Identification

Name
Phenobarbital
Accession Number
DB01174  (APRD00184)
Type
Small Molecule
Groups
Approved, Investigational
Description

A barbituric acid derivative that acts as a nonselective central nervous system depressant. It promotes binding to inhibitory gamma-aminobutyric acid subtype receptors, and modulates chloride currents through receptor channels. It also inhibits glutamate induced depolarizations. [PubChem]

Structure
Thumb
Synonyms
  • 5-ethyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione
  • 5-Ethyl-5-phenyl-pyrimidine-2,4,6-trione
  • 5-Ethyl-5-phenylbarbituric acid
  • 5-ethyl-5-phenylpyrimidine-2,4,6(1H,3H,5H)-trione
  • 5-Phenyl-5-ethylbarbituric acid
  • Phenobarbital
  • Phenobarbitol
  • Phenobarbitone
  • Phenobarbituric Acid
  • Phenylaethylbarbitursaeure
  • Phenylethylbarbiturate
  • Phenylethylbarbituric Acid
  • Phenylethylbarbitursaeure
  • PHENYLETHYLMALONYLUREA
External IDs
NSC-128143 / NSC-9848
Product Ingredients
IngredientUNIICASInChI Key
Phenobarbital sodiumSW9M9BB5K357-30-7WRLGYAWRGXKSKG-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Barbilixir Elx 4mg/mlElixir4 mgOralD.C. Labs Limited1983-12-312005-07-19Canada
PhenobarbTablet100 mgOralPendopharm Division Of De Pharmascience Inc1957-12-31Not applicableCanada
PhenobarbTablet15 mgOralPendopharm Division Of De Pharmascience Inc1957-12-31Not applicableCanada
PhenobarbTablet60 mgOralPendopharm Division Of De Pharmascience Inc1957-12-31Not applicableCanada
PhenobarbTablet30 mgOralPendopharm Division Of De Pharmascience Inc1957-12-31Not applicableCanada
Phenobarb ElixirElixir5 mgOralPendopharm Division Of De Pharmascience Inc1965-12-31Not applicableCanada
Phenobarbital 100mg TabTablet100 mgOralValeant Canada Lp Valeant Canada S.E.C.1975-12-312009-07-02Canada
Phenobarbital Sodium Injection 120mg/mlSolution120 mgIntramuscular; IntravenousHospira, Inc.1981-12-312012-08-03Canada
Phenobarbital Sodium Injection 30mg/mlSolution30 mgIntramuscular; Intravenous; SubcutaneousHospira, Inc.1981-12-312012-08-03Canada
Phenobarbital Sodium Injection, USPSolution120 mgIntramuscular; IntravenousSandoz Canada Incorporated2008-02-29Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Bellergal SpacetabsPhenobarbital (40.0 mg) + Belladonna (0.2 mg) + Ergotamine tartrate (0.6 mg)Tablet, extended releaseOralPaladin Labs Inc1959-01-01Not applicableCanada
Bellergal TabPhenobarbital (20 mg) + Belladonna (.1 mg) + Ergotamine (.3 mg)TabletOralSandoz1951-12-311997-08-12Canada
DiclophenPhenobarbital (15 mg) + Dicyclomine Hydrochloride (10 mg)CapsuleOralPro Doc Limitee1970-12-312009-07-23Canada
Dilantin W Phenobarbital 15mgPhenobarbital (15 mg) + Phenytoin sodium (100 mg)CapsuleOralParke Davis Division, Warner Lambert Canada Inc.1951-12-311999-04-08Canada
Dilantin W Phenobarbital 30mg CapPhenobarbital (30 mg) + Phenytoin sodium (100 mg)CapsuleOralParke Davis Division, Warner Lambert Canada Inc.1969-12-311997-08-25Canada
