Phenobarbital

Identification

Summary

Phenobarbital is a long-lasting barbiturate and anticonvulsant used in the treatment of all types of seizures, except for absent seizures.

Brand Names
Donnatal, Luminal, Phenobarb, Phenohytro, Sezaby
Generic Name
Phenobarbital
DrugBank Accession Number
DB01174
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 232.2353
Monoisotopic: 232.08479226
Chemical Formula
C12H12N2O3
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
  • Fenobarbital
  • Phenobarbital
  • Phenobarbitol
  • Phenobarbitone
  • Phenobarbituric Acid
  • Phenyläthylbarbitursäure
  • Phenylethylbarbiturate
  • Phenylethylbarbituric Acid
  • Phenylethylbarbitursäure
  • Phenylethylmalonylurea
External IDs
  • NSC-128143
  • NSC-9848

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAlcohol withdrawal••• •••••
Treatment ofAnxiety••••••••••••
Treatment ofFebrile seizures••••••••••••
Prophylaxis ofFebrile seizures••••••••••••
Treatment ofHyperbilirubinemia••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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
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
UNMDA receptor
antagonist
Humans
UNuclear receptor subfamily 1 group I member 2
activator
Humans
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).

Hover over products below to view reaction partners

Route of elimination

Not Available

Half-life

53 to 118 hours (mean 79 hours)

Clearance

Not Available

Adverse Effects
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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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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 Phenobarbital.
AbacavirThe metabolism of Abacavir can be increased when combined with Phenobarbital.
AbaloparatidePhenobarbital may increase the hypotensive activities of Abaloparatide.
AbataceptThe metabolism of Phenobarbital can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be increased when combined with Phenobarbital.
Food Interactions
  • Administer vitamin supplements.
  • Avoid alcohol.
  • Limit caffeine intake.
  • Take on an empty stomach. Taking this medication on an empty stomach increases the speed of absorption.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Phenobarbital sodiumSW9M9BB5K357-30-7WRLGYAWRGXKSKG-UHFFFAOYSA-M
Product Images
International/Other Brands
Luminal
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
PhenobarbitalLiquid20 mg/5mLOralbryant ranch prepack2020-09-01Not applicableUS flag
PhenobarbitalTablet16.2 mg/1Oralbryant ranch prepack2002-03-012013-03-01US flag
PhenobarbitalTablet32.4 mg/1OralRemedy Repack2018-06-212018-10-26US flag
PhenobarbitalTablet32.4 mg/1OralREMEDYREPACK INC.2018-10-25Not applicableUS flag
PhenobarbitalTablet15 mg/1Oralbryant ranch prepack2020-03-01Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Bellergal SpacetabsPhenobarbital (40.0 mg) + Belladonna (0.2 mg) + Ergotamine tartrate (0.6 mg)Tablet, extended releaseOralPaladin Labs Inc1959-01-012018-06-05Canada flag
Bellergal TabPhenobarbital (20 mg / tab) + Belladonna (.1 mg / tab) + Ergotamine tartrate (.3 mg / tab)TabletOralSandoz1951-12-311997-08-12Canada flag
DiclophenPhenobarbital (15 mg) + Dicyclomine hydrochloride (10 mg)CapsuleOralPro Doc Limitee1970-12-312009-07-23Canada flag
Dilantin W Phenobarbital 15mgPhenobarbital (15 mg / cap) + Phenytoin sodium (100 mg / cap)CapsuleOralParke Davis Division, Warner Lambert Canada Inc.1951-12-311999-04-08Canada flag
Dilantin W Phenobarbital 30mg CapPhenobarbital (30 mg / cap) + Phenytoin sodium (100 mg / cap)CapsuleOralParke Davis Division, Warner Lambert Canada Inc.1969-12-311997-08-25Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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 flag
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)TabletOralHikma Pharmaceuticals USA Inc.1966-01-012019-07-31US flag
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 flag
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 Distributors Corp2004-08-31Not applicableUS flag
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 flag

Categories

ATC Codes
N05CB01 — Combinations of barbituratesN03AA02 — Phenobarbital
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,3-diazinane / Aromatic heteromonocyclic compound / Azacycle / Barbiturate / Benzenoid / Carbonic acid derivative / Carbonyl group / Carboxylic acid derivative / Dicarboximide / Hydrocarbon derivative
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
barbiturates (CHEBI:8069)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
YQE403BP4D
CAS number
50-06-6
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

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. [Article]
  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. [Article]
  3. Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. [Article]
  4. Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. [Article]
  5. Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. [Article]
  6. Pacifici GM: Clinical Pharmacology of Phenobarbital in Neonates: Effects, Metabolism and Pharmacokinetics. Curr Pediatr Rev. 2016;12(1):48-54. doi: 10.2174/1573397111666151026223914. [Article]
Human Metabolome Database
HMDB0015305
KEGG Drug
D00506
KEGG Compound
C07434
PubChem Compound
4763
PubChem Substance
46505776
ChemSpider
4599
BindingDB
50021437
RxNav
8134
ChEBI
8069
ChEMBL
CHEMBL40
ZINC
ZINC000095588079
Therapeutic Targets Database
DAP000061
PharmGKB
PA450911
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
UQA
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Phenobarbital
PDB Entries
6x3w
MSDS
Download (53 KB)

