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Chemistry

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Also known as: 5104-49-4, Ansaid, Froben, Antadys, 2-(2-fluorobiphenyl-4-yl)propanoic acid, Cebutid

Molecular Formula

C₁₅H₁₃FO₂

Molecular Weight

244.26 g/mol

InChI Key

SYTBZMRGLBWNTM-UHFFFAOYSA-N

FDA UNII

5GRO578KLP

An anti-inflammatory analgesic and antipyretic of the phenylalkynoic acid series. It has been shown to reduce bone resorption in periodontal disease by inhibiting CARBONIC ANHYDRASE.

Flurbiprofen is a Nonsteroidal Anti-inflammatory Drug. The mechanism of action of flurbiprofen is as a Cyclooxygenase Inhibitor.

1 2D Structure

Flurbiprofen

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(3-fluoro-4-phenylphenyl)propanoic acid

2.1.2 InChI

InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)

2.1.3 InChI Key

SYTBZMRGLBWNTM-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

5GRO578KLP

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetic Acid

2. Ansaid

3. Apo Flurbiprofen

4. Apo-flurbiprofen

5. Bts 18322

6. Bts-18322

7. Bts18322

8. Cebutid

9. Dobrofen

10. E 7869

11. E-7869

12. E7869

13. Flubiprofen

14. Flugalin

15. Flurbiprofen Sodium

16. Fluriproben

17. Froben

18. Froben Sr

19. Neo Artrol

20. Novo Flurprofen

21. Novo-flurprofen

22. Nu Flurbiprofen

23. Nu-flurbiprofen

24. Ocufen

25. Ocuflur

26. Ratio Flurbiprofen

27. Ratio-flurbiprofen

28. Strefen

2.3.2 Depositor-Supplied Synonyms

1. 5104-49-4

2. Ansaid

3. Froben

4. Antadys

5. 2-(2-fluorobiphenyl-4-yl)propanoic Acid

6. Cebutid

7. Flurofen

8. 3-fluoro-4-phenylhydratropic Acid

9. 2-(3-fluoro-4-phenylphenyl)propanoic Acid

10. Ocufen

11. Flurbiprofene [inn-french]

12. Flurbiprofenum [inn-latin]

13. Flurbiprofeno [inn-spanish]

14. Bts 18322

15. Bts-18322

16. Fp 70

17. U-27182

18. 2-fluoro-alpha-methyl-(1,1'-biphenyl)-4-acetic Acid

19. (+-)-2-fluoro-alpha-methyl-4-biphenylacetic Acid

20. 2-(2-fluorobiphenyl-4-yl)propionic Acid

21. Mfcd00079303

22. Stayban

23. Zepolas

24. Adfeed

25. U 27182

26. 2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoic Acid

27. 51543-38-5

28. Chembl563

29. Bts 18,322

30. Nsc-757037

31. 5gro578klp

32. 2-(2-fluoro-4-biphenylyl)propionic Acid

33. (r)-flurbiprofen;mpc7869

34. Mls000040873

35. Chebi:5130

36. Flubiprofen

37. Flugalin

38. Einecs 257-262-6

39. U-27,182

40. (1)-2-fluoro-alpha-methyl(1,1'-biphenyl)-4-acetic Acid

41. Flurbiprofene

42. Flurbiprofeno

43. Flurbiprofenum

44. 2-fluoro-alpha-methyl-4-biphenylacetic Acid

45. Ocuflur

46. Smr000042823

47. Dsstox_cid_17231

48. Dsstox_rid_79310

49. Dsstox_gsid_37231

50. C15h13fo2

51. Anmetarin

52. Yakuban

53. Dl-flurbiprofen

54. Flurbiprofen (ansaid)

55. Ansaid (tn)

56. Ccris 3708

57. Sr-01000003043

58. Flp

59. Einecs 225-827-6

60. (+-)-2-(2-fluoro-4-biphenylyl)propionic Acid

61. Unii-5gro578klp