Donnatal ElixirPhenobarbital (16.2 mg) + Atropine Sulfate (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Scopolamine (6.5 mcg)ElixirOralAyerst Laboratories1991-12-311996-09-10Canada
Donnatal ElixirPhenobarbital (16.2 mg) + Atropine Sulfate (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Scopolamine (6.5 mcg)ElixirOralWyeth Ayerst Canada Inc.1994-12-312001-01-16Canada
Donnatal ExtentabsPhenobarbital (48.6 mg) + Atropine Sulfate (0.0582 mg) + Hyoscyamine sulfate (0.3111 mg) + Scopolamine (0.0195 mg)Tablet, extended releaseOralAyerst Laboratories1991-12-311996-09-10Canada
Donnatal Extentabs SrtPhenobarbital (48.6 mg) + Atropine Sulfate (0.0582 mg) + Hyoscyamine sulfate (0.3111 mg) + Scopolamine (0.0195 mg)Tablet, extended releaseOralWyeth Ayerst Canada Inc.1994-12-312001-05-07Canada
Donnatal TabPhenobarbital (16.2 mg) + Atropine Sulfate (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Scopolamine (6.5 mcg)TabletOralWyeth Ayerst Canada Inc.1994-12-312001-05-22Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
B-DonnaPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralWinder Laboratories, LLC2015-12-302016-03-03Us
Belladonna Alkaloids with PhenobarbitalPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralbryant ranch prepack1966-01-012015-05-01Us
Belladonna Alkaloids with PhenobarbitalPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralWest-Ward Pharmaceuticals Corp1966-01-01Not applicableUs0143 114020170720 1564 4ev749
Belladonna Alkaloids with PhenobartbitalPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralLiberty Pharmaceuticals, Inc.2000-12-01Not applicableUs00143 1140 10 nlmimage10 bb045dd2
Belladonna Alkaloids with PhenobartbitalPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralApace Packaging2000-12-012015-01-31Us
Belladonna Alkaloids with PhenobartbitalPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralLegacy Pharmaceutical Packaging2000-12-01Not applicableUs
Belladonna Alkaloids with PhenobartbitalPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralPhysicians Total Care, Inc.2004-08-312013-01-15Us
Belladonna Alkaloids with PhenobartbitalPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralPreferreed Pharmaceuticals Inc.2004-08-312013-04-30Us
Belladonna Alkaloids with PhenobartbitalPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralRebel Distributors2004-08-31Not applicableUs
DonnatalPhenobarbital (16.2 mg/1) + Atropine Sulfate (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)TabletOralMckesson Rxpak Inc2008-05-07Not applicableUs
International/Other Brands
Luminal
Categories
UNII
YQE403BP4D
CAS number
50-06-6
Weight
Average: 232.2353
Monoisotopic: 232.08479226
Chemical Formula
C12H12N2O3
InChI Key
DDBREPKUVSBGFI-UHFFFAOYSA-N
InChI
InChI=1S/C12H12N2O3/c1-2-12(8-6-4-3-5-7-8)9(15)13-11(17)14-10(12)16/h3-7H,2H2,1H3,(H2,13,14,15,16,17)
IUPAC Name
5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione
SMILES
CCC1(C(=O)NC(=O)NC1=O)C1=CC=CC=C1

