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    Chemistry

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    Also known as: 145040-37-5, Atacand, Tcv-116, Amias, Parapres, Kenzen
    Molecular Formula
    C33H34N6O6
    Molecular Weight
    610.7  g/mol
    InChI Key
    GHOSNRCGJFBJIB-UHFFFAOYSA-N
    FDA UNII
    R85M2X0D68
    Candesartan Cilexetil
    Candesartan Cilexetil is a synthetic, benzimidazole-derived angiotensin II receptor antagonist prodrug with antihypertensive activity. After hydrolysis of candesartan cilexetil to candesartan during gastrointestinal absorption, candesartan selectively competes with angiotensin II for the binding of the angiotensin II receptor subtype 1 (AT1) in vascular smooth muscle, blocking angiotensin II-mediated vasoconstriction and inducing vasodilatation. In addition, antagonism of AT1 in the adrenal gland inhibits angiotensin II-stimulated aldosterone synthesis and secretion by the adrenal cortex; sodium and water excretion increase, followed by a reduction in plasma volume and blood pressure.
    1 2D Structure

    Candesartan Cilexetil

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate
    2.1.2 InChI
    InChI=1S/C33H34N6O6/c1-3-42-32-34-28-15-9-14-27(31(40)43-21(2)44-33(41)45-24-10-5-4-6-11-24)29(28)39(32)20-22-16-18-23(19-17-22)25-12-7-8-13-26(25)30-35-37-38-36-30/h7-9,12-19,21,24H,3-6,10-11,20H2,1-2H3,(H,35,36,37,38)
    2.1.3 InChI Key
    GHOSNRCGJFBJIB-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5)C(=O)OC(C)OC(=O)OC6CCCCC6
    2.2 Other Identifiers
    2.2.1 UNII
    R85M2X0D68
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1-(cyclohexylocarbonyloxy)ethyl-2-ethoxy-1-(2'-(1h-tetrazol-5-yl)biphenyl-4-yl)-1h-benzimidazole-7-carboxylate

    2. 1h-benzimidazolium, 7-carboxy-1-(2-((cyclohexylcarbonyl)oxy)ethyl)-2-ethoxy-1-(2'-(1h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)-, Hydroxide, Inner Salt, (+-)-

    3. Amias

    4. Atacand

    5. Blopress

    6. Kenzen

    7. Parapres

    8. Tcv 116

    9. Tcv-116

    2.3.2 Depositor-Supplied Synonyms

    1. 145040-37-5

    2. Atacand

    3. Tcv-116

    4. Amias

    5. Parapres

    6. Kenzen

    7. Candesartan Cilextil

    8. Tcv 116

    9. Candesartancilexetil

    10. Candesartan Cilexetil [usan]

    11. Nsc-758697

    12. Chembl1014

    13. Chebi:3348

    14. 1-(((cyclohexyloxy)carbonyl)oxy)ethyl 1-((2'-(2h-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1h-benzo[d]imidazole-7-carboxylate

    15. R85m2x0d68

    16. 1-(cyclohexyloxycarbonyloxy)ethyl 1-((2'-(1h-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-ethoxy-1h-benzo[d]imidazole-7-carboxylate

    17. 1-cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate

    18. 1-(((cyclohexyloxy)carbonyl)oxy)ethyl 1-((2'-(1h-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1h-benzo[d]imidazole-7-carboxylate

    19. Candesartan 1-(((cyclohexyloxy)carbonyl)oxy)ethyl Ester

    20. Candesartan 1-[[(cyclohexyloxy)carbonyl]oxy]ethyl Ester

    21. Racanda

    22. Unii-r85m2x0d68

    23. Tcy 116

    24. Candesartan Hexetil

    25. 1-cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(1h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate

