Primidone

Identification

Summary

Primidone is an antiepileptic used to treat grand mal, psychomotor, and focal epileptic seizures.

Brand Names
Mysoline
Generic Name
Primidone
DrugBank Accession Number
DB00794
Background

Primidone is an anticonvulsant used to treat essential tremor as well as grand mal, psychomotor, and focal epileptic seizures.15 Primidone was developed by J Yule Bogue and H C Carrington in 1949.10

Primidone was granted FDA Approval on 8 March 1954.15

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 218.2518
Monoisotopic: 218.105527702
Chemical Formula
C12H14N2O2
Synonyms
  • 2-deoxyphenobarbital
  • 5-Phenyl-5-ethyl-Hexahydropyrimidine-4,6-dione
  • Primidon
  • Primidona
  • Primidone
  • Primidonum
External IDs
  • NSC-41701
  • Rö 101

Pharmacology

Indication

Primidone is commonly indicated for the management of grand mal, psychomotor, and focal epileptic seizures.14,15 In addition, it has also been studied and utilized as an effective management of essential tremor.1,2,14

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofEssential tremor••••••••••••••••••••• ••••••••••••
Management ofFocal seizures••••••••••••
Management ofGrand mal seizure••••••••••••
Management ofPsychomotor seizures••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Primidone alters sodium and calcium channel transport, reducing the frequency of nerve firing, which may be responsible for its effect on convulsions and essential tremor.4 Primidone has a wide therapeutic window as doses of 50-1000mg/day were effective.4 Patients should be counselled regarding the risk of status epilepticus with abrupt cessation of primidone.15

Mechanism of action

Primidone and its metabolites, phenobarbital and phenylethylmalonamide (PEMA), are active anticonvulsants.4 Primidone does not directly interact with GABA-A receptors or chloride channels but phenobarbital does.4 Primidone alters transmembrane sodium and calcium channel transport, reducing the frequency of nerve firing, which may be responsible for the primidone’s effect on convulsions and essential tremor.4

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-2
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-3
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-4
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-5
potentiator
Humans
AGamma-aminobutyric acid receptor subunit alpha-6
potentiator
Humans
AGABA(A) Receptor
positive allosteric modulator
Humans
AGamma-aminobutyric acid receptor subunit alpha-1
potentiator
Humans
UNeuronal acetylcholine receptor subunit alpha-4
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-7
antagonist
Humans
UGlutamate receptor 2
antagonist
Humans
UGlutamate receptor ionotropic, kainate 2
antagonist
Humans
Absorption

Oral primidone is up to 80% bioavailable with a Tmax if 2-4h.4,6 A 500mg oral dose of primidone Reaches a Cmax of 2.7±0.4µg/mL with a Tmax of 0.5-7h.7 Data regarding the AUC of primidone is not readily available.15

Volume of distribution

The volume of distribution of primidone is 0.5-0.8L/kg.5,6

Protein binding

Primidone is 10.78-13.70% protein bound in serum.3

Metabolism

Primidone is metabolized to phenobarbitol and phenylethylmalonamide (PEMA).11 This metabolism is largely mediated by CYP2C9,12,4,5 CYP2C19,13,12,5 and CYP2E1.12,5

Hover over products below to view reaction partners

Route of elimination

Primidone is 72.9-80.6% recovered in urine.8

Half-life

The half life of primidone is 7-22h in adults, 5-11h in children, and 8-80h in newborns.6

Clearance

Primidone is cleared at a rate of 30mL/min.7

Adverse Effects
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Toxicity

The oral LD50 in rats is 1500mg/kg and in mice is 280mg/kg.16 The intraperitoneal LD50 in rats was 240mg/kg and in mice was 332mg/kg.16

Patients experiencing a primidone overdose may present with CNS depression, coma, respiratory depression, suppressed reflexes, suppressed response to pain, hypotension, and decreased urine output.9 Overdose should be treated with symptomatic and supportive treatment, including the removal of unabsorbed drug.9