Clinical Trials

Clinical Trials

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 / mL
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
TabletOral100.000 mg
SolutionOral400 mg
TabletOral10 mg
SolutionIntramuscular; Intravenous0.2 g
SolutionParenteral200 mg
InjectionParenteral40 mg
TabletOral100 mg
TabletOral50 mg
Injection, solution
Injection, solutionIntramuscular100 MG/2ML
Injection, solutionIntramuscular30 MG/ML
SolutionIntramuscular; Intravenous40 mg
Injection, solutionIntramuscular100 MG
ElixirOral0.3 %
Injection, solutionIntramuscular; Parenteral200 MG/ML
Syrup
CapsuleOral
TabletOral15 mg
TabletOral30 mg
TabletOral60 mg
SolutionOral5 mg / mL
ElixirOral20 mg/5mL
ElixirOral20.0 mg/5mL
Injection
LiquidOral20 mg/5mL
SolutionOral20 mg/5mL
TabletOral
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
SolutionOral30 mg/7.5mL
SolutionOral60 mg/15mL
InjectionIntramuscular130 mg/1mL
InjectionIntramuscular65 mg/1mL
InjectionIntramuscular; Intravenous130 mg/1mL
InjectionIntramuscular; Intravenous65 mg/1mL
Injection, solutionIntramuscular; Intravenous130 mg/1mL
Injection, solutionIntramuscular; Intravenous65 mg/1mL
SolutionIntramuscular; Intravenous; Subcutaneous30 mg / mL
SolutionIntramuscular; Intravenous120 mg / mL
SolutionIntramuscular; Intravenous30 mg / mL
ElixirOral
TabletOral
SuppositoryRectal
InjectionIntravenous100 mg/1
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
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US11857683No2022-04-072042-04-07US flag