Pharmacology

Indication

For the treatment of all types of seizures except absence seizures.

Associated Conditions
Associated Therapies
Pharmacodynamics

Phenobarbital, the longest-acting barbiturate, is used for its anticonvulsant and sedative-hypnotic properties in the management of all seizure disorders except absence (petit mal).

Mechanism of action

Phenobarbital acts on GABAA receptors, increasing synaptic inhibition. This has the effect of elevating seizure threshold and reducing the spread of seizure activity from a seizure focus. Phenobarbital may also inhibit calcium channels, resulting in a decrease in excitatory transmitter release. The sedative-hypnotic effects of phenobarbital are likely the result of its effect on the polysynaptic midbrain reticular formation, which controls CNS arousal.

TargetActionsOrganism
AGamma-aminobutyric acid receptor subunit alpha-1
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
UNMDA receptor
antagonist
Human
UNuclear receptor subfamily 1 group I member 2
activator
Human
Absorption

Absorbed in varying degrees following oral, rectal or parenteral administration. The salts are more rapidly absorbed than are the acids. The rate of absorption is increased if the sodium salt is ingested as a dilute solution or taken on an empty stomach.

Volume of distribution
Not Available
Protein binding

20 to 45%

Metabolism

Hepatic (mostly via CYP2C19).

Route of elimination
Not Available
Half life

53 to 118 hours (mean 79 hours)

Clearance
Not Available
Toxicity

CNS and respiratory depression which may progress to Cheyne-Stokes respiration, areflexia, constriction of the pupils to a slight degree (though in severe poisoning they may wshow paralytic dilation), oliguria, tachycardia, hypotension, lowered body temperature, and coma. Typical shock syndrome (apnea, circulatory collapse, respiratory arrest, and death) may occur.

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

Interactions

Drug Interactions
DrugInteraction
(2-benzhydryloxyethyl)diethyl-methylammonium iodideThe risk or severity of adverse effects can be increased when Phenobarbital is combined with (2-benzhydryloxyethyl)diethyl-methylammonium iodide.
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Phenobarbital.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Phenobarbital.
1,10-PhenanthrolineThe therapeutic efficacy of Phenobarbital can be decreased when used in combination with 1,10-Phenanthroline.
16-BromoepiandrosteroneThe metabolism of 16-Bromoepiandrosterone can be increased when combined with Phenobarbital.
2,5-Dimethoxy-4-ethylamphetamineThe serum concentration of Phenobarbital can be decreased when it is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe serum concentration of Phenobarbital 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 Phenobarbital.
3,4-MethylenedioxyamphetamineThe serum concentration of Phenobarbital 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 Phenobarbital.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Increase dietary intake of magnesium, folate, vitamin B6, B12, and/or consider taking a multivitamin.
  • Take on an empty stomach for quicker absorption

References

Synthesis Reference

Tong Sun, Shawn Watson, Rajesh Manchanda, "PHENOBARBITAL SALTS; METHODS OF MAKING; AND METHODS OF USE THEREOF." U.S. Patent US20100035904, issued February 11, 2010.