    26. Atacand (tn)

    27. Candesartan Cilexitil

    28. Mfcd00871371

    29. Spectrum_001707

    30. Candesartan (cilexetil)

    31. Dsstox_cid_239

    32. Spectrum2_000485

    33. Spectrum3_000996

    34. Spectrum4_001124

    35. Spectrum5_001462

    36. Candesartan Celexetil Ester

    37. Dsstox_rid_85567

    38. Dsstox_gsid_20239

    39. Schembl40831

    40. Bspbio_002691

    41. Candesartan Cilexetil- Bio-x

    42. Kbiogr_001607

    43. Kbioss_002187

    44. 1h-benzimidazolium, 7-carboxy-1-(2-((cyclohexylcarbonyl)oxy)ethyl)-2-ethoxy-1-(2'-(1h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)-, Hydroxide, Inner Salt, (+-)-

    45. Candesartan Cilexetil-[d11]

    46. Mls004774127

    47. Candesartan Cilexetil , 97%

    48. Spectrum1504261

    49. Spbio_000349

    50. Gtpl8352

    51. Candesartan Cilexetil (atacand)

    52. Dtxsid5020239

    53. Kbio2_002187

    54. Kbio2_004755

    55. Kbio2_007323

    56. Kbio3_001911

    57. Hms1922j09

    58. Hms2093e20

    59. Hms3651i08

    60. Pharmakon1600-01504261

    61. Candesartan Cilexetil (jp17/usp)

    62. Candesartan Cilexetil [jan]

    63. Bcp22050

    64. Tox21_302202

    65. Ac-204

    66. Bdbm50318907

    67. Candesartan Cilexetil [vandf]

    68. Ccg-39530

    69. Nsc758697

    70. S2037

    71. Stl451065

    72. Candesartan Cilexetil [mart.]

    73. Akos015894954

    74. Akos015920180

    75. Candesartan Cilexetil [usp-rs]

    76. Candesartan Cilexetil [who-dd]

    77. Ab07617

    78. Am90293

    79. Bcp9000480

    80. Ccg-222334

    81. Db00796

    82. Ds-1302

    83. Ks-1147

    84. Nsc 758697

    85. Candesartan Cilexetil, >=98% (hplc)

    86. Ncgc00095123-01

    87. Ncgc00095123-02

    88. Ncgc00095123-03

    89. Ncgc00095123-05

    90. Ncgc00095123-10

    91. Ncgc00095123-16

    92. Ncgc00255218-01

    93. (+-)-1-hydroxyethyl 2-ethoxy-1-(p-(o-1h-tetrazol-5-ylphenyl)benzyl)-7-benzimidazolecarboxylate, Cyclohexyl Carbonate (ester)

    94. 1-[[(cyclohexyloxy)carbonyl]oxy]ethyl 2-ethoxy-1-[[2'-(1h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1h-benzimidazole-7-carboxylate

    95. 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-(ethyloxy)-1-{[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methyl}-1h-benzimidazole-7-carboxylate

    96. 1h-benzimidazole-7-carboxylic Acid, 2-ethoxy-1-((2'-(1h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-, 1-(((cyclohexyloxy)carbonyl)oxy)ethyl Ester, (+-)-

    97. 2-ethoxy-1-[[2'-(2h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1h-benzimidazole-7-carboxylic Acid 1-[[(cyclohexyloxy)carbonyl]oxy]ethyl Ester

    98. 2-ethoxy-3-[2'-(1h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3h-benzoimidazole-4-carboxylic Acid 1-cyclohexyloxycarbonyloxy-ethyl Ester

    99. Bc164274

    100. Hy-17505

    101. Smr003500784

    102. Candesartan Cilexetil [orange Book]

    103. Sbi-0206767.p001

    104. Candesartan Cilexetil [ep Monograph]

    105. Candesartan Cilexetil [usp Monograph]

    106. Cas-145040-37-5

    107. Ft-0602914

    108. Sw220041-1

    109. C07709

    110. D00626

    111. Ab01274805-01

    112. Ab01274805_02

    113. Ab01274805_03

    114. 040c375

    115. H212/91

    116. L006257

    117. Sr-05000001976

    118. Camptothecine, Antibiotic For Culture Media Use Only

    119. Q-200786

    120. Sr-05000001976-1

    121. Brd-a65671304-001-02-6

    122. Brd-a65671304-001-03-4

    123. Q27075664

    124. Candesartan 1-(((cyclohexyloxy)carbonyl)oxy)ethyl Ester [mi]

    125. Candesartan Cilexetil, European Pharmacopoeia (ep) Reference Standard

    126. Candesartan Cilexetil, United States Pharmacopeia (usp) Reference Standard

    127. Candesartan Cilexetil For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    128. Candesartan Cilexetil For System Suitability, European Pharmacopoeia (ep) Reference Standard

