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Loperamide Hydrochloride

Synopsis, Chemistry

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TABLET;ORAL - 2MG, CAPSULE;ORAL - 1MG, CAPSULE;ORAL - 2MG

TABLET;ORAL - 2MG
CAPSULE;ORAL - 1MG
CAPSULE;ORAL - 2MG

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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

Loperamide Hydrochloride

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 Formula	C₂₉H₃₄Cl₂N₂O₂
Molecular Weight	513.5 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	7
Exact Mass	512.1997337 g/mol
Monoisotopic Mass	512.1997337 g/mol
Topological Polar Surface Area	43.8 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	623
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 8
Drug Name	Imodium
Active Ingredient	Loperamide hydrochloride
Dosage Form	Capsule
Route	Oral
Strength	2mg
Market Status	Prescription
Company	Mcneil Cons

2 of 8
Drug Name	Imodium a-d ez chews
Active Ingredient	Loperamide hydrochloride
Dosage Form	Tablet, chewable
Route	Oral
Strength	2mg
Market Status	Over the Counter
Company	Mcneil

3 of 8
Drug Name	Loperamide hydrochloride
PubMed Health	Loperamide (By mouth)
Drug Classes	Antidiarrheal, Gastrointestinal Agent
Drug Label	Loperamide 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 Ingredient	Loperamide hydrochloride
Dosage Form	Tablet; Capsule; Suspension; Solution
Route	Oral
Strength	1mg/5ml; 1mg; 2mg; 1mg/7.5ml
Market Status	Over the Counter; Prescription
Company	Wockhardt; Ohm Labs; Teva; Lnk; Banner Pharmacaps; Roxane; Perrigo R And D; Hi Tech Pharma; Perrigo; Contract Pharmacal; Mylan

4 of 8
Drug Name	Loperamide hydrochloride and simethicone
Drug Label	IMODIUM (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 Ingredient	simethicone; Loperamide hydrochloride
Dosage Form	Tablet; Tablet, chewable
Route	Oral
Strength	125mg; 2mg
Market Status	Over the Counter
Company	Ranbaxy; Perrigo

5 of 8
Drug Name	Imodium
Active Ingredient	Loperamide hydrochloride
Dosage Form	Capsule
Route	Oral
Strength	2mg
Market Status	Prescription
Company	Mcneil Cons

6 of 8
Drug Name	Imodium a-d ez chews
Active Ingredient	Loperamide hydrochloride
Dosage Form	Tablet, chewable
Route	Oral
Strength	2mg
Market Status	Over the Counter
Company	Mcneil

7 of 8
Drug Name	Loperamide hydrochloride
PubMed Health	Loperamide (By mouth)
Drug Classes	Antidiarrheal, Gastrointestinal Agent
Drug Label	Loperamide 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 Ingredient	Loperamide hydrochloride
Dosage Form	Tablet; Capsule; Suspension; Solution
Route	Oral
Strength	1mg/5ml; 1mg; 2mg; 1mg/7.5ml
Market Status	Over the Counter; Prescription
Company	Wockhardt; Ohm Labs; Teva; Lnk; Banner Pharmacaps; Roxane; Perrigo R And D; Hi Tech Pharma; Perrigo; Contract Pharmacal; Mylan

8 of 8
Drug Name	Loperamide hydrochloride and simethicone
Drug Label	IMODIUM (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 Ingredient	simethicone; Loperamide hydrochloride
Dosage Form	Tablet; Tablet, chewable
Route	Oral
Strength	125mg; 2mg
Market Status	Over the Counter
Company	Ranbaxy; 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]