U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H21NO2
Molecular Weight 247.3327
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPERIDINE

SMILES

CCOC(=O)C1(CCN(C)CC1)C2=CC=CC=C2

InChI

InChIKey=XADCESSVHJOZHK-UHFFFAOYSA-N
InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C15H21NO2
Molecular Weight 247.3327
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Pethidine, also known as meperidine and Demerol, a narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Meperidine is an opioid agonist with multiple actions qualitatively similar to those of morphine. Most common adverse reactions were lightheadedness, dizziness, sedation, nausea, vomiting, and sweating. Pethidine has serious interactions that can be dangerous with monoamine oxidase inhibitors (e.g., furazolidone, isocarboxazid, moclobemide, phenelzine, procarbazine, selegiline, tranylcypromine). Pethidine can interact with muscle relaxants, some antidepressants, benzodiazepines, and ethanol.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
450.1 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DEMEROL

Cmax

ValueDoseCo-administeredAnalytePopulation
196 ng/mL
30 mg single, intravenous
MEPERIDINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
19.6 μg × min/mL
30 mg single, intravenous
MEPERIDINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
124 min
30 mg single, intravenous
MEPERIDINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
Oral: 50 to 100 mg every 4 hours as needed. IV,IM,subcutaneously: 25 to 100 mg every 4 hours as needed. Continuous IV: 15 to 35 mg/hr.
Route of Administration: Other
In Vitro Use Guide
Pethidine's stimulant action on the 22-day pregnant rat isolated uterus does not involve receptors sensitive to methysergide and is unlikely to involve the synthesis and release of endogenous prostaglandins. Maximal stimulant response occurred with 40 ug/ml.
Substance Class Chemical
Record UNII
9E338QE28F
Record Status Validated (UNII)
Record Version