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    Loperamide HCl

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    ANALYTICAL

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    2D Structure
    Also known as: 34552-83-5, Loperamide hcl, Imodium, Suprasec, Loperamide (hydrochloride), Fortasec
    Molecular Formula
    C29H34Cl2N2O2
    Molecular Weight
    513.5  g/mol
    InChI Key
    PGYPOBZJRVSMDS-UHFFFAOYSA-N
    FDA UNII
    77TI35393C
    One of the long-acting synthetic ANTIDIARRHEALS; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-N,N-dimethyl-2,2-diphenylbutanamide;hydrochloride
    2.1.2 InChI
    InChI=1S/C29H33ClN2O2.ClH/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23;/h3-16,34H,17-22H2,1-2H3;1H
    2.1.3 InChI Key
    PGYPOBZJRVSMDS-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN(C)C(=O)C(CCN1CCC(CC1)(C2=CC=C(C=C2)Cl)O)(C3=CC=CC=C3)C4=CC=CC=C4.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    77TI35393C
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Hydrochloride, Loperamide

    2. Imodium

    3. Loperamide

    4. Loperamide Monohydrochloride

    5. Monohydrochloride, Loperamide

    6. R 18553

    7. R-18553

    8. R18553

    2.3.2 Depositor-Supplied Synonyms

    1. 34552-83-5

    2. Loperamide Hcl

    3. Imodium

    4. Suprasec

    5. Loperamide (hydrochloride)

    6. Fortasec

    7. Imodium A-d

    8. 4-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-n,n-dimethyl-2,2-diphenylbutanamide Hydrochloride

    9. Nsc-696356

    10. Maalox Anti-diarrheal

    11. 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-n,n-dimethyl-2,2-diphenylbutanamide Hydrochloride

    12. 4-[4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl]-n,n-dimethyl-2,2-diphenylbutanamide;hydrochloride

    13. Mls000069779

    14. Chebi:6533

    15. 1-piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-, Hydrochloride

    16. R 18,553

    17. 4-(p-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-1-piperidine Butyramide Hcl

    18. 77ti35393c

    19. 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenylpiperidine-1-butyramide Monohydrochloride

    20. 4-(p-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-1-piperidinebutyramide Monohydrochloride

    21. Dissenten

    22. Lopemid

    23. Lopemin

    24. Loperyl

    25. Smr000058466

    26. Imosec

    27. Tebloc

    28. R-18553

    29. Maalox Antidiarrheal

    30. Blox

    31. Brek

    32. Diamode

    33. Loseramin

    34. Imotil

    35. Anti-diarrheal

    36. Kao-paverin

    37. Diar-aid

    38. Kaopectate 1-d

    39. K-pek Ii

    40. Pepto Diarrhea Control

    41. Imodium A-d Ez Chews

    42. Pj185

    43. Sr-01000075507

    44. Up And Up Anti Diarrheal

    45. Einecs 252-082-4

    46. C29h33cln2o2.hcl

    47. Unii-77ti35393c

    48. Loperamide, Hcl

    49. R 18553

    50. Prestwick_302

    51. Imodium (tn)

    52. Mfcd00058581

    53. Cpd000058466

    54. Loperamide Hydrochloride [usan:usp:jan]

    55. Loperamidi Hydrochloridum

    56. Opera_id_1508

    57. 4-(4-(p-chlorophenyl)-4-hydroxy-1-piperidyl)-n,n-dimethyl-2,2-diphenylbutyramide Hcl

