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Chemistry

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Also known as: Dicycloverine, Dicycloverin, 77-19-0, Bentyl, Diocyl, Di-syntramine

Molecular Formula

C₁₉H₃₅NO₂

Molecular Weight

309.5 g/mol

InChI Key

CURUTKGFNZGFSE-UHFFFAOYSA-N

FDA UNII

4KV4X8IF6V

A muscarinic antagonist used as an antispasmodic and in urinary incontinence. It has little effect on glandular secretion or the cardiovascular system. It does have some local anesthetic properties and is used in gastrointestinal, biliary, and urinary tract spasms.

Dicyclomine is an Anticholinergic. The mechanism of action of dicyclomine is as a Cholinergic Antagonist.

1 2D Structure

Dicyclomine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate

2.1.2 InChI

InChI=1S/C19H35NO2/c1-3-20(4-2)15-16-22-18(21)19(13-9-6-10-14-19)17-11-7-5-8-12-17/h17H,3-16H2,1-2H3

2.1.3 InChI Key

CURUTKGFNZGFSE-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCN(CC)CCOC(=O)C1(CCCCC1)C2CCCCC2

2.2 Other Identifiers

2.2.1 UNII

4KV4X8IF6V

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bentyl

2. Bentylol

3. Di Cyclonex

4. Di Spaz

5. Di-cyclonex

6. Di-spaz

7. Dibent

8. Diclomin

9. Dicyclomine Hydrochloride

10. Dicycloverin

11. Hydrochloride, Dicyclomine

12. Lomine

13. Merbentyl

14. Or Tyl

15. Or-tyl

16. Spascol

2.3.2 Depositor-Supplied Synonyms

1. Dicycloverine

2. Dicycloverin

3. 77-19-0

4. Bentyl

5. Diocyl

6. Di-syntramine

7. Bentylol

8. Dicicloverina

9. Wyovin

10. Dicycloverinum

11. Dicymine

12. Procyclomin

13. Bentomine

14. Mamiesan

15. Sawamin

16. Atumin

17. Dyspas

18. 2-(diethylamino)ethyl 1-cyclohexylcyclohexane-1-carboxylate

19. Oxityl-p

20. Kolantyl

21. Diocyl Hydrochloride

22. Wyovin Hydrochloride

23. Dicycloverin Hydrochloride

24. Dicycloverine (inn)

25. [1,1'-bicyclohexyl]-1-carboxylic Acid, 2-(diethylamino)ethyl Ester

26. (bicyclohexyl)-1-carboxylic Acid, 2-(diethylamino)ethyl Ester

27. (1,1'-bicyclohexyl)-1-carboxylic Acid, 2-(diethylamino)ethyl Ester

28. 4kv4x8if6v

29. Chembl1123

30. 2-(diethylamino)ethyl 1-cyclohexylcyclohexanecarboxylate

31. 2-(diethylamino)ethyl 1,1'-bi(cyclohexyl)-1-carboxylate

32. Chebi:4514

33. Bicyclohexyl-1-carboxylic Acid 2-diethylamino-ethyl Ester

34. Ncgc00015368-06

35. Diethylaminocarbethoxybicyclohexyl Hydrochloride

36. Dicycloverinum [inn-latin]

37. Dicicloverina [inn-spanish]

38. Dsstox_cid_2926

39. Dicycloverine [inn]

40. Dsstox_rid_76790

41. Dsstox_gsid_22926

42. Bentyl Hydrochloride

43. Bentylol; Dicyclomine; Dicycloverin; Dicycloverine

44. Bentylol Hydrochloride

45. Dicycloverine [inn:ban]

46. Cas-77-19-0

47. Dicymine (tn)

48. Dicyclomine [inn]

49. Hsdb 3058

50. Einecs 201-009-4

51. Unii-4kv4x8if6v

52. Bicyclohexyl-1-carbonsaeure-2'diethylaminoethylester

53. Byclomine

54. [bicyclohexyl]-1-carboxylic Acid, 2-(diethylamino)ethyl Ester

55. Bis(cyclohexyl)carboxylic Acid Diethylaminoethyl Ester Hydrochloride

56. 2-diethylaminoethyl 1-cyclohexylcyclohexane-1-carboxylate

57. Spectrum_000934

58. Dicyclomine [mi]

59. Prestwick0_000048

60. Prestwick1_000048

61. Prestwick2_000048

62. Prestwick3_000048

63. Spectrum2_000590

64. Spectrum3_000388

65. Spectrum4_000509

66. Spectrum5_000873

67. Lopac-d-7909

68. Dicyclomine [hsdb]

