Identification

Name
Primidone
Accession Number
DB00794  (APRD00549)
Type
Small Molecule
Groups
Approved, Vet approved
Description

An antiepileptic agent related to the barbiturates; it is partly metabolized to phenobarbital in the body and owes some of its actions to this metabolite. Adverse effects are reported to be more frequent than with phenobarbital. (From Martindale, The Extra Pharmacopoeia, 30th ed, p309)

Structure
Thumb
Synonyms
  • 5-Phenyl-5-ethyl-hexahydropyrimidine-4,6-dione
  • Desoxyphenobarbital
  • Primaclone
  • Primidon
  • Primidona
  • Primidone
  • Primidonum
External IDs
NSC-41701 / Rö 101
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MysolineTablet250 mg/1OralValeant Pharmaceuticals North America2009-06-24Not applicableUs
MysolineTablet50 mg/1OralValeant Pharmaceuticals North America2009-06-24Not applicableUs
Mysoline 250mg TabTablet250 mgOralElan Pharmaceuticals1994-12-312004-08-05Canada
Mysoline Pediatric Chewable Tablets 125mgTablet125 mgOralElan Pharmaceuticals1994-12-312004-08-05Canada
Mysoline Tab 125mgTablet125 mgOralAyerst Laboratories1963-12-311996-09-10Canada
Mysoline Tab 250mgTablet250 mgOralAyerst Laboratories1965-12-311997-08-15Canada
PrimidoneTablet250 mgOralAa Pharma Inc1977-12-31Not applicableCanada
PrimidoneTablet250 mg/1OralVintage Pharmaceuticals, LLC2007-11-272007-11-27Us
PrimidoneTablet125 mgOralAa Pharma Inc1977-12-31Not applicableCanada
PrimidoneTablet50 mg/1OralVintage Pharmaceuticals, LLC2007-11-272007-11-27Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
PrimidoneTablet50 mg/1OralImpax Generics2008-02-122014-02-28Us
PrimidoneTablet250 mg/1OralAmerincan Health Packaging2007-06-14Not applicableUs
PrimidoneTablet250 mg/1OralAv Kare, Inc.2009-11-10Not applicableUs
PrimidoneTablet50 mg/1OralWest Ward Pharmaceutical2006-07-01Not applicableUs
PrimidoneTablet50 mg/1OralDr Reddy's Laboratories2008-10-03Not applicableUs
PrimidoneTablet250 mg/1OralOceanside Pharmaceuticals2018-05-21Not applicableUs
PrimidoneTablet250 mg/1OralMajor2009-12-242018-09-20Us65162 0545 10 nlmimage10 a83e5462
PrimidoneTablet50 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs2001-05-24Not applicableUs
PrimidoneTablet250 mg/1OralPhysicians Total Care, Inc.2009-07-27Not applicableUs
PrimidoneTablet50 mg/1OralMajor2005-04-07Not applicableUs
International/Other Brands
Liskantin (Desitin) / Mizodin (Unia) / Mylepsinum / Mysoline / Pridona (Psicofarma) / Primid (Apsen) / Prysoline (Rekah) / Sertan (Alkaloida)
Categories
UNII
13AFD7670Q
CAS number
125-33-7
Weight
Average: 218.2518
Monoisotopic: 218.105527702
Chemical Formula
C12H14N2O2
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

Pharmacology

Indication

Primidone is commonly indicated for the management of grand mal, psychomotor, and focal epileptic seizures [8]. In addition, it has also been studied and utilized as an effective management of essential tremor [6, 7, 8].

Associated Conditions
Pharmacodynamics

Primidone is a barbiturate with anticonvulsant properties. Primidone, either alone or used 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. Primidone raises electro- or chemoshock seizure thresholds or alters seizure patterns in experimental animals. Primidone per se has anticonvulsant activity as do its two metabolites, phenobarbital and phenylethylmalonamide (PEMA). In addition to its anticonvulsant activity, Primidone potentiates that of phenobarbital in experimental animals.

Mechanism of action

Primidone is a GABA receptor agonist. The mechanism of Primidone's antiepileptic action is not known.

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

90 to 100%

Volume of distribution
Not Available
Protein binding

70%

Metabolism

Hepatic

Route of elimination
Not Available
Half life

3-23 hours

Clearance
Not Available
Toxicity

Symptoms of an overdose typically include sluggishness, incoordination, difficulty in thinking, slowness of speech, faulty judgment, drowsiness or coma, shallow breathing, staggering, and in severe cases coma and death.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Primidone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Primidone.
1,10-PhenanthrolineThe therapeutic efficacy of Primidone can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamineThe serum concentration of Primidone can be decreased when it is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe serum concentration of Primidone can be decreased when it is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be decreased when it is combined with Primidone.
3,4-MethylenedioxyamphetamineThe serum concentration of Primidone can be decreased when it is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Primidone.
4-Bromo-2,5-dimethoxyamphetamineThe serum concentration of Primidone can be decreased when it is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Primidone.
Food Interactions
  • Avoid alcohol.
  • Avoid high doses of caffeine.
  • Take with food to reduce gastric irritation.