    58. Chembl1707

    59. Loperamidehydrochloride

    60. Schembl15048

    61. R-18553 (hydrochloride)

    62. Mls001148627

    63. Mls002222200

    64. Spectrum2300241

    65. Regid_for_cid_71420

    66. Loperamide Hydrochloride ,(s)

    67. Hy-b0418a

    68. Dtxsid00880006

    69. Hms1568m10

    70. Hms1922j18

    71. Pharmakon1600-02300241

    72. Bcp28441

    73. Loperamide Hydrochloride (jan/usp)

    74. Tox21_500708

    75. Ccg-39494

    76. Loperamide Hydrochloride [mi]

    77. Nsc696356

    78. Nsc759568

    79. S2480

    80. Loperamide Hydrochloride [jan]

    81. Akos015846351

    82. Ac-8242

    83. Adl 2-1294

    84. Loperamide Hydrochloride [usan]

    85. Lp00708

    86. Nc00572

    87. Nsc 759568

    88. Nsc-759568

    89. Loperamide Hydrochloride [mart.]

    90. Loperamide Hydrochloride [vandf]

    91. Loperamide Hydrochloride [usp-rs]

    92. Loperamide Hydrochloride [who-dd]

    93. Loperamide Hydrochloride [who-ip]

    94. Ncgc00094059-01

    95. Ncgc00094059-02

    96. Ncgc00094059-03

    97. Ncgc00094059-04

    98. Ncgc00094059-05

    99. Ncgc00180886-01

    100. Ncgc00180886-02

    101. Ncgc00261393-01

    102. 1-piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-.alpha.,.alpha.-diphenyl-, Monohydrochloride

    103. 1-piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-, Monohydrochloride

    104. 4-[4-(4-chlorophenyl)-4-hydroxy-1-piperidinyl]-n,n-dimethyl-2,2-diphenylbutanamide Hydrochloride

    105. As-13181

    106. Bl166178

    107. B1392

    108. Eu-0100708

    109. Ft-0627973

    110. L0154

    111. Sw196602-3

    112. Loperamide Hydrochloride [ep Impurity]

    113. Loperamide Hydrochloride [orange Book]

    114. D00729

    115. D78217

    116. L 4762

    117. Loperamide Hydrochloride [ep Monograph]

    118. Loperamide Hydrochloride [usp Monograph]

    119. Loperamidi Hydrochloridum [who-ip Latin]

    120. 552l835

    121. A822272

    122. Sr-01000075507-1

    123. Sr-01000075507-3

    124. Sr-01000075507-8

    125. W-106729

    126. Q27107231

    127. Loperamide Hydrochloride, Vetranal(tm), Analytical Standard

    128. Imodium Multi-symptom Relief Component Loperamide Hydrochloride

    129. Loperamide Hydrochloride Component Of Imodium Multi-symptom Relief

    130. Loperamide Hydrochloride, British Pharmacopoeia (bp) Reference Standard

    131. Loperamide Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    132. 4-(4-chlorophenyl)-4-hydroxy-n,.alpha.-diphenyl-1-piperidinebutanamide Monohydrochloride

    133. 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-?,?-diphenyl-1-piperidinebutanamide Hydrochloride

    134. Loperamide Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

    135. Loperamide Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    136. 4-(4-chlorophenyl)-1-[4-(dimethylamino)-4-oxo-3,3-diphenylbutyl]-4-hydroxypiperidin-1-ium Chloride

    137. 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide Hydrochloride

    138. 4-(4-chlorophenyl)-4-hydroxy-n,n-dimethyl-alpha,alpha-diphenyl-1-piperidinebutanamidehydrochloride

    139. 4-(p-chlorophenyl)-4-hydroxy-n,n-dimethyl-.alpha.,.alpha.-diphenyl-1-piperidinebutyramide Monohydrochloride

    140. 4-[4-(4-chlorophenyl)-4-oxidanyl-piperidin-1-yl]-n,n-dimethyl-2,2-diphenyl-butanamide Hydrochloride

    141. Loperamide Hydrochloride For System Suitability, European Pharmacopoeia (ep) Reference Standard

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 513.5 g/mol
    Molecular Formula C29H34Cl2N2O2
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count7
    Exact Mass512.1997337 g/mol
    Monoisotopic Mass512.1997337 g/mol
    Topological Polar Surface Area43.8 Ų
    Heavy Atom Count35
    Formal Charge0
    Complexity623
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 8  
    Drug NameImodium
    Active IngredientLoperamide hydrochloride
    Dosage FormCapsule
    RouteOral
    Strength2mg
    Market StatusPrescription
    CompanyMcneil Cons

    2 of 8  
    Drug NameImodium a-d ez chews
    Active IngredientLoperamide hydrochloride
    Dosage FormTablet, chewable
    RouteOral
    Strength2mg
    Market StatusOver the Counter
    CompanyMcneil

