Details
Stereochemistry | ACHIRAL |
Molecular Formula | C22H24ClN5O2 |
Molecular Weight | 425.911 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC=C2N(C3CCN(CCCN4C(=O)NC5=C4C=CC=C5)CC3)C(=O)NC2=C1
InChI
InChIKey=FGXWKSZFVQUSTL-UHFFFAOYSA-N
InChI=1S/C22H24ClN5O2/c23-15-6-7-20-18(14-15)25-22(30)28(20)16-8-12-26(13-9-16)10-3-11-27-19-5-2-1-4-17(19)24-21(27)29/h1-2,4-7,14,16H,3,8-13H2,(H,24,29)(H,25,30)
Molecular Formula | C22H24ClN5O2 |
Molecular Weight | 425.911 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/17488253Curator's Comment: description was created based on several sources, including
https://www.fda.gov/drugs/developmentapprovalprocess/howdrugsaredevelopedandapproved/approvalapplications/investigationalnewdrugindapplication/ucm368736.htm
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17488253
Curator's Comment: description was created based on several sources, including
https://www.fda.gov/drugs/developmentapprovalprocess/howdrugsaredevelopedandapproved/approvalapplications/investigationalnewdrugindapplication/ucm368736.htm
Domperidone is a peripherally selective D2 receptor antagonist. It acts as an antiemetic and a prokinetic agent through its effects on the chemoreceptor trigger zone and motor function of the stomach and small intestine. Domperidone was not approved in USA due to risks of cardiac arrhythmias, cardiac arrest, and sudden death, but is available in other countries. However, FDA allows access to Domperidone through an expanded access investigational new drug application (IND) to patients with gastroesophageal reflux disease with upper GI symptoms, gastroparesis, and chronic constipation. As an “off-label” use, domperidone is prescribed to breastfeeding women to enhance their milk production.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8568818 |
1.0 nM [Ki] | ||
Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14521403 |
3.5 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | MOTILIUM Approved UseMOTILIUM is indicated for the short-term treatment in adults of symptoms associated with idiopathic or diabetic gastroparesis (once control of diabetes has been established by diet and/or insulin, an attempt should be made to discontinue MOTILIUM). |
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Primary | MOTILIUM Approved UseMOTILIUM is indicated for the short-term treatment in adults of intractable nausea and vomiting from any cause. |
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Primary | MOTILIUM Approved UseDomperidone is not officially approved to treat gastroesophageal reflux disease, but FDA recognizes that there are some patients with severe gastrointestinal motility disorders that are difficult to manage with available therapy for whom domperidone’s potential benefits may justify its potential risks. Patients 12 years of age and older with certain gastrointestinal (GI) conditions who have failed standard therapies may be able to receive treatment with domperidone through an expanded access investigational new drug application (IND). These conditions include gastroesophageal reflux disease with upper GI symptoms, gastroparesis, and chronic constipation. |
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Primary | MOTILIUM Approved UseDomperidone is not officially approved to treat gastroesophageal reflux disease, but FDA recognizes that there are some patients with severe gastrointestinal motility disorders that are difficult to manage with available therapy for whom domperidone’s potential benefits may justify its potential risks. Patients 12 years of age and older with certain gastrointestinal (GI) conditions who have failed standard therapies may be able to receive treatment with domperidone through an expanded access investigational new drug application (IND). These conditions include gastroesophageal reflux disease with upper GI symptoms, gastroparesis, and chronic constipation. |
PubMed
Title | Date | PubMed |
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Plasma cytokine concentration and the cytokine producing ability of whole blood cell cultures from healthy females with pharmacologically induced hyperprolactinemia. | 1999 |
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Age-dependent effect of domperidone on dopamine release by the hypoxic carotid body in the rabbit. | 2001 |
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Nonulcer Dyspepsia. | 2001 Aug |
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[Study on relationship between the reflux laryngitis and gastroesophageal reflux disease]. | 2001 Dec |
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Effect of adrenalectomy and dexamethasone treatment on prolactin secretion of lactating rats. | 2001 Dec |
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Centrally mediated effects of bromocriptine on cardiac sympathovagal balance. | 2001 Jul |
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Reduction of glomerular hyperfiltration by dopamine D(2)-like receptor blockade in experimental diabetes mellitus. | 2001 Jul |
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Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review. | 2001 Jul 7 |
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Gastroparesis and its management. | 2001 Jul-Sep |
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Dopamine D2-like receptors and amino acid-induced glomerular hyperfiltration in humans. | 2001 May |
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Central bromocriptine-induced tachycardia is reversed to bradycardia in conscious, deoxycorticosterone acetate-salt hypertensive rats. | 2001 May |
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The broad-spectrum anti-emetic activity of AS-8112, a novel dopamine D2, D3 and 5-HT3 receptors antagonist. | 2001 May |
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Quick titration of pergolide in cotreatment with domperidone is safe and effective. | 2001 May-Jun |
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Pharmacological characterization of cyclosporine A-induced kaolin intake in rats. | 2001 Oct-Nov |
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Treatment of non-ulcer dyspepsia: a meta-analysis of placebo-controlled prospective studies. | 2001 Sep |
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Dopamine D(2) receptor activation causes mitogenesis via p44/42 mitogen-activated protein kinase in opossum kidney cells. | 2001 Sep |
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[A case of the successful treatment of the esophageal leukoplakia with rabeprazole]. | 2002 |
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Hyperprolactinemia does not influence hypothalamic-pituitary-adrenocortical function during hypoglycemia in women. | 2002 |
