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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
Structure of DOMPERIDONE

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)

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.0 nM [Ki]
3.5 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MOTILIUM

Approved Use

MOTILIUM 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).
Primary
MOTILIUM

Approved Use

MOTILIUM is indicated for the short-term treatment in adults of intractable nausea and vomiting from any cause.
Primary
MOTILIUM

Approved Use

Domperidone 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.
Primary
MOTILIUM

Approved Use

Domperidone 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

PubMed

TitleDatePubMed
Plasma cytokine concentration and the cytokine producing ability of whole blood cell cultures from healthy females with pharmacologically induced hyperprolactinemia.
1999
Age-dependent effect of domperidone on dopamine release by the hypoxic carotid body in the rabbit.
2001
Nonulcer Dyspepsia.
2001 Aug
[Study on relationship between the reflux laryngitis and gastroesophageal reflux disease].
2001 Dec
Effect of adrenalectomy and dexamethasone treatment on prolactin secretion of lactating rats.
2001 Dec
Centrally mediated effects of bromocriptine on cardiac sympathovagal balance.
2001 Jul
Reduction of glomerular hyperfiltration by dopamine D(2)-like receptor blockade in experimental diabetes mellitus.
2001 Jul
Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review.
2001 Jul 7
Gastroparesis and its management.
2001 Jul-Sep
Dopamine D2-like receptors and amino acid-induced glomerular hyperfiltration in humans.
2001 May
Central bromocriptine-induced tachycardia is reversed to bradycardia in conscious, deoxycorticosterone acetate-salt hypertensive rats.
2001 May
The broad-spectrum anti-emetic activity of AS-8112, a novel dopamine D2, D3 and 5-HT3 receptors antagonist.
2001 May
Quick titration of pergolide in cotreatment with domperidone is safe and effective.
2001 May-Jun
Pharmacological characterization of cyclosporine A-induced kaolin intake in rats.
2001 Oct-Nov
Treatment of non-ulcer dyspepsia: a meta-analysis of placebo-controlled prospective studies.
2001 Sep
Dopamine D(2) receptor activation causes mitogenesis via p44/42 mitogen-activated protein kinase in opossum kidney cells.
2001 Sep
[A case of the successful treatment of the esophageal leukoplakia with rabeprazole].
2002
Hyperprolactinemia does not influence hypothalamic-pituitary-adrenocortical function during hypoglycemia in women.
2002
Role of tyrosine kinase and p44/42 MAPK in D(2)-like receptor-mediated stimulation of Na(+), K(+)-ATPase in kidney.
2002 Apr
Galactogogues: medications that induce lactation.
2002 Aug
Simultaneous determination of domperidone maleate and cinnarizine in a binary mixture using derivative ratio spectrophotometry and classical least squares calibration.
2002 Aug 22
New insight into the functional role of acetylcholine in developing embryonic rat retinal neurons.
2002 Feb
Opioid mediated anti-nociceptive effect of domperidone and cisapride in mice.
2002 Jan
Dopaminergic modulation of ventilation in obese Zucker rats.
2002 Jan
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
Quantitative and qualitative assessment of milk production after pharmaceutical induction of lactation in the mare.
2002 Jul-Aug
Age-related changes in dopamine D2 receptors in rat heart and coronary vessels.
2002 May-Jun
Blunted central bromocriptine-induced tachycardia in conscious, malnourished rats.
2003 Apr
Bowel cleansing for diagnostic colonoscopy: which method is preferable? Istanbul experience.
2003 Apr
Potentiation of domperidone-induced catalepsy by a P-glycoprotein inhibitor, cyclosporin A.
2003 Apr
Tumoral versus non-tumoral hyperprolactinemia in children and adolescents: possible usefulness of the domperidone test.
2003 Feb
Domperidone. Discovering new choices for lactating mothers.
2003 Feb-Mar
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
Simultaneous determination of domperidone and cinnarizine in a binary mixture using derivative spectrophotometry, partial least squares and principle component regression calibration.
2003 Jan
Substrate-dependent regulation of MAO-A in rat mesangial cells: involvement of dopamine D2-like receptors.
2003 Jan
Area postrema mediates gastric motor response induced by apomorphine in rats.
2003 Jan 17
Neuroprotective effect of nitric oxide against NMDA-induced neurotoxicity in the rat retina is associated with tyrosine hydroxylase expression.
2003 Jul 4
Determination of ambroxol in human plasma using LC-MS/MS.
2003 Jun 1
Olfactory sensitivity to catecholamines and their metabolites in the goldfish.
2003 Mar
Spectrophotometric methods for the determination of anti-emetic drugs in bulk and in pharmaceutical preparations.
2003 May
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
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
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
by admin
on Fri Dec 15 15:16:53 GMT 2023
Edited
by admin
on Fri Dec 15 15:16:53 GMT 2023
Record UNII
5587267Z69
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOMPERIDONE
EP   INN   JAN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
DOMPERIDONE [MART.]
Common Name English
Domperidone [WHO-DD]
Common Name English
DOMPERIDONE [JAN]
Common Name English
NSC-299589
Code English
5-Chloro-1-[1-[3-(2-oxo-1-benzimidazolinyl)propyl]-4-piperidyl]-2-benzimidazolinone
Systematic Name English
2H-BENZIMIDAZOL-2-ONE, 5-CHLORO-1-(1-(3-(2,3-DIHYDRO-2-OXO-1H-BENZIMIDAZOL-1-YL)PROPYL)-4-PIPERIDINYL)-1,3-DIHYDRO-
Systematic Name English
R-33812
Code English
MOTILIUM
Brand Name English
domperidone [INN]
Common Name English
NSC-759575
Code English
DOMPERIDONE [USAN]
Common Name English
R 33,812
Code English
DOMPERIDONE [GREEN BOOK]
Common Name English
DOMPERIDONE [EP MONOGRAPH]
Common Name English
DOMPERIDONE [VANDF]
Common Name English
DOMPERIDONE [MI]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 520.766
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
LIVERTOX NBK548487
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WHO-VATC QA03FA03
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WHO-VATC QP51AX24
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NCI_THESAURUS C29710
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FDA ORPHAN DRUG 336111
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WHO-ATC A03FA03
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Code System Code Type Description
WIKIPEDIA
DOMPERIDONE
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PRIMARY
MERCK INDEX
m4737
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PRIMARY Merck Index
DRUG BANK
DB01184
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PRIMARY
LACTMED
Domperidone
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PRIMARY
ECHA (EC/EINECS)
260-968-7
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PRIMARY
FDA UNII
5587267Z69
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PRIMARY
ChEMBL
CHEMBL219916
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PRIMARY
MESH
D004294
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PRIMARY
DAILYMED
5587267Z69
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PRIMARY
DRUG CENTRAL
945
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PRIMARY
NSC
759575
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PRIMARY
NSC
299589
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PRIMARY
EVMPD
SUB06361MIG
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PRIMARY
EPA CompTox
DTXSID1045116
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PRIMARY
PUBCHEM
3151
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PRIMARY
RXCUI
3626
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PRIMARY RxNorm
IUPHAR
965
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PRIMARY
NCI_THESAURUS
C454
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PRIMARY
SMS_ID
100000092257
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PRIMARY
CHEBI
31515
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PRIMARY
CAS
57808-66-9
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PRIMARY
INN
4110
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PRIMARY
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