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)7.14Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area75.27 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity59.75 m3·mol-1Chemaxon
Polarizability22.59 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-MSsplash10-014i-1940000000-8377cca722b6479ce2fd
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
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0390000000-f2147d068e18223694c5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9310000000-8f28ab4d44583146115c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-3ee2f0a4c65cdb33c0aa
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-b05d6bfef8dfbacd745d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-3940000000-bf59676229ff02f2fa16
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9120000000-73e8d9efbc75ac46d257
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0390000000-b80fd29f5e672b9a3083
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9210000000-8bc75358f3b56e3c0432
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-96f4625a08add32dcca1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-fd502df51e9ef52baa4e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9110000000-9ea8c84e4188051e5b81
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-1930000000-c4d9938ef20de9f70a0d
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
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]-157.4845834
predicted
DarkChem Lite v0.1.0
[M-H]-159.3932
predicted
DeepCCS 1.0 (2019)
[M-H]-157.4845834
predicted
DarkChem Lite v0.1.0
[M-H]-159.3932
predicted
DeepCCS 1.0 (2019)
[M+H]+158.2351834
predicted
DarkChem Lite v0.1.0
[M+H]+161.75119
predicted
DeepCCS 1.0 (2019)
[M+H]+158.2351834
predicted
DarkChem Lite v0.1.0
[M+H]+161.75119
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.8849834
predicted
DarkChem Lite v0.1.0
[M+Na]+167.84435
predicted
DeepCCS 1.0 (2019)
[M+Na]+157.8849834
predicted
DarkChem Lite v0.1.0
[M+Na]+167.84435
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
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. Macdonald RL, McLean MJ: Anticonvulsant drugs: mechanisms of action. Adv Neurol. 1986;44:713-36. [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]
  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. [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]
Kind
Protein group
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. 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. doi: 10.1124/dmd.31.4.421. [Article]
  2. 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. [Article]
  3. Yukawa E, Mamiya K: Effect of CYP2C19 genetic polymorphism on pharmacokinetics of phenytoin and phenobarbital in Japanese epileptic patients using Non-linear Mixed Effects Model approach. J Clin Pharm Ther. 2006 Jun;31(3):275-82. doi: 10.1111/j.1365-2710.2006.00712.x. [Article]
  4. 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. [Article]
  5. Pacifici GM: Clinical Pharmacology of Phenobarbital in Neonates: Effects, Metabolism and Pharmacokinetics. Curr Pediatr Rev. 2016;12(1):48-54. doi: 10.2174/1573397111666151026223914. [Article]
  6. Flockhart Table of Drug Interactions [Link]
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. 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. [Article]
  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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. Pacifici GM: Clinical Pharmacology of Phenobarbital in Neonates: Effects, Metabolism and Pharmacokinetics. Curr Pediatr Rev. 2016;12(1):48-54. doi: 10.2174/1573397111666151026223914. [Article]
  6. Flockhart Table of Drug Interactions [Link]
  7. Phenobarbital Monograph [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. 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. [Article]
  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. doi: 10.1124/dmd.31.4.421. [Article]
  3. Pacifici GM: Clinical Pharmacology of Phenobarbital in Neonates: Effects, Metabolism and Pharmacokinetics. Curr Pediatr Rev. 2016;12(1):48-54. doi: 10.2174/1573397111666151026223914. [Article]
Kind
Protein
Organism
Humans
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. Gervot L, Rochat B, Gautier JC, Bohnenstengel F, Kroemer H, de Berardinis V, Martin H, Beaune P, de Waziers I: Human CYP2B6: expression, inducibility and catalytic activities. Pharmacogenetics. 1999 Jun;9(3):295-306. [Article]
  2. 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. [Article]
  3. Wang H, Faucette SR, Gilbert D, Jolley SL, Sueyoshi T, Negishi M, LeCluyse EL: Glucocorticoid receptor enhancement of pregnane X receptor-mediated CYP2B6 regulation in primary human hepatocytes. Drug Metab Dispos. 2003 May;31(5):620-30. [Article]
  4. 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. doi: 10.1124/dmd.31.4.421. [Article]
  5. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  4. Klose TS, Blaisdell JA, Goldstein JA: Gene structure of CYP2C8 and extrahepatic distribution of the human CYP2Cs. J Biochem Mol Toxicol. 1999;13(6):289-95. doi: 10.1002/(sici)1099-0461(1999)13:6<289::aid-jbt1>3.0.co;2-n. [Article]
  5. Flockhart Table of Drug Interactions [Link]
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. 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. [Article]
  2. 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. [Article]
  3. Zhou SF, Xue CC, Yu XQ, Li C, Wang G: Clinically important drug interactions potentially involving mechanism-based inhibition of cytochrome P450 3A4 and the role of therapeutic drug monitoring. Ther Drug Monit. 2007 Dec;29(6):687-710. doi: 10.1097/FTD.0b013e31815c16f5. [Article]
  4. PHENOBARBITAL SODIUM INJECTION Prescribing Information - Sandoz Canada [Link]
  5. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
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. 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. [Article]
  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. doi: 10.1124/dmd.31.4.421. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
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. 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. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. Yoshinari K, Yoda N, Toriyabe T, Yamazoe Y: Constitutive androstane receptor transcriptionally activates human CYP1A1 and CYP1A2 genes through a common regulatory element in the 5'-flanking region. Biochem Pharmacol. 2010 Jan 15;79(2):261-9. doi: 10.1016/j.bcp.2009.08.008. Epub 2009 Aug 12. [Article]
  2. Sadar MD, Ash R, Sundqvist J, Olsson PE, Andersson TB: Phenobarbital induction of CYP1A1 gene expression in a primary culture of rainbow trout hepatocytes. J Biol Chem. 1996 Jul 26;271(30):17635-43. doi: 10.1074/jbc.271.30.17635. [Article]
  3. Sadar MD, Westlind A, Blomstrand F, Andersson TB: Induction of CYP1A1 by GABA receptor ligands. Biochem Biophys Res Commun. 1996 Dec 4;229(1):231-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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. 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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
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. 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. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
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. Mastyugin V, Aversa E, Bonazzi A, Vafaes C, Mieyal P, Schwartzman ML: Hypoxia-induced production of 12-hydroxyeicosanoids in the corneal epithelium: involvement of a cytochrome P-4504B1 isoform. J Pharmacol Exp Ther. 1999 Jun;289(3):1611-9. [Article]
  2. McKinnon RA, Burgess WM, Gonzalez FJ, Gasser R, McManus ME: Species-specific expression of CYP4B1 in rabbit and human gastrointestinal tissues. Pharmacogenetics. 1994 Oct;4(5):260-70. [Article]
Kind
Protein
Organism
Humans
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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
Curator comments
Enzyme action based on in vivo study in rats. Only one study supports this currently.
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Sakakibara Y, Katoh M, Kondo Y, Nadai M: Effects of Phenobarbital on Expression of UDP-Glucuronosyltransferase 1a6 and 1a7 in Rat Brain. Drug Metab Dispos. 2016 Mar;44(3):370-7. doi: 10.1124/dmd.115.067439. Epub 2015 Dec 18. [Article]
Kind
Protein
Organism
Humans
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. 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. [Article]
  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. doi: 10.1124/dmd.31.4.421. [Article]
  3. Al Koudsi N, Hoffmann EB, Assadzadeh A, Tyndale RF: Hepatic CYP2A6 levels and nicotine metabolism: impact of genetic, physiological, environmental, and epigenetic factors. Eur J Clin Pharmacol. 2010 Mar;66(3):239-51. doi: 10.1007/s00228-009-0762-0. Epub 2009 Dec 9. [Article]
  4. Donato MT, Viitala P, Rodriguez-Antona C, Lindfors A, Castell JV, Raunio H, Gomez-Lechon MJ, Pelkonen O: CYP2A5/CYP2A6 expression in mouse and human hepatocytes treated with various in vivo inducers. Drug Metab Dispos. 2000 Nov;28(11):1321-6. [Article]

Transporters

Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 19, 2024 11:06