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
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
DescriptionCurator'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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21215785 |
450.1 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | DEMEROL Approved UseFor the relief of moderate to severe pain. For preoperative medication. For support of anesthesia. For obstetrical analgesia. Launch Date1942 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
196 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2891328/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
19.6 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2891328/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
124 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2891328/ |
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
Dose | Population | Adverse events |
---|---|---|
10 g single, oral Overdose |
unknown, 17 years |
Other AEs: Myoclonus, Hyperreflexia... Other AEs: Myoclonus (1 patient) Sources: Hyperreflexia (1 patient) Respiratory depression (1 patient) Hypotension (1 patient) Tremor (1 patient) |
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... |
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 n = 1 Health Status: unhealthy Condition: pain Age Group: 37 years Sex: M Population Size: 1 Sources: |
Disc. AE: Muscle twitching, Tremor... AEs leading to discontinuation/dose reduction: Muscle twitching (1 patient) Sources: Tremor (1 patient) |
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 n = 7 Health Status: unknown Age Group: 44 years Sex: M+F Population Size: 7 Sources: |
Other AEs: Jitteriness, Hallucinations... Other AEs: Jitteriness (3 patients) Sources: Hallucinations (3 patients) Seizures (3 patients) |
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... Other AEs: Withdrawal syndrome neonatal 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: |
pregnant, adult Health Status: pregnant Condition: pain Age Group: adult Sex: F Sources: |
Other AEs: Withdrawal syndrome neonatal... Other AEs: Withdrawal syndrome neonatal 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: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
Other AEs: Withdrawal syndrome neonatal... Other AEs: Withdrawal syndrome neonatal 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: |
unhealthy, adult Health Status: unhealthy Condition: pain Age Group: adult Sources: |
Other AEs: Addiction, Respiratory depression... Other AEs: Addiction Sources: 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 Health Status: unhealthy Condition: pain Age Group: adult Sources: |
Other AEs: Addiction, Respiratory depression... Other AEs: Addiction Sources: 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 Health Status: unhealthy Condition: pain Age Group: adult Sources: |
Other AEs: Addiction, Respiratory depression... Other AEs: Addiction Sources: Respiratory depression (serious|grade 5) |
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... Other AEs: Withdrawal syndrome neonatal Sources: |
10 mg/mL multiple, intravenous Recommended Dose: 10 mg/mL Route: intravenous Route: multiple Dose: 10 mg/mL Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Addiction, Respiratory depression... Other AEs: Addiction Sources: Respiratory depression (serious|grade 5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hyperreflexia | 1 patient | 10 g single, oral Overdose |
unknown, 17 years |
Hypotension | 1 patient | 10 g single, oral Overdose |
unknown, 17 years |
Myoclonus | 1 patient | 10 g single, oral Overdose |
unknown, 17 years |
Respiratory depression | 1 patient | 10 g single, oral Overdose |
unknown, 17 years |
Tremor | 1 patient | 10 g single, oral Overdose |
unknown, 17 years |
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 n = 1 Health Status: unhealthy Condition: pain Age Group: 37 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Condition: pain Age Group: 37 years Sex: M Population Size: 1 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 n = 7 Health Status: unknown Age Group: 44 years Sex: M+F Population Size: 7 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 n = 7 Health Status: unknown Age Group: 44 years Sex: M+F Population Size: 7 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 n = 7 Health Status: unknown Age Group: 44 years Sex: M+F Population Size: 7 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 Condition: pain 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 Health Status: unhealthy Condition: pain Age Group: adult Sources: |
|
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 Health Status: unhealthy Condition: pain Age Group: adult Sources: |
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 Health Status: unhealthy Condition: pain Age Group: adult Sources: |
|
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 Health Status: unhealthy Condition: pain Age Group: adult Sources: |
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 Health Status: unhealthy Condition: pain Age Group: adult Sources: |
|
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 Health Status: unhealthy Condition: pain Age Group: adult Sources: |
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 Health Status: unhealthy Age Group: adult Sources: |
|
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 Health Status: unhealthy Age Group: adult Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
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 |
||
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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12388652/ Page: 5.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Adding low dose meperidine to spinal lidocaine prolongs postoperative analgesia. | 1999 Apr |
|
Norpethidine accumulation and generalized seizure during pethidine patient-controlled analgesia. | 1999 Jun |
|
Prolonged analgesic effect of ketamine, an N-methyl-D-aspartate receptor inhibitor, in patients with chronic pain. | 1999 May |
|
