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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C15H21NO2.ClH
Molecular Weight 283.794
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPERIDINE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=WCNLCIJMFAJCPX-UHFFFAOYSA-N
InChI=1S/C15H21NO2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C15H21NO2
Molecular Weight 247.3327
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.pbm.va.gov/clinicalguidance/criteriaforuse/MeperidineCriteriaforUse.pdf | https://www.drugs.com/pro/meperidine.html

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
450.1 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DEMEROL

Approved Use

For the relief of moderate to severe pain. For preoperative medication. For support of anesthesia. For obstetrical analgesia.

Launch Date

1942
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
196 ng/mL
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MEPERIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
19.6 μg × min/mL
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MEPERIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
124 min
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
MEPERIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unknown, 17 years
Health Status: unknown
Age Group: 17 years
Sex: F
Sources:
Other AEs: Respiratory depression, Hypotension...
Other AEs:
Respiratory depression (1 patient)
Hypotension (1 patient)
Tremor (1 patient)
Hyperreflexia (1 patient)
Myoclonus (1 patient)
Sources:
50 mg single, intrathecal
Dose: 50 mg
Route: intrathecal
Route: single
Dose: 50 mg
Sources:
unknown, 24 - 81 years
Health Status: unknown
Age Group: 24 - 81 years
Sex: F
Sources:
Other AEs: Respiratory depression...
Other AEs:
Respiratory depression (2 patients)
Sources:
1000 mg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 1000 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 1000 mg, 1 times / day
Sources:
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: M
Sources:
Disc. AE: Muscle twitching, Tremor...
AEs leading to
discontinuation/dose reduction:
Muscle twitching (1 patient)
Tremor (1 patient)
Sources:
600 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unknown, 44 years
Health Status: unknown
Age Group: 44 years
Sex: M+F
Sources:
Other AEs: Jitteriness, Hallucinations...
Other AEs:
Jitteriness (3 patients)
Hallucinations (3 patients)
Seizures (3 patients)
Sources:
50 mg 6 times / day multiple, intramuscular
Recommended
Dose: 50 mg, 6 times / day
Route: intramuscular
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Other AEs: Withdrawal syndrome neonatal...
50 mg 6 times / day multiple, oral
Recommended
Dose: 50 mg, 6 times / day
Route: oral
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Other AEs: Withdrawal syndrome neonatal...
50 mg 6 times / day multiple, subcutaneous
Recommended
Dose: 50 mg, 6 times / day
Route: subcutaneous
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Other AEs: Withdrawal syndrome neonatal...
50 mg 6 times / day multiple, intramuscular
Recommended
Dose: 50 mg, 6 times / day
Route: intramuscular
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
unhealthy, adult
Other AEs: Addiction, Respiratory depression...
Other AEs:
Addiction
Respiratory depression (serious|grade 5)
Sources:
50 mg 6 times / day multiple, oral
Recommended
Dose: 50 mg, 6 times / day
Route: oral
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
unhealthy, adult
Other AEs: Addiction, Respiratory depression...
Other AEs:
Addiction
Respiratory depression (serious|grade 5)
Sources:
50 mg 6 times / day multiple, subcutaneous
Recommended
Dose: 50 mg, 6 times / day
Route: subcutaneous
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
unhealthy, adult
Other AEs: Addiction, Respiratory depression...
Other AEs:
Addiction
Respiratory depression (serious|grade 5)
Sources:
10 mg/mL multiple, intravenous
Recommended
Dose: 10 mg/mL
Route: intravenous
Route: multiple
Dose: 10 mg/mL
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Other AEs: Withdrawal syndrome neonatal...
10 mg/mL multiple, intravenous
Recommended
Dose: 10 mg/mL
Route: intravenous
Route: multiple
Dose: 10 mg/mL
Sources:
unhealthy, adult
Other AEs: Addiction, Respiratory depression...
Other AEs:
Addiction
Respiratory depression (serious|grade 5)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hyperreflexia 1 patient
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unknown, 17 years
Health Status: unknown
Age Group: 17 years
Sex: F
Sources:
Hypotension 1 patient
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unknown, 17 years
Health Status: unknown
Age Group: 17 years
Sex: F
Sources:
Myoclonus 1 patient
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unknown, 17 years
Health Status: unknown
Age Group: 17 years
Sex: F
Sources:
Respiratory depression 1 patient
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unknown, 17 years
Health Status: unknown
Age Group: 17 years
Sex: F
Sources:
Tremor 1 patient
10 g single, oral
Overdose
Dose: 10 g
Route: oral
Route: single
Dose: 10 g
Sources:
unknown, 17 years
Health Status: unknown
Age Group: 17 years
Sex: F
Sources:
Respiratory depression 2 patients
50 mg single, intrathecal
Dose: 50 mg
Route: intrathecal
Route: single
Dose: 50 mg
Sources:
unknown, 24 - 81 years
Health Status: unknown
Age Group: 24 - 81 years
Sex: F
Sources:
Muscle twitching 1 patient
Disc. AE
1000 mg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 1000 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 1000 mg, 1 times / day
Sources:
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: M
Sources:
Tremor 1 patient
Disc. AE
1000 mg 1 times / day multiple, intramuscular
Highest studied dose
Dose: 1000 mg, 1 times / day
