Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H35NO2.ClH |
Molecular Weight | 345.948 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN(CC)CCOC(=O)C1(CCCCC1)C2CCCCC2
InChI
InChIKey=GUBNMFJOJGDCEL-UHFFFAOYSA-N
InChI=1S/C19H35NO2.ClH/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;1H
Dicyclomine is an anticholinergic tertiary amine used frequently by oral and parenteral route as an effective anti-spasmodic agent. Dicyclomine hydrochloride salt is approved under brand name bentyl for the treatment of functional bowel/irritable bowel syndrome. In addition is known, that dicyclomine is also used in morning and motion sickness, dysmenorrheal, intestinal hypermotility. It was shown, that Dicyclomine is a selective M1 and M3 muscarinic receptors antagonist, but os shown pharmacological activity via the M1 receptor.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL216 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2432979 |
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Target ID: CHEMBL245 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3612532 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | BENTYL Approved UseDicyclomine hydrochloride oral solution is indicated for the treatment of functional bowel/irritable bowel syndrome. Launch Date4.66646401E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
50.47 ng/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICYCLOMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
47.98 ng/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICYCLOMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
202.67 ng × h/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICYCLOMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
207.88 ng × h/mL |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICYCLOMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.66 h |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICYCLOMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
6.09 h |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICYCLOMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.8 h |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
DICYCLOMINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
600 mg single, oral Highest recorded dose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: |
unhealthy, 10 months n = 1 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: 10 months Sex: unknown Population Size: 1 Sources: |
|
1500 mg single, oral Highest recorded dose Dose: 1500 mg Route: oral Route: single Dose: 1500 mg Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 1 Sources: |
|
40 mg 4 times / day multiple, oral Recommended Dose: 40 mg, 4 times / day Route: oral Route: multiple Dose: 40 mg, 4 times / day Sources: |
unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: |
Other AEs: Dry mouth, Dizziness... Other AEs: Dry mouth (33%) Sources: Dizziness (40%) Vision blurred (27%) Nausea (14%) Somnolence (9%) Asthenia (7%) Nervousness (6%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 14% | 40 mg 4 times / day multiple, oral Recommended Dose: 40 mg, 4 times / day Route: oral Route: multiple Dose: 40 mg, 4 times / day Sources: |
unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: |
Vision blurred | 27% | 40 mg 4 times / day multiple, oral Recommended Dose: 40 mg, 4 times / day Route: oral Route: multiple Dose: 40 mg, 4 times / day Sources: |
unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: |
Dry mouth | 33% | 40 mg 4 times / day multiple, oral Recommended Dose: 40 mg, 4 times / day Route: oral Route: multiple Dose: 40 mg, 4 times / day Sources: |
unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: |
Dizziness | 40% | 40 mg 4 times / day multiple, oral Recommended Dose: 40 mg, 4 times / day Route: oral Route: multiple Dose: 40 mg, 4 times / day Sources: |
unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: |
Nervousness | 6% | 40 mg 4 times / day multiple, oral Recommended Dose: 40 mg, 4 times / day Route: oral Route: multiple Dose: 40 mg, 4 times / day Sources: |
unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: |
Asthenia | 7% | 40 mg 4 times / day multiple, oral Recommended Dose: 40 mg, 4 times / day Route: oral Route: multiple Dose: 40 mg, 4 times / day Sources: |
unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: |
Somnolence | 9% | 40 mg 4 times / day multiple, oral Recommended Dose: 40 mg, 4 times / day Route: oral Route: multiple Dose: 40 mg, 4 times / day Sources: |
unhealthy, adult n = 100 Health Status: unhealthy Condition: functional bowel/irritable bowel syndrome Age Group: adult Sex: unknown Population Size: 100 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Dicyclomine: worrying symptoms associated with its use in some small babies. | 1984 Mar 24 |
|
Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells. | 1989 Apr |
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The effect of M1 muscarinic blockade on behavior and physiological responses following traumatic brain injury in the rat. | 1990 Mar 12 |
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Antinociceptive and antiamnesic properties of the presynaptic cholinergic amplifier PG-9. | 1998 Mar |
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Alternative therapies of morning sickness. | 2001 Dec |
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Infantile colic. | 2002 Dec |
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Infantile colic. | 2002 Jun |
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Medical, social, and legal implications of treating nausea and vomiting of pregnancy. | 2002 May |
