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Prestwick3_000243

Prestwick3_000243

Synopsis, Chemistry

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Also known as: 2438-72-4, Bufexamic acid, 2-(4-butoxyphenyl)-n-hydroxyacetamide, Parfenac, Feximac, Droxaryl

Molecular Formula

C₁₂H₁₇NO₃

Molecular Weight

223.27 g/mol

InChI Key

MXJWRABVEGLYDG-UHFFFAOYSA-N

FDA UNII

4T3C38J78L

A benzeneacetamide with anti-inflammatory, analgesic, and antipyretic action. It is administered topically, orally, or rectally.

1 2D Structure

Prestwick3_000243

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(4-butoxyphenyl)-N-hydroxyacetamide

2.1.2 InChI

InChI=1S/C12H17NO3/c1-2-3-8-16-11-6-4-10(5-7-11)9-12(14)13-15/h4-7,15H,2-3,8-9H2,1H3,(H,13,14)

2.1.3 InChI Key

MXJWRABVEGLYDG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCCCOC1=CC=C(C=C1)CC(=O)NO

2.2 Other Identifiers

2.2.1 UNII

4T3C38J78L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Allergipuran

2. Bufal

3. Bufederm

4. Bufexamac Ratiopharm

5. Bufexamac-ratiopharm

6. Bufexamacratiopharm

7. Droxaryl

8. Duradermal

9. Jomax

10. Malipuran

11. P Butoxyphenylacethydroxamic Acid

12. P-butoxyphenylacethydroxamic Acid

13. Paraderm

14. Parfenac

15. Windol

2.3.2 Depositor-Supplied Synonyms

1. 2438-72-4

2. Bufexamic Acid

3. 2-(4-butoxyphenyl)-n-hydroxyacetamide

4. Parfenac

5. Feximac

6. Droxaryl

7. Malipuran

8. Mofenar

9. Norfemac

10. Paraderm

11. Parfenal

12. Anderm

13. 4-butoxy-n-hydroxybenzeneacetamide

14. Bufexamaco

15. Bufexamacum

16. Flogicid

17. P-butoxyphenylacetohydroxamic Acid

18. 4-butoxyphenylacetohydroxamic Acid

19. 2-(p-butoxyphenyl)-acetohydroxamic Acid

20. Flogocid N Plastigel

21. Acide P-butoxyphenylacethydroxamique

22. 2-(p-butoxyphenyl)acetohydroxamic Acid

23. Cp 1044 J3

24. Benzeneacetamide, 4-butoxy-n-hydroxy-

25. Cp 1044

26. Chebi:31317

27. Acetohydroxamic Acid, 2-(p-butoxyphenyl)-

28. Cp-1044-j3

29. Nsc-758153

30. Chembl94394

31. Mls000028409

32. 4t3c38j78l

33. J3

34. Ncgc00016611-01

35. Smr000058407

36. Cas-2438-72-4

37. Dsstox_cid_25368

38. Dsstox_rid_80831

39. Dsstox_gsid_45368

40. Bufessamac [dcit]

41. Bufessamac

42. Droxarol

43. Ml392

44. Bufexamacum [inn-latin]

45. Bufexamaco [inn-spanish]

46. Bufexamac [inn:ban:dcf:jan]

47. Sr-01000003067

48. Einecs 219-451-1

49. 2-(4-butoxyphenyl)acetohydroxamic Acid

50. Brn 2646848

51. Unii-4t3c38j78l

52. Acide P-butoxyphenylacethydroxamique [french]

53. Bufexamac,(s)

54. Prestwick_676

55. Anderm (tn)

56. Spectrum_001754

57. Bufexamac (jan/inn)

58. Bufexamac [inn]

59. Bufexamac [jan]

60. Opera_id_1503

61. Prestwick0_000243

62. Prestwick1_000243

63. Prestwick2_000243

64. Prestwick3_000243

65. Spectrum2_001457

66. Spectrum3_000938

67. Spectrum4_001037

68. Spectrum5_001117

69. Bufexamac [mart.]

70. Epitope Id:180855

71. Bufexamac [who-dd]

72. Cid_2466

73. Regid_for_cid_2466

74. Schembl25215

75. Bspbio_000026

76. Kbiogr_001593

77. Kbioss_002234

78. Mls001148632

79. Bufexamac, Analytical Standard

80. Butoxyphenylacethydroxamic Acid

81. Divk1c_000108

82. Spectrum1502003

83. Spbio_001353

84. Spbio_002245

85. Bpbio1_000030

86. Gtpl7498

87. Bufexamac [ep Impurity]

88. Bufexamac [ep Monograph]

89. Dtxsid7045368

90. Benzylchloroacetylcarbamate

91. Hms500f10

92. Kbio1_000108

93. Kbio2_002234

94. Kbio2_004802

95. Kbio2_007370

96. Kbio3_001976

97. Ninds_000108

98. Hms1568b08

99. Hms1921b18

100. Hms2095b08

101. Hms2235i13

102. Hms3371k16

103. Hms3656h16

104. Hms3712b08

105. Hms3885k03

106. Kuc105648n

107. Pharmakon1600-01502003

108. Act07664

109. Caa43872

110. Hy-b0494

111. Zinc3871797

112. Para-butoxyphenylacetohydroxamic Acid

