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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

Dicyclomine
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 Weight 309.5 g/mol
Molecular Formula C19H35NO2
XLogP35.5
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count8
Exact Mass309.266779359 g/mol
Monoisotopic Mass309.266779359 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count22
Formal Charge0
Complexity326
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
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 NameBentyl
PubMed HealthDicyclomine
Drug ClassesGastrointestinal Agent
Drug LabelDicyclomine 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 IngredientDicyclomine hydrochloride
Dosage FormInjectable; Tablet; Syrup; Capsule
RouteInjection; Oral
Strength10mg/5ml; 10mg; 10mg/ml; 20mg
Market StatusPrescription
CompanyAptalis Pharma Us; Forest Labs

2 of 2  
Drug NameBentyl
PubMed HealthDicyclomine
Drug ClassesGastrointestinal Agent
Drug LabelDicyclomine 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 IngredientDicyclomine hydrochloride
Dosage FormInjectable; Tablet; Syrup; Capsule
RouteInjection; Oral
Strength10mg/5ml; 10mg; 10mg/ml; 20mg
Market StatusPrescription
CompanyAptalis 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 Tmax 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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B5 (pt) & B6 (pt) SIPCOT INDUSTRIAL PARK, IRUNGATTUKOTTAI"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1714501800,"product":"DICYCLOMINE HCL","address":"7\/1,CORPORATE PARK,SION-TROMBAY","city":"MUMBAI","supplier":"OLON S.P.A","supplierCountry":"ITALY","foreign_port":"MILAN - MALPENSA","customer":"FLAMINGO PHARMACEUTICALS LIMITED","customerCountry":"INDIA","quantity":"25.00","actualQuantity":"25","unit":"KGS","unitRateFc":"650","totalValueFC":"16515.6","currency":"USD","unitRateINR":"54860","date":"01-May-2024","totalValueINR":"1371500","totalValueInUsd":"16515.6","indian_port":"Bombay Air","hs_no":"29221990","bill_no":"3292284","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"DIREZIONE E UFFICISTR.RIVOLTANA KM 6\/720053 RODANA (MI) ITALY","customerAddress":"7\/1,CORPORATE PARK,SION-TROMBAY"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1717698600,"product":"DICYCLOMINE HCL USP","address":"LINCOLN HOUSE, B\/H SATYAM","city":"AHMEDABAD ,GUJARAT","supplier":"OLON S.P.A","supplierCountry":"ITALY","foreign_port":"MILAN - MALPENSA","customer":"LINCOLN PHARMACEUTICALS","customerCountry":"INDIA","quantity":"33.00","actualQuantity":"33","unit":"KGS","unitRateFc":"295","totalValueFC":"9882.4","currency":"USD","unitRateINR":"24868.5","date":"07-Jun-2024","totalValueINR":"820660.5","totalValueInUsd":"9882.4","indian_port":"Ahmedabad Air","hs_no":"29221990","bill_no":"3875462","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"VIA RIVOLTANA KM 6 7RODANO MI 20053 ITITALY IT","customerAddress":"LINCOLN HOUSE, B\/H SATYAM"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1719253800,"product":"DICYCLOMINE HYDROCHLORIDE BP","address":"NO.49D, BOMMASANDRA INDUSTRIAL","city":"BANGALORE","supplier":"OLON S.P.A","supplierCountry":"ITALY","foreign_port":"MILAN - MALPENSA","customer":"ADCOCK INGRAM","customerCountry":"INDIA","quantity":"25.00","actualQuantity":"25","unit":"KGS","unitRateFc":"290","totalValueFC":"7962.2","currency":"EUR","unitRateINR":"26448","date":"25-Jun-2024","totalValueINR":"661200","totalValueInUsd":"7962.2","indian_port":"Bangalore Air","hs_no":"29420011","bill_no":"4169972","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"STRADA RIVOLTANA KM 6\/720053 RODANO MISDNF ITALY","customerAddress":"NO.49D, BOMMASANDRA INDUSTRIAL"}]
14-Jan-2021
28-Aug-2024
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