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
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
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 |
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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 Date1.46396165E12 |
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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 Date1.46396165E12 |
|||
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 Date1.46396165E12 |
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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Ischemic induction of protooncogene expression in gerbil brain. | 1991 |
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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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The effect of pentobarbital anesthesia on the autonomic nervous system control of heart rate during baroreceptor activation. | 1991 Nov |
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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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Learning of rats under amnesia caused by pentobarbital. | 1992 May |
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LHRH neurons express cJun protein during the proestrous surge of luteinizing hormone. | 1992 May |
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Effects of radiocontrast, mannitol, and endothelin on blood pressure and renal damage in the aging male spontaneously hypertensive rat. | 1999 Jul |
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Role of hypotension in brain-death associated impairment of liver microcirculation and viability. | 2000 |
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Ketamine potentiates cerebrocortical damage induced by the common anaesthetic agent nitrous oxide in adult rats. | 2000 Aug |
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Anaesthetic agents inhibit gastrin-stimulated but not basal histamine release from rat stomach ECL cells. | 2000 Jun |
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Pentobarbital, but not propofol, suppresses vasopressin-stimulated heat shock protein 27 induction in aortic smooth muscle cells. | 2000 Jun |
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Genomewide search for epistasis in a complex trait: pentobarbital withdrawal convulsions in mice. | 2001 Jan |
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Gonadotropin regulation of NGFI-B messenger ribonucleic acid expression during ovarian follicle development in the rat. | 2001 Jul |
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Neuropeptide Y alters sedation through a hypothalamic Y1-mediated mechanism. | 2001 Jun |
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Brain-derived neurotrophic factor superinduction parallels anti-epileptic--neuroprotective treatment in the pilocarpine epilepsy model. | 2001 Mar |
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Inhibition of cardiac potassium currents by pentobarbital. | 2002 Jan |
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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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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 |
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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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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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Key structural features of ligands for activation of human pregnane X receptor. | 2004 Apr |
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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 |
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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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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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Transgenic mice with a hypomorphic NADPH-cytochrome P450 reductase gene: effects on development, reproduction, and microsomal cytochrome P450. | 2005 Jan |
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Effect of N-methyl-D-aspartate receptor epsilon1 subunit gene disruption of the action of general anesthetic drugs in mice. | 2005 Mar |
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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 |
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Valproate hepatotoxicity in a 5-year-old boy with cerebral palsy due to neonatal asphyxia. | 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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Genomic and functional conservation of sedative-hypnotic targets in the zebrafish. | 2007 Apr |
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Isoflurane improves survival and protects against renal and hepatic injury in murine septic peritonitis. | 2007 Apr |
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[Effects of intravenous anesthetics on acidosis induced apoptosis in primary brain cell culture]. | 2007 Aug |
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Modulation of neuronal activity in CNS pain pathways following propofol administration in rats: Fos and EEG analysis. | 2007 May |
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The differential effect of cyclosporine on hypnotic response and pain reaction in mice. | 2007 Nov |
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[Expression of mRNA for corticoliberin and vasopressin in hypothalamus and amygdala on the background of administration of psychoactive drugs in rats]. | 2008 Jul-Aug |
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Impact of anesthesia on valvular function in normal rats during echocardiography. | 2008 Oct |
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Anesthetic pentobarbital inhibits proliferation and migration of malignant glioma cells. | 2009 Sep 8 |
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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 |
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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.
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 522.2444B
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CFR |
21 CFR 522.1704
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CFR |
21 CFR 522.900
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NCI_THESAURUS |
C67084
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DEA NO. |
2270
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M8513
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PRIMARY | Merck Index | ||
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57-33-0
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203085
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200-323-9
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NJJ0475N0S
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SUB03691MIG
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CHEMBL448
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14075609
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DBSALT000442
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NJJ0475N0S
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C47662
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10816
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DTXSID9021712
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ACTIVE MOIETY
SUBSTANCE RECORD