285

73. Kbioss_000908

74. 5-22-05-00241 (beilstein Handbook Reference)

75. Mls000028440

76. Mls006010622

77. Divk1c_000490

78. Spectrum1500666

79. Spbio_001143

80. Spbio_002451

81. Acemetacin, Analytical Standard

82. Bpbio1_000256

83. Dtxsid7022540

84. Hms501i12

85. Kbio1_000490

86. Kbio2_000908

87. Kbio2_003476

88. Kbio2_006044

89. Kbio3_002818

90. Acemetacin [ep Monograph]

91. Ninds_000490

92. Hms1568l14

93. Hms1921a08

94. Hms2090e21

95. Hms2095l14

96. Hms2230g08

97. Hms3372k20

98. Hms3656e22

99. Hms3712l14

100. Hms3884p10

101. Pharmakon1600-01500666

102. Zinc601272

103. Bcp13127

104. Hy-b0482

105. Tvx-1322

106. Tox21_113473

107. (1-(p-chlorbenzoyl)-5-methoxy-2-methylindol-3-acetoxy)essigsaeure

108. Bdbm50336272

109. Ccg-39550

110. Nsc757413

111. S2602

112. Akos015895194

113. Tox21_113473_1

114. Ab03974

115. Db13783

116. Nsc 757413

117. Tv-1322

118. {2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]acetoxy}acetic Acid

119. Idi1_000490

120. Ncgc00016868-01

121. Ncgc00016868-02

122. Ncgc00016868-03

123. Ncgc00016868-04

124. Ncgc00016868-05

125. Ncgc00016868-06

126. Ncgc00016868-07

127. Ncgc00016868-08

128. Ncgc00016868-11

129. Ncgc00016868-12

130. Ncgc00022084-03

131. Ncgc00022084-04

132. Ncgc00022084-05

133. Ncgc00022084-06

134. Ncgc00022084-07

135. Bs-16970

136. Sbi-0051585.p002

137. Db-052263

138. A2452

139. Ab00052149

140. Ft-0630659

141. Sw196824-3

142. D01582

143. D88520

144. Ab00052149-15

145. Ab00052149_16

146. Ab00052149_17

147. From D:/data/p.sapui/gsas_26052012/ps1.cif

148. 164a059

149. A936725

150. Q2723146

151. Sr-01000000070-2

152. Sr-01000000070-3

153. Brd-k67563174-001-05-1

154. Brd-k67563174-001-09-3

155. Acemetacin, European Pharmacopoeia (ep) Reference Standard

156. [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetoxyacetic Acid

157. [1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxy]-acetic Acid

158. [({1-[(4-chlorophenyl)carbonyl]-5-methoxy-2-methyl-1h-indol-3-yl}acetyl)oxy]acetic Acid

159. [1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1h-indol-3-yl]-acetic Acid Carboxymethyl Ester

160. [({1-[(4-chlorophenyl)carbonyl]-2-methyl-5-(methyloxy)-1h-indol-3-yl}acetyl)oxy]acetic Acid

161. [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetoxyacetic Acid[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetoxyacetic Acid

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₁₈ClNO₆
Molecular Weight	415.8 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	7
Exact Mass	415.0822650 g/mol
Monoisotopic Mass	415.0822650 g/mol
Topological Polar Surface Area	94.8 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	620
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Acemetacin is not FDA, Canada or EMA approved, but in the countries where it is marketed it is indicated for the symptomatic treatment of pain and swelling in acute inflammation of the joints in rheumathoid arthritis, osteoarthritis, low back pain and post-surgical pain. It is also indicated for the treatment of chronic inflammation of the joints in presence of rheumatoid arthritis, treatment of ankylosing spondylitis, treatment of irritation in the joints and spinal column caused by degenerative disorders, treatment of inflammatory soft-tissue rheumatism syndrome and painful swelling and inflammation caused by injury.

5 Pharmacology and Biochemistry

5.1 Pharmacology

The effect of acemetacin causes a weak reduction of prostaglandin synthesis which generates an anti-inflammatory and analgesic effect. The weak inhibition of prostaglandin reduces significantly the damage caused in the mucous membrane of the gastrointestinal tract. Studies have shown that acemetacin strongly inhibits the release of histamine from mast cells and the generation of hyperthermia. Acemetacin effect also causes changes in systolic and diastolic blood pressure as well as inhibition of platelet aggregation.

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.)

5.3 ATC Code

M01AB11

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

M01AB11 - Acemetacin

5.4 Absorption, Distribution and Excretion

Absorption

After 8 days of oral administration twice daily of acemetacin there was an age-dependant Cmax of 276.8 ng/ml in elderly compared to 187 ng/ml for younger individuals. There was also a Tmax of 2.5 h and AUC in a range of 483-712 ng h/ml. The bioavailability of acemetacin after repeated doses is aproximately 66% in plasma and 64% in urine.

Route of Elimination

The elimination of acemetacin is divided in renal elimination that covers 40% of the complete administered dose and the restant 60% is excreted in feces.

Volume of Distribution

The apparent volume of distribution of acemetacin is in a range of 0.5-0.7 L/kg.

Clearance

Intravenous administration of acemetacin in healthy subjects reported a clearance rate of 4.59 ml min/kg.

5.5 Metabolism/Metabolites

Acemetacin is highly metabolized and degraded by esterolytic cleavage to form its major and active metabolite indometacin. It presents other inactive metabolites made by reaction of O-demethylation, N-desacylation and part of them are also transformed by conjugation with glucuronic acid.

5.6 Biological Half-Life

The elimination half-life of acemetacin after steady-state is 4.5 hours.

5.7 Mechanism of Action

Acemetacin is a non-selective inhibitor of the production of pro-inflammatory mediators derived from the action of the enzyme COX. COX is essential for the synthesis of prostaglandin E2 and F2 which are molecules derived from fatty acids and stored in the cell membrane. Acetometacine is metabolized and forms its major metabolite indometacin which is also a non-selective inhibitor of COX and exhibits the capacity to inhibit the motility of polymorphonuclear leukocytes and decreased cerebral flow by modulating the nitric oxide pathway and vasoconstriction.