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Role of tyrosine kinase and p44/42 MAPK in D(2)-like receptor-mediated stimulation of Na(+), K(+)-ATPase in kidney. | 2002 Apr |
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Galactogogues: medications that induce lactation. | 2002 Aug |
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Simultaneous determination of domperidone maleate and cinnarizine in a binary mixture using derivative ratio spectrophotometry and classical least squares calibration. | 2002 Aug 22 |
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New insight into the functional role of acetylcholine in developing embryonic rat retinal neurons. | 2002 Feb |
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Opioid mediated anti-nociceptive effect of domperidone and cisapride in mice. | 2002 Jan |
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Dopaminergic modulation of ventilation in obese Zucker rats. | 2002 Jan |
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Synthesis and structure-activity relationships of 4-amino-5-chloro-N-(1,4-dialkylhexahydro-1,4-diazepin-6-yl)-2-methoxybenzamide derivatives, novel and potent serotonin 5-HT3 and dopamine D2 receptors dual antagonist. | 2002 Jul |
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Quantitative and qualitative assessment of milk production after pharmaceutical induction of lactation in the mare. | 2002 Jul-Aug |
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Age-related changes in dopamine D2 receptors in rat heart and coronary vessels. | 2002 May-Jun |
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Blunted central bromocriptine-induced tachycardia in conscious, malnourished rats. | 2003 Apr |
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Bowel cleansing for diagnostic colonoscopy: which method is preferable? Istanbul experience. | 2003 Apr |
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Potentiation of domperidone-induced catalepsy by a P-glycoprotein inhibitor, cyclosporin A. | 2003 Apr |
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Tumoral versus non-tumoral hyperprolactinemia in children and adolescents: possible usefulness of the domperidone test. | 2003 Feb |
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Domperidone. Discovering new choices for lactating mothers. | 2003 Feb-Mar |
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Prolactin-releasing peptide and its homolog RFRP-1 act in hypothalamus but not in anterior pituitary gland to stimulate stress hormone secretion. | 2003 Feb-Mar |
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Simultaneous determination of domperidone and cinnarizine in a binary mixture using derivative spectrophotometry, partial least squares and principle component regression calibration. | 2003 Jan |
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Substrate-dependent regulation of MAO-A in rat mesangial cells: involvement of dopamine D2-like receptors. | 2003 Jan |
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Area postrema mediates gastric motor response induced by apomorphine in rats. | 2003 Jan 17 |
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Neuroprotective effect of nitric oxide against NMDA-induced neurotoxicity in the rat retina is associated with tyrosine hydroxylase expression. | 2003 Jul 4 |
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Determination of ambroxol in human plasma using LC-MS/MS. | 2003 Jun 1 |
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Olfactory sensitivity to catecholamines and their metabolites in the goldfish. | 2003 Mar |
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Spectrophotometric methods for the determination of anti-emetic drugs in bulk and in pharmaceutical preparations. | 2003 May |
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Studies on the interactions between drug and estrogen. II. On the inhibitory effect of 29 drugs reported to induce gynecomastia on the oxidation of estradiol at C-2 or C-17. | 2003 May |
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Effects of antireflux treatment on bronchial hyper-responsiveness and lung function in asthmatic patients with gastroesophageal reflux disease. | 2003 May |
Patents
Sample Use Guides
Domperidone should be taken 15-30 minutes before meals and, if necessary, before retiring. Adult dose of the drug is 10 mg three times daily. Domperidone is also available as suppository or as a solution for intramuscular injection.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8568818
After dissection, rat striata were homogenized by seven manual strokes in a Wheaton Teflon-glass homogenizer with ice cold 50 mM HEPES buffer, centrifuged at 27000g, the supernatant was discarded. The pellet was homogenized (five strokes), resuspended in ice cold buffer, and centrifuged again. Nonspecific binding of [3H]Spiperone (ca.0.07 nM) was defined by adding unlabeled chlorpromazine. Binding was terminated by filtering with 15 mL of ice cold buffer. Radioactivity was determined on an LKB-1219 Rack-Beta liquid scintillation counter. Domperidone binds to D2 receptorss with Ki of 1 nM
Substance Class |
Chemical
Created
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admin
on
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Record UNII |
5587267Z69
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Record Status |
Validated (UNII)
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CFR |
21 CFR 520.766
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NBK548487
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QA03FA03
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QP51AX24
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NCI_THESAURUS |
C29710
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FDA ORPHAN DRUG |
336111
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A03FA03
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DOMPERIDONE
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m4737
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DB01184
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Domperidone
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260-968-7
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5587267Z69
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C454
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE | |||
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METABOLIC ENZYME -> INHIBITOR |
IC50
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METABOLIC ENZYME -> SUBSTRATE |
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OFF-TARGET->INHIBITOR |
IC50
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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ACTIVE MOIETY |
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