PENTOBARBITAL SODIUM

First marketed in 1921

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H17N2O3.Na
Molecular Weight	248.254
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O

InChI

InChIKey=QGMRQYFBGABWDR-UHFFFAOYSA-M

InChI=1S/C11H18N2O3.Na/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);/q;+1/p-1

HIDE SMILES / InChI

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 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15247320	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Highest Phase	Product
Anxiety 267 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9f4b344-b092-4eec-b49d-d8cfe8ebc05d	Primary	Approved 8429	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 8429	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 108 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e9f4b344-b092-4eec-b49d-d8cfe8ebc05d	Primary	Approved 8429	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 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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	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
Sigma-Aldrich	1507002_USP	https://www.sigmaaldrich.com/catalog/product/usp/1507002?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
Luteinizing hormone-releasing hormone neurons express Fos protein during the proestrous surge of luteinizing hormone.	1990 Jul	2114646
The early acquisition of two-way (shuttle-box) avoidance as an anxiety-mediated behavior: psychopharmacological validation.	1991 Jan	1673080
Transient expression of progesterone receptor messenger RNA in ovarian granulosa cells after the preovulatory luteinizing hormone surge.	1991 Jul	1840636
Ethanol sensitivity of the GABAA receptor expressed in Xenopus oocytes requires 8 amino acids contained in the gamma 2L subunit.	1991 Jul	1712603
GABA/BZ-and NMDA-receptor interaction in digoxin-induced convulsions in rats.	1991 Jul	1665475
Reversal of antihypertensive agent-induced postural hypotension with physostigmine.	1991 May-Jun	1665057
The effect of pentobarbital anesthesia on the autonomic nervous system control of heart rate during baroreceptor activation.	1991 Nov	1765616
Improved heart failure protection by FK664, a novel positive inotropic agent, in dog heart-lung preparations.	1992	1386131
Transient ischemia stimulates glial fibrillary acid protein and vimentin gene expression in the gerbil neocortex, striatum and hippocampus.	1992 Apr	1317493
Amyloid precursor protein mRNA encoding the Kunitz protease inhibitor domain is increased by kainic acid-induced seizures in rat hippocampus.	1992 Dec	1306490
Learning of rats under amnesia caused by pentobarbital.	1992 May	1616457
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
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
Evidence for a stabilizer element in the untranslated regions of Drosophila glutathione S-transferase D1 mRNA.	2002 Sep 20	12118001
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
Myoclonus and urinary retention following subarachnoid morphine injection in a dog.	2003 Oct	12925183
A single M1 residue in the beta2 subunit alters channel gating of GABAA receptor in anesthetic modulation and direct activation.	2003 Oct 31	12939268
Validation of a modified mirrored chamber sensitive to anxiolytics and anxiogenics in mice.	2003 Sep	12783153
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
Abnormalities in uridine homeostatic regulation and pyrimidine nucleotide metabolism as a consequence of the deletion of the uridine phosphorylase gene.	2005 Jun 3	15772079
Effect of N-methyl-D-aspartate receptor epsilon1 subunit gene disruption of the action of general anesthetic drugs in mice.	2005 Mar	15731593
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 Aug 25	16828057
Valproate hepatotoxicity in a 5-year-old boy with cerebral palsy due to neonatal asphyxia.	2006 Dec	17168987
Changes in expression of GABAA alpha4 subunit mRNA in the brain under anesthesia induced by volatile and intravenous anesthetics.	2006 Mar	16733821
Effects of isoflurane, pentobarbital, and urethane on apoptosis and apoptotic signal transduction in rat kidney.	2006 Nov	16978161
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.	2007 Apr	17496723
Isoflurane improves survival and protects against renal and hepatic injury in murine septic peritonitis.	2007 Apr	17414419
The lack of CB1 receptors prevents neuroadapatations of both NMDA and GABA(A) receptors after chronic ethanol exposure.	2007 Aug	17442049
Regulation of mRNA stability through a pentobarbital-responsive element.	2007 Mar 1	17234150
Modulation of neuronal activity in CNS pain pathways following propofol administration in rats: Fos and EEG analysis.	2007 May	17136530
Both orexin receptors are expressed in rat ovaries and fluctuate with the estrous cycle: effects of orexin receptor antagonists on gonadotropins and ovulation.	2007 Oct	17638707
Microarray analysis of choroid/RPE gene expression in marmoset eyes undergoing changes in ocular growth and refraction.	2008 Aug 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 Jul	18313124
Pentobarbital coma for refractory intra-cranial hypertension after severe traumatic brain injury: mortality predictions and one-year outcomes in 55 patients.	2010 Aug	20699736

