Details
| Stereochemistry | RACEMIC |
| Molecular Formula | 2C11H17N2O3.Ca |
| Molecular Weight | 490.607 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Ca++].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O.CCCC(C)C2(CC)C(=O)NC(=O)[N-]C2=O
InChI
InChIKey=VBJLHIJEIVBIHF-UHFFFAOYSA-L
InChI=1S/2C11H18N2O3.Ca/c2*1-4-6-7(3)11(5-2)8(14)12-10(16)13-9(11)15;/h2*7H,4-6H2,1-3H3,(H2,12,13,14,15,16);/q;;+2/p-2
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093872 |
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 |
|||
| 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 |
|---|---|---|
| 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.
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| Code System | Code | Type | Description | ||
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7563-42-0
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NON-SPECIFIC STOICHIOMETRY | |||
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SUB03690MIG
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231-460-2
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100000085545
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66V4W08X7J
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24876-35-5
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m8513
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CHEMBL448
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656845
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ACTIVE MOIETY
SUBSTANCE RECORD
