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Chemistry

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Also known as: 26807-65-8, Noranat, Veroxil, Tertensif, Lozol, Indaflex
Molecular Formula
C16H16ClN3O3S
Molecular Weight
365.8  g/mol
InChI Key
NDDAHWYSQHTHNT-UHFFFAOYSA-N
FDA UNII
F089I0511L

Indapamide
A benzamide-sulfonamide-indole derived DIURETIC that functions by inhibiting SODIUM CHLORIDE SYMPORTERS.
Indapamide is a Thiazide-like Diuretic. The physiologic effect of indapamide is by means of Increased Diuresis.
1 2D Structure

Indapamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide
2.1.2 InChI
InChI=1S/C16H16ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23)
2.1.3 InChI Key
NDDAHWYSQHTHNT-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1CC2=CC=CC=C2N1NC(=O)C3=CC(=C(C=C3)Cl)S(=O)(=O)N
2.2 Other Identifiers
2.2.1 UNII
F089I0511L
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Metindamide

2. S 1520

3. S-1520

4. S1520

5. Se 1520

6. Se-1520

7. Se1520

2.3.2 Depositor-Supplied Synonyms

1. 26807-65-8

2. Noranat

3. Veroxil

4. Tertensif

5. Lozol

6. Indaflex

7. Arifon

8. Fludex

9. Indamol

10. Bajaten

11. Ipamix

12. Tandix

13. Natrilix

14. Damide

15. Pressurai

16. Indapamida

17. Indapamidum

18. Natrix

19. Indapamidum [inn-latin]

20. Indapamida [inn-spanish]

21. Se-1520

22. Flupamid

23. Indamide

24. 1-(4-chloro-3-sulfamoylbenzamido)-2-methylindoline

25. Fludin

26. Lorvas

27. 4-chloro-n-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoylbenzamide

28. S-1520

29. Benzamide, 3-(aminosulfonyl)-4-chloro-n-(2,3-dihydro-2-methyl-1h-indol-1-yl)-

30. 4-chloro-n-(2-methyl-1-indolinyl)-3-sulfamoylbenzamide

31. Indapamide (lozol)

32. Flubest

33. 4-chloro-n-(2-methyl-2,3-dihydro-1h-indol-1-yl)-3-sulfamoylbenzamide

34. Metindamide

35. Cormil

36. Nsc-757075

37. N-(4-chloro-3-sulfamoylbenzamido)-2-methylindoline

38. Mls000028554

39. Chebi:5893

40. 26807-65-8(free Base)

41. Kyd-041

42. Benzamide, 4-chloro-n-(2-methyl-1-indolinyl)-3-sulfamoyl-

43. F089i0511l

44. Ncgc00018172-03

45. Smr000058829

46. 4-chloro-n-(2-methylindolin-1-yl)-3-sulfamoylbenzamide

47. Dsstox_cid_24633

48. Dsstox_rid_80366

49. Dsstox_gsid_44633

50. Se 1520

51. Rhc 2555

52. Usv 2555

53. Natrix (tn)

54. Lozol (tn)

55. Sr-01000003079

56. Einecs 248-012-7

57. Mfcd00079375

58. Brn 1604026

59. Unii-f089i0511l

60. Hypen Sr

61. 3-(aminosulfonyl)-4-chloro-n-(2,3-dihydro-2-methyl-1h-indol-1-yl)benzamide

62. Indapamide [usan:usp:inn:ban:jan]

63. Spectrum_000917

64. Indapamide [mi]

65. Opera_id_110

66. Indapamide [inn]

67. Indapamide [jan]

68. Prestwick3_000220

69. Spectrum2_000980

70. Spectrum3_000467

71. Spectrum4_000017

72. Spectrum5_000866

73. Indapamide [usan]

74. S1520

75. Indapamide [vandf]

76. Chembl406

77. Indapamide (jp17/usp)

78. Indapamide [mart.]

79. Indapamide [usp-rs]

80. Indapamide [who-dd]

81. Schembl41303

82. Bspbio_000239

83. Bspbio_002174

84. Kbiogr_000393

85. Kbioss_001397

86. 5-20-06-00348 (beilstein Handbook Reference)