    129. Candesartan Cilexetil, Pharmaceutical Secondary Standard; Certified Reference Material

    130. (+/-)-1-(cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[2'-(1h-tetrazol-5-yl) Biphenyl-4-yl]methylbenzimidazole-7-carboxylate

    131. (+/-)-1-(cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7-carboxylate

    132. (+/-)1-hydroxyethyl 2-ethoxy-1-(p-(o-1h-tetrazol-5-ylphenyl)benzyl)-7-benzimidazolecarboxylate, Cyclohexyl Carbonate (ester)

    133. 1-(((cyclohexyloxy)carbonyl)oxy)ethyl1-((2'-(2h-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1h-benzo[d]imidazole-7-carboxylate

    134. 1-(cyclohexyloxycarbonyloxy)ethyl-2-ethoxy-1-[[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazol-7-carboxylate

    135. 1-{[(cyclohexyloxy)carbonyl]oxy}ethyl 2-ethoxy-1-{[2'-(1h-tetrazol-5-yl)biphenyl-4-yl]methyl}-1h-benzimidazole-7-carboxylate

    136. 1-cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl] Methyl]benzimidazole-4-carboxylate

    137. 1-cyclohexyloxycarbonyloxyethyl 2-ethoxy-3-[[4-[2-(2h-tetrazol-5-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate.

    138. 1h-benzimidazole-7-carboxylic Acid, 2-ethoxy-1-((2'-(1h-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-, 1-(((cyclohexyloxy)carbonyl)oxy)ethyl Ester, (+/-)-

    139. 1h-benzimidazole-7-carboxylic Acid, 2-ethoxy-1-[[2'-(2h-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-, 1-[[(cyclohexyloxy)carbonyl]oxy]ethyl Ester

    140. 2-ethoxy-1-[2'-(1h-tetrazole-5-yl)-4-biphenylylmethyl]-1h-benzimidazole-7-carboxylic Acid 1-(cyclohexyloxycarbonyloxy)ethyl Ester

    141. 2-ethoxy-3-[2''-(1h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3h-benzoimidazole-4-carboxylic Acid 1-cyclohexyloxycarbonyloxy-ethyl Ester

    142. 2-ethoxy-3-[2''-(2h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3h-benzoimidazole-4-carboxylic Acid 1-cyclohexyloxycarbonyloxy-ethyl Ester

    143. 2-ethoxy-3-[2'-(1h-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3h-benzoimidazole-4-carboxylic Acid 1-cyclohe

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 610.7 g/mol
    Molecular Formula C33H34N6O6
    XLogP37
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count13
    Exact Mass610.25398283 g/mol
    Monoisotopic Mass610.25398283 g/mol
    Topological Polar Surface Area143 Ų
    Heavy Atom Count45
    Formal Charge0
    Complexity962
    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 6  
    Drug NameAtacand
    PubMed HealthCandesartan (By mouth)
    Drug ClassesAngiotensin II Receptor Antagonist/Thiazide Combination
    Drug LabelATACAND (candesartan cilexetil), a prodrug, is hydrolyzed to candesartan during absorption from the gastrointestinal tract. Candesartan is a selective AT1 subtype angiotensin II receptor antagonist.Candesartan cilexetil, a nonpeptide, is chemically d...
    Active IngredientCandesartan cilexetil
    Dosage FormTablet
    RouteOral
    Strength32mg; 4mg; 16mg; 8mg
    Market StatusPrescription
    CompanyAstrazeneca