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be increased when combined with Primidone.
AbacavirThe metabolism of Abacavir can be increased when combined with Primidone.
AbaloparatidePrimidone may increase the hypotensive activities of Abaloparatide.
AbataceptThe metabolism of Primidone can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Primidone.
Food Interactions
  • Avoid alcohol.
  • Avoid St. John's Wort.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Product Images
International/Other Brands
Liskantin (Desitin) / Mizodin (Unia) / Mylepsinum / Pridona (Psicofarma) / Primid (Apsen) / Prysoline (Rekah) / Sertan (Alkaloida)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MysolineTablet250 mg/1OralBausch Health US, LLC2009-06-24Not applicableUS flag
MysolineTablet50 mg/1OralBausch Health US, LLC2009-06-24Not applicableUS flag
Mysoline 250mg TabTablet250 mgOralElan Pharmaceuticals1994-12-312004-08-05Canada flag
Mysoline Pediatric Chewable Tablets 125mgTablet125 mgOralElan Pharmaceuticals1994-12-312004-08-05Canada flag
Mysoline Tab 125mgTablet125 mg / tabOralAyerst Laboratories1963-12-311996-09-10Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PrimidoneTablet50 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2001-05-24Not applicableUS flag
PrimidoneTablet50 mg/1OralDirect Rx2021-05-11Not applicableUS flag
PrimidoneTablet50 mg/1OralPar Pharmaceutical2005-02-242021-10-31US flag
PrimidoneTablet250 mg/1OralMajor Pharmaceuticals2005-04-072019-01-11US flag
PrimidoneTablet50 mg/1OralPhysicians Total Care, Inc.2009-01-29Not applicableUS flag

Categories

ATC Codes
N05CB01 — Combinations of barbituratesN03AA03 — Primidone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hydropyrimidines. These are compounds containing a hydrogenated pyrimidine ring (i.e. containing less than the maximum number of double bonds.).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Hydropyrimidines
Alternative Parents
Benzene and substituted derivatives / Cyclic carboximidic acids / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
2,5-dihydropyrimidine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Cyclic carboximidic acid / Hydrocarbon derivative / Hydropyrimidine / Monocyclic benzene moiety / Organic 1,3-dipolar compound / Organic nitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidone (CHEBI:8412)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
13AFD7670Q
CAS number
125-33-7
InChI Key
DQMZLTXERSFNPB-UHFFFAOYSA-N
InChI
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)
IUPAC Name
5-ethyl-5-phenyl-1,3-diazinane-4,6-dione
SMILES
CCC1(C(=O)NCNC1=O)C1=CC=CC=C1

