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Substance Name: Loperamide [INN:BAN]
RN: 53179-11-6
UNII: 6X9OC3H4II
InChIKey: RDOIQAHITMMDAJ-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

Molecular Weight

  • 477.0447
 

Classification Codes

  • Antidiarrheals
  • Drug / Therapeutic Agent
  • Gastrointestinal Agents

Names and Synonyms

Name of Substance

  • Loperamide
  • Loperamide [INN:BAN]

MeSH Heading

  • Loperamide

Synonyms

  • 4-(4-Chlorophenyl)-N,N-dimethyl-alpha,alpha-diphenyl-4-hydroxy-1-piperidinebutanamide
  • 5-21-02-00379 (Beilstein Handbook Reference)
  • BRN 1558273
  • EC 258-416-5
  • EINECS 258-416-5
  • HSDB 8344
  • Ioperamide
  • Loperamida
  • Loperamida [INN-Spanish]
  • Loperamide
  • Loperamidum
  • Loperamidum [INN-Latin]
  • UNII-6X9OC3H4II

Systematic Names

  • 1-Piperidinebutanamide, 4-(4-chlorophenyl)-4-hydroxy-N,N-dimethyl-alpha,alpha-diphenyl-
  • Loperamide

Registry Numbers

CAS Registry Number

  • 53179-11-6

FDA UNII

  • 6X9OC3H4II

Related Registry Number

  • 34552-83-5 (mono-hydrochloride)

System Generated Number

  • 0053179116

Structure Descriptors

InChI

1S/C29H33ClN2O2/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

InChIKey

RDOIQAHITMMDAJ-UHFFFAOYSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intravenous 2800ug/kg (2.8mg/kg) BEHAVIORAL: TREMOR

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
dog LD50 oral 40mg/kg (40mg/kg) BEHAVIORAL: TREMOR

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
guinea pig LD50 oral 42mg/kg (42mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
guinea pig LD50 oral 42mg/kg (42mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: TREMOR
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
mouse LD50 intraperitoneal 28mg/kg (28mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
mouse LD50 intraperitoneal 28mg/kg (28mg/kg) BEHAVIORAL: TREMOR

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
mouse LD50 oral 105mg/kg (105mg/kg) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: TREMOR
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
mouse LD50 subcutaneous 75mg/kg (75mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
mouse LD50 subcutaneous 75mg/kg (75mg/kg) BEHAVIORAL: TREMOR

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
rat LD50 intravenous 5100ug/kg (5.1mg/kg) BEHAVIORAL: TREMOR

SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 461, 1981.
rat LD50 oral 98mg/kg (98mg/kg)   Drug Development Research. Vol. 8, Pg. 279, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 5.150 (none)   EST
Atmospheric OH Rate Constant 1.38E-10 cm3/molecule-sec 25 EST

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