Route: intramuscular
Route: multiple
Dose: 1000 mg, 1 times / day
Sources:
unhealthy, 37 years
Health Status: unhealthy
Age Group: 37 years
Sex: M
Sources:
Hallucinations 3 patients
600 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unknown, 44 years
Health Status: unknown
Age Group: 44 years
Sex: M+F
Sources:
Jitteriness 3 patients
600 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unknown, 44 years
Health Status: unknown
Age Group: 44 years
Sex: M+F
Sources:
Seizures 3 patients
600 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 600 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
unknown, 44 years
Health Status: unknown
Age Group: 44 years
Sex: M+F
Sources:
Withdrawal syndrome neonatal
50 mg 6 times / day multiple, intramuscular
Recommended
Dose: 50 mg, 6 times / day
Route: intramuscular
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Withdrawal syndrome neonatal
50 mg 6 times / day multiple, oral
Recommended
Dose: 50 mg, 6 times / day
Route: oral
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Withdrawal syndrome neonatal
50 mg 6 times / day multiple, subcutaneous
Recommended
Dose: 50 mg, 6 times / day
Route: subcutaneous
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Addiction
50 mg 6 times / day multiple, intramuscular
Recommended
Dose: 50 mg, 6 times / day
Route: intramuscular
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
unhealthy, adult
Respiratory depression serious|grade 5
50 mg 6 times / day multiple, intramuscular
Recommended
Dose: 50 mg, 6 times / day
Route: intramuscular
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
unhealthy, adult
Addiction
50 mg 6 times / day multiple, oral
Recommended
Dose: 50 mg, 6 times / day
Route: oral
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
unhealthy, adult
Respiratory depression serious|grade 5
50 mg 6 times / day multiple, oral
Recommended
Dose: 50 mg, 6 times / day
Route: oral
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
unhealthy, adult
Addiction
50 mg 6 times / day multiple, subcutaneous
Recommended
Dose: 50 mg, 6 times / day
Route: subcutaneous
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
unhealthy, adult
Respiratory depression serious|grade 5
50 mg 6 times / day multiple, subcutaneous
Recommended
Dose: 50 mg, 6 times / day
Route: subcutaneous
Route: multiple
Dose: 50 mg, 6 times / day
Sources:
unhealthy, adult
Withdrawal syndrome neonatal
10 mg/mL multiple, intravenous
Recommended
Dose: 10 mg/mL
Route: intravenous
Route: multiple
Dose: 10 mg/mL
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Addiction
10 mg/mL multiple, intravenous
Recommended
Dose: 10 mg/mL
Route: intravenous
Route: multiple
Dose: 10 mg/mL
Sources:
unhealthy, adult
Respiratory depression serious|grade 5
10 mg/mL multiple, intravenous
Recommended
Dose: 10 mg/mL
Route: intravenous
Route: multiple
Dose: 10 mg/mL
Sources:
unhealthy, adult
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
likely (co-administration study)
Comment: The concomitant use of DEMEROL Injection and CYP3A4 or CYP2B6 inhibitors can increase the plasma concentration of meperidine, resulting in increased or prolonged opioid effects; The concomitant use of DEMEROL Injection and CYP3A4 inducers, or CYP2B6 inducers can decrease the plasma concentration of meperidine
Page: 20.0
yes
likely (co-administration study)
Comment: The concomitant use of DEMEROL Injection and CYP3A4 or CYP2B6 inhibitors can increase the plasma concentration of meperidine, resulting in increased or prolonged opioid effects; The concomitant use of DEMEROL Injection and CYP3A4 inducers, or CYP2B6 inducers can decrease the plasma concentration of meperidine
Page: 20.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Single-dose dipyrone for acute postoperative pain.
2001
Tramadol for postoperative shivering: a double-blind comparison with pethidine.
2001 Apr
Determination of pethidine in rabbit plasma by capillary gas chromatography.
2001 Dec
Renal colic and recurrent urinary calculi. Management and prevention.
2001 Jan
Preoperative rectal diclofenac versus paracetamol for tonsillectomy: effects on pain and blood loss.
2001 Jan
Remifentanil versus meperidine for monitored anesthesia care: a comparison study in older patients undergoing ambulatory colonoscopy.
2001 Jan
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg.
2001 Jan 10
Use of a new finger-mounted device to compare mechanical nociceptive thresholds in cats given pethidine or no medication after castration.
2001 Jun
Postoperative pain management using intravenous patient-controlled analgesia for pediatric patients.
2001 Mar
Safety and efficacy of peribulbar block as adjunct to general anaesthesia for paediatric ophthalmic surgery.
2001 Mar
Patient-controlled pethidine after major upper abdominal surgery: comparison of the epidural and intravenous routes.
2001 Nov
Use of opioid analgesics in a patient with chronic abdominal pain.
2002 Apr
Infective endocarditis: too ill to be operated?
2002 Apr
Selegiline: a second look. Six years later: too risky in Parkinson's disease.
2002 Aug
Synergistic sedation with midazolam and propofol versus midazolam and pethidine in colonoscopies: a prospective, randomized study.
2002 Aug
Parenteral opioids for labor pain relief: a systematic review.
2002 May
Transdermal fentanyl for the management of acute pancreatitis pain.
2002 May
Lack of microbiological concordance between bone and non-bone specimens in chronic osteomyelitis: an observational study.
2002 May 16
The low normothermia concept--maintaining a core body temperature between 36 and 37 degrees C in acute stroke unit patients.
2002 Oct
Characterisation of silent and active genes for a variable large protein of Borrelia recurrentis.
2002 Oct 14
Patents

