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

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

Similar Structures

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

Associated Therapies

Sedation

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.

Target	Actions	Organism
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

Phenobarbital
- p-Hydroxyphenobarbital
  - Phenobarbital O-glucuronide
  - Phenobarbital O-sulfate

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.

Drug	Interaction
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1,2-Benzodiazepine	The metabolism of 1,2-Benzodiazepine can be increased when combined with Phenobarbital.
Abacavir	The metabolism of Abacavir can be increased when combined with Phenobarbital.
Abatacept	The metabolism of Phenobarbital can be increased when combined with Abatacept.
Abemaciclib	The metabolism of Abemaciclib can be increased when combined with Phenobarbital.
Abiraterone	The metabolism of Abiraterone can be increased when combined with Phenobarbital.
Acalabrutinib	The metabolism of Acalabrutinib can be increased when combined with Phenobarbital.
Acebutolol	Phenobarbital may increase the hypotensive activities of Acebutolol.
Acemetacin	The metabolism of Acemetacin can be increased when combined with Phenobarbital.
Acenocoumarol	The metabolism of Acenocoumarol can be increased when combined with Phenobarbital.
Acetazolamide	The serum concentration of Phenobarbital can be decreased when it is combined with Acetazolamide.

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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

Ingredient	UNII	CAS	InChI Key
Phenobarbital sodium	SW9M9BB5K3	57-30-7	WRLGYAWRGXKSKG-UHFFFAOYSA-M

Product Images

International/Other Brands

Luminal

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Phenobarbital	Tablet	32.4 mg/1	Oral	PD-Rx Pharmaceuticals, Inc.	2003-02-01	2019-09-12
Phenobarbital	Tablet	30 mg/1	Oral	Mylan Institutional	2006-09-11	2013-02-28
Phenobarbital	Tablet	97.2 mg/1	Oral	Par Pharmaceutical	2001-12-01	Not applicable
Phenobarbital	Tablet	15 mg/1	Oral	Rising Pharma Holdings, Inc.	2020-11-01	Not applicable
Phenobarbital	Tablet	16.2 mg/1	Oral	McKesson Corporation dba SKY Packaging	2017-02-24	Not applicable
Phenobarbital	Tablet	32.4 mg/1	Oral	Sterling-Knight Pharmaceuticals, LLC	2017-03-28	Not applicable
Phenobarbital	Tablet	64.8 mg/1	Oral	ECI Pharmaceuticals, LLC	2014-11-24	Not applicable
Phenobarbital	Liquid	20 mg/5mL	Oral	bryant ranch prepack	2020-09-01	Not applicable
Phenobarbital	Tablet	64.8 mg/1	Oral	Amerincan Health Packaging	2015-10-05	2017-12-31
Phenobarbital	Elixir	20.0 mg/5mL	Oral	Atlantic Biologicals Corps	1997-01-01	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Bellergal Spacetabs	Phenobarbital (40.0 mg) + Belladonna (0.2 mg) + Ergotamine tartrate (0.6 mg)	Tablet, extended release	Oral	Paladin Labs Inc	1959-01-01	2018-06-05
Bellergal Tab	Phenobarbital (20 mg / tab) + Belladonna (.1 mg / tab) + Ergotamine (.3 mg / tab)	Tablet	Oral	Sandoz	1951-12-31	1997-08-12
Diclophen	Phenobarbital (15 mg) + Dicyclomine hydrochloride (10 mg)	Capsule	Oral	Pro Doc Limitee	1970-12-31	2009-07-23
Dilantin W Phenobarbital 15mg	Phenobarbital (15 mg / cap) + Phenytoin sodium (100 mg / cap)	Capsule	Oral	Parke Davis Division, Warner Lambert Canada Inc.	1951-12-31	1999-04-08
Dilantin W Phenobarbital 30mg Cap	Phenobarbital (30 mg / cap) + Phenytoin sodium (100 mg / cap)	Capsule	Oral	Parke Davis Division, Warner Lambert Canada Inc.	1969-12-31	1997-08-25
Donnatal Elixir	Phenobarbital (16.2 mg) + Atropine sulfate anyhdrous (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Scopolamine (6.5 mcg)	Elixir	Oral	Wyeth Ayerst Canada Inc.	1994-12-31	2001-01-16
Donnatal Elixir	Phenobarbital (16.2 mg) + Atropine sulfate anyhdrous (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Scopolamine (6.5 mcg)	Elixir	Oral	Ayerst Laboratories	1991-12-31	1996-09-10
Donnatal Extentabs	Phenobarbital (48.6 mg) + Atropine sulfate anyhdrous (0.0582 mg) + Hyoscyamine sulfate (0.3111 mg) + Scopolamine (0.0195 mg)	Tablet, extended release	Oral	Ayerst Laboratories	1991-12-31	1996-09-10
Donnatal Extentabs Srt	Phenobarbital (48.6 mg) + Atropine sulfate anyhdrous (0.0582 mg) + Hyoscyamine sulfate (0.3111 mg) + Scopolamine (0.0195 mg)	Tablet, extended release	Oral	Wyeth Ayerst Canada Inc.	1994-12-31	2001-05-07
Donnatal Tab	Phenobarbital (16.2 mg) + Atropine sulfate anyhdrous (0.0194 mg) + Hyoscyamine sulfate (0.1037 mg) + Scopolamine (6.5 mcg)	Tablet	Oral	Wyeth Ayerst Canada Inc.	1994-12-31	2001-05-22