87. Mls001148152

88. Mls002222229

89. Mls006011900

90. Divk1c_000508

91. Spectrum1500349

92. Spbio_001019

93. Bpbio1_000263

94. Gtpl7203

95. Dtxsid7044633

96. Indapamide [ep Impurity]

97. Indapamide [orange Book]

98. Bdbm25901

99. Hms501j10

100. Kbio1_000508

101. Kbio2_001397

102. Kbio2_003965

103. Kbio2_006533

104. Kbio3_001394

105. Indapamide [ep Monograph]

106. Ninds_000508

107. Hms1920f19

108. Hms2090m16

109. Hms2091n07

110. Hms2095l21

111. Hms2231g13

112. Hms3259c14

113. Hms3369j20

114. Hms3655e06

115. Hms3712l21

116. Hms3748k05

117. Indapamide [usp Monograph]

118. Pharmakon1600-01500349

119. Indapamide 1.0 Mg/ml In Methanol

120. Amy31945

121. Bcp04140

122. Hy-b0259

123. Tox21_110775

124. Tox21_113182

125. Tox21_302687

126. Ccg-40198

127. Nsc757075

128. S1730

129. Stl257105

130. Stl455045

131. 3-(aminosulfonyl)-4-chloro-n-(2-methyl-2,3-dihydro-1h-indol-1-yl)benzamide

132. Akos015888148

133. Tox21_110775_1

134. Ab03037

135. Ac-2073

136. Db00808

137. Ks-5219

138. Nc00568

139. Nsc 757075

140. Benzamide, 3-(aminosulfonyl)-4-chloro-n-(2,3-dihydro-2-methyl-1h-indol-l-yl)-

141. Idi1_000508

142. Ncgc00018172-02

143. Ncgc00018172-04

144. Ncgc00018172-06

145. Ncgc00018172-08

146. Ncgc00018172-09

147. Ncgc00089727-02

148. Ncgc00089727-03

149. Ncgc00256884-01

150. Sbi-0051415.p003

151. Db-047020

152. Ab00052021

153. I0730

154. Sw198686-2

155. A23574

156. D00345

157. Ab00052021-14

158. Ab00052021-15

159. Ab00052021_16

160. Ab00052021_17

161. 807i658

162. Indapamide, Analytical Standard, For Drug Analysis

163. J-016554

164. Q1078392

165. Sr-01000003079-2

166. Sr-01000003079-3

167. Brd-a95869247-001-04-6

168. Brd-a95869247-001-14-5

169. Z2786158257

170. Indapamide, British Pharmacopoeia (bp) Reference Standard

171. Indapamide, European Pharmacopoeia (ep) Reference Standard

172. Indapamide, United States Pharmacopeia (usp) Reference Standard

173. 3-aminosulfonyl-4-chloro-n-(2,3-dihydro-2-methyl-1h-indol-1-yl)benzamide

174. 4-chloro-3-aminosulphonyl-n-(2,3-dihydro2-methyl-1h-indol-1-yl)benzamide

175. Indapamide, Pharmaceutical Secondary Standard; Certified Reference Material

176. 3-(aminosulphonyl)-4-chloro-n-(2-methyl-2,3-dihydro-1h-indol-1--yl)benzamide

177. 3-(aminosulphonyl)-4-chloro-n-(2-methyl-2,3-dihydro-1h-indol-1-yl)benzamide

178. 4-chloro-n-(2-methyl-2,3-dihydro-1h-indol-1-yl)-3-sulfamoylbenzenecarboximidic Acid

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 365.8 g/mol
Molecular Formula C16H16ClN3O3S
XLogP32.9
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count3
Exact Mass365.0600902 g/mol
Monoisotopic Mass365.0600902 g/mol
Topological Polar Surface Area101 Ų
Heavy Atom Count24
Formal Charge0
Complexity580
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 2  
Drug NameIndapamide
PubMed HealthIndapamide (By mouth)
Drug ClassesCardiovascular Agent
Drug LabelIndapamide is an oral antihypertensive/diuretic. Its molecule contains both a polar sulfamoyl chlorobenzamide moiety and a lipid-soluble methylindoline moiety. It differs chemically from the thiazides in that it does not possess the thiazide ring sys...
Active IngredientIndapamide
Dosage FormTablet
RouteOral
Strength2.5mg; 1.25mg
Market StatusPrescription
CompanyMylan Pharms; Ivax Sub Teva Pharms; Actavis Elizabeth; Mylan