    2 of 6  
    Drug NameAtacand hct
    PubMed HealthCandesartan/Hydrochlorothiazide (By mouth)
    Active Ingredienthydrochlorothiazide; Candesartan cilexetil
    Dosage FormTablet
    RouteOral
    Strength32mg; 25mg; 16mg; 12.5mg
    Market StatusPrescription
    CompanyAstrazeneca

    3 of 6  
    Drug NameCandesartan cilexetil
    Drug LabelCandesartan cilexetil, a prodrug, is hydrolyzed to candesartan during absorption from the gastrointestinal tract. Candesartan is a selective AT1 subtype angiotensin II receptor antagonist.Candesartan cilexetil, a nonpeptide, is chemically described a...
    Active IngredientCandesartan cilexetil
    Dosage FormTablet
    Routeoral; Oral
    Strength32mg; 4mg; 16mg; 8mg
    Market StatusTentative Approval; Prescription
    CompanyMatrix Labs; Apotex; Sandoz

    4 of 6  
    Drug NameAtacand
    PubMed HealthCandesartan (By mouth)
    Drug ClassesAngiotensin II Receptor Antagonist/Thiazide Combination
    Drug LabelATACAND (candesartan cilexetil), a prodrug, is hydrolyzed to candesartan during absorption from the gastrointestinal tract. Candesartan is a selective AT1 subtype angiotensin II receptor antagonist.Candesartan cilexetil, a nonpeptide, is chemically d...
    Active IngredientCandesartan cilexetil
    Dosage FormTablet
    RouteOral
    Strength32mg; 4mg; 16mg; 8mg
    Market StatusPrescription
    CompanyAstrazeneca

    5 of 6  
    Drug NameAtacand hct
    PubMed HealthCandesartan/Hydrochlorothiazide (By mouth)
    Active Ingredienthydrochlorothiazide; Candesartan cilexetil
    Dosage FormTablet
    RouteOral
    Strength32mg; 25mg; 16mg; 12.5mg
    Market StatusPrescription
    CompanyAstrazeneca

    6 of 6  
    Drug NameCandesartan cilexetil
    Drug LabelCandesartan cilexetil, a prodrug, is hydrolyzed to candesartan during absorption from the gastrointestinal tract. Candesartan is a selective AT1 subtype angiotensin II receptor antagonist.Candesartan cilexetil, a nonpeptide, is chemically described a...
    Active IngredientCandesartan cilexetil
    Dosage FormTablet
    Routeoral; Oral
    Strength32mg; 4mg; 16mg; 8mg
    Market StatusTentative Approval; Prescription
    CompanyMatrix Labs; Apotex; Sandoz

    4.2 Drug Indication

    May be used as a first line agent to treat uncomplicated hypertension, isolated systolic hypertension and left ventricular hypertrophy. May be used as a first line agent to delay progression of diabetic nephropathy. Candesartan may be also used as a second line agent in the treatment of congestive heart failure, systolic dysfunction, myocardial infarction and coronary artery disease in those intolerant of ACE inhibitors.

    FDA Label

    Diabetic retinopathy, Essential hypertension, Heart Failure

    Diabetic retinopathy, Essential hypertension, Heart Failure

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Candesartan cilexetil is an ARB prodrug that is rapidly converted to candesartan, its active metabolite, during absorption from the gastrointestinal tract. Candesartan confers blood pressure lowering effects by antagonizing the hypertensive effects of angiotensin II via the RAAS. RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from granular cells of the juxtaglomerular apparatus in the kidneys. Renin cleaves circulating angiotensinogen to angiotensin I, which is cleaved by angiotensin converting enzyme (ACE) to angiotensin II. Angiotensin II increases blood pressure by increasing total peripheral resistance, increasing sodium and water reabsorption in the kidneys via aldosterone secretion, and altering cardiovascular structure. Angiotensin II binds to two receptors: type-1 angiotensin II receptor (AT1) and type-2 angiotensin II receptor (AT2). AT1 is a G-protein coupled receptor (GPCR) that mediates the vasoconstrictive and aldosterone-secreting effects of angiotensin II. Studies performed in recent years suggest that AT2 antagonizes AT1-mediated effects and directly affects long-term blood pressure control by inducing vasorelaxation and increasing urinary sodium excretion. Angiotensin receptor blockers (ARBs) are non-peptide competitive inhibitors of AT1. ARBs block the ability of angiotensin II to stimulate pressor and cell proliferative effects. Unlike ACE inhibitors, ARBs do not affect bradykinin-induced vasodilation. The overall effect of ARBs is a decrease in blood pressure.