62. (+/-)-2-fluoro-alpha-methyl-4-biphenylacetic Acid

63. Mpc7869

64. U 27,182

65. Flurbiprofen O

66. Mks-11

67. Rac-flurbiprofen

68. Flurbiprofen,(s)

69. Ncgc00016654-01

70. (+-)flurbiprofen

71. Cas-5104-49-4

72. Ocufen (salt/mix)

73. [1,1'-biphenyl]-4-acetic Acid, 2-fluoro-?-methyl-

74. Flurbiprofen [usan:usp:inn:ban:jan]

75. Spectrum_001096

76. Opera_id_777

77. Prestwick0_000917

78. Prestwick1_000917

79. Prestwick2_000917

80. Prestwick3_000917

81. Spectrum2_001025

82. Spectrum3_000435

83. Spectrum4_000558

84. Spectrum5_000720

85. Flurbiprofen [mi]

86. 2-(3-fluoro-4-phenyl-phenyl)propanoic Acid

87. F0371

88. (.+/-.)-flurbiprofen

89. Flurbiprofen [inn]

90. Flurbiprofen [jan]

91. 4-biphenylacetic Acid, 2-fluoro-alpha-methyl-

92. Flurbiprofen [usan]

93. Schembl2248

94. Flurbiprofen [vandf]

95. 4-biphenylacetic Acid, 2-fluoro-.alpha.-methyl-

96. Bspbio_000794

97. Bspbio_002050

98. Flurbiprofen [mart.]

99. Kbiogr_001255

100. Kbioss_001576

101. 2-(2-fluoro[1,1'-biphenyl]-4-yl)propanoic Acid

102. Mls000028441

103. Mls000758198

104. Mls001201729

105. Mls001401361

106. Mls006011431

107. Mls006011931

108. Divk1c_000804

109. Flurbiprofen [usp-rs]

110. Flurbiprofen [who-dd]

111. Spectrum1500308

112. 2-(2-fluoro-[1,1'-biphenyl-4-yl])propanoic Acid

113. Spbio_001209

114. Spbio_002983

115. Bpbio1_000874

116. Gtpl4194

117. Dtxsid0037231

118. Schembl10029029

119. Flurbiprofen (jp17/usp/inn)

120. Hms502i06

121. Kbio1_000804

122. Kbio2_001576

123. Kbio2_004144

124. Kbio2_006712

125. Kbio3_001270

126. Sytbzmrglbwntm-uhfffaoysa-

127. [1,1'-biphenyl]-4-acetic Acid, 2-fluoro-.alpha.-methyl-

128. Ninds_000804

129. Flurbiprofen [orange Book]

130. Hms1570h16

131. Hms1920o20

132. Hms2051a05

133. Hms2090i06

134. Hms2091f21

135. Hms2097h16

136. Hms2232i08

137. Hms3259i12

138. Hms3268e10

139. Hms3370n14

140. Hms3371i05

141. Hms3393a05

142. Hms3414n17

143. Hms3649k11

144. Hms3655g19

145. Hms3678n15

146. Hms3714h16

147. Pharmakon1600-01500308

148. Flurbiprofen [ep Monograph]

149. (1,1'-biphenyl)-4-acetic Acid, 2-fluoro-alpha-methyl-, (+-)-

150. Bcp09086

151. Bcp13426

152. Flurbiprofen [usp Monograph]

153. Tox21_110547

154. Tox21_302353

155. Bbl010980

156. Bdbm50074922

157. Ccg-40243

158. Flurbiprofen - Cas 5104-49-4

159. Nsc685701

160. Nsc755404

161. Nsc757037

162. Stk802101

163. Flurbiprofen, Cyclooxygenase Inhibitor

164. Akos004119934

165. Akos016340701

166. Ac-8106

167. Ccg-100759

168. Db00712

169. Ks-5035

170. Nc00009

171. Nc00563

172. Nsc 757037

173. Nsc-685701

174. Nsc-755404

175. 2(2-fluoro-4-biphenylyl)propionic Acid

176. Idi1_000804

177. Ncgc00018157-03

178. Ncgc00018157-04

179. Ncgc00018157-05

180. Ncgc00018157-08

181. Ncgc00018157-11

182. Ncgc00018157-13

183. Ncgc00025287-03

184. Ncgc00025287-04

185. Ncgc00255457-01

186. Hy-10582

