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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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    14-Jan-2021
    28-Aug-2024
    KGS
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