    5.2 MeSH Pharmacological Classification

    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.)

    Angiotensin II Type 1 Receptor Blockers

    Agents that antagonize ANGIOTENSIN II TYPE 1 RECEPTOR. Included are ANGIOTENSIN II analogs such as SARALASIN and biphenylimidazoles such as LOSARTAN. Some are used as ANTIHYPERTENSIVE AGENTS. (See all compounds classified as Angiotensin II Type 1 Receptor Blockers.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Angiotensin 2 Receptor Blocker [EPC]; Angiotensin 2 Receptor Antagonists [MoA]
    5.4 Absorption, Distribution and Excretion

    Absorption

    Following administration of the candesartan cilexetil prodrug, the absolute bioavailability of candesartan was estimated to be 15%. Food with a high fat content has no effect on the bioavailability of candesartan from candesartan cilexetil.

    Route of Elimination

    When candesartan is administered orally, about 26% of the dose is excreted unchanged in urine. Candesartan is mainly excreted unchanged in urine and feces (via bile).

    Volume of Distribution

    0.13 L/kg

    Clearance

    0.37 mL/min/kg

    5.5 Metabolism/Metabolites

    The prodrug candesartan cilexetil undergoes rapid and complete ester hydrolysis in the intestinal wall to form the active drug, candesartan. Elimination of candesartan is primarily as unchanged drug in the urine and, by the biliary route, in the feces. Minor hepatic metabolism of candesartan (<20%) occurs by O-deethylation via cytochrome P450 2C9 to form an inactive metabolite. Candesartan undergoes N-glucuronidation in the tetrazole ring by uridine diphosphate glucuronosyltransferase 1A3 (UGT1A3). O-glucuronidation may also occur. 75% of candesartan is excreted as unchanged drug in urine and feces.

    5.6 Biological Half-Life

    Approximately 9 hours.

    5.7 Mechanism of Action

    Candesartan selectively blocks the binding of angiotensin II to AT1 in many tissues including vascular smooth muscle and the adrenal glands. This inhibits the AT1-mediated vasoconstrictive and aldosterone-secreting effects of angiotensin II and results in an overall decrease in blood pressure. Candesartan is greater than 10,000 times more selective for AT1 than AT2. Inhibition of aldosterone secretion may increase sodium and water excretion while decreasing potassium excretion.

    API Reference Price

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    18-Feb-2021
    30-Aug-2024
    KGS
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    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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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - TABLET;ORAL - 16MG

    USFDA APPLICATION NUMBER - 20838

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    DOSAGE - TABLET;ORAL - 32MG

    USFDA APPLICATION NUMBER - 20838

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    DOSAGE - TABLET;ORAL - 4MG

    USFDA APPLICATION NUMBER - 20838

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    DOSAGE - TABLET;ORAL - 8MG

    USFDA APPLICATION NUMBER - 20838

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    DOSAGE - TABLET;ORAL - 16MG;12.5MG

    USFDA APPLICATION NUMBER - 21093

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    DOSAGE - TABLET;ORAL - 32MG;12.5MG

    USFDA APPLICATION NUMBER - 21093

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    DOSAGE - TABLET;ORAL - 32MG;25MG

    USFDA APPLICATION NUMBER - 21093

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    DATA COMPILATION #PharmaFlow

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    REF. STANDARDS & IMPURITIES

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