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Chemistry

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Also known as: 77-36-1, Chlortalidone, Phthalamudine, Chlorphthalidolone, Hygroton, Chlorthalidon
Molecular Formula
C14H11ClN2O4S
Molecular Weight
338.8  g/mol
InChI Key
JIVPVXMEBJLZRO-UHFFFAOYSA-N
FDA UNII
Q0MQD1073Q

Chlorthalidone
A benzenesulfonamide-phthalimidine that tautomerizes to a BENZOPHENONES form. It is considered a thiazide-like diuretic.
Chlorthalidone is a Thiazide-like Diuretic. The physiologic effect of chlorthalidone is by means of Increased Diuresis.
1 2D Structure

Chlorthalidone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-chloro-5-(1-hydroxy-3-oxo-2H-isoindol-1-yl)benzenesulfonamide
2.1.2 InChI
InChI=1S/C14H11ClN2O4S/c15-11-6-5-8(7-12(11)22(16,20)21)14(19)10-4-2-1-3-9(10)13(18)17-14/h1-7,19H,(H,17,18)(H2,16,20,21)
2.1.3 InChI Key
JIVPVXMEBJLZRO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C2C(=C1)C(=O)NC2(C3=CC(=C(C=C3)Cl)S(=O)(=O)N)O
2.2 Other Identifiers
2.2.1 UNII
Q0MQD1073Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Chlorphthalidolone

2. Chlortalidone

3. Hygroton

4. Oxodoline

5. Phthalamudine

6. Thalitone

2.3.2 Depositor-Supplied Synonyms

1. 77-36-1

2. Chlortalidone

3. Phthalamudine

4. Chlorphthalidolone

5. Hygroton

6. Chlorthalidon

7. Phthalamodine

8. Natriuran

9. Thalitone

10. Chlorothalidone

11. Chlorphthalidone

12. Saluretin

13. Zambesil

14. Igroton

15. Isoren

16. Oradil

17. Renon

18. Hydro-long

19. Chlortalidonum

20. Oxodolin

21. Oksodolin (oxodolin)

22. Racemic Chlorthalidone

23. 2-chloro-5-(1-hydroxy-3-oxoisoindolin-1-yl)benzenesulfonamide

24. Demi-regroton

25. G-33182

26. 2-chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)benzenesulfonamide

27. 1-keto-3-(3'-sulfamyl-4'-chlorophenyl)-3-hydroxyisoindoline

28. 3-hydroxy-3-(4-chloro-3-sulfamylphenyl)phthalimidine

29. 2-chloro-5-(1-hydroxy-3-oxo-2h-isoindol-1-yl)benzenesulfonamide

30. 3-(4'-chloro-3'-sulfamoylphenyl)-3-hydroxyphthalimidine

31. 1-oxo-3-(3-sulfamyl-4-chlorophenyl)-3-hydroxyisoindoline

32. G 33182

33. Nsc-69200

34. Benzenesulfonamide, 2-chloro-5-(2,3-dihydro-1-hydroxy-3-oxo-1h-isoindol-1-yl)-

35. Chlortalidone [inn]

36. Benzenesulfonamide, 2-chloro-5-(1-hydroxy-3-oxo-1-isoindolinyl)-

37. 2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1h-isoindol-1-yl)benzenesulfonamide

38. Mls000069531

39. Chebi:3654

40. Q0mqd1073q

41. Clortalidone

42. Famolin

43. Higroton

44. Urolin

45. 2-chloro-5-(2,3-dihydro-1-hydroxy-3-oxo-1h-isoindol-1-yl)benzenesulfonamide

46. Clortalidona

47. Smr000058635

48. (+-)-hygroton

49. Clortalidone [dcit]

50. (+-)-chlorthalidone

51. Dsstox_cid_2812

52. 2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1h-isoindol-1-yl)benzene-1-sulfonamide