187. Nci60_030812

188. 2 -(2-fluoro-4-biphenylyl)propionic Acid

189. 2-(2-fluoro-4-biphenylyl)-propionic Acid

190. 2-(2-fluoro-biphenyl-4-yl)propionic Acid

191. Sbi-0051387.p003

192. Db-051888

193. Flurbiprofen 100 Microg/ml In Acetonitrile

194. 2-(2-fluoro-biphenyl-4-yl)-propionic Acid

195. Ab00051999

196. Ft-0603668

197. Ft-0660285

198. Ft-0668760

199. Ft-0771103

200. Alpha-methyl-2-fluoro-4-biphenylylacetic Acid

201. (rs)-2-(2-fluorobiphenyl-4-yl)propionic Acid

202. 2-fluoro-.alpha.-methyl-4-biphenylacetic Acid

203. Bim-0051387.0001

204. C07013

205. D00330

206. Ab00051999-17

207. Ab00051999_18

208. 104f494

209. 2-(2-fluoro-1,1'-biphenyl-4-yl)propanoic Acid

210. 2-fluoro--methyl-(1,1'-biphenyl)-4-acetic Acid

211. Ao-295/42284050

212. Q419890

213. (.+/-.)-2-(2-fluoro-4-biphenylyl)propionic Acid

214. (r/s)-2-fluoro-alpha-methyl-4-biphenylacetic Acid

215. 2-fluoro-?-methyl-[1,1'-biphenyl]-4-acetic Acid

216. Flurbiprofen, Antibiotic For Culture Media Use Only

217. Q-201129

218. Sr-01000003043-2

219. Sr-01000003043-5

220. Sr-01000003043-6

221. (s)-(+)-2-fluoro-alpha-methyl-4-biphenylaceticacid

222. 2-(2-fluoro-[1,1''-biphenyl-4-yl])propanoic Acid

223. 2-(2-fluoro[1,1'-biphenyl]-4-yl)propanoic Acid #

224. Brd-a86044036-001-05-9

225. Sr-01000003043-14

226. (+/-)-2-(2-fluoro-4-biphenylyl)propionic Acid

227. (.+/-.)-2-fluoro-.alpha.-methyl-4-biphenylacetic Acid

228. 2-fluoro-.alpha.-methyl(1,1'-biphenyl)-4-acetic Acid

229. 2-fluoro-alpha-methyl-(1,1''-biphenyl)-4-acetic Acid

230. 2-fluoro-alpha-methyl-[1,1'-biphenyl]-4-a Cetic Acid

231. (+/-)-2-fluoro-.alpha.-methyl-4-biphenylacetic Acid

232. Flurbiprofen, European Pharmacopoeia (ep) Reference Standard

233. (1,1'-biphenyl)-4-acetic Acid, 2-fluoro-alpha-methyl-, (+/-)-

234. Flurbiprofen, United States Pharmacopeia (usp) Reference Standard

235. [1,1'-biphenyl]-4-acetic Acid, 2-fluoro-.alpha.-methyl-, (.+/-.)-

236. (1,1'-biphenyl)-4-acetic Acid, 2-fluoro-.alpha.-methyl-, (+/-)-

237. Flurbiprofen, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₃FO₂
Molecular Weight	244.26 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	244.08995782 g/mol
Monoisotopic Mass	244.08995782 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	286
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	1

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Ansaid
PubMed Health	Flurbiprofen
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent, NSAID, Ophthalmologic Agent, Propionic Acid
Drug Label	Flurbiprofen tablet, USP contain flurbiprofen, which is a member of the phenylalkanoic acid derivative group of nonsteroidal anti-inflammatory drugs. Flurbiprofen tablet, USP are white, oval, film-coated tablets for oral administration. Flurbiprofen...
Active Ingredient	Flurbiprofen
Dosage Form	Tablet
Route	Oral
Strength	100mg; 50mg
Market Status	Prescription
Company	Pharmacia And Upjohn