2 of 2  
Drug NameIndapamide
PubMed HealthIndapamide (By mouth)
Drug ClassesCardiovascular Agent
Drug LabelIndapamide is an oral antihypertensive/diuretic. Its molecule contains both a polar sulfamoyl chlorobenzamide moiety and a lipid-soluble methylindoline moiety. It differs chemically from the thiazides in that it does not possess the thiazide ring sys...
Active IngredientIndapamide
Dosage FormTablet
RouteOral
Strength2.5mg; 1.25mg
Market StatusPrescription
CompanyMylan Pharms; Ivax Sub Teva Pharms; Actavis Elizabeth; Mylan

4.2 Drug Indication

Indapamide is a diuretic indicated for use as monotherapy or in combination with other blood pressure-lowering agents to treat hypertension. It may also be used to treat fluid and salt retention associated with congestive heart failure.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Classified as a sulfonamide diuretic, indapamide is an effective antihypertensive agent and by extension, has shown efficacy in the prevention of target organ damage. Administration of indapamide produces water and electrolyte loss, with higher doses associated with increased diuresis. Severe and clinically significant electrolyte disturbances may occur with indapamide use - for example, hypokalemia resulting from renal potassium loss may lead to QTc prolongation. Further electrolyte imbalances may occur due to renal excretion of sodium, chloride, and magnesium. Other indapamide induced changes include increases in plasma renin and aldosterone, and reduced calcium excretion in the urine. In many studies investigating the effects of indapamide in both non-diabetic and diabetic hypertensive patients, glucose tolerance was not significantly altered. However, additional studies are necessary to assess the long term metabolic impacts of indapamide, since thiazide related impaired glucose tolerance can take several years to develop in non-diabetic patients.


5.2 MeSH Pharmacological Classification

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.)


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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
INDAPAMIDE
5.3.2 FDA UNII
F089I0511L
5.3.3 Pharmacological Classes
Thiazide-like Diuretic [EPC]; Increased Diuresis [PE]
5.4 ATC Code

C03BA11

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


C - Cardiovascular system

C03 - Diuretics

C03B - Low-ceiling diuretics, excl. thiazides

C03BA - Sulfonamides, plain

C03BA11 - Indapamide


5.5 Absorption, Distribution and Excretion

Absorption

The bioavailability of indapamide is virtually complete after an oral dose and is unaffected by food or antacids. Indapamide is highly lipid-soluble due to its indoline moiety - a characteristic that likely explains why indapamides renal clearance makes up less than 10% of its total systemic clearance. The Tmax occurs approximately 2.3 hours after oral administration. The Cmax and AUC0-24 values are 263 ng/mL and 2.95 ug/hr/mL, respectively.


Route of Elimination

An estimated 60-70% of indapamide is eliminated in the urine, while 16-23% is eliminated in the feces.


Volume of Distribution

Some sources report an apparent volume of distribution of 25 L for indapamide, while others report a value of approximately 60 L.


Clearance

Indapamide's renal and hepatic clearance values are reported to be 1.71 mL/min and 20-23.4 mL/min, respectively.


5.6 Metabolism/Metabolites

As a result of extensive metabolism in the liver, the majority of indapamide excreted is metabolized, with only 7% remaining unchanged. In humans, as many as 19 distinct indapamide metabolites may be produced, although not all have been identified. There are several metabolic routes through which indapamide may be metabolized, and CYP3A4 is the main enzyme involved in the corresponding hydroxylation, carboxylation, and dehydrogenation reactions. Indapamide can undergo dehydrogenation to form M5, then oxidation to form M4, then further hydroxylation at the indole moiety to form M2. These reactions are facilitated by CYP3A4. Another route of metabolism occurs when indapamide is first hydroxylated to M1 by CYP3A4. M1 then undergoes dehydrogenation to form M3 and is further oxidized to form M2. Hydroxylation of indapamides indole moiety is thought to form the major metabolite (M1), which is less pharmacologically active compared to its parent compound according to animal studies. Indapamide may also undergo epoxidation via CYP3A4 to form a reactive epoxide intermediate. The unstable epoxide intermediate may then undergo dihydroxylation via microsomal epoxide hydrolase to form M6, or glutathione conjugation to form M7.