|
Prenatal prescription of macrolide antibiotics and infantile hypertrophic pyloric stenosis. | 2003 Apr |
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Infantile colic. | 2003 Dec |
|
Variable effects of previously untested muscarinic receptor antagonists on experimental myopia. | 2003 Mar |
|
Infantile colic. | 2004 Jun |
|
The negative impact of litigation on women's health care. | 2005 Dec |
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Infantile colic. | 2005 Jun |
|
Muscarinic M2 and M4 receptors in anterior cingulate cortex: relation to neuropsychiatric symptoms in dementia with Lewy bodies. | 2005 Jun 20 |
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Pharmacodynamic effects of darifenacin, a muscarinic M selective receptor antagonist for the treatment of overactive bladder, in healthy volunteers. | 2005 Nov |
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Interaction between M1-muscarinic and glutamatergic NMDA receptors on an inhibitory avoidance task. | 2005 Nov 30 |
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[Drug treatment of irritable bowel syndrome: an unmet need]. | 2007 Mar |
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Improving the detection limits of antispasmodic drugs electrodes by using modified membrane sensors with inner solid contact. | 2007 May 9 |
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Blockade of M1 muscarinic acetylcholine receptors modulates the methamphetamine-induced psychomotor stimulant effect. | 2008 Jun 2 |
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Dicyclomine, an M1 muscarinic antagonist, reduces biomarker levels, but not neuronal degeneration, in fluid percussion brain injury. | 2008 Nov |
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Effect of fibre, antispasmodics, and peppermint oil in the treatment of irritable bowel syndrome: systematic review and meta-analysis. | 2008 Nov 13 |
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Development of functional gastrointestinal disorders after Giardia lamblia infection. | 2009 Apr 21 |
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Antispasmodic and bronchodilator activities of Artemisia vulgaris are mediated through dual blockade of muscarinic receptors and calcium influx. | 2009 Dec 10 |
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Self-medication for infants with colic in Lagos, Nigeria. | 2009 Feb 4 |
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[Characterization of muscarinic receptors in undifferentiated thyroid cells in Fisher rats]. | 2009 Mar |
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Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method. | 2010 Dec |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
Patents
Sample Use Guides
Adults-Oral. The only oral dose clearly shown to be effective is 160 mg per day (in 4 equally divided doses). Since this dose is associated with a significant incidence of side effects, it is prudent to begin with 80 mg per day (in 4 equally divided doses). Depending upon the patient’s response during the first week of therapy, the dose should be increased to 160 mg per day unless side effects limit dosage escalation. If efficacy is not achieved within 2 weeks or side effects require doses below 80 mg per day, the drug should be discontinued. Documented safety data are not available for doses above 80 mg daily for periods longer than 2 weeks.
Adults-Intramuscular Injection. NOT FOR INTRAVENOUS USE. The intramuscular dosage form is to be used temporarily when the patient cannot take oral medication. Intramuscular injection is about twice as bioavailable as oral dosage forms; consequently, the recommended intramuscular dose is 80 mg daily (in 4 equally divided doses). Oral dicyclomine hydrochloride should be started as soon as possible and the intramuscular form should not be used for periods longer than 1 or 2 days.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14723484
Dicyclomine showed inhibitory action against several pathogenic bacteria. Dicyclomine inhibited most of the bacterial isolates tested at 25-100 microg/ml concentration, and a few were sensitive even at a lower concentration (10 microg/ml). Dicyclomine was found to be bacteriostatic in nature against Shigella dysenteriae 7, and bactericidal against S. aureus NCTC 6571, 8530, and 8531.
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CFR |
21 CFR 310.201
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NCI_THESAURUS |
C29704
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C29698
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C28987
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441344
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100000090526
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CQ903KQA31
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SUB01676MIG
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67-92-5
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DTXSID0058778
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m4378
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CHEMBL1123
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200-671-1
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DBSALT000698
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4515
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404381
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CQ903KQA31
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ACTIVE MOIETY
SUBSTANCE RECORD