US20100035904
General References
  1. Kwan P, Brodie MJ: Phenobarbital for the treatment of epilepsy in the 21st century: a critical review. Epilepsia. 2004 Sep;45(9):1141-9. [PubMed:15329080]
  2. Taylor S, Tudur Smith C, Williamson PR, Marson AG: Phenobarbitone versus phenytoin monotherapy for partial onset seizures and generalized onset tonic-clonic seizures. Cochrane Database Syst Rev. 2001;(4):CD002217. [PubMed:11687150]
  3. Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. [PubMed:12535420]
  4. Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. [PubMed:16142991]
  5. Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. [PubMed:15495087]
External Links
Human Metabolome Database
HMDB0015305
KEGG Drug
D00506
KEGG Compound
C07434
PubChem Compound
4763
PubChem Substance
46505776
ChemSpider
4599
BindingDB
50021437
ChEBI
8069
ChEMBL
CHEMBL40
Therapeutic Targets Database
DAP000061
PharmGKB
PA450911
IUPHAR
2804
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Phenobarbital
ATC Codes
N03AA02 — PhenobarbitalN05CB01 — Combinations of barbiturates
AHFS Codes
  • 28:12.04 — Barbiturates
  • 28:24.04 — Barbiturates
MSDS
Download (53 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentDrug/Agent Toxicity by Tissue/Organ / Malignant Lymphomas / Neutropenias / Small Intestine Cancer / Unspecified Adult Solid Tumor, Protocol Specific1
1, 2Not Yet RecruitingTreatmentNeonatal Convulsions1
1, 2RecruitingTreatmentNeonatal Convulsions1
2Not Yet RecruitingTreatmentDrug withdrawal syndrome neonatal1
2RecruitingTreatmentGeneralized Convulsive Status Epilepticus1
3Active Not RecruitingTreatmentDrug withdrawal syndrome neonatal / Neonatal Opioid Withdrawal1
3CompletedPreventionInfant, Low Birth Weight / Infant, Small for Gestational Age / Infants, Premature / Intracranial Hemorrhages / Newborn Infants1
3CompletedTreatmentDrug withdrawal syndrome neonatal1
3CompletedTreatmentEpilepsies1
3CompletedTreatmentPediatric Status Epilepticus1
3Not Yet RecruitingTreatmentNeonatal Convulsions1
3TerminatedTreatmentAnxiety Disorders / Dementias / Depression / Psychosomatic Disorders / Schizophrenic Disorders1
3WithdrawnTreatmentEpilepsies / Refractory seizure disorders1
4CompletedTreatmentDrug withdrawal syndrome neonatal1
4RecruitingTreatmentAcute Kidney Injury (AKI) / Impaired Renal Function / Pharmacokinetics / Renal Failure1
4RecruitingTreatmentNeonatal Convulsions1
4TerminatedTreatmentNeonatal Convulsions1
Not AvailableCompletedNot AvailableEpilepsies1
Not AvailableCompletedNot AvailableNeonatal Convulsions1
Not AvailableNot Yet RecruitingTreatmentAlcohol Withdrawal Delirium / Alcohol Withdrawal Seizures / Alcohol Withdrawal Syndrome(AWS)1
Not AvailableRecruitingNot AvailableEpilepsies1
Not AvailableTerminatedTreatmentDrug withdrawal syndrome neonatal1
Not AvailableWithdrawnTreatmentEpilepsies1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Actavis Group
  • Amend
  • Apotheca Inc.
  • Baxter International Inc.
  • Breckenridge Pharmaceuticals
  • C.O. Truxton Inc.
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Century Pharmaceuticals Inc.
  • Comprehensive Consultant Services Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Econolab Inc.
  • Excellium Pharmaceutical Inc.
  • Group Health Cooperative
  • Heartland Repack Services LLC
  • Hikma Pharmaceuticals
  • Hl Moore Drug Exchange
  • Hospira Inc.
  • Kaiser Foundation Hospital
  • Kraft Pharmaceutical Co. Inc.
  • Lake Erie Medical and Surgical Supply
  • Lundbeck Inc.
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nucare Pharmaceuticals Inc.
  • Ohm Laboratories Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Association
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Qualitest
  • Ranbaxy Laboratories
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • River's Edge Pharmaceuticals
  • Stanley Pharmaceuticals Ltd.
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vintage Pharmaceuticals Inc.
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
ElixirOral4 mg
ElixirOral
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
TabletOral
CapsuleOral
TabletOral100 mg
TabletOral15 mg
TabletOral30 mg
TabletOral60 mg
ElixirOral5 mg
ElixirOral20 mg/5mL
ElixirOral20.0 mg/5mL
LiquidOral20 mg/5mL
TabletOral100 mg/1
TabletOral15 mg/1
TabletOral16.2 mg/1
TabletOral30 mg/1
TabletOral32.4 mg/1
TabletOral60 mg/1
TabletOral64.8 mg/1
TabletOral97.2 mg/1
InjectionIntramuscular; Intravenous130 mg/1mL