Sample Use Guides

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
Created
by admin
on Mon Mar 31 17:50:43 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:43 GMT 2025
Record UNII
N8E7F7Q170
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PETHIDINE HYDROCHLORIDE
EP   MART.   WHO-DD   WHO-IP  
Preferred Name English
MEPERIDINE HYDROCHLORIDE
MI   ORANGE BOOK   USAN   USP   VANDF  
USAN  
Official Name English
DEMEROL
Brand Name English
MEPERIDINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
4-PIPERIDINECARBOXYLIC ACID, 1-METHYL-4-PHENYL-, ETHYL ESTER, HYDROCHLORIDE
Common Name English
NSC-400479
Code English
PETHIDINE HYDROCHLORIDE [WHO-IP]
Common Name English
PETHIDINE HYDROCHLORIDE [EP IMPURITY]
Common Name English
MEPERIDINE HYDROCHLORIDE [MI]
Common Name English
PETHIDINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
MEPERIDINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
MEPERIDINE HYDROCHLORIDE CII [USP-RS]
Common Name English
PETHIDINE HYDROCHLORIDE [MART.]
Common Name English
MEPERGAN COMPONENT MEPERIDINE HYDROCHLORIDE
Common Name English
NIH 10522
Code English
MEPERIDINE HYDROCHLORIDE [USAN]
Common Name English
MEPERIDINE HYDROCHLORIDE CII
USP-RS  
Common Name English
MEPERIDINE HCL
Common Name English
PETHIDINE HYDROCHLORIDE [JAN]
Common Name English
PETHIDINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
MEPERIDINE HYDROCHLORIDE [VANDF]
Common Name English
Ethyl 1-methyl-4-phenylisonipecotate hydrochloride
Systematic Name English
Pethidine hydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
DEA NO. 9230
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
NCI_THESAURUS C67413
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID30950620
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
DAILYMED
N8E7F7Q170
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
CHEBI
31984
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
SMS_ID
100000091068
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
NSC
400479
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
ChEMBL
CHEMBL607
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
DRUG BANK
DBSALT000628
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
CHEBI
6754
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
NCI_THESAURUS
C635
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
FDA UNII
N8E7F7Q170
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
MERCK INDEX
m7186
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY Merck Index
PUBCHEM
5750
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
MEPERIDINE HYDROCHLORIDE
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY Description: A white, crystalline powder; odourless. Solubility: Very soluble in water; soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Narcotic analgesic. Storage: Pethidine hydrochloride should be kept in a well-closed container, protected from light. Additional information: Even in the absence of light, Pethidine hydrochloride is gradually degraded on exposure to a humidatmosphere, the decomposition being faster at higher temperatures. Definition: Pethidine hydrochloride contains not less than 98.0% and not more than 101.0% of C15H21NO2,HCl, calculated withreference to the dried substance.
CAS
50-13-5
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
RS_ITEM_NUM
1383001
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
EVMPD
SUB03726MIG
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
RXCUI
103755
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
200-013-3
Created by admin on Mon Mar 31 17:50:43 GMT 2025 , Edited by admin on Mon Mar 31 17:50:43 GMT 2025
PRIMARY
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