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.

Name

Type

Language

PENTOBARBITAL SODIUM

Common Name

English

NARCOREN

Brand Name

English

SODIUM PENTOBARBITONE

Common Name

English

Pentobarbital sodium [WHO-DD]

Common Name

English

V-PENTO

Common Name

English

AUROPAN

Common Name

English

SODIUM-PENT

Common Name

English

844

Common Name

English

MEBUMAL SODIUM

Common Name

English

NSC-10816

Code

English

SAGATAL

Brand Name

English

NEMBUTAL SODIUM

Brand Name

English

SODIUM NEMBUTAL

Common Name

English

DIABUTAL

Brand Name

English

PENTOBARBITAL SODIUM SALT

Common Name

English

EUTHATAL

Brand Name

English

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

Common Name

English

SODIUM PENTOBARBITAL

Brand Name

English

SOPENTAL

Common Name

English

PENTOBARBITAL SODIUM [MART.]

Common Name

English

ISOBARB

Brand Name

English

PENTOBARBITAL SODIUM [VANDF]

Common Name

English

NAPENTAL

Common Name

English

MEBUBARBITAL SODIUM

Common Name

English

PENTAL

Brand Name

English

SODIUM PENTOBARBITURATE

Common Name

English

BARPENTAL

Brand Name

English

VETBUTAL

Common Name

English

PRAECICALM

Brand Name

English

ETAMINAL SODIUM

Common Name

English

PENTOBARBITAL SODIUM SALT [MI]

Common Name

English

SOMNOTOL

Common Name

English

PENTOBARBITAL SODIUM [USP MONOGRAPH]

Common Name

English

Sodium 5-ethyl-5-(1-methylbutyl)barbiturate

Systematic Name

English

5-ETHYL-5-(1-METHYLBUTYL) BARBITURIC ACID SODIUM SALT

Common Name

English

PENTOBARBITAL SODIUM [EP MONOGRAPH]

Common Name

English

SOLUBLE PENTOBARBITAL

Common Name

English

SOMNOPENTYL

Common Name

English

PENTOBARBITAL SODIUM [GREEN BOOK]

Common Name

English

PENTOBARBITAL SODIUM [JAN]

Common Name

English

PENTONE

Brand Name

English

EMBUTAL

Brand Name

English

SODIUM PENTAL

Common Name

English

BARBITURIC ACID, 5-ETHYL-5-(1-METHYLBUTYL)-, SODIUM SALT

Common Name

English

SODIUM ETHAMINAL

Common Name

English

PENTOBARBITAL SODIUM [ORANGE BOOK]

Common Name

English

ETHAMINAL SODIUM

Common Name

English

PENTONAL

Common Name

English

PENTOBARBITAL SODIUM [EP IMPURITY]

Common Name

English

ENTOBAR

Brand Name

English

EUTHANYL

Brand Name

English

RS-PENTOBARBITAL SODIUM

Common Name

English

2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-5-(1-METHYLBUTYL)-, SODIUM SALT (1:1)

Common Name

English

PACIFAN

Brand Name

English

BIOSEDAN

Brand Name

English

SOTYL

Common Name

English

PENTOBARBITONE SODIUM

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.2444B