PENTOBARBITAL

First marketed in 1921

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H18N2O3
Molecular Weight	226.2722
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC(C)C1(CC)C(=O)NC(=O)NC1=O

InChI

InChIKey=WEXRUCMBJFQVBZ-UHFFFAOYSA-N

InChI=1S/C11H18N2O3/c1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15/h7H,4-6H2,1-3H3,(H2,12,13,14,15,16)

HIDE SMILES / InChI

Molecular Formula	C11H18N2O3
Molecular Weight	226.2722
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9f4b344-b092-4eec-b49d-d8cfe8ebc05d#s3

Pentobarbital belongs to the class of a short-acting barbiturate is used as sedatives, hypnotics, for the short-term treatment of insomnia, since they appear to lose their effectiveness for sleep induction and sleep maintenance after 2 weeks; preanesthetics and anticonvulsant, in anesthetic doses, in the emergency control of certain acute convulsive episodes, e.g., those associated with status epilepticus, cholera, eclampsia, meningitis, tetanus, and toxic reactions to strychnine or local anesthetics. Pentobarbital binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15247320	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Highest Phase	Product
Anxiety 275 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9f4b344-b092-4eec-b49d-d8cfe8ebc05d	Primary	Approved 8583	PENTOBARBITAL SODIUM Approved Use Parenteral a. Sedatives. b. Hypnotics, for the short-term treatment of insomnia, since they appear to lose their effectiveness for sleep induction and sleep maintenance after 2 weeks. c. Preanesthetics. d. Anticonvulsant, in anesthetic doses, in the emergency control of certain acute convulsive episodes, e.g., those associated with status epilepticus, cholera, eclampsia, meningitis, tetanus, and toxic reactions to strychnine or local anesthetics. Launch Date 2016
Convulsive episodes 4 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9f4b344-b092-4eec-b49d-d8cfe8ebc05d	Primary	Approved 8583	PENTOBARBITAL SODIUM Approved Use Parenteral a. Sedatives. b. Hypnotics, for the short-term treatment of insomnia, since they appear to lose their effectiveness for sleep induction and sleep maintenance after 2 weeks. c. Preanesthetics. d. Anticonvulsant, in anesthetic doses, in the emergency control of certain acute convulsive episodes, e.g., those associated with status epilepticus, cholera, eclampsia, meningitis, tetanus, and toxic reactions to strychnine or local anesthetics. Launch Date 2016
Insomnia 111 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9f4b344-b092-4eec-b49d-d8cfe8ebc05d	Primary	Approved 8583	PENTOBARBITAL SODIUM Approved Use Parenteral a. Sedatives. b. Hypnotics, for the short-term treatment of insomnia, since they appear to lose their effectiveness for sleep induction and sleep maintenance after 2 weeks. c. Preanesthetics. d. Anticonvulsant, in anesthetic doses, in the emergency control of certain acute convulsive episodes, e.g., those associated with status epilepticus, cholera, eclampsia, meningitis, tetanus, and toxic reactions to strychnine or local anesthetics. Launch Date 2016

C_max

Value	Dose	Co-administered	Analyte	Population
1.15 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7062221/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:		PENTOBARBITAL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
8.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7062221/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:		PENTOBARBITAL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
50 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7062221/	50 mg single, intravenous dose: 50 mg route of administration: Intravenous experiment type: SINGLE co-administered:		PENTOBARBITAL plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/11862331/