53. Dsstox_rid_76738

54. Dsstox_gsid_22812

55. Chlortalidonum [inn-latin]

56. Clortalidona [inn-spanish]

57. Thalitone (tn)

58. Hygroton (tn)

59. Chlorthalidone (usp)

60. Hsdb 3035

61. Sr-01000721929

62. Einecs 201-022-5

63. Nsc 69200

64. Chlortalidone (jan/inn)

65. Brn 0312295

66. Chlorthalidone [usan:usp]

67. Unii-q0mqd1073q

68. Oksodolin

69. Cas-77-36-1

70. Ncgc00016317-01

71. Prestwick_759

72. Regroton (salt/mix)

73. Combipres (salt/mix)

74. Spectrum_000146

75. Opera_id_138

76. (.+/-.)-hygroton

77. Prestwick0_000351

78. Prestwick1_000351

79. Prestwick2_000351

80. Prestwick3_000351

81. Spectrum2_000099

82. Spectrum3_000349

83. Spectrum4_000957

84. Spectrum5_000743

85. (.+/-.)-chlorthalidone

86. Chlortalidone [jan]

87. Chlorthalidone [mi]

88. Chembl1055

89. Schembl26234

90. Bspbio_000441

91. Bspbio_002017

92. Chlorthalidone [hsdb]

93. Chlorthalidone [usan]

94. Kbiogr_001574

95. Kbioss_000626

96. 5-22-07-00602 (beilstein Handbook Reference)