References

General References
  1. Rajput AH, Rajput A: Medical treatment of essential tremor. J Cent Nerv Syst Dis. 2014 Apr 21;6:29-39. doi: 10.4137/JCNSD.S13570. eCollection 2014. [Article]
  2. Schneider SA, Deuschl G: The treatment of tremor. Neurotherapeutics. 2014 Jan;11(1):128-38. doi: 10.1007/s13311-013-0230-5. [Article]
  3. Haidukewych D, Rodin EA: Serial free and plasma valproic acid and phenytoin monitoring and drug interactions. Ther Drug Monit. 1981;3(3):303-7. doi: 10.1097/00007691-198103000-00013. [Article]
  4. Hedera P, Cibulcik F, Davis TL: Pharmacotherapy of essential tremor. J Cent Nerv Syst Dis. 2013 Dec 22;5:43-55. doi: 10.4137/JCNSD.S6561. [Article]
  5. Marvanova M: Pharmacokinetic characteristics of antiepileptic drugs (AEDs). Ment Health Clin. 2016 Mar 8;6(1):8-20. doi: 10.9740/mhc.2015.01.008. eCollection 2016 Jan. [Article]
  6. Patsalos PN, Spencer EP, Berry DJ: Therapeutic Drug Monitoring of Antiepileptic Drugs in Epilepsy: A 2018 Update. Ther Drug Monit. 2018 Oct;40(5):526-548. doi: 10.1097/FTD.0000000000000546. [Article]
  7. Lee CS, Marbury TC, Perchalski RT, Wilder BJ: Pharmacokinetics of primidone elimination by uremic patients. J Clin Pharmacol. 1982 Jul;22(7):301-8. doi: 10.1002/j.1552-4604.1982.tb02679.x. [Article]
  8. Treston AM, Hooper WD: Urinary metabolites of phenobarbitone, primidone, and their N-methyl and N-ethyl derivatives in humans. Xenobiotica. 1992 Apr;22(4):385-94. doi: 10.3109/00498259209046650. [Article]
  9. van Heijst AN, de Jong W, Seldenrijk R, van Dijk A: Coma and crystalluria: a massive primidone intoxication treated with haemoperfusion. J Toxicol Clin Toxicol. 1983 Jun;20(4):307-18. doi: 10.3109/15563658308990598. [Article]
  10. HANDLEY R, STEWART AS: Mysoline; a new drug in the treatment of epilepsy. Lancet. 1952 Apr 12;1(6711):742-4. doi: 10.1016/s0140-6736(52)90500-x. [Article]
  11. El-Masri HA, Portier CJ: Physiologically based pharmacokinetics model of primidone and its metabolites phenobarbital and phenylethylmalonamide in humans, rats, and mice. Drug Metab Dispos. 1998 Jun;26(6):585-94. [Article]
  12. Zaccara G, Perucca E: Interactions between antiepileptic drugs, and between antiepileptic drugs and other drugs. Epileptic Disord. 2014 Dec;16(4):409-31. doi: 10.1684/epd.2014.0714. [Article]
  13. Tanaka E: Clinically significant pharmacokinetic drug interactions between antiepileptic drugs. J Clin Pharm Ther. 1999 Apr;24(2):87-92. doi: 10.1046/j.1365-2710.1999.00201.x. [Article]
  14. Electronic Medicines Compendium: Primidone 50 mg Tablet Monograph [Link]
  15. FDA Approved Drug Products: Mysoline Primidone Oral Tablets [Link]
  16. Cayman Chemical: Primidone MSDS [Link]
Human Metabolome Database
HMDB0014932
KEGG Drug
D00474
KEGG Compound
C07371
PubChem Compound
4909
PubChem Substance
46507775
ChemSpider
4740
BindingDB
50248152
RxNav
8691
ChEBI
8412
ChEMBL
CHEMBL856
ZINC
ZINC000000001979
Therapeutic Targets Database
DAP000678
PharmGKB
PA451105
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Primidone
FDA label
Download (108 KB)
MSDS
Download (65.5 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2WithdrawnTreatmentClopidogrel Resistance / Secondary Stroke Prevention1
1CompletedBasic ScienceTherapeutic Equivalency1
1CompletedTreatmentHealthy Subjects (HS)1
Not AvailableCompletedNot AvailableEpilepsy1
Not AvailableCompletedNot AvailableEssential Tremor1