Sourcing

Vendor/Aggregator	ID	URL
AHH Chemical co.,ltd	MT-57763	http://www.ahhchemical.com/product/MT-57763.html
Alsachim	3010	http://www.alsachim.com/product-C4084-glo.bal-view.html
Ambinter	Amb17939822	http://www.ambinter.com/reference/17939822
Aurora Fine Chemicals LLC	A17.921.634	http://online.aurorafinechemicals.com/info?ID=A17.921.634
Avantor Inc	75835-288	https://us.vwr.com/store/product/21998648/exempted-drug-of-abuse-reference-standards-restek
ChemMol	44024586	http://www.chemmol.com/chemmol/44024586.html
ChemMol	49416700	http://www.chemmol.com/chemmol/49416700.html
ChemShuttle	140537	http://www.chemshuttle.com/catalogsearch/result/?q=76-74-4&cat=
Chemspace	CSSS00000011403	https://chem-space.com/CSSS00000011403
Clearsynth	CS-EB-01634	https://www.clearsynth.com/en/CSEB01634.html
Clearsynth	CS-ER-01626	https://www.clearsynth.com/en/CSER01626.html
Debye Scientific	DB-056119	http://www.debyesci.com/cas_76-74-4.html
LGC Standards	LGCAMP1357.00-01	https://www.lgcstandards.com/US/en/p/LGCAMP1357.00-01
LGC Standards	LGCAMP1357.00-02	https://www.lgcstandards.com/US/en/p/LGCAMP1357.00-02
LGC Standards	LGCFOR1357.00	https://www.lgcstandards.com/US/en/p/LGCFOR1357.00
LGC Standards	MM1357.00	https://www.lgcstandards.com/US/en/p/MM1357.00
OChem	4718	http://www.ocheminc.com/index.php?act=psearch&pid=057P561
Sigma-Aldrich	1507002_USP	https://www.sigmaaldrich.com/catalog/product/usp/1507002?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P-010_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/p010?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	P0500000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/p0500000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S007937	http://www.sinfoobiotech.com/product/1011335
Smolecule	S538991	http://www.smolecule.com/products/s538991
THE BioTek	bt-279101	https://www.thebiotek.com/product/inhibitors/bt-279101
Vitas-M Laboratory	BBL028072	http://www.request.vitasmlab.biz/index.php?option=com_search_stk&Itemid=22&stk=BBL028072&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
Vitas-M Laboratory	STL367899	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL367899&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink

PubMed

Title	Date	PubMed
Pentobarbital coma for refractory intra-cranial hypertension after severe traumatic brain injury: mortality predictions and one-year outcomes in 55 patients.	2010-08	20699736
Regulation of cytochrome P450 expression in Drosophila: Genomic insights.	2010-06-01	20582327
Striatal FoxP2 is actively regulated during songbird sensorimotor learning.	2010-01-06	20062527
The effectiveness of ethanolic extract of Amaranthus tricolor L.: A natural hepatoprotective agent.	2010	21061460
The use of barbiturate coma as salvage therapy in a postoperative Jehovah's Witness patient with life-threatening anemia.	2009-12	19999907
Intestinal microbiota regulate xenobiotic metabolism in the liver.	2009-09-09	19742318
Anesthetic pentobarbital inhibits proliferation and migration of malignant glioma cells.	2009-09-08	19346066
Evaluation of atrial fibrillation induced during anesthesia with fentanyl and pentobarbital in German Shepherd Dogs with inherited arrhythmias.	2008-11	18980425
Impact of anesthesia on valvular function in normal rats during echocardiography.	2008-10	18455290
[Expression of mRNA for corticoliberin and vasopressin in hypothalamus and amygdala on the background of administration of psychoactive drugs in rats].	2008-09-30	18819432
Microarray analysis of choroid/RPE gene expression in marmoset eyes undergoing changes in ocular growth and refraction.	2008-08-11	18698376
Targeted deletion of the GABRA2 gene encoding alpha2-subunits of GABA(A) receptors facilitates performance of a conditioned emotional response, and abolishes anxiolytic effects of benzodiazepines and barbiturates.	2008-07	18313124
mRNA Decay analysis in Drosophila melanogaster drug-induced changes in glutathione S-transferase D21 mRNA stability.	2008	19111182
The differential effect of cyclosporine on hypnotic response and pain reaction in mice.	2007-11	17959987
Both orexin receptors are expressed in rat ovaries and fluctuate with the estrous cycle: effects of orexin receptor antagonists on gonadotropins and ovulation.	2007-10	17638707
The reduction of tumor necrosis factor-alpha release and tissue damage by pentobarbital in the experimental endotoxemia model.	2007-09	17545946
[Effects of intravenous anesthetics on acidosis induced apoptosis in primary brain cell culture].	2007-08	17715682
The lack of CB1 receptors prevents neuroadapatations of both NMDA and GABA(A) receptors after chronic ethanol exposure.	2007-08	17442049
Modulation of neuronal activity in CNS pain pathways following propofol administration in rats: Fos and EEG analysis.	2007-05	17136530
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.	2007-04	17496723
Isoflurane improves survival and protects against renal and hepatic injury in murine septic peritonitis.	2007-04	17414419
Regulation of mRNA stability through a pentobarbital-responsive element.	2007-03-01	17234150
Valproate hepatotoxicity in a 5-year-old boy with cerebral palsy due to neonatal asphyxia.	2006-12	17168987
Brainstem thyrotropin-releasing hormone regulates food intake through vagal-dependent cholinergic stimulation of ghrelin secretion.	2006-12	16959836
Effects of isoflurane, pentobarbital, and urethane on apoptosis and apoptotic signal transduction in rat kidney.	2006-11	16978161
Peroxisome proliferator-activated receptor (PPAR)-binding protein (PBP) but not PPAR-interacting protein (PRIP) is required for nuclear translocation of constitutive androstane receptor in mouse liver.	2006-08-25	16828057
Changes in expression of GABAA alpha4 subunit mRNA in the brain under anesthesia induced by volatile and intravenous anesthetics.	2006-03	16733821
Abnormalities in uridine homeostatic regulation and pyrimidine nucleotide metabolism as a consequence of the deletion of the uridine phosphorylase gene.	2005-06-03	15772079
Effect of N-methyl-D-aspartate receptor epsilon1 subunit gene disruption of the action of general anesthetic drugs in mice.	2005-03	15731593
Monitoring expression of cytochrome P450 genes during postischemic rat liver reperfusion using DNA microarrays.	2005-01	15655285
Contrasting anesthetic sensitivities of T-type Ca2+ channels of reticular thalamic neurons and recombinant Ca(v)3.3 channels.	2005-01	15644869
Transgenic mice with a hypomorphic NADPH-cytochrome P450 reductase gene: effects on development, reproduction, and microsomal cytochrome P450.	2005-01	15328377
Differential protective effects of volatile anesthetics against renal ischemia-reperfusion injury in vivo.	2004-12	15564938
Etomidate versus pentobarbital for sedation of children for head and neck CT imaging.	2004-08	15295244
[Development of oral vaccine carrying GCPII gene and its role in reducing the dosage of pentobarbital in rat: a primitive research].	2004-07-17	15387974
Pathophysiological and pharmacological mechanisms of acute cocaine toxicity in conscious rats.	1992-09	1527734
Learning of rats under amnesia caused by pentobarbital.	1992-05	1616457
LHRH neurons express cJun protein during the proestrous surge of luteinizing hormone.	1992-05	1572316
Modulation of ornithine decarboxylase mRNA following transient ischemia in the gerbil brain.	1991-11	1939391
The effect of pentobarbital anesthesia on the autonomic nervous system control of heart rate during baroreceptor activation.	1991-11	1765616
Recovery of costal and crural diaphragmatic contractility from partial paralysis.	1991-07	2064036
Transient expression of progesterone receptor messenger RNA in ovarian granulosa cells after the preovulatory luteinizing hormone surge.	1991-07	1840636
Ethanol sensitivity of the GABAA receptor expressed in Xenopus oocytes requires 8 amino acids contained in the gamma 2L subunit.	1991-07	1712603
GABA/BZ-and NMDA-receptor interaction in digoxin-induced convulsions in rats.	1991-07	1665475
Reversal of antihypertensive agent-induced postural hypotension with physostigmine.	1991-05-01	1665057
The early acquisition of two-way (shuttle-box) avoidance as an anxiety-mediated behavior: psychopharmacological validation.	1991-01	1673080
Ischemic induction of protooncogene expression in gerbil brain.	1991	1905565
GABAA-receptor expressed from rat brain alpha- and beta-subunit cDNAs displays potentiation by benzodiazepine receptor ligands.	1990-08	1977069
Functional characteristics and sites of gene expression of the alpha 1, beta 1, gamma 2-isoform of the rat GABAA receptor.	1990-07	2165521
Luteinizing hormone-releasing hormone neurons express Fos protein during the proestrous surge of luteinizing hormone.	1990-07	2114646