113. Tox21_110522

114. Bdbm50015144

115. Ccg-39191

116. Mfcd00078936

117. Nsc758153

118. S3023

119. Bufexamac 1.0 Mg/ml In Acetonitrile

120. Akos015895401

121. Kuc105648n-02

122. Kuc105648n-03

123. Tox21_110522_1

124. Db13346

125. Ksc-10-210

126. Nsc 758153

127. Idi1_000108

128. Ksc-390-003

129. Ncgc00016611-02

130. Ncgc00016611-03

131. Ncgc00016611-04

132. Ncgc00016611-05

133. Ncgc00016611-06

134. Ncgc00016611-07

135. Ncgc00016611-09

136. Ncgc00016611-10

137. Ncgc00021813-03

138. Ncgc00021813-04

139. 2-(4-butoxy-phenyl)-n-hydroxy-acetamide

140. 2-(4-butoxyphenyl)-n-hydroxyacetamide #

141. Ac-18729

142. As-12207

143. Ksc-285-073-1

144. Sbi-0051694.p002

145. Ab00052252

146. B4179

147. Ft-0603607

148. Sw196831-3

149. C74254

150. D01271

151. Ab00052252_19

152. Ab00052252_20

153. A817259

154. Q412699

155. J-015485

156. Sr-01000003067-3

157. Sr-01000003067-4

158. Brd-k36660044-001-15-0

159. Bufexamac, European Pharmacopoeia (ep) Reference Standard

160. A4z

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₂H₁₇NO₃
Molecular Weight	223.27 g/mol
XLogP3	1.9
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	6
Exact Mass	223.12084340 g/mol
Monoisotopic Mass	223.12084340 g/mol
Topological Polar Surface Area	58.6 Å²
Heavy Atom Count	16
Formal Charge	0
Complexity	200
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

Indicated for the treatment of various skin conditions, such as atopic eczema and other inflammatory dermatoses.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Bufexamac is a topically-active anti-inflammatory agent that inhibits the cyclooxygenase enzyme. In cutaneous and deep experimental inflammation, topical administration of bufexamac exerted a dose-related anti-inflammatory effect. In guinea pigs, bufexamax was shown to be more active than topical acetylsalicylic acid 5% or phenylbutazone 5% in delaying the local increase in temperature resulting from UV exposure. Bufexamac is unlikely to have any effect on wound healing.

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

M - Musculo-skeletal system

M01 - Antiinflammatory and antirheumatic products

M01A - Antiinflammatory and antirheumatic products, non-steroids

M01AB - Acetic acid derivatives and related substances

M01AB17 - Bufexamac

M - Musculo-skeletal system

M02 - Topical products for joint and muscular pain

M02A - Topical products for joint and muscular pain

M02AA - Antiinflammatory preparations, non-steroids for topical use

M02AA09 - Bufexamac

5.4 Absorption, Distribution and Excretion

Absorption

Method of application affects the extent of cutaneous absorption. Following rectal administration as suppositories, the systemic absorption was reported to be low.

Route of Elimination

Following topical administration of 5% bufexamac, the recovery in the urine was 3.5% of the applied dose within 144 hours. Studies in healthy volunteers receiving an oral dose of 125 to 500 mg indicate that an average of 80% of the total dose is excreted in the urine within 48 hours.

Volume of Distribution

No data available.

Clearance

No data available.

5.5 Metabolism/Metabolites

No data available.

5.6 Biological Half-Life

No data available.

5.7 Mechanism of Action

The full mechanism of action is unclear. It is proposed that bufexamac acts similarly to other non-steroidal anti-inflammatory drugs to inhibit prostaglandin biosynthesis _in vitro_, via inhibiting cyclo-oxygenase (COX) enzymes. Systematically administered bufexamac may accumulate preferentially in the adrenal cortex of rats and may play a role in adrenal stimulation; however its topical anti-inflammatory action is likely to be independent of this effect.