69. Dicyclomine [vandf]

70. Dicycloverine (dicyclomine)

71. Schembl3317

72. Lopac0_000432

73. Bspbio_000175

74. Bspbio_002175

75. Gtpl355

76. Kbiogr_001057

77. Kbioss_001414

78. Divk1c_000162

79. Spbio_000440

80. Spbio_002096

81. Dicycloverine [who-dd]

82. Bpbio1_000193

83. Dtxsid1022926

84. Curutkgfnzgfse-uhfffaoysa-

85. Hy-b1339a

86. Kbio1_000162

87. Kbio2_001414

88. Kbio2_003982

89. Kbio2_006550

90. Kbio3_001395

91. Ninds_000162

92. Hms3604h12

93. Zinc1530613

94. Tox21_113571

95. 2-diethylaminoethyl 1-cyclohexylcyclohexane-1-carboxylate Hydrochloride

96. Bdbm50010101

97. Nsc404381

98. Stl356799

99. [bicyclohexyl]-1-carboxylic Acid, 2-(diethylamino)ethyl Ester Hydrochloride

100. Akos022107181

101. Tox21_113571_1

102. Ccg-204524

103. Db00804

104. Sdccgsbi-0050417.p005

105. Cas-67-92-5

106. Idi1_000162

107. Ncgc00015368-01

108. Ncgc00015368-02

109. Ncgc00015368-03

110. Ncgc00015368-04

111. Ncgc00015368-05

112. Ncgc00015368-07

113. Ncgc00015368-08

114. Ncgc00015368-11

115. Ncgc00015368-17

116. Ncgc00016300-01

117. Ncgc00024386-03

118. Ncgc00024386-04

119. Sbi-0050417.p004

120. Ab00053456

121. Cs-0013567

122. Wln: L6tj A- Al6tj Avo2n2&2 &gh

123. (bicyclohexyl)-1-carboxylic Acid, Hydrochloride

124. C06951

125. D07820

126. [1, 2-(diethylamino)ethyl Ester, Hydrochloride

127. Ab00053456_14

128. Ab00053456_15

129. L000680

130. Q2662662

131. 2-diethylaminoethyl 1-cyclohexylcyclohexanecarboxylate

132. Brd-k68507560-003-05-5

133. Brd-k68507560-003-15-4

134. 2-(diethylamino)ethyl (bicyclohexyl)-1-carboxylate

135. .beta.-diethylaminoethyl-1-cyclohexylhexahydrobenzoate Hydrochloride

136. .beta.-diethylaminoethyl 1-cyclohexylcyclohexanecarboxylate Hydrochloride

137. 104959-55-9

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₃₅NO₂
Molecular Weight	309.5 g/mol
XLogP3	5.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	8
Exact Mass	309.266779359 g/mol
Monoisotopic Mass	309.266779359 g/mol
Topological Polar Surface Area	29.5 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	326
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	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Bentyl
PubMed Health	Dicyclomine
Drug Classes	Gastrointestinal Agent
Drug Label	Dicyclomine hydrochloride is an antispasmodic and anticholinergic (antimuscarinic) agent available in the following dosageforms:Dicyclomine Hydrochloride Capsules, USP for oral use contain 10 mg dicyclomine hydrochloride, USP. Dicyclomine hydroch...
Active Ingredient	Dicyclomine hydrochloride
Dosage Form	Injectable; Tablet; Syrup; Capsule
Route	Injection; Oral
Strength	10mg/5ml; 10mg; 10mg/ml; 20mg
Market Status	Prescription
Company	Aptalis Pharma Us; Forest Labs

2 of 2
Drug Name	Bentyl
PubMed Health	Dicyclomine
Drug Classes	Gastrointestinal Agent
Drug Label	Dicyclomine hydrochloride is an antispasmodic and anticholinergic (antimuscarinic) agent available in the following dosageforms:Dicyclomine Hydrochloride Capsules, USP for oral use contain 10 mg dicyclomine hydrochloride, USP. Dicyclomine hydroch...
Active Ingredient	Dicyclomine hydrochloride
Dosage Form	Injectable; Tablet; Syrup; Capsule
Route	Injection; Oral
Strength	10mg/5ml; 10mg; 10mg/ml; 20mg
Market Status	Prescription
Company	Aptalis Pharma Us; Forest Labs

