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
Functional characteristics and sites of gene expression of the alpha 1, beta 1, gamma 2-isoform of the rat GABAA receptor.	1990 Jul	2165521
Transient expression of progesterone receptor messenger RNA in ovarian granulosa cells after the preovulatory luteinizing hormone surge.	1991 Jul	1840636
LHRH neurons express cJun protein during the proestrous surge of luteinizing hormone.	1992 May	1572316
Pathophysiological and pharmacological mechanisms of acute cocaine toxicity in conscious rats.	1992 Sep	1527734
Expression of c-fos protein in rat brain elicited by electrical stimulation of the pontine parabrachial nucleus.	1992 Sep	1527597
Changes of [3H]muscimol binding and GABA(A) receptor beta2-subunit mRNA level by tolerance to and withdrawal from pentobarbital in rats.	1999 Dec	10591412
GLUT1-deficiency: barbiturates potentiate haploinsufficiency in vitro.	1999 Dec	10590023
Anticonvulsants for soman-induced seizure activity.	1999 Mar-Apr	10087439
Role of hypotension in brain-death associated impairment of liver microcirculation and viability.	2000	11140241
Ketamine potentiates cerebrocortical damage induced by the common anaesthetic agent nitrous oxide in adult rats.	2000 Aug	10928976
Pentobarbital induces nocifensive yhyperreflexia, not hyperalgesia in rats.	2000 Jul	10930210
Anaesthetic agents inhibit gastrin-stimulated but not basal histamine release from rat stomach ECL cells.	2000 Jun	10864877
Pentobarbital, but not propofol, suppresses vasopressin-stimulated heat shock protein 27 induction in aortic smooth muscle cells.	2000 Jun	10839933
N-Methyl-D-aspartate receptor NR1 subunit mRNA level was decreased in rat brain during pentobarbital withdrawal.	2000 Mar 24	10717408
The effects of pentobarbital, isoflurane, and propofol on immediate-early gene expression in the vital organs of the rat.	2000 May	10781476
Gonadotropin regulation of NGFI-B messenger ribonucleic acid expression during ovarian follicle development in the rat.	2001 Jul	11416027
Neuropeptide Y alters sedation through a hypothalamic Y1-mediated mechanism.	2001 Jun	11454027
Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model.	2001 Mar	11259499
Effects of anaesthetic agents on gastrin-stimulated and histamine-stimulated gastric acid secretion in the totally isolated vascularly perfused rat stomach.	2002 Jul	12190085
Changes of the level of G protein alpha-subunit mRNA by tolerance to and withdrawal from pentobarbital in rats.	2002 Jun	12199159
Co-assembly of GABA rho subunits with the GABA(A) receptor gamma(2) subunit cloned from white perch retina.	2002 Jun 30	12106692
Spinal carbonic anhydrase contributes to nociceptive reflex enhancement by midazolam, pentobarbital, and propofol.	2003 Apr	12657854
Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase.	2003 Apr 11	12566435
Liver-specific deletion of the NADPH-cytochrome P450 reductase gene: impact on plasma cholesterol homeostasis and the function and regulation of microsomal cytochrome P450 and heme oxygenase.	2003 Jul 11	12697746
Pharmacological agents, hippocampal EEG, and anticonvulsant effects on soman-induced seizures in rats.	2003 Jun	12782101
2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) stimulates gonadotropin secretion in the immature female Sprague-Dawley rat through a pentobarbital- and estradiol-sensitive mechanism but does not alter gonadotropin-releasing hormone (GnRH) secretion by immortalized GnRH neurons in vitro.	2003 Jun	12606454
Pharmacological characterization of the homomeric and heteromeric UNC-49 GABA receptors in C. elegans.	2003 Mar	12642390
Validation of a modified mirrored chamber sensitive to anxiolytics and anxiogenics in mice.	2003 Sep	12783153
Etomidate versus pentobarbital for sedation of children for head and neck CT imaging.	2004 Aug	15295244
Differential protective effects of volatile anesthetics against renal ischemia-reperfusion injury in vivo.	2004 Dec	15564938
Inhibition of activator protein 1 by barbiturates is mediated by differential effects on mitogen-activated protein kinases and the small G proteins ras and rac-1.	2004 Dec	15263067
Influence of different anaesthetics on pro-inflammatory cytokine expression in rat spleen.	2004 Jul	15207038
Influence of O(3)/O(2)-pneumoperitoneum as an oxidative stressor on duration of anaesthesia, loss of different reflexes and cytokine mRNA expression.	2004 Jul	15207037
[Development of oral vaccine carrying GCPII gene and its role in reducing the dosage of pentobarbital in rat: a primitive research].	2004 Jul 17	15387974
Discriminative stimulus effects of ethanol in mice lacking the gamma-aminobutyric acid type A receptor delta subunit.	2004 Jun	15201633
Monitoring expression of cytochrome P450 genes during postischemic rat liver reperfusion using DNA microarrays.	2005 Jan	15655285
Contrasting anesthetic sensitivities of T-type Ca2+ channels of reticular thalamic neurons and recombinant Ca(v)3.3 channels.	2005 Jan	15644869
Transgenic mice with a hypomorphic NADPH-cytochrome P450 reductase gene: effects on development, reproduction, and microsomal cytochrome P450.	2005 Jan	15328377
[Effects of intravenous anesthetics on acidosis induced apoptosis in primary brain cell culture].	2007 Aug	17715682
Regulation of mRNA stability through a pentobarbital-responsive element.	2007 Mar 1	17234150
The differential effect of cyclosporine on hypnotic response and pain reaction in mice.	2007 Nov	17959987
mRNA Decay analysis in Drosophila melanogaster drug-induced changes in glutathione S-transferase D21 mRNA stability.	2008	19111182
The use of barbiturate coma as salvage therapy in a postoperative Jehovah's Witness patient with life-threatening anemia.	2009 Dec	19999907

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)`
Record Version

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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