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
| 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 |
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: Respiratory depression, Hypotension... Other AEs: Respiratory depression (1 patient) Sources: Hypotension (1 patient) Tremor (1 patient) Hyperreflexia (1 patient) Myoclonus (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 |
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 |
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 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 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 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 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 Health Status: unhealthy 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 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 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 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 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 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 |
|---|---|---|
| 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 |
|
| Leptospirosis: skin wounds and control strategies, Thailand, 1999. | 2002-12 |
|
| Intraperitoneal pethidine versus intramuscular pethidine for the relief of pain after laparoscopic cholecystectomy: randomized trial. | 2002-12 |
|
| Plication darn for the repair of inguinal hernia. A university hospital experience. | 2002-11 |
|
| [Long-memory of labor pain]. | 2002-10-14 |
|
| Characterisation of silent and active genes for a variable large protein of Borrelia recurrentis. | 2002-10-14 |
|
| Comparison of intravenous ketorolac and meperidine in the treatment of biliary colic. | 2002-10 |
|
| The low normothermia concept--maintaining a core body temperature between 36 and 37 degrees C in acute stroke unit patients. | 2002-10 |
|
| Two in one: patient-controlled epidural analgesia (PCEA) to prevent erection and control pain in adult hypospadias-surgery patients. | 2002-09 |
|
| Can ketamine potentiate the analgesic effect of epidural morphine, preincisional or postincisional administration? | 2002-09 |
|
| Effects of intravenous opioids on eye movements in humans: possible mechanisms. | 2002-09 |
|
| Retroperitoneal laparoscopic radical nephrectomy and nephroureterectomy and comparison with open surgery. | 2002-09 |
|
| Application of gas chromatography-surface ionization organic mass spectrometry to forensic toxicology. | 2002-08-25 |
|
| Laparoscopic hysterectomy versus abdominal hysterectomy: a controlled study of clinical and functional outcomes. | 2002-08 |
|
| Pulmonary function in infants exposed to pethidine. | 2002-08 |
|
| Selegiline: a second look. Six years later: too risky in Parkinson's disease. | 2002-08 |
|
| Synergistic sedation with midazolam and propofol versus midazolam and pethidine in colonoscopies: a prospective, randomized study. | 2002-08 |
|
| Upper gastrointestinal endoscopic ultrasound and its impact on patient management: 1990-2000. | 2002-08 |
|
| 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. | 2002-08 |
|
| Nasal administration of opioids for pain management in adults. | 2002-08 |
|
| Noninvasive anesthesia, analgesia and radiation-free extracorporeal shock wave lithotripsy for stones in the most distal ureter: experience with 165 patients. | 2002-08 |
|
| Primary thoracoscopic evaluation of pleural effusion with local anesthesia: an alternative approach. | 2002-07-13 |
|
| Mini cholecystectomy now a day stay surgery: anaesthetic management with multi modal analgesia. | 2002-07 |
|
| Severe hypokalaemia secondary to dicloxacillin. | 2002-07 |
|
| Pruritus: a useful sign for predicting the haemodynamic changes that occur following administration of vancomycin. | 2002-06 |
|
| A thermal threshold testing device for evaluation of analgesics in cats. | 2002-06 |
|
| Intra-arterial injection of metoclopramide, midazolam, propofol and pethidine. | 2002-06 |
|
| Double-blind, randomized trial comparing Harmonic Scalpel hemorrhoidectomy, bipolar scissors hemorrhoidectomy, and scissors excision: ligation technique. | 2002-06 |
|
| Lack of microbiological concordance between bone and non-bone specimens in chronic osteomyelitis: an observational study. | 2002-05-16 |
|
| Liquid-phase microextraction of protein-bound drugs under non-equilibrium conditions. | 2002-05 |
|
| Parenteral opioids for labor pain relief: a systematic review. | 2002-05 |
|
| Transdermal fentanyl for the management of acute pancreatitis pain. | 2002-05 |
|
| Anxiolytic premedication reduces preoperative anxiety and pain during oocyte retrieval. A randomized double-blinded placebo-controlled trial. | 2002-05 |
|
| Next generation of everyday analgesics. | 2002-04-10 |
|
| A placebo-controlled, randomized trial of droperidol versus metoclopramide for outpatients undergoing gynecological laparoscopy under conscious sedation. | 2002-04 |
|
| Use of opioid analgesics in a patient with chronic abdominal pain. | 2002-04 |
|
| Infective endocarditis: too ill to be operated? | 2002-04 |
|
| Improved procedure of colonoscopy under accompanying music therapy. | 2002-03-28 |
|
| [Survey of anesthesia practice in Morocco]. | 2002-01 |
|
| 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 novel approach to the prevention of postoperative delirium in the elderly after gastrointestinal surgery. | 2002 |
|
| Intrathecal pethidine as sole anaesthetic agent for operative procedures of the lower limb, inguinal area and perineum. | 2001-12 |
|
| Morphine, pethidine and buprenorphine disposition in the cat. | 2001-12 |
|
| [Comparison of vaginal misoprostol and oxytocin for labor induction in post-term pregnancy]. | 2001-12 |
|
| [Prospective double-blind randomized trial of cryoanalgesia: experimental and clinical study]. | 2001-11 |
|
| Upper and mid-ureteric stones: a prospective unrandomized comparison of retroperitoneoscopic and open ureterolithotomy. | 2001-11 |
|
| Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria. | 2001-03 |
|
| [Anesthesia and analgesia for lower limb amputation]. | 2001 |
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
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| Record UNII |
9E338QE28F
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Validated (UNII)
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WHO-VATC |
QN02AG03
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NCI_THESAURUS |
C67413
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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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57-42-1
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PETHIDINE
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Meperidine
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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METABOLIC ENZYME -> SUBSTRATE |
MINOR
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BINDER->LIGAND |
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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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