Pharmacoeconomics

Manufacturers
  • Xcel pharmaceuticals
  • Valeant pharmaceuticals international
  • Amneal pharmaceutical
  • Dr reddys laboratories ltd
  • Impax laboratories inc
  • Lannett co inc
  • Mutual pharmaceutical co inc
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
Packagers
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Astellas Pharma Inc.
  • Atlantic Biologicals Corporation
  • Avkare Incorporated
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Global Pharmaceuticals
  • Heartland Repack Services LLC
  • Impax Laboratories Inc.
  • Kaiser Foundation Hospital
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Patheon Inc.
  • PCA LLC
  • Pharmaceutical Packaging Center
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Professional Co.
  • Qualitest
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Richmond Pharmacy
  • Valeant Ltd.
  • Vangard Labs Inc.
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
SuspensionOral125 mg
TabletOral0.25 G
TabletOral250 mg
TabletOral250.000 mg
TabletOral125 mg
TabletOral125 mg/1
TabletOral250 mg/1
TabletOral50 mg/1
TabletOral125 mg / tab
TabletOral250 mg / tab
TabletOral
Prices
Unit descriptionCostUnit
Primidone powder10.56USD g
Mysoline 250 mg tablet6.52USD tablet
Mysoline 50 mg tablet1.26USD tablet
Primidone 250 mg tablet1.02USD tablet
Primidone 50 mg tablet0.51USD tablet
Apo-Primidone 250 mg Tablet0.09USD tablet
Apo-Primidone 125 mg Tablet0.06USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)281.5 °CPhysProp
water solubility500 mg/L (at 22 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP0.91HANSCH,C ET AL. (1995)
logS-2.64ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility1.04 mg/mLALOGPS
logP0.62ALOGPS
logP1.12Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)11.5Chemaxon
pKa (Strongest Basic)-6.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area58.2 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity59.04 m3·mol-1Chemaxon
Polarizability22.44 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9907
Blood Brain Barrier+0.9642
Caco-2 permeable-0.5593
P-glycoprotein substrateSubstrate0.5222
P-glycoprotein inhibitor INon-inhibitor0.536
P-glycoprotein inhibitor IINon-inhibitor0.9048
Renal organic cation transporterNon-inhibitor0.8298
CYP450 2C9 substrateNon-substrate0.7961
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6863
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.924
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7814
BiodegradationNot ready biodegradable0.982
Rat acute toxicity2.1941 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9912
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.01 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-014i-2920000000-48e0e1759e3b8f3d22ce
GC-MS Spectrum - EI-BGC-MSsplash10-014i-8900000000-0e7a89b14902d3718a96
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03di-2910000000-b7efd09b00e06dbafb8a
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-03di-1910000000-bd08d6489b18d57466ef
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-015c-4900000000-628ede89a2ff3a714388
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0900000000-cd2ff1c9796dadddc1c4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03k9-0900000000-2791dd2c8b88ef3746e2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0590000000-248d62cc8fce49dbc8ac
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03xr-1910000000-defb3cb3827732984417
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-01ox-4900000000-2a6eec3c8ff19123ac27
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9800000000-6cf73d06072a870130a9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9500000000-f9d1e48f1afbc27fce53
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9400000000-ee42f86b57749afa5326
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-0590000000-c6e3ad2d87e33ccd0249
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03xr-1910000000-4f481052510ee71cb8ae
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03dl-4900000000-b796d864e3b38d92a1d4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9700000000-c6a71612fcf884b362c6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9400000000-2509c88567fd37a64f08
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9400000000-70b4eb639de5cd82206d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03k9-0900000000-32676f955580c7b188af
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0gb9-0790000000-85b9730b3c1a612616dd
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0uxr-1950000000-9a26803c7d536d7535be
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-1000-7940000000-13c974e8220bfde7b936
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0aou-9400000000-e6ac3896e41d100eb94d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-052f-9000000000-bdd6d5c0f8bd8a00b144
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-8900000000-8251f44f80079a017e49
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0006-9500000000-eca07632eb70021d3678
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03k9-0900000000-104ab34d91923122fa54
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-03k9-0900000000-523cfc5e1d739d54e0f5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-1910000000-bd08d6489b18d57466ef
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-2910000000-b7efd09b00e06dbafb8a
MS/MS Spectrum - , positiveLC-MS/MSsplash10-015c-4900000000-628ede89a2ff3a714388
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03xu-2900000000-c1f7b0b63b199254dd07
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-c6baa1759ce7e2d42782
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00r6-9870000000-6ac7af9bfbc0a803432f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0970000000-877664a9e7e0131f8885
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-dcd39f1c6d787b2808cf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-2720336a9e20f6f3ee25
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-6900000000-d31b138dede6a048a7c7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-152.5808268
predicted
DarkChem Lite v0.1.0
[M-H]-152.6351268
predicted
DarkChem Lite v0.1.0
[M-H]-152.5837268
predicted
DarkChem Lite v0.1.0
[M-H]-151.50157
predicted
DeepCCS 1.0 (2019)
[M+H]+153.7144268
predicted
DarkChem Lite v0.1.0
[M+H]+153.5146268
predicted
DarkChem Lite v0.1.0
[M+H]+153.6865268
predicted
DarkChem Lite v0.1.0
[M+H]+153.85959
predicted
DeepCCS 1.0 (2019)
[M+Na]+153.0126268
predicted
DarkChem Lite v0.1.0
[M+Na]+162.9773134
predicted
DarkChem Lite v0.1.0
[M+Na]+159.95273
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA2
Uniprot ID
P47869
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-2
Molecular Weight
51325.85 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA3
Uniprot ID
P34903
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-3
Molecular Weight
55164.055 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA4
Uniprot ID
P48169
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-4
Molecular Weight
61622.645 Da
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Transporter activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA5
Uniprot ID
P31644
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-5
Molecular Weight
52145.645 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel.
Gene Name
GABRA6
Uniprot ID
Q16445
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-6
Molecular Weight
51023.69 Da
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
  2. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Positive allosteric modulator
Curator comments
This activity is performed by phenobarbital, a metabolite of primidone.
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...