InjectionIntramuscular; Intravenous65 mg/1mL
SolutionIntramuscular; Intravenous; Subcutaneous30 mg
SolutionIntramuscular; Intravenous120 mg
SolutionIntramuscular; Intravenous30 mg
LiquidOral
Prices
Unit descriptionCostUnit
Phenobarbital 130 mg/ml vial4.32USD ml
Phenobarbital 65 mg/ml vial1.63USD ml
Phenobarbital sodium powder0.36USD g
Pms-Phenobarbital 100 mg Tablet0.15USD tablet
Phenobarbital powder0.13USD g
Pms-Phenobarbital 60 mg Tablet0.11USD tablet
Phenobarbital 97.2 mg tablet0.1USD tablet
Phenobarbital 64.8 mg tablet0.09USD tablet
Pms-Phenobarbital 5 mg/ml Elixir0.09USD ml
Phenobarbital 16.2 mg tablet0.08USD tablet
Phenobarbital 30 mg tablet0.08USD tablet
Phenobarbital 32.4 mg tablet0.08USD tablet
Pms-Phenobarbital 30 mg Tablet0.08USD tablet
Phenobarbital 100 mg tablet0.07USD tablet
Pms-Phenobarbital 15 mg Tablet0.07USD tablet
PHENobarbital 20 mg/5ml Elixir0.06USD ml
Phenobarbital 60 mg tablet0.03USD tablet
Phenobarbital 15 mg tablet0.02USD 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)174 °CPhysProp
water solubility1110 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.47HANSCH,C ET AL. (1995)
pKa7.3BUDAVARI,S ET AL. (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.276 mg/mLALOGPS
logP1.4ALOGPS
logP1.41ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.14ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.75 m3·mol-1ChemAxon
Polarizability22.61 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9935
Blood Brain Barrier+0.9736
Caco-2 permeable-0.5561
P-glycoprotein substrateSubstrate0.5157
P-glycoprotein inhibitor INon-inhibitor0.6472
P-glycoprotein inhibitor IINon-inhibitor0.9869
Renal organic cation transporterNon-inhibitor0.9235
CYP450 2C9 substrateNon-substrate0.6962
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.7702
CYP450 1A2 substrateNon-inhibitor0.84
CYP450 2C9 inhibitorNon-inhibitor0.9023
CYP450 2D6 inhibitorNon-inhibitor0.9593
CYP450 2C19 inhibitorNon-inhibitor0.8664
CYP450 3A4 inhibitorNon-inhibitor0.9236
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9164
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7469
BiodegradationNot ready biodegradable0.9894
Rat acute toxicity3.1244 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.99
hERG inhibition (predictor II)Non-inhibitor0.9354
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.44 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0udi-5970000000-7bda34bd3bb88b5fd9fd
GC-MS Spectrum - CI-BGC-MSsplash10-001i-0090000000-55265fc1e12027dc6454
Mass Spectrum (Electron Ionization)MSsplash10-0uxr-6950000000-193bf296d3e5d1705628
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-QFT , negativeLC-MS/MSsplash10-001i-0190000000-8cf53cd66a890256ea98
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-001i-1290000000-73d0e0b25f99ffc6a500
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0016-3950000000-ab62a9483b8a2a65b563
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0900000000-4121e8dd703c01c1161c
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0900000000-4976dfc244184e5d627b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-1890000000-a12eb2be0b05b9f234de
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-1920000000-43ed71cd16bfceef49e6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-08fr-2900000000-236ae1dab83b15539a86
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-053u-3900000000-2a994f0e45c022cca640
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-053u-4900000000-066a53ca113150f58406
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05o3-6900000000-b8f9c9d0f71b6d2c6c2f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0uy3-8900000000-6bcd457bfff85f05fe9c
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-9500000000-0ecfff7e43e9e78d677e
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0uxs-9300000000-7413ad1c764a1ae4a98e
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as barbituric acid derivatives. These are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Barbituric acid derivatives
Alternative Parents
N-acyl ureas / Diazinanes / Benzene and substituted derivatives / Dicarboximides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Barbiturate / Ureide / N-acyl urea / Monocyclic benzene moiety / 1,3-diazinane / Benzenoid / Dicarboximide / Urea / Carbonic acid derivative / Carboxylic acid derivative
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
barbiturates (CHEBI:8069)

