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Substance Name: Loperamide hydrochloride [USAN:USP:JAN]
RN: 34552-83-5
UNII: 77TI35393C
InChIKey: PGYPOBZJRVSMDS-UHFFFAOYSA-N

Note

  • One of the long-acting synthetic ANTIDIARRHEALS; it is not significantly absorbed from the gut, and has no effect on the adrenergic system or central nervous system, but may antagonize histamine and interfere with acetylcholine release locally.

Molecular Formula

  • C29-H33-Cl-N2-O2.Cl-H

Molecular Weight

  • 513.5056
 

Classification Codes

  • Antiperistaltic
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Loperamide hydrochloride [USAN:USP:JAN]

Synonyms

  • 4-(4-(p-Chlorophenyl)-4-hydroxy-1-piperidyl)-N,N-dimethyl-2,2-diphenylbutyramide HCl
  • 4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenyl-1-piperidine butyramide HCl
  • 4-(p-Chlorophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenyl-1-piperidinebutyramide monohydrochloride
  • Anti-diarrheal
  • BLOX
  • BREK
  • Diamode
  • Diar-Aid
  • Dissenten
  • EINECS 252-082-4
  • Fortasec
  • Imodium
  • Imodium A-D
  • Imodium A-D EZ chews
  • Imosec
  • Imotil
  • K-Pek II
  • Kao-Paverin
  • Kaopectate 1-D
  • Lopemid
  • Lopemin
  • Loperamide HCl
  • Loperamide hydrochloride
  • Loperyl
  • Maalox Anti-Diarrheal
  • Maalox Antidiarrheal
  • NSC 759568
  • Pepto Diarrhea Control
  • PJ185
  • R 18,553
  • R 18553
  • Suprasec
  • Tebloc
  • UNII-77TI35393C
  • Up and up anti diarrheal

Systematic Names

  • 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenyl-, hydrochloride
  • 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenyl-, monohydrochloride
  • 4-(4-Chlorophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenylpiperidine-1-butyramide monohydrochloride

Registry Numbers

CAS Registry Number

  • 34552-83-5

FDA UNII

  • 77TI35393C

Related Registry Number

  • 53179-11-6 (Parent)

System Generated Number

  • 0034552835

Molecular Formulas

Molecular Formula

  • C29-H33-Cl-N2-O2.Cl-H

Molecular Formula Fragments

  • C29-H33-Cl-N2-O2
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

InChI=1S/C29H33ClN2O2.ClH/c1-31(2)27(33)29(24-9-5-3-6-10-24,25-11-7-4-8-12-25)19-22-32-20-17-28(34,18-21-32)23-13-15-26(30)16-14-23;/h3-16,34H,17-22H2,1-2H3;1H

InChIKey

PGYPOBZJRVSMDS-UHFFFAOYSA-N

Smiles

Cl.CN(C)C(=O)C(CCN1CCC(O)(CC1)c2ccc(Cl)cc2)(c3ccccc3)c4ccccc4

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 125ug/kg (0.125mg/kg) BEHAVIORAL: COMA

BEHAVIORAL: IRRITABILITY

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
British Medical Journal. Vol. 294, Pg. 1383, 1987.
dog LDLo oral > 40mg/kg (40mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1633, 1974.
guinea pig LD50 oral 41500ug/kg (41.5mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 12, Pg. 1204, 1981.
monkey LD50 oral > 40mg/kg (40mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2419, 1977.
mouse LD50 intraperitoneal 28mg/kg (28mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1636, 1974.
mouse LD50 intravenous 12640ug/kg (12.64mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2419, 1977.
mouse LD50 oral 105mg/kg (105mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1633, 1974.
mouse LD50 subcutaneous 75mg/kg (75mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1636, 1974.
rabbit LDLo oral 160mg/kg (160mg/kg) GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2419, 1977.
rat LD50 intravenous 7490ug/kg (7.49mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2419, 1977.
rat LD50 oral 185mg/kg (185mg/kg) GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION Journal of Medicinal Chemistry. Vol. 16, Pg. 782, 1973.
rat LD50 subcutaneous 78700ug/kg (78.7mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2419, 1977.