Components:
References
  1. Hedera P, Cibulcik F, Davis TL: Pharmacotherapy of essential tremor. J Cent Nerv Syst Dis. 2013 Dec 22;5:43-55. doi: 10.4137/JCNSD.S6561. [Article]
  2. ChEMBL Compound Report Card [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Potentiator
General Function
Inhibitory extracellular ligand-gated ion channel activity
Specific Function
Component of the heteropentameric receptor for GABA, the major inhibitory neurotransmitter in the vertebrate brain. Functions also as histamine receptor and mediates cellular responses to histamine...
Gene Name
GABRA1
Uniprot ID
P14867
Uniprot Name
Gamma-aminobutyric acid receptor subunit alpha-1
Molecular Weight
51801.395 Da
References
  1. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [Article]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
  3. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  4. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  6. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  7. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [Article]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Arias HR, Bhumireddy P: Anesthetics as chemical tools to study the structure and function of nicotinic acetylcholine receptors. Curr Protein Pept Sci. 2005 Oct;6(5):451-72. [Article]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Ionotropic glutamate receptor activity
Specific Function
Receptor for glutamate that functions as ligand-gated ion channel in the central nervous system and plays an important role in excitatory synaptic transmission. L-glutamate acts as an excitatory ne...
Gene Name
GRIA2
Uniprot ID
P42262
Uniprot Name
Glutamate receptor 2
Molecular Weight
98820.32 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
General Function
Kainate selective glutamate receptor activity
Specific Function
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L-glutamate induces a co...
Gene Name
GRIK2
Uniprot ID
Q13002
Uniprot Name
Glutamate receptor ionotropic, kainate 2
Molecular Weight
102582.475 Da
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [Article]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zaccara G, Perucca E: Interactions between antiepileptic drugs, and between antiepileptic drugs and other drugs. Epileptic Disord. 2014 Dec;16(4):409-31. doi: 10.1684/epd.2014.0714. [Article]
  2. Hedera P, Cibulcik F, Davis TL: Pharmacotherapy of essential tremor. J Cent Nerv Syst Dis. 2013 Dec 22;5:43-55. doi: 10.4137/JCNSD.S6561. [Article]
  3. Marvanova M: Pharmacokinetic characteristics of antiepileptic drugs (AEDs). Ment Health Clin. 2016 Mar 8;6(1):8-20. doi: 10.9740/mhc.2015.01.008. eCollection 2016 Jan. [Article]
  4. primidone - Drug Summary [Link]
  5. MONOGRAPH, Primidone [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
Curator comments
As the major active metabolite of primidone is phenobarbital, this drug is an inducer of CYP2C19.
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Tanaka E: Clinically significant pharmacokinetic drug interactions between antiepileptic drugs. J Clin Pharm Ther. 1999 Apr;24(2):87-92. doi: 10.1046/j.1365-2710.1999.00201.x. [Article]
  2. Zaccara G, Perucca E: Interactions between antiepileptic drugs, and between antiepileptic drugs and other drugs. Epileptic Disord. 2014 Dec;16(4):409-31. doi: 10.1684/epd.2014.0714. [Article]