5.7 Biological Half-Life

Indapamide is characterized by biphasic elimination. In healthy subjects, indapamide's elimination half-life can range from 13.9 to 18 hours. The long half-life is conducive to once-daily dosing.


5.8 Mechanism of Action

Indapamide acts on the nephron, specifically at the proximal segment of the distal convoluted tubule where it inhibits the Na+/Cl- cotransporter, leading to reduced sodium reabsorption. As a result, sodium and water are retained in the lumen of the nephron for urinary excretion. The effects that follow include reduced plasma volume, reduced venous return, lower cardiac output, and ultimately decreased blood pressure. Interestingly, it is likely that thiazide-like diuretics such as indapamide have additional blood pressure lowering mechanisms that are unrelated to diuresis. This is exemplified by the observation that the antihypertensive effects of thiazides are sustained 4-6 weeks after initiation of therapy, despite recovering plasma and extracellular fluid volumes. Some studies have suggested that indapamide may decrease responsiveness to pressor agents while others have suggested it can decrease peripheral resistance. Although it is clear that diuresis contributes to the antihypertensive effects of indapamide, further studies are needed to investigate the medications ability to decrease peripheral vascular resistance and relax vascular smooth muscle.


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Axplora

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Bioindustria L.I.M. Spa

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Axplora

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Indapamide

About the Company : Axplora, created from the merger of Farmabios, Novasep & PharmaZell, is a leading API manufacturing partner to the world’s leading pharma & biotech companies, delivering top-qual...

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About the Company : LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, ...

LGM Pharma is a global leader in sourcing hard-to-find APIs and intermediates for the pharmaceutical and biotech industries. LGM is also a full service CDMO providing formulation, analytical method development and testing, and commercial manufacturing. LGM Pharma offers custom API synthesis, analytical development, and regulatory services. With a network of over 300 accredited CGMP manufacturing partners, LGM provides unparalleled supply chain security. And, with over 100,000 square feet of FDA-inspected cGMP manufacturing and warehouse capacity, LGM Pharma provides a one-stop solution for solid dose, powder, semi-solid and liquid drugs.
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About the Company : Bioindustria Laboratorio Italiano Medicinali L.I.M. S.p.A. has a long tradition in the pharmaceutical business and specializes in: large and small volume injectables with termin...

Bioindustria Laboratorio Italiano Medicinali L.I.M. S.p.A. has a long tradition in the pharmaceutical business and specializes in: large and small volume injectables with terminal sterilization or with aseptic process, lyophilised dosage forms, syrups, drops, tablets, capsules.
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CHEMO

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About the Company : More than 35 years of dedication to quality, service and pursuit of excellence, CHEMO was founded by Hugo Sigman, M.D., and Silvia Gold, Biochemist, in Spain (Barcelona), in 1977, ...

More than 35 years of dedication to quality, service and pursuit of excellence, CHEMO was founded by Hugo Sigman, M.D., and Silvia Gold, Biochemist, in Spain (Barcelona), in 1977, and starts business activities trading with pharmaceutical raw materials. In the 80's, the company expanded its operations into the Industrial Business, developing and manufacturing active pharmaceutical ingredients (APIs) in Italy (Industriale Chimica) and in Spain (Quimica Sintetica). In the 90's, CHEMO starts developing and manufacturing high quality and technology finished dosage forms (FDFs).
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About the Company : Guangzhou Tosun Pharmaceutical was founded in 1999, which mainly focuses on importation & exportation of Active Pharmaceutical Ingrediants, Chemical Raw Materials, Intermediate, Ex...

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Indapamide

About the Company : Ipca Laboratories, headquartered in Mumbai, India, is a prominent pharmaceutical enterprise established in 1949. Over the years, Ipca has emerged as a leading player in India's pha...

Ipca Laboratories, headquartered in Mumbai, India, is a prominent pharmaceutical enterprise established in 1949. Over the years, Ipca has emerged as a leading player in India's pharmaceutical landscape, specializing in the manufacturing and commercialization of a diverse range of healthcare products, including APIs, formulations, and generic drugs. Renowned for its exceptional research and development capabilities, Ipca is dedicated to delivering high-quality and cost-effective medications across various therapeutic domains, including anti-malarial, anti-infective, anti-inflammatory, cardiovascular, central nervous system, among others.
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08

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Pharma Manufacturing 2024
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Indapamide

About the Company : Located in beautiful Spring City-Jinan,Jiwan is a high-tech pharmaceutical company,specializing in R&D, technology transfer and technical consulting of biotechnology and pharmaceut...

