Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H21NO2 |
Molecular Weight | 247.3333 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)C1(CCN(C)CC1)c2ccccc2
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
Molecular Formula | C15H21NO2 |
Molecular Weight | 247.3333 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 Date-8.5656961E11 |
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 |
---|---|---|
[Anesthesia and analgesia for lower limb amputation]. | 2001 |
|
[Condition of patients after surgical wisdom tooth extraction under general anesthesia with different premedication variants--a prospective study based on a post-anesthesia questionnaire]. | 2001 |
|
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 |
|
[Comparison of vaginal misoprostol and oxytocin for labor induction in post-term pregnancy]. | 2001 Dec |
|
[Evaluation of analgesia after cesarean section]. | 2001 Jul-Aug |
|
Use of a new finger-mounted device to compare mechanical nociceptive thresholds in cats given pethidine or no medication after castration. | 2001 Jun |
|
Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria. | 2001 Mar |
|
Influence of doxepin used in preemptive analgesia on the nociception in the perioperative period. Experimental and clinical study. | 2001 May-Jun |
|
[Prospective double-blind randomized trial of cryoanalgesia: experimental and clinical study]. | 2001 Nov |
|
Upper and mid-ureteric stones: a prospective unrandomized comparison of retroperitoneoscopic and open ureterolithotomy. | 2001 Nov |
|
Prevention and treatment of respiratory syncytial virus bronchiolitis and postbronchiolitic wheezing. | 2002 |
|
A novel approach to the prevention of postoperative delirium in the elderly after gastrointestinal surgery. | 2002 |
|
A placebo-controlled, randomized trial of droperidol versus metoclopramide for outpatients undergoing gynecological laparoscopy under conscious sedation. | 2002 Apr |
|
Use of opioid analgesics in a patient with chronic abdominal pain. | 2002 Apr |
|
Infective endocarditis: too ill to be operated? | 2002 Apr |
|
Primary thoracoscopic evaluation of pleural effusion with local anesthesia: an alternative approach. | 2002 Apr-Jun |
|
Pulmonary function in infants exposed to pethidine. | 2002 Aug |
|
Upper gastrointestinal endoscopic ultrasound and its impact on patient management: 1990-2000. | 2002 Aug |
|
A prospective randomized trial comparing patient-controlled sedation using propofol and alfentanil and physician-administered sedation using diazepam and pethidine during transvaginal ultrasound-guided oocyte retrieval. | 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 |
|
Application of gas chromatography-surface ionization organic mass spectrometry to forensic toxicology. | 2002 Aug 25 |
|
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 |
|
A comparison of patient-controlled analgesia administered by the intravenous or intranasal route during the early postoperative period. | 2002 Jan |
|
Use of meperidine in patient-controlled analgesia and the development of a normeperidine toxic reaction. | 2002 Jan |
|
An outbreak of community-acquired foodborne illness caused by methicillin-resistant Staphylococcus aureus. | 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 |
|
Severe hypokalaemia secondary to dicloxacillin. | 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 |
|
Intra-arterial injection of metoclopramide, midazolam, propofol and pethidine. | 2002 Jun |
|
Double-blind, randomized trial comparing Harmonic Scalpel hemorrhoidectomy, bipolar scissors hemorrhoidectomy, and scissors excision: ligation technique. | 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 |
|
Liquid-phase microextraction of protein-bound drugs under non-equilibrium conditions. | 2002 May |
|
Parenteral opioids for labor pain relief: a systematic review. | 2002 May |
|
Transdermal fentanyl for the management of acute pancreatitis pain. | 2002 May |
|
Anxiolytic premedication reduces preoperative anxiety and pain during oocyte retrieval. A randomized double-blinded placebo-controlled trial. | 2002 May |
|
Lack of microbiological concordance between bone and non-bone specimens in chronic osteomyelitis: an observational study. | 2002 May 16 |
|
Next generation of everyday analgesics. | 2002 May-Jun |
|
Plication darn for the repair of inguinal hernia. A university hospital experience. | 2002 Nov |
|
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 |
|
Two in one: patient-controlled epidural analgesia (PCEA) to prevent erection and control pain in adult hypospadias-surgery patients. | 2002 Sep |
|
Effects of intravenous opioids on eye movements in humans: possible mechanisms. | 2002 Sep |
|
Retroperitoneal laparoscopic radical nephrectomy and nephroureterectomy and comparison with open surgery. | 2002 Sep |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 00:23:02 UTC 2021
by
admin
on
Sat Jun 26 00:23:02 UTC 2021
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Record UNII |
9E338QE28F
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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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 |
600
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NDF-RT |
N0000175690
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DEA NO. |
9230
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WHO-ATC |
N02AB52
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NDF-RT |
N0000175684
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WHO-VATC |
QN02AB72
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WHO-VATC |
QN02AB02
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WHO-ATC |
N02AB02
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WHO-VATC |
QN02AB52
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WHO-ATC |
N02AG03
Created by
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57-42-1
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6754
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57-42-1
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7221
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200-329-1
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PETHIDINE
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DB00454
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Meperidine
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4058
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CHEMBL607
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D008614
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C71632
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9E338QE28F
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3116
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SUB09738MIG
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M7186
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1690
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC PHARMACOKINETIC |
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