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Substance Name: Domperidone [USAN:INN:BAN:JAN]
RN: 57808-66-9
UNII: 5587267Z69
InChIKey: FGXWKSZFVQUSTL-UHFFFAOYSA-N

Note

  • A specific blocker of dopamine receptors. It speeds gastrointestinal peristalsis, causes prolactin release, and is used as antiemetic and tool in the study of dopaminergic mechanisms.

Molecular Formula

  • C22-H24-Cl-N5-O2

Molecular Weight

  • 425.9176
 

Classification Codes

  • Anti-Emetic
  • Antiemetics
  • Autonomic Agents
  • Central Nervous System Agents
  • Dopamine Agents
  • Dopamine Antagonists
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents
  • Human Data
  • Neurotransmitter Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Domperidone
  • Domperidone [USAN:INN:BAN:JAN]

MeSH Heading

  • Domperidone

Synonyms

  • 2H-Benzimidazol-2-one, 5-chloro-1-(1-(3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl)-4-piperidinyl)-1,3-dihydro-
  • 5-24-02-00402 (Beilstein Handbook Reference)
  • 5-Chloro-1-(1-(3-(2-oxo-1-benzimidazolinyl)propyl)-4-piperidyl)-2-benzimidazolinone
  • BRN 0903774
  • Domperidona
  • Domperidona [INN-Spanish]
  • Domperidone
  • Domperidonum
  • Domperidonum [INN-Latin]
  • EINECS 260-968-7
  • KW-5338
  • Motilium
  • R 33,812
  • UNII-5587267Z69

Systematic Names

  • 2H-Benzimidazol-2-one, 1,3-dihydro-5-chloro-1-(1-(3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl)-4-piperidinyl)-
  • 2H-Benzimidazol-2-one, 5-chloro-1-(1-(3-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)propyl)-4-piperidinyl)-1,3-dihydro-
  • Domperidone

Mixture Name

  • Ovaprim

Registry Numbers

CAS Registry Number

  • 57808-66-9

FDA UNII

  • 5587267Z69

Related Registry Numbers

  • 83898-65-1 (maleate (1:1))
  • 99497-03-7 (maleate)

System Generated Number

  • 0057808669

Structure Descriptors

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)

InChIKey

FGXWKSZFVQUSTL-UHFFFAOYSA-N

Smiles

Clc1ccc2N(C3CCN(CCCN4C(=O)Nc5ccccc45)CC3)C(=O)Nc2c1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 42700ug/kg (42.7mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: ANTIPSYCHOTIC

GASTROINTESTINAL: NAUSEA OR VOMITING
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 244, Pg. 130, 1980.
dog LD50 oral > 160mg/kg (160mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 244, Pg. 130, 1980.
dog LD50 rectal > 120mg/kg (120mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 625, 1984.
dog LD50 subcutaneous > 160mg/kg (160mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 244, Pg. 130, 1980.
guinea pig LD50 intravenous 42900ug/kg (42.9mg/kg) BEHAVIORAL: ATAXIA

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: ANTIPSYCHOTIC
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 244, Pg. 130, 1980.
human LDLo intravenous 429ug/kg (0.429mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD British Medical Journal. Vol. 288, Pg. 1728, 1984.
human TDLo intravenous 714ug/kg (0.714mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD British Medical Journal. Vol. 288, Pg. 1728, 1984.
infant TDLo oral 1170ug/kg/1D- (1.17mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE Journal of Pediatrics. Vol. 108, Pg. 630, 1986.
man TDLo intramuscular 200ug/kg (0.2mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Lancet. Vol. 2, Pg. 1259, 1980.
man TDLo oral 234mg/kg/39W- (234mg/kg) ENDOCRINE: GYNECOMASTIA Postgraduate Medical Journal. Vol. 67, Pg. 401, 1991.
mouse LD50 intraperitoneal > 8gm/kg (8000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
mouse LD50 intravenous 46500ug/kg (46.5mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
mouse LD50 oral > 8gm/kg (8000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 1128, 1982.
mouse LD50 subcutaneous > 8gm/kg (8000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
rat LD50 intraperitoneal 61200ug/kg (61.2mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 13, Pg. 1128, 1982.
rat LD50 intravenous 41700ug/kg (41.7mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
rat LD50 oral 5243mg/kg (5243mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
rat LD50 rectal > 250mg/kg (250mg/kg)   Yakkyoku. Pharmacy. Vol. 35, Pg. 625, 1984.
rat LD50 subcutaneous > 8gm/kg (8000mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 3991, 1980.
women TDLo intravenous 600ug/kg/1D (0.6mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) Lancet. Vol. 2, Pg. 385, 1985.
women TDLo intravenous 1mg/kg (1mg/kg) CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) British Medical Journal. Vol. 289, Pg. 1579, 1984.
women TDLo rectal 7200ug/kg/30H (7.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE Journal of Pediatrics. Vol. 105, Pg. 852, 1984.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 242.5 deg C   EXP
pKa Dissociation Constant 7.9 (none)   EXP
log P (octanol-water) 3.9 (none)   EXP
Water Solubility 0.986 mg/L 25 EST
Vapor Pressure 1.15E-14 mm Hg 25 EST
Henry's Law Constant 6.11E-22 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.57E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.