Located in beautiful Spring City-Jinan,Jiwan is a high-tech pharmaceutical company,specializing in R&D, technology transfer and technical consulting of biotechnology and pharmaceutical technology. Moreover, Jiwan has the right of dealing import and export business of APIs,intermediates and fine chemical goods. Jiwan has a group of high-level specialists from various fields of pharmaceutics and its related sciences who have rich experence and professional research talents and have been working together for more than 10 years.
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09

Pharma Manufacturing 2024
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Pharma Manufacturing 2024
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Indapamide

About the Company : Alchemia is dedicated to the production of high-quality active ingredients and intermediates for the pharmaceutical industry. Our goal is to offer products manufactured to the hig...

Alchemia is dedicated to the production of high-quality active ingredients and intermediates for the pharmaceutical industry. Our goal is to offer products manufactured to the highest standards of excellence in accordance with the following business philosophy: • State-of-the-art manufacturing facilities • Process optimization and continued improvement • Ongoing education and training of personnel • Long-term partnerships with suppliers and customers built on transparency • A constant exchange of ideas with the academic community.
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10

Pharma Manufacturing 2024
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Pharma Manufacturing 2024
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Indapamide

About the Company : Suzhou Bichal Biological Technology Co.,Ltd is an ISO 9001:2008 Certified Organization,established plants in Yancheng and Lianyungang.focus on R&D synthesis,manufacture,analysis gm...

Suzhou Bichal Biological Technology Co.,Ltd is an ISO 9001:2008 Certified Organization,established plants in Yancheng and Lianyungang.focus on R&D synthesis,manufacture,analysis gm-kg scale new biological and chemical Generic Pharmas and intermediates in Antiviral,Hypotensives,Antianginal,Peripheral vasodilator,Anticoagulant,Anti-cancer and antineoplastic,Gastric mucosa protectives,Anti-asthamatics,Central nervous stimulants,Immunomodulators,Antidiabetic,Antigout.Prostaglandins,Corticosteroids,peptide reagents etc.welcome to contact with us. Our quality and service are what you expected!
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BOX 6901 LUGANO SWITZERLAND , , Swi tzerland Switzerland","customerAddress":"PIRAMAL ANANTA, PIRAMAL AGASTYA PARK"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q4","strtotime":1729621800,"product":"INDAPAMIDE MICRONIZED","address":"PIRAMAL ANANTA, PIRAMAL AGASTYA PARK","city":"KURLA, MUMBAI","supplier":"CHEMO","supplierCountry":"SPAIN","foreign_port":"MADRID","customer":"PIRAMAL PHARMA SOLUTIONS","customerCountry":"INDIA","quantity":"11.47","actualQuantity":"11.47","unit":"KGS","unitRateFc":"2600","totalValueFC":"30149.7","currency":"USD","unitRateINR":"220870","date":"23-Oct-2024","totalValueINR":"2533378.9","totalValueInUsd":"30149.7","indian_port":"Bombay Air","hs_no":"29359090","bill_no":"6291611","productDescription":"API","marketType":"REGULATED MARKET","country":"SPAIN","selfForZScoreResived":"Micronized","supplierPort":"MADRID","supplierAddress":"LUGANO BRANCH VIA.F.PELLI 17 , P.O. BOX 6901 LUGANO SWITZERLAND , , Swi tzerland Switzerland","customerAddress":"PIRAMAL ANANTA, PIRAMAL AGASTYA PARK"}]
13-Jan-2021
23-Oct-2024
KGS
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Average Price (USD/KGS)

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
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Average Price
(USD/KGS)
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INTERMEDIATES SUPPLIERS

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American Pharma Summit
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American Pharma Summit
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CAS Number : 102789-79-7

End Use API : Indapamide

About The Company : Actis Generics Pvt Ltd is a fast emerging APIs (Active Pharmaceutical Ingredients) & Intermediates manufacturer & supplier in India set up by a group of young p...

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