4.2 Therapeutic Uses

Muscarinic Antagonists; Parasympatholytics

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

...OFTEN CLASSIFIED WITH ANTIMUSCARINIC AGENTS AS "ANTISPASMODICS," DO NOT PROPERLY BELONG TO GROUP OF ANTIMUSCARINIC AGENTS. ...DICYCLOMINE HYDROCHLORIDE, VSP-DECR SPASM OF GI TRACT, BILIARY TRACT, URETER, & UTERUS WITHOUT PRODUCING CHARACTERISTIC ATROPINIC EFFECTS ON SALIVARY, SWEAT, OR GI GLANDS, EYE, CV SYSTEM... /HCL/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 527

IT DECR MOTILITY BUT DOES NOT SUPPRESS GASTRIC SECRETION. IT IS USED IN TREATMENT OF IRRITABLE COLON, SPASTIC CONSTIPATION, MUCOUS COLITIS, SPASTIC COLITIS, PYLOROSPASM, & BILIARY DYSKINESIA. IN TREATMENT OF PEPTIC ULCER IT IS USED TO DELAY GASTRIC EMPTYING. /HYDROCHLORIDE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 844

ANTICHOLINERGIC /HYDROCHLORIDE/

The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc., 1976., p. 409

4.3 Drug Warning

DICYCLOMINE SHOULD BE USED CAUTIOUSLY IN PT WITH PROSTATIC HYPERTROPHY, BLADDER NECK OBSTRUCTION, PYLORIC OBSTRUCTION, & CARDIOSPASM. EVEN THOUGH IT DOES NOT APPEAR TO RAISE INTRAOCULAR PRESSURE IN NARROW-ANGLE GLAUCOMA, IT IS ADVISABLE TO MONITOR PRESSURE OF SUCH PT.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 844

CLINICAL USE OF.../BENTYL/ HAS BEEN DISAPPOINTING.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 527

A 3-YR-OLD MALE INGESTED APPROX 100 TABLETS OF BENDECTIN & DEVELOPED TONIC-CLONIC SEIZURES FOLLOWED BY CARDIAC ARREST. ANALYSIS YIELDED HIGH LEVELS OF DOXYLAMINE, DICYCLOMINE & PYRIDOXINE. DOXYLAMINE APPEARS TO BE TOXIC CONSTITUENT.

BAYLEY M ET AL; FATAL OVERDOSE FROM BENDECTIN; CLIN PEDIATR (PHILA) 14: 507 (1975)

4.4 Drug Indication

Dicyclomine is indicated for the treatment of functional bowel disorder and irritable bowel syndrome.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Dicyclomine is an anticholinergic drug used to relax the smooth muscles of the intestines. It's duration of action is not especially long as it is usually taken 4 times daily with individual doses of 20-40mg orally or 10-20mg by intramuscular injection. Dicyclomine should not be administered intravenously.

5.2 MeSH Pharmacological Classification

Parasympatholytics

Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)

Muscarinic Antagonists

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

DICYCLOMINE

5.3.2 FDA UNII

4KV4X8IF6V

5.3.3 Pharmacological Classes

Mechanisms of Action [MoA] - Cholinergic Antagonists

5.4 ATC Code

A - Alimentary tract and metabolism

A03 - Drugs for functional gastrointestinal disorders

A03A - Drugs for functional gastrointestinal disorders

A03AA - Synthetic anticholinergics, esters with tertiary amino group

A03AA07 - Dicycloverine

5.5 Absorption, Distribution and Excretion

Absorption

The bioavailability of dicyclomine has not been determined, though it is likely well absorbed as the primary route of elimination is in the urine. Dicyclomine has a T_max of 1-1.5h.

Route of Elimination

Dicyclomine is 79.5% eliminated in the urine and 8.4% in the feces.

Volume of Distribution

The volume of distribution for a 20mg oral dose is 3.65L/kg.

Clearance

Data regarding the clearance of dicyclomine is not readily available.

5.6 Metabolism/Metabolites

The metabolism of dicyclomine has not been well researched.

5.7 Biological Half-Life

The mean plasma elimination half life is approximately 1.8 hours.

5.8 Mechanism of Action

Dicyclomine achieves its action partially through direct antimuscarinic activity of the M1, M3, and M2 receptors; and partially through antagonism of bradykinin and histamine. Dicyclomine non-competitively inhibits the action of bradykinin and histamine, resulting in direct action on the smooth muscle, and decreased strength of contractions seen in spasms of the ileum.

...MAJOR ACTION APPEARS TO BE NONSPECIFIC DIRECT RELAXANT ACTION ON SMOOTH MUSLCE RATHER THAN COMPETITIVE ANTAGONISM OF ACH.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 527

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