2 of 6
Drug Name	Flurbiprofen
PubMed Health	Flurbiprofen
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent, NSAID, Ophthalmologic Agent, Propionic Acid
Drug Label	OCUFEN (flurbiprofen sodium ophthalmic solution, USP) 0.03% is a sterile topical nonsteroidal anti-inflammatory product for ophthalmic use. Chemical Name:Sodium ()-2-(2-fluoro-4-biphenylyl) propionate dihydrate. Structural Formula:C15H12FNaO22...
Active Ingredient	Flurbiprofen
Dosage Form	Tablet
Route	Oral
Strength	100mg; 50mg
Market Status	Prescription
Company	Teva; Sun Pharm Inds; Mylan

3 of 6
Drug Name	Ocufen
PubMed Health	Flurbiprofen
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent, NSAID, Ophthalmologic Agent, Propionic Acid
Active Ingredient	Flurbiprofen sodium
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.03%
Market Status	Prescription
Company	Allergan

4 of 6
Drug Name	Ansaid
PubMed Health	Flurbiprofen
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent, NSAID, Ophthalmologic Agent, Propionic Acid
Drug Label	Flurbiprofen tablet, USP contain flurbiprofen, which is a member of the phenylalkanoic acid derivative group of nonsteroidal anti-inflammatory drugs. Flurbiprofen tablet, USP are white, oval, film-coated tablets for oral administration. Flurbiprofen...
Active Ingredient	Flurbiprofen
Dosage Form	Tablet
Route	Oral
Strength	100mg; 50mg
Market Status	Prescription
Company	Pharmacia And Upjohn

5 of 6
Drug Name	Flurbiprofen
PubMed Health	Flurbiprofen
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent, NSAID, Ophthalmologic Agent, Propionic Acid
Drug Label	OCUFEN (flurbiprofen sodium ophthalmic solution, USP) 0.03% is a sterile topical nonsteroidal anti-inflammatory product for ophthalmic use. Chemical Name:Sodium ()-2-(2-fluoro-4-biphenylyl) propionate dihydrate. Structural Formula:C15H12FNaO22...
Active Ingredient	Flurbiprofen
Dosage Form	Tablet
Route	Oral
Strength	100mg; 50mg
Market Status	Prescription
Company	Teva; Sun Pharm Inds; Mylan

6 of 6
Drug Name	Ocufen
PubMed Health	Flurbiprofen
Drug Classes	Analgesic, Antirheumatic, Central Nervous System Agent, Musculoskeletal Agent, NSAID, Ophthalmologic Agent, Propionic Acid
Active Ingredient	Flurbiprofen sodium
Dosage Form	Solution/drops
Route	Ophthalmic
Strength	0.03%
Market Status	Prescription
Company	Allergan

4.2 Drug Indication

Flurbiprofen tablets are indicated for the acute or long-term symptomatic treatment of rheumatoid arthritis, osteorarthritis and anklosing spondylitis. It may also be used to treat pain associated with dysmenorrhea and mild to moderate pain accompanied by inflammation (e.g. bursitis, tendonitis, soft tissue trauma). Topical ophthalmic formulations may be used pre-operatively to prevent intraoperative miosis.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Flurbiprofen, a nonsteroidal anti-inflammatory agent (NSAIA) of the propionic acid class, is structually and pharmacologically related to fenoprofen, ibuprofen, and ketoprofen, and has similar pharmacological actions to other prototypica NSAIAs. Flurbiprofen exhibits antiinflammatory, analgesic, and antipyretic activities. The commercially available flurbiprofen is a racemic mixture of (+)S- and (-) R-enantiomers. The S-enantiomer appears to possess most of the anti-inflammatory, while both enantiomers may possess analgesic activity.

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.)

Analgesics

Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

FLURBIPROFEN

5.3.2 FDA UNII

5GRO578KLP

5.3.3 Pharmacological Classes

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

5.4 ATC Code

R02AX01

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

M01AE - Propionic acid derivatives

M01AE09 - Flurbiprofen

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

M02AA19 - Flurbiprofen

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AX - Other throat preparations

R02AX01 - Flurbiprofen

S - Sensory organs

S01 - Ophthalmologicals

S01B - Antiinflammatory agents

S01BC - Antiinflammatory agents, non-steroids

S01BC04 - Flurbiprofen

5.5 Absorption, Distribution and Excretion

Absorption

Fluribiprofen is rapidly and almost completely absorbed following oral administration. Peak plasma concentrations are reached 0.5 - 4 hours after oral administration.

