Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H14N2O2 |
Molecular Weight | 218.2522 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC1(c2ccccc2)C(=NCN=C1O)O
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 | 218.2522 |
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 |
---|---|---|
Prediction of adsorption from multicomponent solutions by activated carbon using single-solute parameters. Part II--Proposed equation. | 2002 |
|
Fate of pharmaceuticals during indirect potable reuse. | 2002 |
|
Treatment of epilepsy in women of reproductive age: pharmacokinetic considerations. | 2002 |
|
Management of essential tremor. | 2002 Jul |
|
Clinical and electromyographic assessment of essential tremor treatment. | 2002 Jun |
|
Some common issues in the use of antiepileptic drugs. | 2002 Mar |
|
Primary standardization of assays for anticonvulsant drugs: comparison of accuracy and precision. | 2002 Nov |
|
Prolonged anticonvulsant hypersensitivity syndrome related to lamotrigine in a patient with human immunodeficiency virus. | 2002 Nov-Dec |
|
QT length and heart function in primidone hypocalcaemia. | 2002 Oct |
|
Benefits and risks of pharmacological treatments for essential tremor. | 2003 |
|
Drug treatment of epilepsy in elderly people: focus on valproic Acid. | 2003 |
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Effects of barbiturates on human platelet aggregation differ depending on their chemical structures. | 2003 Aug |
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Clinically important drug interactions in epilepsy: interactions between antiepileptic drugs and other drugs. | 2003 Aug |
|
Tremor. | 2003 Aug |
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Essential tremor: differential diagnosis and current therapy. | 2003 Aug 1 |
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[Late compensation for a recalled drug]. | 2003 Dec 15 |
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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 |
|
The absorption of gabapentin following high dose escalation. | 2003 Jan |
|
Simultaneous plasma lamotrigine analysis with carbamazepine, carbamazepine 10,11 epoxide, primidone, phenytoin, phenobarbital, and PEMA by micellar electrokinetic capillary chromatography (MECC). | 2003 Jul-Aug |
|
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 |
|
The ideal pharmacokinetic properties of an antiepileptic drug: how close does levetiracetam come? | 2003 May |
|
[Oxcarbazepine induced interstitial nephritis in a patient with drug hypersensitivity syndrome]. | 2003 Nov 16-30 |
|
[Antiepileptic primidone shortly to be withdrawn from sale: change medication now]. | 2003 Nov 22 |
|
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 |
|
Use of primidone in low doses (250 mg/day) versus high doses (750 mg/day) in the management of essential tremor. Double-blind comparative study with one-year follow-up. | 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 |
|
Key structural features of ligands for activation of human pregnane X receptor. | 2004 Apr |
|
Fatal mix-up between prednisone and primidone. | 2004 Aug 1 |
|
When breastfeeding mothers need CNS-acting drugs. | 2004 Fall |
|
[Drug interactions with antiepileptic agents]. | 2004 Feb 28 |
|
Natural history and syndromic associations of orthostatic tremor: a review of 41 patients. | 2004 Jul |
|
Levetiracetam in focal epilepsy and hepatic porphyria: a case report. | 2004 May |
|
Anticonvulsant efficacy of the low-affinity partial benzodiazepine receptor agonist ELB 138 in a dog seizure model and in epileptic dogs with spontaneously recurrent seizures. | 2004 Oct |
|
Pilot efficacy and tolerability: a randomized, placebo-controlled trial of levetiracetam for essential tremor. | 2004 Oct |
|
Simple and rapid micellar electrokinetic capillary chromatographic method for simultaneous determination of four antiepileptics in human serum. | 2004 Oct |
|
Efficacy and tolerability of the new antiepileptic drugs: comparison of two recent guidelines. | 2004 Oct |
|
Essential tremor. Epidemiology, diagnosis, and treatment. | 2004 Sep |
|
Epilepsy in the United Kingdom: seizure frequency and severity, anti-epileptic drug utilization and impact on life in 1652 people with epilepsy. | 2004 Sep |
|
[Population pharmacokinetics of carbamazepine in adults with epilepsy]. | 2005 Jan-Feb |
|
Drug-induced hypersensitivity syndrome in a premature infant. | 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 |
|
Primidone is associated with interictal depression in patients with epilepsy. | 2005 May |
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
Fri Jun 25 21:05:20 UTC 2021
by
admin
on
Fri Jun 25 21:05:20 UTC 2021
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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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-
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QN03AA03
Created by
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NCI_THESAURUS |
C67084
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WHO-ATC |
N03AA03
Created by
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NDF-RT |
N0000008486
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LIVERTOX |
798
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CFR |
21 CFR 862.3680
Created by
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NDF-RT |
N0000175753
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NCI_THESAURUS |
C264
Created by
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CFR |
21 CFR 520.1900
Created by
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Code System | Code | Type | Description | ||
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5338
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125-33-7
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PRIMARY | |||
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DB00794
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PRIMARY | |||
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M9135
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PRIMARY | Merck Index | ||
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4909
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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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248
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PRIMIDONE
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125-33-7
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2267
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D011324
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C47686
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3169
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1562000
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PRIMARY | USP-RS |
Related Record | Type | Details | ||
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METABOLIC ENZYME -> INDUCER | |||
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BINDER->LIGAND |
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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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