Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H14N2O2 |
Molecular Weight | 218.2518 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1(C(=O)NCNC1=O)C2=CC=CC=C2
InChI
InChIKey=DQMZLTXERSFNPB-UHFFFAOYSA-N
InChI=1S/C12H14N2O2/c1-2-12(9-6-4-3-5-7-9)10(15)13-8-14-11(12)16/h3-7H,2,8H2,1H3,(H,13,15)(H,14,16)
Molecular Formula | C12H14N2O2 |
Molecular Weight | 218.2518 |
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
https://www.ncbi.nlm.nih.gov/pubmed/?term=2871724
http://www.rxlist.com/mysoline-drug/side-effects-interactions.htm
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=2871724
http://www.rxlist.com/mysoline-drug/side-effects-interactions.htm
Primidone is an anticonvulsant of the barbiturate class. It was introduced in 1954 under the brand name Mysoline by Wyeth in the United States. Mysoline, used alone or concomitantly with other anticonvulsants, is indicated in the control of grand mal, psychomotor, and focal epileptic seizures. It may control grand mal seizures refractory to other anticonvulsant therapy. Mysoline raises electro- or chemoshock seizure thresholds or alters seizure patterns in experimental animals. The mechanism(s) of primidone’s antiepileptic action is not known. Primidone per se has anticonvulsant activity, as do its two metabolites, phenobarbital and phenylethylmalonamide (PEMA). In addition to its anticonvulsant activity, PEMA potentiates the anticonvulsant activity of phenobarbital in experimental animals. Primidone itself doesn’t act on GABA-A receptors. It is active metabolite - phenobarbital primary acts via modulation of GABA -A receptors. The most frequently occurring early side effects are ataxia and vertigo. These tend to disappear with continued therapy, or with reduction of initial dosage. Occasionally, the following have been reported: nausea, anorexia, vomiting, fatigue, hyperirritability, emotional disturbances, sexual impotency, diplopia, nystagmus, drowsiness, and morbilliform skin eruptions.Granulocytopenia, agranulocytosis, and red-cell hypoplasia and aplasia, have been reported rarely. These and, occasionally, other persistant or severe side effects may necessitate withdrawal of the drug. Megaloblastic anemia may occur as a rare idiosyncrasy to Mysoline and to other anticonvulsants. The anemia responds to folic acid without necessity of discontinuing medication.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13359420
Curator's Comment: The effectiveness of primidone was demonstrated by Yule Bogue in the Imperial Chemical Industries' Laboratories in 1949 and the results published in 1953.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=2871724 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | MYSOLINE Approved UseMysoline, used alone or concomitantly with other anticonvulsants, is indicated in the control of grand mal, psychomotor, and focal epileptic seizures. It may control grand mal seizures refractory to other anticonvulsant therapy. Launch Date-4.99219202E11 |
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Primary | MYSOLINE Approved UseMysoline, used alone or concomitantly with other anticonvulsants, is indicated in the control of grand mal, psychomotor, and focal epileptic seizures. It may control grand mal seizures refractory to other anticonvulsant therapy. Launch Date-4.99219202E11 |
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Primary | MYSOLINE Approved UseMysoline, used alone or concomitantly with other anticonvulsants, is indicated in the control of grand mal, psychomotor, and focal epileptic seizures. It may control grand mal seizures refractory to other anticonvulsant therapy. Launch Date-4.99219202E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.45 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9688064 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMIDONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
140.5 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9688064 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMIDONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.9 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9688064 |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
PRIMIDONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
62.5 mg 1 times / day multiple, oral Studied dose Dose: 62.5 mg, 1 times / day Route: oral Route: multiple Dose: 62.5 mg, 1 times / day Sources: Page: p.316 |
unhealthy, 18-83 n = 19 Health Status: unhealthy Condition: Essential tremor Age Group: 18-83 Sex: M+F Population Size: 19 Sources: Page: p.316 |
Disc. AE: Nausea, Ataxia... AEs leading to discontinuation/dose reduction: Nausea (acute) Sources: Page: p.316Ataxia (acute) Dizziness (acute) Confusion (acute) |
15 mg single, oral (max) Overdose |
healthy, 34 n = 1 Health Status: healthy Age Group: 34 Sex: F Population Size: 1 Sources: |
Disc. AE: Coma, Crystalluria... AEs leading to discontinuation/dose reduction: Coma Sources: Crystalluria |
500 mg 4 times / day multiple, oral Recommended Dose: 500 mg, 4 times / day Route: oral Route: multiple Dose: 500 mg, 4 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Epileptic seizures Sources: Page: p.2 |
Disc. AE: Suicidal behavior, Suicidal ideation... AEs leading to discontinuation/dose reduction: Suicidal behavior Sources: Page: p.2Suicidal ideation |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Ataxia | acute Disc. AE |