Patents

Sample Use Guides

In Vivo Use Guide

Intramuscular Administration: IM injection of the sodium salts of barbiturates should be made deeply into a large muscle, and a volume of 5 mL should not be exceeded at any one site because of possible tissue irritation. After IM injection of a hypnotic dose, the patient's vital signs should be monitored. The usual adult dosage of Pentobarbital Sodium is 150 to 200 mg as a single IM injection; the recommended pediatric dosage ranges from 2 to 6 mg/kg as a single IM injection not to exceed 100 mg. Intravenous Administration: Pentobarbital Sodium should not be admixed with any other medication or solution. IV injection is restricted to conditions in which other routes are not feasible, either because the patient is unconscious (as in cerebral hemorrhage, eclampsia, or status epilepticus), or because the patient resists (as in delirium), or because prompt action is imperative. Slow IV injection is essential, and patients should be carefully observed during administration. This requires that blood pressure, respiration, and cardiac function be maintained, vital signs be recorded, and equipment for resuscitation and artificial ventilation be available. The rate of IV injection should not exceed 50 mg/min for Pentobarbital Sodium. There is no average intravenous dose of Pentobarbital Sodium that can be relied on to produce similar effects in different patients. The possibility of overdose and respiratory depression is remote when the drug is injected slowly in fractional doses. A commonly used initial dose for the 70 kg adult is 100 mg. Proportional reduction in dosage should be made for pediatric or debilitated patients. At least one minute is necessary to determine the full effect of intravenous pentobarbital. If necessary, additional small increments of the drug may be given up to a total of from 200 to 500 mg for normal adults.

Route of Administration: Other

In Vitro Use Guide

It was studied the effects of pentobarbital on extracellular activity in ventrobasal thalamic slices. Pentobarbital at sedative-hypnotic concentration (20 microM) reversibly induced 1-15 Hz oscillations. Sustained oscillations required electrical stimulation of internal capsule, but not elevated temperature or low [Mg2+]. Anesthetic concentration (200 microM) of pentobarbital evoked only transient oscillations.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:29:08 GMT 2025` Edited by `admin` on `Mon Mar 31 19:29:08 GMT 2025`
Record UNII	I4744080IR
Record Status	`Validated (UNII)`
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Name

Type

Language

PENTOBARBITAL CII

Preferred Name

English

PENTOBARBITAL

Official Name

English

MEBUMAL

Common Name

English

MEBUBARBITAL

Common Name

English

PENTOBARBITAL [EP MONOGRAPH]

Common Name

English

Pentobarbital [WHO-DD]

Common Name

English

NEMBUTAL

Brand Name

English

PENTOBARBITAL [GREEN BOOK]

Common Name

English

THIOPENTAL SODIUM IMPURITY B [EP IMPURITY]

Common Name

English

PENTOBARBITAL CII [USP-RS]

Common Name

English

PENTOBARBITAL [USP MONOGRAPH]

Common Name

English

PENTOBARBITONE

Common Name

English

(±)-5-ETHYL-5-(1-METHYLBUTYL)BARBITURIC ACID

Systematic Name

English

PENTOBARBITAL [VANDF]

Common Name

English

2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-5-(1-METHYLBUTYL)-, (±)-

Systematic Name

English

NSC-28708

Code

English

pentobarbital [INN]

Common Name

English

PENTOBARBITAL [MI]

Common Name

English

PENTOBARBITAL [HSDB]

Common Name

English

PENTOBARBITAL [MART.]

Common Name

English

PENTOBARBITAL [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.380