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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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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Transient expression of progesterone receptor messenger RNA in ovarian granulosa cells after the preovulatory luteinizing hormone surge. | 1991 Jul |
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LHRH neurons express cJun protein during the proestrous surge of luteinizing hormone. | 1992 May |
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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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Changes of [3H]muscimol binding and GABA(A) receptor beta2-subunit mRNA level by tolerance to and withdrawal from pentobarbital in rats. | 1999 Dec |
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GLUT1-deficiency: barbiturates potentiate haploinsufficiency in vitro. | 1999 Dec |
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Anticonvulsants for soman-induced seizure activity. | 1999 Mar-Apr |
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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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Pentobarbital induces nocifensive yhyperreflexia, not hyperalgesia in rats. | 2000 Jul |
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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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N-Methyl-D-aspartate receptor NR1 subunit mRNA level was decreased in rat brain during pentobarbital withdrawal. | 2000 Mar 24 |
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The effects of pentobarbital, isoflurane, and propofol on immediate-early gene expression in the vital organs of the rat. | 2000 May |
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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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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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Co-assembly of GABA rho subunits with the GABA(A) receptor gamma(2) subunit cloned from white perch retina. | 2002 Jun 30 |
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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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Pharmacological agents, hippocampal EEG, and anticonvulsant effects on soman-induced seizures in rats. | 2003 Jun |
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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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Validation of a modified mirrored chamber sensitive to anxiolytics and anxiogenics in mice. | 2003 Sep |
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Etomidate versus pentobarbital for sedation of children for head and neck CT imaging. | 2004 Aug |
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Differential protective effects of volatile anesthetics against renal ischemia-reperfusion injury in vivo. | 2004 Dec |
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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 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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Transgenic mice with a hypomorphic NADPH-cytochrome P450 reductase gene: effects on development, reproduction, and microsomal cytochrome P450. | 2005 Jan |
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[Effects of intravenous anesthetics on acidosis induced apoptosis in primary brain cell culture]. | 2007 Aug |
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Regulation of mRNA stability through a pentobarbital-responsive element. | 2007 Mar 1 |
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The differential effect of cyclosporine on hypnotic response and pain reaction in mice. | 2007 Nov |
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mRNA Decay analysis in Drosophila melanogaster drug-induced changes in glutathione S-transferase D21 mRNA stability. | 2008 |
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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 |
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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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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7983
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C61885
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D010424
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PENTOBARBITAL
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DB00312
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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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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 |