97. Chlortalidone [mart.]

98. Chlorthalidone (chlortalidone)

99. Chlorthalidone [vandf]

100. Divk1c_000731

101. Spectrum1500187

102. Spbio_000058

103. Spbio_002362

104. Chlortalidone [who-dd]

105. Chlortalidone [who-ip]

106. Bpbio1_000487

107. Gtpl7147

108. Chlorthalidone [usp-rs]

109. Dtxsid4022812

110. Bdbm25900

111. Hms502e13

112. Kbio1_000731

113. Kbio2_000626

114. Kbio2_003194

115. Kbio2_005762

116. Kbio3_001237

117. Ninds_000731

118. Hms1569g03

119. Hms1920m09

120. Hms2091e12

121. Hms2096g03

122. Hms2236d07

123. Hms3259h04

124. Hms3372a07

125. Hms3713g03

126. Pharmakon1600-01500187

127. Chlortalidone [ep Impurity]

128. Bcp27835

129. Nsc69200

130. Chlortalidone [ep Monograph]

131. Chlorthalidone [orange Book]

132. Tox21_110369

133. Ccg-38917

134. Mfcd00036257

135. Nsc756692

136. S3074

137. Stk686335

138. Chlortalidone 1.0 Mg/ml In Methanol

139. Chlortalidonum [who-ip Latin]

140. Chlorthalidone [usp Monograph]

141. Akos005599810

142. Tox21_110369_1

143. Db00310

144. Ks-1342

145. Nc00690

146. Nsc-756692

147. Clorpres Component Chlorthalidone

148. Idi1_000731

149. Kerledex Component Chlorthalidone

150. Regroton Component Chlorthalidone

151. Combipres Component Chlorthalidone

152. Ncgc00094616-01

153. Ncgc00094616-02

154. Ncgc00094616-03

155. Ncgc00094616-04

156. Ncgc00094616-07

157. Tenoretic Component Chlorthalidone

158. Ac-11367

159. Hy-15833

160. Chlorthalidone Component Of Clorpres

161. Chlorthalidone Component Of Kerledex

162. Chlorthalidone Component Of Regroton

163. Sbi-0051313.p003

164. Chlorthalidone Component Of Combipres

165. Chlorthalidone Component Of Tenoretic

166. Db-056211

167. Lopressidone Component Chlorthalidone

168. [(3,5-difluorophenyl)amino](oxo)aceticacid

169. Ab00051946

170. Demi-regroton Component Chlorthalidone

171. C76474

172. Chlorthalidone Component Of Lopressidone

173. D00272

174. Ab00051946_12

175. Chlorthalidone Component Of Demi-regroton

176. 036c257

177. A839067

178. Q425289

179. Sr-01000721929-2

180. Sr-01000721929-3

181. W-104322

182. Brd-a26384407-001-05-3

183. Brd-a26384407-001-15-2

184. 2-chloro-5-(1-hydroxy-3-oxo-1h-isoindolinyl)benzenesulfonamide

185. Chlorthalidone, European Pharmacopoeia (ep) Reference Standard

186. 2-chloro-5-(1,3-dihydroxy-1h-isoindol-1-yl)benzene-1-sulfonamide

187. Benzenesulfonamide,3-dihydro-1-hydroxy-3-oxo-1h-isoindol-1-yl)-

188. Chlorthalidone, United States Pharmacopeia (usp) Reference Standard

189. 2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1h-isoindol-1-yl)benzenesulfonamide #

190. 2-chloro-5-[(1s)-1-hydroxy-3-oxo-isoindolin-1-yl]benzenesulfonamide;chlorthalidone

191. Chlortalidone For Peak Identification, European Pharmacopoeia (ep) Reference Standard

192. 74658-80-3

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 338.8 g/mol
Molecular Formula C14H11ClN2O4S
XLogP30.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass338.0128057 g/mol
Monoisotopic Mass338.0128057 g/mol
Topological Polar Surface Area118 Ų
Heavy Atom Count22
Formal Charge0
Complexity564
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 Information
1 of 4  
Drug NameChlorthalidone
PubMed HealthChlorthalidone (By mouth)
Drug ClassesCardiovascular Agent
Drug LabelChlorthalidone is an oral antihypertensive/diuretic. It is a monosulfamyl diuretic that differs chemically from thiazide diuretics in that a double-ring system is incorporated in its structure. It is 2-chloro-5(1-hydroxy-3-oxo-1- isoindolinyl) benzen...
Active IngredientChlorthalidone
Dosage FormTablet
RouteOral
Strength25mg; 50mg
Market StatusPrescription
CompanyMylan

2 of 4  
Drug NameThalitone
PubMed HealthChlorthalidone (By mouth)
Drug ClassesCardiovascular Agent
Drug LabelThalitone (chlorthalidone USP) is an antihypertensive/diuretic supplied as 15 mg tablets for oral use. It is a monosulfamyl diuretic that differs chemically from thiazide diuretics in that a double ring system is incorporated in its structure. It i...
Active IngredientChlorthalidone
Dosage FormTablet
RouteOral
Strength15mg
Market StatusPrescription
CompanyCitron Pharma

3 of 4  
Drug NameChlorthalidone
PubMed HealthChlorthalidone (By mouth)
Drug ClassesCardiovascular Agent
Drug LabelChlorthalidone is an oral antihypertensive/diuretic. It is a monosulfamyl diuretic that differs chemically from thiazide diuretics in that a double-ring system is incorporated in its structure. It is 2-chloro-5(1-hydroxy-3-oxo-1- isoindolinyl) benzen...
Active IngredientChlorthalidone
Dosage FormTablet
RouteOral
Strength25mg; 50mg
Market StatusPrescription
CompanyMylan

4 of 4  
Drug NameThalitone
PubMed HealthChlorthalidone (By mouth)
Drug ClassesCardiovascular Agent
Drug LabelThalitone (chlorthalidone USP) is an antihypertensive/diuretic supplied as 15 mg tablets for oral use. It is a monosulfamyl diuretic that differs chemically from thiazide diuretics in that a double ring system is incorporated in its structure. It i...
Active IngredientChlorthalidone
Dosage FormTablet
RouteOral
Strength15mg
Market StatusPrescription
CompanyCitron Pharma