Successful treatment of normeperidine neurotoxicity by hemodialysis. | 2000 Jan |
|
Urticaria induced by meperidine allergy. | 2000 Mar |
|
Co-administration of drugs and blood products. | 2001 Apr |
|
Analgesic effects in dogs of carprofen and pethidine together compared with the effects of either drug alone. | 2001 Apr 7 |
|
Intrathecal pethidine as sole anaesthetic agent for operative procedures of the lower limb, inguinal area and perineum. | 2001 Dec |
|
Morphine, pethidine and buprenorphine disposition in the cat. | 2001 Dec |
|
Renal colic and recurrent urinary calculi. Management and prevention. | 2001 Jan |
|
Meperidine--a liability. | 2001 Jan |
|
Tris(2,2'-bipyridine)ruthenium(II) electrogenerated chemiluminescence of alkaloid type drugs with solid phase extraction sample preparation. | 2001 Jan |
|
Serotonin syndrome: potential consequences of Meridia combined with Demerol or fentanyl. | 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 |
|
Opiate-sensitivity: clinical characteristics and the role of skin prick testing. | 2001 Jul |
|
Sensitive determination of pethidine in body fluids by surface ionization organic mass spectrometry. | 2001 Jul 5 |
|
[Evaluation of analgesia after cesarean section]. | 2001 Jul-Aug |
|
Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria. | 2001 Mar |
|
Maternal analgesia during labor disturbs newborn behavior: effects on breastfeeding, temperature, and crying. | 2001 Mar |
|
Safety and efficacy of peribulbar block as adjunct to general anaesthesia for paediatric ophthalmic surgery. | 2001 Mar |
|
Prospective, randomized trial comparing diathermy and Harmonic Scalpel hemorrhoidectomy. | 2001 May |
|
Upper and mid-ureteric stones: a prospective unrandomized comparison of retroperitoneoscopic and open ureterolithotomy. | 2001 Nov |
|
Ipsilateral dislocation of the shoulder and elbow. | 2001 Nov |
|
Patient-controlled pethidine after major upper abdominal surgery: comparison of the epidural and intravenous routes. | 2001 Nov |
|
Iatrogenic cardiopulmonary arrest during pediatric sedation with meperidine, promethazine, and chlorpromazine. | 2001 Oct |
|
From hit to lead. Combining two complementary methods for focused library design. Application to mu opiate ligands. | 2001 Oct 11 |
|
Clinical experience and results of ESWL treatment for 3,093 urinary calculi with the Storz Modulith SL 20 lithotripter at the Singapore general hospital. | 2002 |
|
A novel approach to the prevention of postoperative delirium in the elderly after gastrointestinal surgery. | 2002 |
|
Primary thoracoscopic evaluation of pleural effusion with local anesthesia: an alternative approach. | 2002 Apr-Jun |
|
Pulmonary function in infants exposed to pethidine. | 2002 Aug |
|
Nasal administration of opioids for pain management in adults. | 2002 Aug |
|
Noninvasive anesthesia, analgesia and radiation-free extracorporeal shock wave lithotripsy for stones in the most distal ureter: experience with 165 patients. | 2002 Aug |
|
Intraperitoneal pethidine versus intramuscular pethidine for the relief of pain after laparoscopic cholecystectomy: randomized trial. | 2002 Dec |
|
[Survey of anesthesia practice in Morocco]. | 2002 Jan |
|
Use of meperidine in patient-controlled analgesia and the development of a normeperidine toxic reaction. | 2002 Jan |
|
Vitamin K and childhood cancer: analysis of individual patient data from six case-control studies. | 2002 Jan 7 |
|
The management of metastatic bone pain in a developing country: the role of radiotherapy as an adjunct to weak opioids. | 2002 Jan-Feb |
|
Mini cholecystectomy now a day stay surgery: anaesthetic management with multi modal analgesia. | 2002 Jul |
|
Pruritus: a useful sign for predicting the haemodynamic changes that occur following administration of vancomycin. | 2002 Jun |
|
A thermal threshold testing device for evaluation of analgesics in cats. | 2002 Jun |
|
Treatment patterns of isolated benign headache in US emergency departments. | 2002 Mar |
|
Improved procedure of colonoscopy under accompanying music therapy. | 2002 Mar 28 |
|
Anxiolytic premedication reduces preoperative anxiety and pain during oocyte retrieval. A randomized double-blinded placebo-controlled trial. | 2002 May |
|
Next generation of everyday analgesics. | 2002 May-Jun |
|
The low normothermia concept--maintaining a core body temperature between 36 and 37 degrees C in acute stroke unit patients. | 2002 Oct |
|
Comparison of colonoscopies performed under sedation with propofol or with midazolam or without sedation. | 2003 |
|
Demographics, assessment and management of pain in the elderly. | 2003 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/meperidine.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2886612
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.
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WHO-VATC |
QN02AG03
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NCI_THESAURUS |
C67413
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WHO-ATC |
N02AB72
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LIVERTOX |
NBK548764
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NDF-RT |
N0000175690
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DEA NO. |
9230
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N02AB52
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NDF-RT |
N0000175684
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QN02AB72
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QN02AB02
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N02AB02
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WHO-VATC |
QN02AB52
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WHO-ATC |
N02AG03
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6754
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57-42-1
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PETHIDINE
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DB00454
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Meperidine
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)