References

General References
  1. Murphy K, Delanty N: Primary Generalized Epilepsies. Curr Treat Options Neurol. 2000 Nov;2(6):527-542. [PubMed:11096777]
  2. Kagitani-Shimono K, Imai K, Okamoto N, Ono J, Okada S: Unverricht-Lundborg disease with cystatin B gene abnormalities. Pediatr Neurol. 2002 Jan;26(1):55-60. [PubMed:11814737]
  3. Brown GM, Stone GH, Rathbone MP: Primidone and rapid cycling affective disorders. Lancet. 1993 Oct 9;342(8876):925. [PubMed:8105181]
  4. Schaffer LC, Schaffer CB, Caretto J: The use of primidone in the treatment of refractory bipolar disorder. Ann Clin Psychiatry. 1999 Jun;11(2):61-6. [PubMed:10440522]
  5. Young MC, Hughes IA: Loss of therapeutic control in congenital adrenal hyperplasia due to interaction between dexamethasone and primidone. Acta Paediatr Scand. 1991 Jan;80(1):120-4. [PubMed:2028784]
  6. 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. [PubMed:24812533]
  7. Schneider SA, Deuschl G: The treatment of tremor. Neurotherapeutics. 2014 Jan;11(1):128-38. doi: 10.1007/s13311-013-0230-5. [PubMed:24142589]
  8. Electronic Medicines Compendium: Primidone 50 mg Tablet Monograph [Link]
External Links
Human Metabolome Database
HMDB0014932
KEGG Drug
D00474
KEGG Compound
C07371
PubChem Compound
4909
PubChem Substance
46507775
ChemSpider
4740
ChEBI
8412
ChEMBL
CHEMBL856
Therapeutic Targets Database
DAP000678
PharmGKB
PA451105
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Primidone
ATC Codes
N03AA03 — PrimidoneN05CB01 — Combinations of barbiturates
AHFS Codes
  • 28:12.04 — Barbiturates
FDA label
Download (108 KB)
MSDS
Download (65.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceTherapeutic Equivalency1
1CompletedTreatmentHealthy Volunteers1
2WithdrawnTreatmentClopidogrel Resistance / Secondary Stroke Prevention1

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
TabletOral125 mg
TabletOral250 mg
TabletOral250 mg/1
TabletOral50 mg/1
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-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-014i-8900000000-0e7a89b14902d3718a96
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Benzenoid / 2,5-dihydropyrimidine / Hydropyrimidine / Monocyclic benzene moiety / Cyclic carboximidic acid / Azacycle / Organic 1,3-dipolar compound / Propargyl-type 1,3-dipolar organic compound / Organic nitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidone (CHEBI:8412)

Targets

Kind
Protein
Organism
Human
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. [PubMed:14579514]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
  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. [PubMed:11264449]
  4. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  6. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  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. [PubMed:17016423]
Kind
Protein
Organism
Human
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. [PubMed:11264449]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
Kind
Protein
Organism
Human
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. [PubMed:11264449]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
Kind
Protein
Organism
Human
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. [PubMed:10209232]
Kind
Protein
Organism
Human
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. [PubMed:11264449]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232]
Kind
Protein
Organism
Human
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. [PubMed:10209232]
  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. [PubMed:11264449]
Kind
Protein
Organism
Human
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. [PubMed:11264449]
  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. [PubMed:16248797]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
Kind
Protein
Organism
Human
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. [PubMed:11264449]
  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. [PubMed:16248797]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
Kind
Protein
Organism
Human
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. [PubMed:11264449]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]
Kind
Protein
Organism
Human
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. [PubMed:11264449]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207]

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:10380060]
  2. Primidine Prescribing Information, Canada [File]
  3. Primidone FDA label [File]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. primidone - Drug Summary [Link]
  3. MONOGRAPH, Primidone [File]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Kalsi SS, Wood DM, Waring WS, Dargan PI: Does cytochrome P450 liver isoenzyme induction increase the risk of liver toxicity after paracetamol overdose? Open Access Emerg Med. 2011 Oct 13;3:69-76. doi: 10.2147/OAEM.S24962. eCollection 2011. [PubMed:27147854]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
No
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...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Interactions [Link]

Drug created on June 13, 2005 07:24 / Updated on November 14, 2018 12:46