    3 of 8  
    Drug NameLoperamide hydrochloride
    PubMed HealthLoperamide (By mouth)
    Drug ClassesAntidiarrheal, Gastrointestinal Agent
    Drug LabelLoperamide hydrochloride is a white to slightly yellow powder and is freely soluble in methanol, isopropyl alcohol, chloroform and slightly soluble in water.Loperamide hydrochloride, 4-(p-chlorophenyl)-4-hydroxy-N,N-dimethyl-monohydrochloride, is a s...
    Active IngredientLoperamide hydrochloride
    Dosage FormTablet; Capsule; Suspension; Solution
    RouteOral
    Strength1mg/5ml; 1mg; 2mg; 1mg/7.5ml
    Market StatusOver the Counter; Prescription
    CompanyWockhardt; Ohm Labs; Teva; Lnk; Banner Pharmacaps; Roxane; Perrigo R And D; Hi Tech Pharma; Perrigo; Contract Pharmacal; Mylan

    4 of 8  
    Drug NameLoperamide hydrochloride and simethicone
    Drug LabelIMODIUM (loperamide hydrochloride), 4-(p-chlorophenyl)-4-hydroxy-N,N-dimethyl-a,a-diphenyl-1-piperidinebutyramide monohydrochloride, is a synthetic antidiarrheal for oral use.IMODIUM is available in 2mg capsules.The inactive ingredients are: Lact...
    Active Ingredientsimethicone; Loperamide hydrochloride
    Dosage FormTablet; Tablet, chewable
    RouteOral
    Strength125mg; 2mg
    Market StatusOver the Counter
    CompanyRanbaxy; Perrigo

    5 of 8  
    Drug NameImodium
    Active IngredientLoperamide hydrochloride
    Dosage FormCapsule
    RouteOral
    Strength2mg
    Market StatusPrescription
    CompanyMcneil Cons

    6 of 8  
    Drug NameImodium a-d ez chews
    Active IngredientLoperamide hydrochloride
    Dosage FormTablet, chewable
    RouteOral
    Strength2mg
    Market StatusOver the Counter
    CompanyMcneil

    7 of 8  
    Drug NameLoperamide hydrochloride
    PubMed HealthLoperamide (By mouth)
    Drug ClassesAntidiarrheal, Gastrointestinal Agent
    Drug LabelLoperamide hydrochloride is a white to slightly yellow powder and is freely soluble in methanol, isopropyl alcohol, chloroform and slightly soluble in water.Loperamide hydrochloride, 4-(p-chlorophenyl)-4-hydroxy-N,N-dimethyl-monohydrochloride, is a s...
    Active IngredientLoperamide hydrochloride
    Dosage FormTablet; Capsule; Suspension; Solution
    RouteOral
    Strength1mg/5ml; 1mg; 2mg; 1mg/7.5ml
    Market StatusOver the Counter; Prescription
    CompanyWockhardt; Ohm Labs; Teva; Lnk; Banner Pharmacaps; Roxane; Perrigo R And D; Hi Tech Pharma; Perrigo; Contract Pharmacal; Mylan

    8 of 8  
    Drug NameLoperamide hydrochloride and simethicone
    Drug LabelIMODIUM (loperamide hydrochloride), 4-(p-chlorophenyl)-4-hydroxy-N,N-dimethyl-a,a-diphenyl-1-piperidinebutyramide monohydrochloride, is a synthetic antidiarrheal for oral use.IMODIUM is available in 2mg capsules.The inactive ingredients are: Lact...
    Active Ingredientsimethicone; Loperamide hydrochloride
    Dosage FormTablet; Tablet, chewable
    RouteOral
    Strength125mg; 2mg
    Market StatusOver the Counter
    CompanyRanbaxy; Perrigo

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antidiarrheals

    Miscellaneous agents found useful in the symptomatic treatment of diarrhea. They have no effect on the agent(s) that cause diarrhea, but merely alleviate the condition. (See all compounds classified as Antidiarrheals.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Opioid Agonists [MoA]; Opioid Agonist [EPC]