4.2 Therapeutic Uses

Antihypertensive Agents; Diuretics, Sulfamyl

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


...ORALLY EFFECTIVE DIURETIC USEFUL IN TREATMENT OF EDEMA ASSOC WITH CONGESTIVE HEART FAILURE, RENAL DISEASE, HEPATIC CIRRHOSIS, PREGNANCY, OBESITY, & PREMENSTRUAL SYNDROME. DIURETIC EFFECTS START WITHIN 2 HR AFTER ADMIN, REACH PEAK IN 6 HR, & PERSIST FOR 48 TO 72 HR.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871


MOST OF THIAZIDES ARE GIVEN IN DIVIDED DAILY DOSES FOR TREATMENT OF HYPERTENSION, BUT SINGLE DAILY DOSE MAY BE PREFERABLE FOR MOBILIZATION OF EDEMA FLUID. ...CHLORTHALIDONE...SHOULD BE GIVEN LESS FREQUENTLY, SINCE.../IT HAS/ DURATION OF ACTION LONGER THAN 24 HR.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 832


CHLORTHALIDONE ALSO EXERTS ANTIHYPERTENSIVE EFFECT & MAY BE ADMIN WITH OTHER AGENTS, SUCH AS RESERPINE, GANGLIONIC BLOCKING AGENTS, HYDRALAZINE, & GUANETHIDINE. SINCE.../IT/ CONTAINS SULFONAMIDE GROUP, ITS PHARMACOLOGICAL ACTIONS & MANY OF ITS UNTOWARD EFFECTS ARE SIMILAR TO THOSE OF OTHER ORALLY ADMIN DIURETICS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871


For more Therapeutic Uses (Complete) data for CHLORTHALIDONE (11 total), please visit the HSDB record page.


4.3 Drug Warning

CHLORTHALIDONE IS CONTRAINDICATED IN PT WITH SEVERE RENAL OR HEPATIC DISEASE. PT ON THIS DRUG SHOULD BE WATCHED CLOSELY FOR SYMPTOMS OF RENAL DAMAGE OR OF ELECTROLYTE DISTURBANCE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871


May suppress lactation ... /Thiazide diuretics; from table/

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 45-29


Many experts consider diuretics contraindicated in pregnancy except for patients with heart disease, since they do not prevent or alter course of toxemia and may decrease placental perfusion. /Chlorothiazide; from table/

Young, L.Y., M.A. Koda-Kimble (eds.). Applied Therapeutics. The Clinical Use of Drugs. 6th ed. Vancouver, WA., Applied Therapeutics, Inc. 1995., p. 45-9


Maternal Medication usually Compatible with Breast-Feeding: Chlorthalidone: Reported Sign or Symptom in Infant or Effect on Lactation: Excreted slowly. /from Table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 140 (1994)


For more Drug Warnings (Complete) data for CHLORTHALIDONE (14 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

3. 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-239


4.5 Drug Indication

Chlorthalidone is indicated in the management of hypertension either as the sole therapeutic agent or to enhance the effect of other antihypertensive drugs in the more severe forms of hypertension. Chlorthalidone is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. Chlorthalidone has also been found useful in edema due to various forms of renal dysfunction, such as nephrotic syndrome, acute glomerulonephritis, and chronic renal failure.


FDA Label


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Sodium Chloride Symporter Inhibitors

Agents that inhibit SODIUM CHLORIDE SYMPORTERS. They act as DIURETICS. Excess use is associated with HYPOKALEMIA. (See all compounds classified as Sodium Chloride Symporter Inhibitors.)


Diuretics

Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)


Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Active Moiety
CHLORTHALIDONE
5.2.2 FDA UNII
Q0MQD1073Q
5.2.3 Pharmacological Classes
Thiazide-like Diuretic [EPC]; Increased Diuresis [PE]
5.3 ATC Code

C - Cardiovascular system

C03 - Diuretics

C03B - Low-ceiling diuretics, excl. thiazides

C03BA - Sulfonamides, plain

C03BA04 - Chlortalidone


5.4 Absorption, Distribution and Excretion

Route of Elimination

Approximately 50% of the administered dose is excreted unmetabolized through the kidney, and excretion is characterized by biphasic elimination with a rapid phase followed by a slow secretory phase.