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. Macdonald RL, McLean MJ: Anticonvulsant drugs: mechanisms of action. Adv Neurol. 1986;44:713-36. [PubMed:2871724]
  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
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]
  3. Jin LJ, Schlesinger F, Song YP, Dengler R, Krampfl K: The interaction of the neuroprotective compounds riluzole and phenobarbital with AMPA-type glutamate receptors: a patch-clamp study. Pharmacology. 2010;85(1):54-62. doi: 10.1159/000268641. Epub 2009 Dec 23. [PubMed:20051697]
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]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Voltage-gated cation channel activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...

Components:
References
  1. Daniell LC: Effect of anesthetic and convulsant barbiturates on N-methyl-D-aspartate receptor-mediated calcium flux in brain membrane vesicles. Pharmacology. 1994 Nov;49(5):296-307. [PubMed:7862741]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Activator
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Faucette SR, Wang H, Hamilton GA, Jolley SL, Gilbert D, Lindley C, Yan B, Negishi M, LeCluyse EL: Regulation of CYP2B6 in primary human hepatocytes by prototypical inducers. Drug Metab Dispos. 2004 Mar;32(3):348-58. [PubMed:14977870]
  2. Kobayashi K, Yamagami S, Higuchi T, Hosokawa M, Chiba K: Key structural features of ligands for activation of human pregnane X receptor. Drug Metab Dispos. 2004 Apr;32(4):468-72. [PubMed:15039302]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
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. 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. Madan A, Graham RA, Carroll KM, Mudra DR, Burton LA, Krueger LA, Downey AD, Czerwinski M, Forster J, Ribadeneira MD, Gan LS, LeCluyse EL, Zech K, Robertson P Jr, Koch P, Antonian L, Wagner G, Yu L, Parkinson A: Effects of prototypical microsomal enzyme inducers on cytochrome P450 expression in cultured human hepatocytes. Drug Metab Dispos. 2003 Apr;31(4):421-31. [PubMed:12642468]
  3. Mamiya K, Hadama A, Yukawa E, Ieiri I, Otsubo K, Ninomiya H, Tashiro N, Higuchi S: CYP2C19 polymorphism effect on phenobarbitone. Pharmacokinetics in Japanese patients with epilepsy: analysis by population pharmacokinetics. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):821-5. [PubMed:10805060]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. 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]
  3. Kawalek JC, Howard KD, Farrell DE, Derr J, Cope CV, Jackson JD, Myers MJ: Effect of oral administration of low doses of pentobarbital on the induction of cytochrome P450 isoforms and cytochrome P450-mediated reactions in immature Beagles. Am J Vet Res. 2003 Sep;64(9):1167-75. [PubMed:13677397]
  4. Chen Y, Ferguson SS, Negishi M, Goldstein JA: Induction of human CYP2C9 by rifampicin, hyperforin, and phenobarbital is mediated by the pregnane X receptor. J Pharmacol Exp Ther. 2004 Feb;308(2):495-501. Epub 2003 Nov 4. [PubMed:14600250]
  5. Zhou D, Sunzel M, Ribadeneira MD, Smith MA, Desai D, Lin J, Grimm SW: A clinical study to assess CYP1A2 and CYP3A4 induction by AZD7325, a selective GABA(A) receptor modulator - an in vitro and in vivo comparison. Br J Clin Pharmacol. 2012 Jul;74(1):98-108. doi: 10.1111/j.1365-2125.2011.04155.x. [PubMed:22122233]
  6. Phenobarbital Monograph [File]
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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. Kawalek JC, Howard KD, Farrell DE, Derr J, Cope CV, Jackson JD, Myers MJ: Effect of oral administration of low doses of pentobarbital on the induction of cytochrome P450 isoforms and cytochrome P450-mediated reactions in immature Beagles. Am J Vet Res. 2003 Sep;64(9):1167-75. [PubMed:13677397]
  2. Gerbal-Chaloin S, Pascussi JM, Pichard-Garcia L, Daujat M, Waechter F, Fabre JM, Carrere N, Maurel P: Induction of CYP2C genes in human hepatocytes in primary culture. Drug Metab Dispos. 2001 Mar;29(3):242-51. [PubMed:11181490]
  3. Dvorak Z, Modriansky M, Pichard-Garcia L, Balaguer P, Vilarem MJ, Ulrichova J, Maurel P, Pascussi JM: Colchicine down-regulates cytochrome P450 2B6, 2C8, 2C9, and 3A4 in human hepatocytes by affecting their glucocorticoid receptor-mediated regulation. Mol Pharmacol. 2003 Jul;64(1):160-9. doi: 10.1124/mol.64.1.160. [PubMed:12815172]