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
B-Donna	Phenobarbital (16.2 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)	Tablet	Oral	Winder Laboratories, LLC	2015-12-30	2016-03-03
Belladonna Alkaloids with Phenobarbital	Phenobarbital (16.2 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)	Tablet	Oral	bryant ranch prepack	1966-01-01	2015-05-01
Belladonna Alkaloids with Phenobarbital	Phenobarbital (16.2 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)	Tablet	Oral	Hikma Pharmaceuticals USA Inc.	1966-01-01	2019-07-31
Belladonna Alkaloids with Phenobartbital	Phenobarbital (16.2 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)	Tablet	Oral	Liberty Pharmaceuticals, Inc.	2000-12-01	Not applicable
Belladonna Alkaloids with Phenobartbital	Phenobarbital (16.2 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)	Tablet	Oral	Physicians Total Care, Inc.	2004-08-31	2013-01-15
Belladonna Alkaloids with Phenobartbital	Phenobarbital (16.2 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)	Tablet	Oral	Apace Packaging	2000-12-01	2015-01-31
Belladonna Alkaloids with Phenobartbital	Phenobarbital (16.2 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)	Tablet	Oral	Preferreed Pharmaceuticals Inc.	2004-08-31	2013-04-30
Belladonna Alkaloids with Phenobartbital	Phenobarbital (16.2 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)	Tablet	Oral	Legacy Pharmaceutical Packaging	2000-12-01	Not applicable
Belladonna Alkaloids with Phenobartbital	Phenobarbital (16.2 mg/1) + Atropine sulfate anyhdrous (0.0194 mg/1) + Hyoscyamine sulfate dihydrate (0.1037 mg/1) + Scopolamine (0.0065 mg/1)	Tablet	Oral	Rebel Distributors	2004-08-31	Not applicable
Donnatal	Phenobarbital (16.2 mg/5mL) + Atropine sulfate anyhdrous (0.0194 mg/5mL) + Hyoscyamine sulfate dihydrate (0.1037 mg/5mL) + Scopolamine (0.0065 mg/5mL)	Elixir	Oral	Unit Dose Services	2009-11-01	2017-12-31

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

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]
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]
Tudur Smith C, Marson AG, Williamson PR: Carbamazepine versus phenobarbitone monotherapy for epilepsy. Cochrane Database Syst Rev. 2003;(1):CD001904. [Article]
Kalviainen R, Eriksson K, Parviainen I: Refractory generalised convulsive status epilepticus : a guide to treatment. CNS Drugs. 2005;19(9):759-68. [Article]
Booth D, Evans DJ: Anticonvulsants for neonates with seizures. Cochrane Database Syst Rev. 2004 Oct 18;(4):CD004218. [Article]
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]

External Links

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

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Drug withdrawal syndrome neonatal	1
4	Recruiting	Prevention	Epilepsy, Intractable / Gliomas, Malignant / Seizures Disorders	1
4	Recruiting	Treatment	Alcohol Withdrawal Delirium / Alcohol Withdrawal Syndrome	1
4	Terminated	Treatment	Neonatal Convulsions	1
4	Unknown Status	Treatment	Neonatal Convulsions	1
4	Withdrawn	Treatment	Alcohol Withdrawal Syndrome	1
3	Completed	Prevention	Infants, Premature / Intracranial Hemorrhages / Low Birth Weight Infants / Newborn Infants / Small for Gestational Age Infants	1
3	Completed	Treatment	Drug withdrawal syndrome neonatal	1
3	Completed	Treatment	Drug withdrawal syndrome neonatal / Neonatal Opioid Withdrawal	1
3	Completed	Treatment	Epilepsies	1