62.5 mg 1 times / day multiple, oral Studied dose Dose: 62.5 mg, 1 times / day Route: oral Route: multiple Dose: 62.5 mg, 1 times / day Sources: Page: p.316 |
unhealthy, 18-83 n = 19 Health Status: unhealthy Condition: Essential tremor Age Group: 18-83 Sex: M+F Population Size: 19 Sources: Page: p.316 |
Confusion | acute Disc. AE |
62.5 mg 1 times / day multiple, oral Studied dose Dose: 62.5 mg, 1 times / day Route: oral Route: multiple Dose: 62.5 mg, 1 times / day Sources: Page: p.316 |
unhealthy, 18-83 n = 19 Health Status: unhealthy Condition: Essential tremor Age Group: 18-83 Sex: M+F Population Size: 19 Sources: Page: p.316 |
Dizziness | acute Disc. AE |
62.5 mg 1 times / day multiple, oral Studied dose Dose: 62.5 mg, 1 times / day Route: oral Route: multiple Dose: 62.5 mg, 1 times / day Sources: Page: p.316 |
unhealthy, 18-83 n = 19 Health Status: unhealthy Condition: Essential tremor Age Group: 18-83 Sex: M+F Population Size: 19 Sources: Page: p.316 |
Nausea | acute Disc. AE |
62.5 mg 1 times / day multiple, oral Studied dose Dose: 62.5 mg, 1 times / day Route: oral Route: multiple Dose: 62.5 mg, 1 times / day Sources: Page: p.316 |
unhealthy, 18-83 n = 19 Health Status: unhealthy Condition: Essential tremor Age Group: 18-83 Sex: M+F Population Size: 19 Sources: Page: p.316 |
Coma | Disc. AE | 15 mg single, oral (max) Overdose |
healthy, 34 n = 1 Health Status: healthy Age Group: 34 Sex: F Population Size: 1 Sources: |
Crystalluria | Disc. AE | 15 mg single, oral (max) Overdose |
healthy, 34 n = 1 Health Status: healthy Age Group: 34 Sex: F Population Size: 1 Sources: |
Suicidal behavior | Disc. AE | 500 mg 4 times / day multiple, oral Recommended Dose: 500 mg, 4 times / day Route: oral Route: multiple Dose: 500 mg, 4 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Epileptic seizures Sources: Page: p.2 |
Suicidal ideation | Disc. AE | 500 mg 4 times / day multiple, oral Recommended Dose: 500 mg, 4 times / day Route: oral Route: multiple Dose: 500 mg, 4 times / day Sources: Page: p.2 |
unhealthy Health Status: unhealthy Condition: Epileptic seizures Sources: Page: p.2 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no | ||||
no | ||||
no | ||||
no | ||||
unlikely | ||||
weak | ||||
yes [Activation 39.81072 uM] | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/29955442/ |
yes | |||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/ |
yes | |||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/29955442/ |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/29955442/ |
yes | |||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/11996015/ |
yes | |||
yes | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/29955442/ |
yes | |||
yes | yes (co-administration study) Comment: The mean serum concentration of carbamazepine is lower when the drug is given in combination with primidone (58·2%) than when carbamazepine is given alone (100%). |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
major | ||||
no | ||||
no | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Anticonvulsant-induced dyskinesias: a comparison with dyskinesias induced by neuroleptics. | 1976 Dec |
|
Seizure-inducing paradoxical reaction to antiepileptic drugs. | 2000 Jun |
|
Giant cell myocarditis as a manifestation of drug hypersensitivity. | 2000 Sep-Oct |
|
[Febrile convulsions, Treatment and prognosis]. | 2001 Feb 19 |
|
Neural tube defects in relation to use of folic acid antagonists during pregnancy. | 2001 May 15 |
|
Pharmacologic management of epilepsy in the elderly. | 2001 May-Jun |
|
Fate of pharmaceuticals during indirect potable reuse. | 2002 |
|
Ecological data of Travassosnema travassosi travassosi (Dracunculoidea: Guyanemidae) from the humour of the eyes of Acestrorhynchus lacustris from Tibagi River, Paraná, Brazil. | 2002 Jan |
|
Antiepileptic hypersensitivity syndrome: clinicians beware and be aware. | 2002 Jan |
|
Unverricht-Lundborg disease with cystatin B gene abnormalities. | 2002 Jan |
|
Management of essential tremor. | 2002 Jul |
|
Serum concentrations of topiramate in patients with epilepsy: influence of dose, age, and comedication. | 2002 Jun |
|
Some common issues in the use of antiepileptic drugs. | 2002 Mar |
|
The management of tremor. | 2002 Mar |
|
Occurrence, fate, and removal of pharmaceutical residues in the aquatic environment: a review of recent research data. | 2002 May 10 |
|
Benefits and risks of pharmacological treatments for essential tremor. | 2003 |
|
Drug treatment of epilepsy in elderly people: focus on valproic Acid. | 2003 |
|
Effects of antiepileptic comedication on levetiracetam pharmacokinetics: a pooled analysis of data from randomized adjunctive therapy trials. | 2003 Feb |
|
Effects of concomitant antiepileptic drugs on serum carbamazepine concentration in epileptic patients: quantitative analysis based on extracellular water volume as a transforming factor. | 2003 Jan |
|
Clinically important drug interactions in epilepsy: general features and interactions between antiepileptic drugs. | 2003 Jun |
|
Orthostatic tremor: report of a case and review of the literature. | 2003 Mar |
|
Clinical features, assessment and treatment of essential tremor. | 2003 Mar |
|
Tremor--easily seen but difficult to describe and treat. | 2003 Mar |
|
Microemulsion electrokinetic chromatography applied for separation of levetiracetam from other antiepileptic drugs in polypharmacy. | 2003 Mar |
|