Volume of Distribution

Chlorthalidone has been shown to rapidly concentrate within erythrocytes and subsequently equilibrate via a slow diffusion back into the serum compartment, resulting in a large volume of distribution.


BIOCHEM STUDIES SUGGEST THAT PROLONGED DURATION OF ACTION IS DUE TO SLOW GI ABSORPTION & ENTEROHEPATIC RECIRCULATION. DRUG IS EXCRETED UNCHANGED BY KIDNEY.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871


MOST /THIAZIDE/ COMPD ARE RAPIDLY EXCRETED WITHIN 3 TO 6 HR. /THIAZIDE COMPD/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 831


STUDY OF DOSE-DEPENDENT URINARY EXCRETION OF CHLORTHALIDONE.

FLEUREN HLJ ET AL; DOSE-DEPENDENT URINARY EXCRETION OF CHLORTHALIDONE; CLIN PHARMACOL THER 25(6) 806-812 (1979)


5.5 Metabolism/Metabolites

Liver


5.6 Biological Half-Life

40-50 hours


5.7 Mechanism of Action

Chlorthalidone prevents reabsorption of sodium and chloride through inhibition of the Na+/Cl- symporter in the cortical diluting segment of the ascending limb of the loop of Henle. Reduction of sodium reabsorption subsequently reduces extracellular fluid and plasma volume via an osmotic, sodium-driven diuresis. By increasing the delivery of sodium to the distal renal tubule, Chlorthalidone indirectly increases potassium excretion via the sodium-potassium exchange mechanism. The exact mechanism of chlorthalidone's anti-hypertensive effect is under debate, however, it is thought that increased diuresis results in decreased plasma and extracellular fluid volume which therefore requires decreased cardiac output and overall lowers blood pressure. Chlorthalidone has also been shown to decrease platelet aggregation and vascular permeability, as well as promote angiogenesis in vitro, which is thought to be partly the result of reductions in carbonic anhydrasedependent pathways. These pathways may play a role in chlorthalidone's cardiovascular risk reduction effects.


...ACT BY INHIBITING RENAL TUBULAR TRANSPORT OF VARIOUS IONS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 871


Decreased plasma volume and decreased extracellular fluid volume; decreased cardiac output initially, followed by decreased total peripheral resistance with normalization of cardiac output ... /from table/

Ellenhorn, M.J., S. Schonwald, G. Ordog, J. Wasserberger. Ellenhorn's Medical Toxicology: Diagnosis and Treatment of Human Poisoning. 2nd ed. Baltimore, MD: Williams and Wilkins, 1997., p. 552


...ANTIHYPERTENSIVE EFFECT OF CHLORTHALIDONE IS THOUGHT TO BE DUE TO DECR CARDIAC OUTPUT.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 862


The exact mechanism for reduction of arterial blood pressure by diuretics is not certain. Initially the drugs decrease extracellular volume and cardiac output. However, the hypotensive effect is maintained during long-term therapy because of reduced vascular resistance ... /Diuretics/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 781


For more Mechanism of Action (Complete) data for CHLORTHALIDONE (8 total), please visit the HSDB record page.


API Reference Price

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12-Jan-2021
30-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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Fillers, Diluents & Binders

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Coating Systems & Additives

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Direct Compression

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Disintegrants & Superdisintegrants

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Controlled & Modified Release

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Lubricants & Glidants

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Granulation

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Co-Processed Excipients

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Taste Masking

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Thickeners and Stabilizers

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Chewable & Orodispersible Aids

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Film Formers & Plasticizers

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Solubilizers

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Parenteral

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API Stability Enhancers

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Empty Capsules

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Coloring Agents

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Vegetarian Capsules

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Emulsifying Agents

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Rheology Modifiers

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Topical

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Surfactant & Foaming Agents

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NEWS #PharmaBuzz

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