  4. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
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]
  2. von Bahr C, Steiner E, Koike Y, Gabrielsson J: Time course of enzyme induction in humans: effect of pentobarbital on nortriptyline metabolism. Clin Pharmacol Ther. 1998 Jul;64(1):18-26. [PubMed:9695715]
  3. Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Nortriptyline E-10-hydroxylation in vitro is mediated by human CYP2D6 (high affinity) and CYP3A4 (low affinity): implications for interactions with enzyme-inducing drugs. J Clin Pharmacol. 1999 Jun;39(6):567-77. [PubMed:10354960]
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]
  2. Sakuma T, Ohtake M, Katsurayama Y, Jarukamjorn K, Nemoto N: Induction of CYP1A2 by phenobarbital in the livers of aryl hydrocarbon-responsive and -nonresponsive mice. Drug Metab Dispos. 1999 Mar;27(3):379-84. [PubMed:10064569]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 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. Kawalek JC, Howard KD, Farrell DE, Derr J, Cope CV, Jackson JD, Myers MJ: Effect of oral administration of low doses of pentobarbital on the induction of cytochrome P450 isoforms and cytochrome P450-mediated reactions in immature Beagles. Am J Vet Res. 2003 Sep;64(9):1167-75. [PubMed:13677397]
Kind
Protein
Organism
Human
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. 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. Lee AM, Joshi M, Yue J, Tyndale RF: Phenobarbital induces monkey brain CYP2E1 protein but not hepatic CYP2E1, in vitro or in vivo chlorzoxazone metabolism. Eur J Pharmacol. 2006 Dec 15;552(1-3):151-8. Epub 2006 Sep 16. [PubMed:17049344]
  3. Madan A, Graham RA, Carroll KM, Mudra DR, Burton LA, Krueger LA, Downey AD, Czerwinski M, Forster J, Ribadeneira MD, Gan LS, LeCluyse EL, Zech K, Robertson P Jr, Koch P, Antonian L, Wagner G, Yu L, Parkinson A: Effects of prototypical microsomal enzyme inducers on cytochrome P450 expression in cultured human hepatocytes. Drug Metab Dispos. 2003 Apr;31(4):421-31. [PubMed:12642468]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
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
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 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. Hukkanen J, Lassila A, Paivarinta K, Valanne S, Sarpo S, Hakkola J, Pelkonen O, Raunio H: Induction and regulation of xenobiotic-metabolizing cytochrome P450s in the human A549 lung adenocarcinoma cell line. Am J Respir Cell Mol Biol. 2000 Mar;22(3):360-6. [PubMed:10696073]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Leukotriene-b4 20-monooxygenase activity
Specific Function
Catalyzes the omega- and (omega-1)-hydroxylation of various fatty acids such as laurate, myristate and palmitate. Has little activity toward prostaglandins A1 and E1. Oxidizes arachidonic acid to 2...
Gene Name
CYP4A11
Uniprot ID
Q02928
Uniprot Name
Cytochrome P450 4A11
Molecular Weight
59347.31 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
Vitamin d 24-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
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 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
Oxygen binding
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
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 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
CYP2C18
Uniprot ID
P33260
Uniprot Name
Cytochrome P450 2C18
Molecular Weight
55710.075 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
Oxygen binding
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
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 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. Schuetz EG, Schuetz JD, Strom SC, Thompson MT, Fisher RA, Molowa DT, Li D, Guzelian PS: Regulation of human liver cytochromes P-450 in family 3A in primary and continuous culture of human hepatocytes. Hepatology. 1993 Nov;18(5):1254-62. [PubMed:8225233]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
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
CYP4B1
Uniprot ID
P13584