Route of Elimination

Flurbiprofen is poorly excreted into human milk. Following dosing with flurbiprofen, less than 3% of flurbiprofen is excreted unchanged in the urine, with about 70% of the dose eliminated in the urine as parent drug and metabolites. Renal elimination is a significant pathway of elimination of flurbiprofen metabolites.

Volume of Distribution

14 L [Normal Healthy Adults]

12 L [Geriatric Arthritis Patients]

10 L [End Stage Renal Disease Patients]

14 L [Alcoholic Cirrhosis Patients]

0.12 L/kg

5.6 Metabolism/Metabolites

Hepatic. Cytochrome P450 2C9 plays an important role in the metabolism of flurbiprofen to its major metabolite, 4’-hydroxy-flurbiprofen. The 4’-hydroxy-flurbiprofen metabolite showed little anti-inflammatory activity in animal models of inflammation.

5.7 Biological Half-Life

R-flurbiprofen, 4.7 hours; S-flurbiprofen, 5.7 hours

5.8 Mechanism of Action

Similar to other NSAIAs, the anti-inflammatory effect of flurbiprofen occurs via reversible inhibition of cyclooxygenase (COX), the enzyme responsible for the conversion of arachidonic acid to prostaglandin G2 (PGG2) and PGG2 to prostaglandin H2 (PGH2) in the prostaglandin synthesis pathway. This effectively decreases the concentration of prostaglandins involved in inflammation, pain, swelling and fever. Flurbiprofen is a non-selective COX inhibitor and inhibits the activity of both COX-1 and -2. It is also one of the most potent NSAIAs in terms of prostaglandin inhibitory activity.

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API Reference Price

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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Fillers, Diluents & Binders

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Direct Compression

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Granulation

Disintegrants & Superdisintegrants

Solubilizers

Lubricants & Glidants

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Topical

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Parenteral

Emulsifying Agents

Taste Masking

Empty Capsules

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US Medicaid Prescriptions

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Flurbiprofen

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

40 API Suppliers

12 USDMF

9 CEP/COS

11 JDMF

5 EU WC

8 KDMF

14 NDC API

19 Listed Suppliers

$ API Reference Price

INTERMEDIATES

5 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

41 FDF Dossiers

16 FDA Orange Book

12 Europe

2 Canada

5 South Africa

6 Listed Dossiers

RELATED EXCIPIENT COMPANIES

1 SPI Pharma

2 Seqens

4 DKSH

2 Jai Radhe Sales

4 Faran Shimi Pharmaceutical

9 Gangwal Healthcare

3 Nanjing Well Pharmaceutical

1 ACG Worldwide

5 Actylis

6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

15 BASF

1 Clariant

10 Corel Pharma Chem

6 DFE Pharma

1 Finar

9 Gangwal Chemicals

5 Ideal Cures Pvt Ltd

1 Ingredion Pharma Solutions

35 Kerry

3 Kima Chemical

6 Lonza Capsugel

11 Microlex e.U

1 Nanjing Bold Chemical

2 Nomisma Healthcare

1 Novo Excipients

1 Pharmatrans-Sanaq

4 Pluviaendo

3 Prachin Chemical

1 Qianhao Chemical (Hebei) Co., Ltd

1 Qualicaps

10 Roquette

12 Seppic

4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

10 Sigachi Industries

2 The Dow Chemical Company

3 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

50 Fillers, Diluents & Binders

46 Coating Systems & Additives

25 Controlled & Modified Release

24 Direct Compression

19 Thickeners and Stabilizers

17 Granulation

15 Disintegrants & Superdisintegrants

15 Solubilizers

13 Lubricants & Glidants

13 Co-Processed Excipients

12 Topical

11 Film Formers & Plasticizers

9 Parenteral

7 Emulsifying Agents

6 Taste Masking

5 Empty Capsules

5 API Stability Enhancers