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

Form	Route	Strength
Elixir	Oral	4 mg / mL
Tablet	Oral
Tablet, film coated, extended release	Oral
Solution	Oral	400 mg
Solution	Intramuscular; Intravenous	0.2 g
Solution	Parenteral	200 mg
Injection	Parenteral	40 mg
Tablet	Oral	100 mg
Tablet	Oral	50 mg
Injection, solution
Injection, solution	Intramuscular
Solution	Intramuscular; Intravenous	40 mg
Injection, solution	Intramuscular	100 MG
Elixir	Oral	0.3 %
Injection, solution	Intramuscular; Parenteral	200 MG/ML
Tablet	Oral	15 MG
Syrup
Suppository	Rectal
Capsule	Oral
Tablet	Oral	30 mg
Solution	Oral	5 mg / mL
Elixir	Oral	20 mg/5mL
Elixir	Oral	20 ug/5mL
Elixir	Oral	20.0 mg/5mL
Injection
Liquid	Oral	20 mg/5mL
Solution	Oral	20 mg/5mL
Tablet	Oral
Tablet	Oral	100 mg/1
Tablet	Oral	15 mg/1
Tablet	Oral	16.2 mg/1
Tablet	Oral	30 mg/1
Tablet	Oral	32.4 mg/1
Tablet	Oral	60 mg/1
Tablet	Oral	64.8 mg/1
Tablet	Oral	97.2 mg/1
Solution	Oral	30 mg/7.5mL
Solution	Oral	60 mg/15mL
Injection	Intramuscular	130 mg/1mL
Injection	Intramuscular	65 mg/1mL
Injection	Intramuscular; Intravenous	130 mg/1mL
Injection	Intramuscular; Intravenous	65 mg/1mL
Solution	Intramuscular; Intravenous; Subcutaneous	30 mg / mL
Solution	Intramuscular; Intravenous	120 mg / mL
Solution	Intramuscular; Intravenous	30 mg / mL
Tablet	Oral	10 mg
Tablet	Oral	60 mg
Elixir	Oral
Tablet, extended release	Oral
Liquid	Oral

Prices

Unit description	Cost	Unit
Phenobarbital 130 mg/ml vial	4.32USD	ml
Phenobarbital 65 mg/ml vial	1.63USD	ml
Phenobarbital sodium powder	0.36USD	g
Pms-Phenobarbital 100 mg Tablet	0.15USD	tablet
Phenobarbital powder	0.13USD	g
Pms-Phenobarbital 60 mg Tablet	0.11USD	tablet
Phenobarbital 97.2 mg tablet	0.1USD	tablet
Phenobarbital 64.8 mg tablet	0.09USD	tablet
Pms-Phenobarbital 5 mg/ml Elixir	0.09USD	ml
Phenobarbital 16.2 mg tablet	0.08USD	tablet
Phenobarbital 30 mg tablet	0.08USD	tablet
Phenobarbital 32.4 mg tablet	0.08USD	tablet
Pms-Phenobarbital 30 mg Tablet	0.08USD	tablet
Phenobarbital 100 mg tablet	0.07USD	tablet
Pms-Phenobarbital 15 mg Tablet	0.07USD	tablet
PHENobarbital 20 mg/5ml Elixir	0.06USD	ml
Phenobarbital 60 mg tablet	0.03USD	tablet
Phenobarbital 15 mg tablet	0.02USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	174 °C	PhysProp
water solubility	1110 mg/L (at 25 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	1.47	HANSCH,C ET AL. (1995)
pKa	7.3	BUDAVARI,S ET AL. (1996)

Predicted Properties

Property	Value	Source
Water Solubility	0.276 mg/mL	ALOGPS
logP	1.4	ALOGPS
logP	1.41	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	59.75 m³·mol^-1	ChemAxon
Polarizability	22.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9935
Blood Brain Barrier	+	0.9736
Caco-2 permeable	-	0.5561
P-glycoprotein substrate	Substrate	0.5157
P-glycoprotein inhibitor I	Non-inhibitor	0.6472
P-glycoprotein inhibitor II	Non-inhibitor	0.9869
Renal organic cation transporter	Non-inhibitor	0.9235
CYP450 2C9 substrate	Non-substrate	0.6962
CYP450 2D6 substrate	Non-substrate	0.9116
CYP450 3A4 substrate	Non-substrate	0.7702
CYP450 1A2 substrate	Non-inhibitor	0.84
CYP450 2C9 inhibitor	Non-inhibitor	0.9023
CYP450 2D6 inhibitor	Non-inhibitor	0.9593
CYP450 2C19 inhibitor	Non-inhibitor	0.8664
CYP450 3A4 inhibitor	Non-inhibitor	0.9236
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9164
Ames test	AMES toxic	0.9107
Carcinogenicity	Non-carcinogens	0.7469
Biodegradation	Not ready biodegradable	0.9894
Rat acute toxicity	3.1244 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.99
hERG inhibition (predictor II)	Non-inhibitor	0.9354

