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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 of PENTOBARBITAL SODIUM

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

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 ( + / - )

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.

Originator

Curator's Comment: # Volwiler and Tabern (Abbott Laboratories)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.15 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
8.2 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
50 h
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
GABAA-receptor expressed from rat brain alpha- and beta-subunit cDNAs displays potentiation by benzodiazepine receptor ligands.
1990 Aug
Functional characteristics and sites of gene expression of the alpha 1, beta 1, gamma 2-isoform of the rat GABAA receptor.
1990 Jul
Luteinizing hormone-releasing hormone neurons express Fos protein during the proestrous surge of luteinizing hormone.
1990 Jul
Ischemic induction of protooncogene expression in gerbil brain.
1991
The early acquisition of two-way (shuttle-box) avoidance as an anxiety-mediated behavior: psychopharmacological validation.
1991 Jan
Recovery of costal and crural diaphragmatic contractility from partial paralysis.
1991 Jul
Transient expression of progesterone receptor messenger RNA in ovarian granulosa cells after the preovulatory luteinizing hormone surge.
1991 Jul
Ethanol sensitivity of the GABAA receptor expressed in Xenopus oocytes requires 8 amino acids contained in the gamma 2L subunit.
1991 Jul
GABA/BZ-and NMDA-receptor interaction in digoxin-induced convulsions in rats.
1991 Jul
Reversal of antihypertensive agent-induced postural hypotension with physostigmine.
1991 May-Jun
Modulation of ornithine decarboxylase mRNA following transient ischemia in the gerbil brain.
1991 Nov
The effect of pentobarbital anesthesia on the autonomic nervous system control of heart rate during baroreceptor activation.
1991 Nov
Learning of rats under amnesia caused by pentobarbital.
1992 May
LHRH neurons express cJun protein during the proestrous surge of luteinizing hormone.
1992 May
Pathophysiological and pharmacological mechanisms of acute cocaine toxicity in conscious rats.
1992 Sep
Etomidate versus pentobarbital for sedation of children for head and neck CT imaging.
2004 Aug
Differential protective effects of volatile anesthetics against renal ischemia-reperfusion injury in vivo.
2004 Dec
[Development of oral vaccine carrying GCPII gene and its role in reducing the dosage of pentobarbital in rat: a primitive research].
2004 Jul 17
Monitoring expression of cytochrome P450 genes during postischemic rat liver reperfusion using DNA microarrays.
2005 Jan
Contrasting anesthetic sensitivities of T-type Ca2+ channels of reticular thalamic neurons and recombinant Ca(v)3.3 channels.
2005 Jan
Transgenic mice with a hypomorphic NADPH-cytochrome P450 reductase gene: effects on development, reproduction, and microsomal cytochrome P450.
2005 Jan
Abnormalities in uridine homeostatic regulation and pyrimidine nucleotide metabolism as a consequence of the deletion of the uridine phosphorylase gene.
2005 Jun 3
Effect of N-methyl-D-aspartate receptor epsilon1 subunit gene disruption of the action of general anesthetic drugs in mice.
2005 Mar
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
Valproate hepatotoxicity in a 5-year-old boy with cerebral palsy due to neonatal asphyxia.
2006 Dec
Brainstem thyrotropin-releasing hormone regulates food intake through vagal-dependent cholinergic stimulation of ghrelin secretion.
2006 Dec
Changes in expression of GABAA alpha4 subunit mRNA in the brain under anesthesia induced by volatile and intravenous anesthetics.
2006 Mar
Effects of isoflurane, pentobarbital, and urethane on apoptosis and apoptotic signal transduction in rat kidney.
2006 Nov
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.
2007 Apr
Isoflurane improves survival and protects against renal and hepatic injury in murine septic peritonitis.
2007 Apr
[Effects of intravenous anesthetics on acidosis induced apoptosis in primary brain cell culture].
2007 Aug
The lack of CB1 receptors prevents neuroadapatations of both NMDA and GABA(A) receptors after chronic ethanol exposure.
2007 Aug
Regulation of mRNA stability through a pentobarbital-responsive element.
2007 Mar 1
Modulation of neuronal activity in CNS pain pathways following propofol administration in rats: Fos and EEG analysis.
2007 May
The differential effect of cyclosporine on hypnotic response and pain reaction in mice.
2007 Nov
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
The reduction of tumor necrosis factor-alpha release and tissue damage by pentobarbital in the experimental endotoxemia model.
2007 Sep
mRNA Decay analysis in Drosophila melanogaster drug-induced changes in glutathione S-transferase D21 mRNA stability.
2008
Microarray analysis of choroid/RPE gene expression in marmoset eyes undergoing changes in ocular growth and refraction.
2008 Aug 11
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
[Expression of mRNA for corticoliberin and vasopressin in hypothalamus and amygdala on the background of administration of psychoactive drugs in rats].
2008 Jul-Aug
Evaluation of atrial fibrillation induced during anesthesia with fentanyl and pentobarbital in German Shepherd Dogs with inherited arrhythmias.
2008 Nov
Impact of anesthesia on valvular function in normal rats during echocardiography.
2008 Oct
The use of barbiturate coma as salvage therapy in a postoperative Jehovah's Witness patient with life-threatening anemia.
2009 Dec
Anesthetic pentobarbital inhibits proliferation and migration of malignant glioma cells.
2009 Sep 8
Intestinal microbiota regulate xenobiotic metabolism in the liver.
2009 Sep 9
The effectiveness of ethanolic extract of Amaranthus tricolor L.: A natural hepatoprotective agent.
2010
Pentobarbital coma for refractory intra-cranial hypertension after severe traumatic brain injury: mortality predictions and one-year outcomes in 55 patients.
2010 Aug
Striatal FoxP2 is actively regulated during songbird sensorimotor learning.
2010 Jan 6
Regulation of cytochrome P450 expression in Drosophila: Genomic insights.
2010 Jun 1
Patents

Sample Use Guides

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
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 Fri Dec 15 14:59:52 GMT 2023
Edited
by admin
on Fri Dec 15 14:59:52 GMT 2023
Record UNII
NJJ0475N0S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENTOBARBITAL SODIUM
EP   GREEN BOOK   JAN   MART.   ORANGE BOOK   USP   VANDF   WHO-DD  
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
MI  
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
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
CFR 21 CFR 522.1704
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
CFR 21 CFR 522.900
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
DEA NO. 2270
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
Code System Code Type Description
MERCK INDEX
m8513
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY Merck Index
CAS
57-33-0
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
RXCUI
203085
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY RxNorm
SMS_ID
100000090048
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-323-9
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
FDA UNII
NJJ0475N0S
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
EVMPD
SUB03691MIG
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
ChEMBL
CHEMBL448
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
PUBCHEM
14075609
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
DRUG BANK
DBSALT000442
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
DAILYMED
NJJ0475N0S
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
NCI_THESAURUS
C47662
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
NSC
10816
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID9021712
Created by admin on Fri Dec 15 14:59:53 GMT 2023 , Edited by admin on Fri Dec 15 14:59:53 GMT 2023
PRIMARY
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
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ACTIVE MOIETY