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
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)
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18568113
Curator's Comment: # Volwiler and Tabern (Abbott Laboratories)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15247320 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | PENTOBARBITAL SODIUM Approved UseParenteral
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 Date2016 |
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Primary | PENTOBARBITAL SODIUM Approved UseParenteral
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 Date2016 |
|||
Primary | PENTOBARBITAL SODIUM Approved UseParenteral
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 Date2016 |
Cmax
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 |
T1/2
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 |
PubMed
Title | Date | PubMed |
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GABAA-receptor expressed from rat brain alpha- and beta-subunit cDNAs displays potentiation by benzodiazepine receptor ligands. | 1990 Aug |
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Functional characteristics and sites of gene expression of the alpha 1, beta 1, gamma 2-isoform of the rat GABAA receptor. | 1990 Jul |
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Luteinizing hormone-releasing hormone neurons express Fos protein during the proestrous surge of luteinizing hormone. | 1990 Jul |
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The early acquisition of two-way (shuttle-box) avoidance as an anxiety-mediated behavior: psychopharmacological validation. | 1991 Jan |
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Recovery of costal and crural diaphragmatic contractility from partial paralysis. | 1991 Jul |
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Transient expression of progesterone receptor messenger RNA in ovarian granulosa cells after the preovulatory luteinizing hormone surge. | 1991 Jul |
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Ethanol sensitivity of the GABAA receptor expressed in Xenopus oocytes requires 8 amino acids contained in the gamma 2L subunit. | 1991 Jul |
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GABA/BZ-and NMDA-receptor interaction in digoxin-induced convulsions in rats. | 1991 Jul |
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Reversal of antihypertensive agent-induced postural hypotension with physostigmine. | 1991 May-Jun |
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Modulation of ornithine decarboxylase mRNA following transient ischemia in the gerbil brain. | 1991 Nov |
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The effect of pentobarbital anesthesia on the autonomic nervous system control of heart rate during baroreceptor activation. | 1991 Nov |
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Improved heart failure protection by FK664, a novel positive inotropic agent, in dog heart-lung preparations. | 1992 |
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Transient ischemia stimulates glial fibrillary acid protein and vimentin gene expression in the gerbil neocortex, striatum and hippocampus. | 1992 Apr |
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Amyloid precursor protein mRNA encoding the Kunitz protease inhibitor domain is increased by kainic acid-induced seizures in rat hippocampus. | 1992 Dec |
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Pathophysiological and pharmacological mechanisms of acute cocaine toxicity in conscious rats. | 1992 Sep |
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Expression of c-fos protein in rat brain elicited by electrical stimulation of the pontine parabrachial nucleus. | 1992 Sep |
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Effects of anaesthetic agents on gastrin-stimulated and histamine-stimulated gastric acid secretion in the totally isolated vascularly perfused rat stomach. | 2002 Jul |
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Changes of the level of G protein alpha-subunit mRNA by tolerance to and withdrawal from pentobarbital in rats. | 2002 Jun |
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Spinal carbonic anhydrase contributes to nociceptive reflex enhancement by midazolam, pentobarbital, and propofol. | 2003 Apr |
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Inactivation of the hepatic cytochrome P450 system by conditional deletion of hepatic cytochrome P450 reductase. | 2003 Apr 11 |
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Pharmacological agents, hippocampal EEG, and anticonvulsant effects on soman-induced seizures in rats. | 2003 Jun |
|
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 |
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Pharmacological characterization of the homomeric and heteromeric UNC-49 GABA receptors in C. elegans. | 2003 Mar |
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Preprocedural fasting state and adverse events in children undergoing procedural sedation and analgesia in a pediatric emergency department. | 2003 Nov |
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Myoclonus and urinary retention following subarachnoid morphine injection in a dog. | 2003 Oct |
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A single M1 residue in the beta2 subunit alters channel gating of GABAA receptor in anesthetic modulation and direct activation. | 2003 Oct 31 |
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Validation of a modified mirrored chamber sensitive to anxiolytics and anxiogenics in mice. | 2003 Sep |
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Key structural features of ligands for activation of human pregnane X receptor. | 2004 Apr |
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Etomidate versus pentobarbital for sedation of children for head and neck CT imaging. | 2004 Aug |
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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 |
|
Pentobarbital-mediated regulation of alternative polyadenylation in Drosophila glutathione S-transferase D21 mRNAs. | 2004 Feb 6 |
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Inhibition of small ubiquitin-related modifier-1 expression by luteinizing hormone receptor stimulation is linked to induction of progesterone receptor during ovulation in mouse granulosa cells. | 2004 Jan |
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Influence of different anaesthetics on pro-inflammatory cytokine expression in rat spleen. | 2004 Jul |
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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 |
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[Development of oral vaccine carrying GCPII gene and its role in reducing the dosage of pentobarbital in rat: a primitive research]. | 2004 Jul 17 |
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Discriminative stimulus effects of ethanol in mice lacking the gamma-aminobutyric acid type A receptor delta subunit. | 2004 Jun |
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Monitoring expression of cytochrome P450 genes during postischemic rat liver reperfusion using DNA microarrays. | 2005 Jan |
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Contrasting anesthetic sensitivities of T-type Ca2+ channels of reticular thalamic neurons and recombinant Ca(v)3.3 channels. | 2005 Jan |
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Brainstem thyrotropin-releasing hormone regulates food intake through vagal-dependent cholinergic stimulation of ghrelin secretion. | 2006 Dec |
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Changes in expression of GABAA alpha4 subunit mRNA in the brain under anesthesia induced by volatile and intravenous anesthetics. | 2006 Mar |
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Effects of isoflurane, pentobarbital, and urethane on apoptosis and apoptotic signal transduction in rat kidney. | 2006 Nov |
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[Effects of intravenous anesthetics on acidosis induced apoptosis in primary brain cell culture]. | 2007 Aug |
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The differential effect of cyclosporine on hypnotic response and pain reaction in mice. | 2007 Nov |
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The reduction of tumor necrosis factor-alpha release and tissue damage by pentobarbital in the experimental endotoxemia model. | 2007 Sep |
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Microarray analysis of choroid/RPE gene expression in marmoset eyes undergoing changes in ocular growth and refraction. | 2008 Aug 11 |
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The use of barbiturate coma as salvage therapy in a postoperative Jehovah's Witness patient with life-threatening anemia. | 2009 Dec |
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The effectiveness of ethanolic extract of Amaranthus tricolor L.: A natural hepatoprotective agent. | 2010 |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15555633
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
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Record UNII |
I4744080IR
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 522.380
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WHO-ATC |
N05CA01
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WHO-VATC |
QN51AA01
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LIVERTOX |
757
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WHO-VATC |
QN05CA01
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NCI_THESAURUS |
C67084
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WHO-VATC |
QN51AA51
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DEA NO. |
2270
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m8513
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100000088686
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SUB09699MIG
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I4744080IR
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I4744080IR
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CHEMBL448
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1507002
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Pentobarbital
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2095
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C61885
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D010424
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PENTOBARBITAL
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703
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DTXSID7023435
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76-74-4
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8004
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200-983-8
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3151
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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LABELED -> NON-LABELED |
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |