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Details

Stereochemistry ACHIRAL
Molecular Formula C22H24ClN5O2.C4H4O4
Molecular Weight 541.983
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DOMPERIDONE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.ClC1=CC2=C(C=C1)N(C3CCN(CCCN4C(=O)NC5=C4C=CC=C5)CC3)C(=O)N2

InChI

InChIKey=OAUUYDZHCOULIO-BTJKTKAUSA-N
InChI=1S/C22H24ClN5O2.C4H4O4/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;5-3(6)1-2-4(7)8/h1-2,4-7,14,16H,3,8-13H2,(H,24,29)(H,25,30);1-2H,(H,5,6)(H,7,8)/b;2-1-

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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
17.67 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
87.08 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
327 ng × h/mL
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
289 ng × h/mL
10 mg single, intramuscular
dose: 10 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
57.7 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
259 ng × h/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
243 ng × h/mL
60 mg single, rectal
dose: 60 mg
route of administration: Rectal
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
463 ng × h/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
249 ng × h/mL
60 mg single, oral
dose: 60 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
13.68 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.45 h
10 mg single, intravenous
dose: 10 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5.5%
DOMPERIDONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
20 mg 4 times / day multiple, oral
Recommended
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Disc. AE: CNS disorder (NOS)...
AEs leading to
discontinuation/dose reduction:
CNS disorder (NOS) (2%)
Sources:
20 mg 4 times / day multiple, oral
Recommended
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Disc. AE: Facial swelling, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Facial swelling (3.2%)
Abdominal pain (3.2%)
Abdominal distension (3.2%)
Galactorrhoea (3.2%)
Mastalgia (6.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
CNS disorder (NOS) 2%
Disc. AE
20 mg 4 times / day multiple, oral
Recommended
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Abdominal distension 3.2%
Disc. AE
20 mg 4 times / day multiple, oral
Recommended
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Abdominal pain 3.2%
Disc. AE
20 mg 4 times / day multiple, oral
Recommended
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Facial swelling 3.2%
Disc. AE
20 mg 4 times / day multiple, oral
Recommended
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Galactorrhoea 3.2%
Disc. AE
20 mg 4 times / day multiple, oral
Recommended
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
Mastalgia 6.4%
Disc. AE
20 mg 4 times / day multiple, oral
Recommended
Dose: 20 mg, 4 times / day
Route: oral
Route: multiple
Dose: 20 mg, 4 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [IC50 15.8489 uM]
inconclusive [IC50 6.3096 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
yes [EC50 106 uM]
yes [IC50 14.8 uM]
yes [IC50 2.3 uM]
yes [IC50 3.1623 uM]
yes [IC50 7.9 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
likely
likely
weak
weak
weak
weak
weak
weak
yes
yes
yes
Tox targets
PubMed

PubMed

TitleDatePubMed
Age-dependent effect of domperidone on dopamine release by the hypoxic carotid body in the rabbit.
2001
Excitation of rat striatal large neurons by dopamine and/or glutamate released from nerve terminals via presynaptic nicotinic receptor (A4beta2 type) stimulation.
2001 Aug
Effects of dopaminergic drugs on inflammatory bowel disease induced with 2,4-dinitrofluorbenzene in BALB/c mice.
2001 Aug
[Evidence-based therapy of systemic sclerosis].
2001 Dec
Effect of adrenalectomy and dexamethasone treatment on prolactin secretion of lactating rats.
2001 Dec
Gastroparesis: prevalence, clinical significance and treatment.
2001 Dec
Effects of gastrointestinal stimulant and suppressant pretreatment on the pharmacokinetics of AS-924, a novel ester-type cephem antibiotic.
2001 Nov
Heart rate response to hypoxic exercise: role of dopamine D2-receptors and effect of oxygen supplementation.
2001 Oct
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
Occurrence of dopaminergic (D(2)) receptors within the rabbit pulmonary circulation.
2002
Hyperprolactinemia does not influence hypothalamic-pituitary-adrenocortical function during hypoglycemia in women.
2002
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
Blockade of spinal dopamine D2 receptors enhances the pressor effect of intravenous quinpirole in normotensive, conscious rats.
2002 Feb
[Prokinetics of gastrointestinal system; its newer aspects with regard to motillity stimulants].
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
KDR-5169, a new gastrointestinal prokinetic agent, enhances gastric contractile and emptying activities in dogs and rats.
2002 Jan 11
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
D2 -like receptor stimulation decreases effective renal plasma flow and glomerular filtration rate in spontaneously hypertensive rats.
2002 Jul
Quantitative and qualitative assessment of milk production after pharmaceutical induction of lactation in the mare.
2002 Jul-Aug
[Digestive manifestations in systemic sclerosis].
2002 Jun
Pharmacology and toxicity of nicotinamide combined with domperidone during fractionated radiotherapy.
2002 Jun
Gastric emptying in diabetes: clinical significance and treatment.
2002 Mar
Dopaminergic metabolism in carotid bodies and high-altitude acclimatization in female rats.
2002 Mar
Ranitidine alone and in combination with domperidone in reflux-type dyspepsia.
2002 Mar-Apr
Distribution of domperidone into the rat brain is increased by brain ischaemia or treatment with the P-glycoprotein inhibitor verapamil.
2002 May
A dose-finding study of carboplatin-epirubicin-docetaxel in advanced epithelial ovarian cancer.
2002 May 6
Age-related changes in dopamine D2 receptors in rat heart and coronary vessels.
2002 May-Jun
Severe ventricular arrhythmia and sudden death on neuroleptics.
2002 Oct
Calcitonin gene-related peptide and adrenomedullin release in humans: effects of exercise and hypoxia.
2002 Oct 15
Dynamic modelling of a challenge-escalation cross-over study of treatment of capsaicin-induced coughing.
2002 Oct 30
Blunted central bromocriptine-induced tachycardia in conscious, malnourished rats.
2003 Apr
Bowel cleansing for diagnostic colonoscopy: which method is preferable? Istanbul experience.
2003 Apr
Activation of dopamine D2-like receptors attenuates pulmonary C-fiber hypersensitivity in rats.
2003 Apr 15
Tumoral versus non-tumoral hyperprolactinemia in children and adolescents: possible usefulness of the domperidone test.
2003 Feb
Dopamine-induced protection against indomethacin-evoked intestinal lesions in rats--role of anti-intestinal motility mediated by D2 receptors.
2003 Feb
Double-blind, single-dose, cross-over study of the effects of pramipexole, pergolide, and placebo on rest tremor and UPDRS part III in Parkinson's disease.
2003 Feb
Simultaneous determination of domperidone and cinnarizine in a binary mixture using derivative spectrophotometry, partial least squares and principle component regression calibration.
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
Effects of gonadotropin-releasing hormone agonist and dopamine antagonist on hypothalamus-pituitary-gonadal axis of pre-pubertal female red seabream (Pagrus major).
2003 May
Melatonin in the duodenal lumen is a potent stimulant of mucosal bicarbonate secretion.
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 Mon Mar 31 19:22:18 GMT 2025
Edited
by admin
on Mon Mar 31 19:22:18 GMT 2025
Record UNII
899U5WF46A
Record Status Validated (UNII)
Record Version
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Name Type Language
DOMPERIDONE MALEATE
EP   MART.   WHO-DD  
Common Name English
DOMPERIDONE (AS MALEATE)
Preferred Name English
DOMPERIDONE MALEATE [EP MONOGRAPH]
Common Name English
Domperidone maleate [WHO-DD]
Common Name English
DOMPERIDONE MALEATE [MART.]
Common Name English
5-CHLORO-1-(1-(3-(2-OXOBENZIMIDAZOLIN-1-YL)PROPYL)-4-PIPERIDYL)BENZIMIDAZOLIN-2-ONE MALEATE
Systematic Name English
Code System Code Type Description
DRUG BANK
DBSALT002902
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
PRIMARY
RXCUI
236099
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID901019221
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
PRIMARY
FDA UNII
899U5WF46A
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
PRIMARY
SMS_ID
100000087542
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
PRIMARY
PUBCHEM
6604595
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
PRIMARY
EVMPD
SUB01815MIG
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
PRIMARY
CAS
83898-65-1
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
PRIMARY
ECHA (EC/EINECS)
281-277-7
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
PRIMARY
CAS
99497-03-7
Created by admin on Mon Mar 31 19:22:18 GMT 2025 , Edited by admin on Mon Mar 31 19:22:18 GMT 2025
NON-SPECIFIC STOICHIOMETRY
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ACTIVE MOIETY