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 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 |
---|---|---|
Adding low dose meperidine to spinal lidocaine prolongs postoperative analgesia. | 1999 Apr |
|
Low frequency of meperidine-associated seizures in sickle cell disease. | 1999 Aug |
|
Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. | 1999 Jul |
|
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 |
|
Pseudotumor cerebri induced by all-trans-retinoic acid in a child treated for acute promyelocytic leukemia. | 2000 Apr |
|
[Meperidine (pethidine) outdated as analgesic in acute pancreatitis]. | 2000 Apr 1 |
|
Successful treatment of normeperidine neurotoxicity by hemodialysis. | 2000 Jan |
|
Urticaria induced by meperidine allergy. | 2000 Mar |
|
Single-dose dipyrone for acute postoperative pain. | 2001 |
|
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 |
|
Efficacy and safety of patient-controlled opioid analgesia for acute postoperative pain. A quantitative systematic review. | 2001 Aug |
|
Renal colic and recurrent urinary calculi. Management and prevention. | 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 |
|
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 |
|
Use of a new finger-mounted device to compare mechanical nociceptive thresholds in cats given pethidine or no medication after castration. | 2001 Jun |
|
Safety and efficacy of peribulbar block as adjunct to general anaesthesia for paediatric ophthalmic surgery. | 2001 Mar |
|
Influence of doxepin used in preemptive analgesia on the nociception in the perioperative period. Experimental and clinical study. | 2001 May-Jun |
|
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 |
|
Needlescopic, laparoscopic, and open appendectomy: a comparative study. | 2001 Oct |
|
From hit to lead. Combining two complementary methods for focused library design. Application to mu opiate ligands. | 2001 Oct 11 |
|
A placebo-controlled, randomized trial of droperidol versus metoclopramide for outpatients undergoing gynecological laparoscopy under conscious sedation. | 2002 Apr |
|
Selegiline: a second look. Six years later: too risky in Parkinson's disease. | 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 |
|
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 |
|
Intra-arterial injection of metoclopramide, midazolam, propofol and pethidine. | 2002 Jun |
|
Treatment patterns of isolated benign headache in US emergency departments. | 2002 Mar |
|
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 |
|
Plication darn for the repair of inguinal hernia. A university hospital experience. | 2002 Nov |
|
Characterisation of silent and active genes for a variable large protein of Borrelia recurrentis. | 2002 Oct 14 |
|
Comparison of colonoscopies performed under sedation with propofol or with midazolam or without sedation. | 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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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 |
NBK548764
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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
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DTXSID9023253
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6754
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PRIMARY | RxNorm | ||
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57-42-1
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7221
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411
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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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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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6754
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)