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
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
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 |
---|---|---|
[Meperidine (pethidine) outdated as analgesic in acute pancreatitis]. | 2000 Apr 1 |
|
Urticaria induced by meperidine allergy. | 2000 Mar |
|
Single-dose dipyrone for acute postoperative pain. | 2001 |
|
Sedation and analgesia for transvaginal oocyte retrieval: an audit resulting in a change of clinical practice. | 2001 |
|
Co-administration of drugs and blood products. | 2001 Apr |
|
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 |
|
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg. | 2001 Jan 10 |
|
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 |
|
Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria. | 2001 Mar |
|
Postoperative pain management using intravenous patient-controlled analgesia for pediatric patients. | 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 |
|
Prospective, randomized, comparative study of Misgav Ladach versus traditional cesarean section at Nazareth Hospital, Kenya. | 2001 Sep |
|
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 |
|
Prevention and treatment of respiratory syncytial virus bronchiolitis and postbronchiolitic wheezing. | 2002 |
|
A placebo-controlled, randomized trial of droperidol versus metoclopramide for outpatients undergoing gynecological laparoscopy under conscious sedation. | 2002 Apr |
|
Infective endocarditis: too ill to be operated? | 2002 Apr |
|
Laparoscopic hysterectomy versus abdominal hysterectomy: a controlled study of clinical and functional outcomes. | 2002 Aug |
|
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 |
|
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 |
|
Leptospirosis: skin wounds and control strategies, Thailand, 1999. | 2002 Dec |
|
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 |
|
Vitamin K and childhood cancer: analysis of individual patient data from six case-control studies. | 2002 Jan 7 |
|
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 |
|
Liquid-phase microextraction of protein-bound drugs under non-equilibrium conditions. | 2002 May |
|
Plication darn for the repair of inguinal hernia. A university hospital experience. | 2002 Nov |
|
Comparison of intravenous ketorolac and meperidine in the treatment of biliary colic. | 2002 Oct |
|
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 |
|
Can ketamine potentiate the analgesic effect of epidural morphine, preincisional or postincisional administration? | 2002 Sep |
|
Effects of intravenous opioids on eye movements in humans: possible mechanisms. | 2002 Sep |
|
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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Classification Tree | Code System | Code | ||
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DEA NO. |
9230
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NCI_THESAURUS |
C67413
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DTXSID30950620
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N8E7F7Q170
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31984
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100000091068
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400479
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CHEMBL607
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DBSALT000628
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6754
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C635
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N8E7F7Q170
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m7186
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5750
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MEPERIDINE HYDROCHLORIDE
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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. | ||
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50-13-5
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1383001
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SUB03726MIG
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103755
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200-013-3
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ACTIVE MOIETY
SUBSTANCE RECORD