Uniprot Name
Cytochrome P450 4B1
Molecular Weight
58990.64 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]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. [PubMed:8632764]
  2. Luna-Tortos C, Fedrowitz M, Loscher W: Several major antiepileptic drugs are substrates for human P-glycoprotein. Neuropharmacology. 2008 Dec;55(8):1364-75. doi: 10.1016/j.neuropharm.2008.08.032. Epub 2008 Sep 11. [PubMed:18824002]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Organic anion transmembrane transporter activity
Specific Function
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocyte...
Gene Name
ABCC3
Uniprot ID
O15438
Uniprot Name
Canalicular multispecific organic anion transporter 2
Molecular Weight
169341.14 Da
References
  1. Kiuchi Y, Suzuki H, Hirohashi T, Tyson CA, Sugiyama Y: cDNA cloning and inducible expression of human multidrug resistance associated protein 3 (MRP3). FEBS Lett. 1998 Aug 14;433(1-2):149-52. [PubMed:9738950]
  2. Cherrington NJ, Slitt AL, Maher JM, Zhang XX, Zhang J, Huang W, Wan YJ, Moore DD, Klaassen CD: Induction of multidrug resistance protein 3 (mrp3) in vivo is independent of constitutive androstane receptor. Drug Metab Dispos. 2003 Nov;31(11):1315-9. [PubMed:14570762]
  3. Slitt AL, Cherrington NJ, Maher JM, Klaassen CD: Induction of multidrug resistance protein 3 in rat liver is associated with altered vectorial excretion of acetaminophen metabolites. Drug Metab Dispos. 2003 Sep;31(9):1176-86. [PubMed:12920174]
  4. Ogawa K, Suzuki H, Hirohashi T, Ishikawa T, Meier PJ, Hirose K, Akizawa T, Yoshioka M, Sugiyama Y: Characterization of inducible nature of MRP3 in rat liver. Am J Physiol Gastrointest Liver Physiol. 2000 Mar;278(3):G438-46. [PubMed:10712264]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Kast HR, Goodwin B, Tarr PT, Jones SA, Anisfeld AM, Stoltz CM, Tontonoz P, Kliewer S, Willson TM, Edwards PA: Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor. J Biol Chem. 2002 Jan 25;277(4):2908-15. Epub 2001 Nov 12. [PubMed:11706036]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Kiuchi Y, Suzuki H, Hirohashi T, Tyson CA, Sugiyama Y: cDNA cloning and inducible expression of human multidrug resistance associated protein 3 (MRP3). FEBS Lett. 1998 Aug 14;433(1-2):149-52. [PubMed:9738950]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, a...
Gene Name
SLCO2A1
Uniprot ID
Q92959
Uniprot Name
Solute carrier organic anion transporter family member 2A1
Molecular Weight
70043.33 Da
References
  1. Hagenbuch N, Reichel C, Stieger B, Cattori V, Fattinger KE, Landmann L, Meier PJ, Kullak-Ublick GA: Effect of phenobarbital on the expression of bile salt and organic anion transporters of rat liver. J Hepatol. 2001 Jun;34(6):881-7. [PubMed:11451172]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Courtois A, Payen L, Le Ferrec E, Scheffer GL, Trinquart Y, Guillouzo A, Fardel O: Differential regulation of multidrug resistance-associated protein 2 (MRP2) and cytochromes P450 2B1/2 and 3A1/2 in phenobarbital-treated hepatocytes. Biochem Pharmacol. 2002 Jan 15;63(2):333-41. [PubMed:11841808]
  2. Schrenk D, Baus PR, Ermel N, Klein C, Vorderstemann B, Kauffmann HM: Up-regulation of transporters of the MRP family by drugs and toxins. Toxicol Lett. 2001 Mar 31;120(1-3):51-7. [PubMed:11323161]
  3. Kast HR, Goodwin B, Tarr PT, Jones SA, Anisfeld AM, Stoltz CM, Tontonoz P, Kliewer S, Willson TM, Edwards PA: Regulation of multidrug resistance-associated protein 2 (ABCC2) by the nuclear receptors pregnane X receptor, farnesoid X-activated receptor, and constitutive androstane receptor. J Biol Chem. 2002 Jan 25;277(4):2908-15. Epub 2001 Nov 12. [PubMed:11706036]
  4. Kauffmann HM, Schrenk D: Sequence analysis and functional characterization of the 5'-flanking region of the rat multidrug resistance protein 2 (mrp2) gene. Biochem Biophys Res Commun. 1998 Apr 17;245(2):325-31. [PubMed:9571149]
  5. Johnson DR, Habeebu SS, Klaassen CD: Increase in bile flow and biliary excretion of glutathione-derived sulfhydryls in rats by drug-metabolizing enzyme inducers is mediated by multidrug resistance protein 2. Toxicol Sci. 2002 Mar;66(1):16-26. [PubMed:11861969]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:35