Low doses of topiramate are effective in essential tremor: a report of three cases. | 2003 Nov-Dec |
|
Sedation caused by primidone may exacerbate dementia. | 2003 Oct |
|
AstraZeneca postpones discontinuation of Mysoline. | 2003 Oct |
|
Comparison of human exposures to selected chemicals with thresholds from NTP carcinogenicity studies in rodents. | 2003 Sep |
|
Essential tremor: diagnosis and treatment. | 2003 Sep |
|
Antiepileptic drug pharmacokinetics during pregnancy and lactation. | 2003 Sep 1 |
|
Fatal mix-up between prednisone and primidone. | 2004 Aug 1 |
|
Natural history and syndromic associations of orthostatic tremor: a review of 41 patients. | 2004 Jul |
|
Spectrum of epilepsy in tuberous sclerosis. | 2004 Jun |
|
Antiepileptic drugs: indications other than epilepsy. | 2004 Jun |
|
Levetiracetam in focal epilepsy and hepatic porphyria: a case report. | 2004 May |
|
Essential tremor in the older adult: coping with primary symptoms. | 2004 Sep |
|
Essential tremor. Epidemiology, diagnosis, and treatment. | 2004 Sep |
|
[Hyperhomocysteinemia and treatment with antiepileptic drugs. Effects of different doses of folic acid]. | 2005 Apr 16 |
|
[Population pharmacokinetics of carbamazepine in adults with epilepsy]. | 2005 Jan-Feb |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Practice parameter: therapies for essential tremor: report of the Quality Standards Subcommittee of the American Academy of Neurology. | 2005 Jun 28 |
|
Pharmacological treatment of disabling tremor. | 2005 Mar |
|
Genetic essential tremor in gamma-aminobutyric acidA receptor alpha1 subunit knockout mice. | 2005 Mar |
|
Primidone is associated with interictal depression in patients with epilepsy. | 2005 May |
|
Determination of levetiracetam in human plasma with minimal sample pretreatment. | 2005 May 5 |
Sample Use Guides
Patients 8 years of age and older who have received no previous treatment may be started according to the following regimen using either 50 mg or scored 250 mg tablets:
Days 1 to 3: 100 to 125 mg at bedtime.
Days 4 to 6: 100 to 125 mg b.i.d.
Days 7 to 9: 100 to 125 mg t.i.d.
Day 10 to maintenance: 250 mg t.i.d.
Route of Administration:
Oral
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:36:46 UTC 2023
by
admin
on
Wed Jul 05 22:36:46 UTC 2023
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Record UNII |
13AFD7670Q
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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 |
QN03AA03
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NCI_THESAURUS |
C67084
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WHO-ATC |
N03AA03
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NDF-RT |
N0000008486
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LIVERTOX |
NBK548512
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CFR |
21 CFR 862.3680
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NDF-RT |
N0000175753
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NCI_THESAURUS |
C264
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CFR |
21 CFR 520.1900
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5338
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DTXSID7023510
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DB00794
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M9135
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41701
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4909
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8412
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8691
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SUB10045MIG
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204-737-0
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13AFD7670Q
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Primidone
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CHEMBL856
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100000081656
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248
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PRIMIDONE
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125-33-7
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2267
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1562000
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D011324
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C47686
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13AFD7670Q
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3169
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Related Record | Type | Details | ||
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BINDER->LIGAND |
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METABOLIC ENZYME -> INDUCER |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
Metabolite to parent drug ratio in non-uraemic human plasma.
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
|
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METABOLITE -> PARENT |
Metabolite to parent drug ratio in non-uraemic human plasma.
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
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METABOLITE -> PARENT |
Percent of dose excreted in urine as metabolite.
Primidone is converted in man to phenobarbitone.
AMOUNT EXCRETED
URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Population PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC PHARMACOKINETIC |
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