  3. Marvanova M: Pharmacokinetic characteristics of antiepileptic drugs (AEDs). Ment Health Clin. 2016 Mar 8;6(1):8-20. doi: 10.9740/mhc.2015.01.008. eCollection 2016 Jan. [Article]
  4. Primidine Prescribing Information, Canada [File]
  5. Primidone FDA label [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Zaccara G, Perucca E: Interactions between antiepileptic drugs, and between antiepileptic drugs and other drugs. Epileptic Disord. 2014 Dec;16(4):409-31. doi: 10.1684/epd.2014.0714. [Article]
  2. Marvanova M: Pharmacokinetic characteristics of antiepileptic drugs (AEDs). Ment Health Clin. 2016 Mar 8;6(1):8-20. doi: 10.9740/mhc.2015.01.008. eCollection 2016 Jan. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Spina E, Pisani F, Perucca E: Clinically significant pharmacokinetic drug interactions with carbamazepine. An update. Clin Pharmacokinet. 1996 Sep;31(3):198-214. doi: 10.2165/00003088-199631030-00004. [Article]
  2. Benit CP, Vecht CJ: Seizures and cancer: drug interactions of anticonvulsants with chemotherapeutic agents, tyrosine kinase inhibitors and glucocorticoids. Neurooncol Pract. 2016 Dec;3(4):245-260. doi: 10.1093/nop/npv038. Epub 2015 Oct 11. [Article]
  3. Tanaka E: Clinically significant pharmacokinetic drug interactions between antiepileptic drugs. J Clin Pharm Ther. 1999 Apr;24(2):87-92. doi: 10.1046/j.1365-2710.1999.00201.x. [Article]
  4. Hedera P, Cibulcik F, Davis TL: Pharmacotherapy of essential tremor. J Cent Nerv Syst Dis. 2013 Dec 22;5:43-55. doi: 10.4137/JCNSD.S6561. [Article]
  5. Marvanova M: Pharmacokinetic characteristics of antiepileptic drugs (AEDs). Ment Health Clin. 2016 Mar 8;6(1):8-20. doi: 10.9740/mhc.2015.01.008. eCollection 2016 Jan. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Johannessen SI, Landmark CJ: Antiepileptic drug interactions - principles and clinical implications. Curr Neuropharmacol. 2010 Sep;8(3):254-67. doi: 10.2174/157015910792246254. [Article]
  2. Hedera P, Cibulcik F, Davis TL: Pharmacotherapy of essential tremor. J Cent Nerv Syst Dis. 2013 Dec 22;5:43-55. doi: 10.4137/JCNSD.S6561. [Article]
  3. Marvanova M: Pharmacokinetic characteristics of antiepileptic drugs (AEDs). Ment Health Clin. 2016 Mar 8;6(1):8-20. doi: 10.9740/mhc.2015.01.008. eCollection 2016 Jan. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...

Components:
References
  1. Johannessen SI, Landmark CJ: Antiepileptic drug interactions - principles and clinical implications. Curr Neuropharmacol. 2010 Sep;8(3):254-67. doi: 10.2174/157015910792246254. [Article]
  2. Marvanova M: Pharmacokinetic characteristics of antiepileptic drugs (AEDs). Ment Health Clin. 2016 Mar 8;6(1):8-20. doi: 10.9740/mhc.2015.01.008. eCollection 2016 Jan. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Calcium channel mediating constitutive calcium ion entry. Its activity is increased by reduction in extracellular osmolarity, by store depletion and muscarinic receptor activation.
Specific Function
Calcium activated cation channel activity
Gene Name
TRPM3
Uniprot ID
Q9HCF6
Uniprot Name
Transient receptor potential cation channel subfamily M member 3
Molecular Weight
197569.225 Da
References
  1. Krugel U, Straub I, Beckmann H, Schaefer M: Primidone inhibits TRPM3 and attenuates thermal nociception in vivo. Pain. 2017 May;158(5):856-867. doi: 10.1097/j.pain.0000000000000846. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55