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

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Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-0udi-5970000000-7bda34bd3bb88b5fd9fd
GC-MS Spectrum - CI-B	GC-MS	splash10-001i-0090000000-55265fc1e12027dc6454
Mass Spectrum (Electron Ionization)	MS	splash10-0uxr-6950000000-193bf296d3e5d1705628
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-001i-0190000000-8cf53cd66a890256ea98
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-001i-1290000000-73d0e0b25f99ffc6a500
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0016-3950000000-ab62a9483b8a2a65b563
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0006-0900000000-4121e8dd703c01c1161c
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0006-0900000000-4976dfc244184e5d627b
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-001i-1890000000-a12eb2be0b05b9f234de
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-03di-1920000000-43ed71cd16bfceef49e6
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-08fr-2900000000-236ae1dab83b15539a86
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-053u-3900000000-2a994f0e45c022cca640
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-053u-4900000000-066a53ca113150f58406
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-05o3-6900000000-b8f9c9d0f71b6d2c6c2f
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0uy3-8900000000-6bcd457bfff85f05fe9c
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0udi-9500000000-0ecfff7e43e9e78d677e
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0uxs-9300000000-7413ad1c764a1ae4a98e
1H NMR Spectrum	1D NMR	Not Applicable
13C NMR Spectrum	1D NMR	Not Applicable

Targets

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Details1. Gamma-aminobutyric acid receptor subunit alpha-1

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

Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [Article]
Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [Article]
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]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
Macdonald RL, McLean MJ: Anticonvulsant drugs: mechanisms of action. Adv Neurol. 1986;44:713-36. [Article]
Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
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]

Details2. Neuronal acetylcholine receptor subunit alpha-4

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

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]
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]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Details3. Neuronal acetylcholine receptor subunit alpha-7

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

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]
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]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Details4. Glutamate receptor 2

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

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]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]
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]

Details5. Glutamate receptor ionotropic, kainate 2

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

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]
Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [Article]

Details6. NMDA receptor (Protein Group)

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:

Name	UniProt ID
Glutamate receptor ionotropic, NMDA 1	Q05586
Glutamate receptor ionotropic, NMDA 2A	Q12879
Glutamate receptor ionotropic, NMDA 2B	Q13224
Glutamate receptor ionotropic, NMDA 2C	Q14957
Glutamate receptor ionotropic, NMDA 2D	O15399
Glutamate receptor ionotropic, NMDA 3A	Q8TCU5
Glutamate receptor ionotropic, NMDA 3B	O60391

References

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]

Details7. Nuclear receptor subfamily 1 group I member 2

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

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]
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

Details1. Cytochrome P450 2C19

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

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]
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]
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]
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]
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]
Flockhart Table of Drug Interactions [Link]

Details2. Cytochrome P450 2C9

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

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]
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]
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]
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]
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]
Flockhart Table of Drug Interactions [Link]
Phenobarbital Monograph [File]

Details3. Cytochrome P450 2E1

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

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]
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]
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]

Details4. Cytochrome P450 2B6

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

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]
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]
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]
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]
Flockhart Table of Drug Interactions [Link]

Details5. Cytochrome P450 2C8

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

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]
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]
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]
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]
Flockhart Table of Drug Interactions [Link]

Details6. Cytochrome P450 3A4

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

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]
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]
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]
PHENOBARBITAL SODIUM INJECTION Prescribing Information - Sandoz Canada [Link]
Flockhart Table of Drug Interactions [Link]

Details7. Cytochrome P450 1A2

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

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]
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]

Details8. Cytochrome P450 3A5

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

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]
Flockhart Table of Drug Interactions [Link]

Details9. Cytochrome P450 1A1

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

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]
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]
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]

Details10. Cytochrome P450 2C18

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

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]

Details11. Cytochrome P450 3A7

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

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]
Flockhart Table of Drug Interactions [Link]

Details12. Cytochrome P450 4B1

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

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]
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]

Details13. UDP-glucuronosyltransferase 1-1

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

Interactions [Link]

Details14. UDP-glucuronosyltransferase 2B7

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

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]

Details15. Cytochrome P450 2A6

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

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]
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]
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]
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

Details1. P-glycoprotein 1

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

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]
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]

Details2. Canalicular multispecific organic anion transporter 2

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

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]
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]
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]
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]

Details3. Bile salt export pump

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

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]

Details4. Multidrug resistance-associated protein 1

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

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]

Details5. Solute carrier organic anion transporter family member 2A1

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

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]

Details6. Canalicular multispecific organic anion transporter 1

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

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]
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]
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]
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]
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 on June 13, 2005 13:24 / Updated on October 24, 2021 16:00

Phenobarbital

Identification

Structure for Phenobarbital (DB01174)

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Components:

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Enzymes

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Transporters

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