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
| 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 | ( + / - ) |
| Molecular Formula | Ca |
| Molecular Weight | 40.078 |
| Charge | 2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Prolonged vertical nystagmus after pentobarbital sodium administration. | 1975 Jul |
|
| 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 |
|
| Transient expression of progesterone receptor messenger RNA in ovarian granulosa cells after the preovulatory luteinizing hormone surge. | 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 |
|
| Transient ischemia stimulates glial fibrillary acid protein and vimentin gene expression in the gerbil neocortex, striatum and hippocampus. | 1992 Apr |
|
| Amyloid precursor protein mRNA encoding the Kunitz protease inhibitor domain is increased by kainic acid-induced seizures in rat hippocampus. | 1992 Dec |
|
| 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 |
|
| Expression of c-fos protein in rat brain elicited by electrical stimulation of the pontine parabrachial nucleus. | 1992 Sep |
|
| Role of hypotension in brain-death associated impairment of liver microcirculation and viability. | 2000 |
|
| Pentobarbital induces nocifensive yhyperreflexia, not hyperalgesia in rats. | 2000 Jul |
|
| Genomewide search for epistasis in a complex trait: pentobarbital withdrawal convulsions in mice. | 2001 Jan |
|
| Neuropeptide Y alters sedation through a hypothalamic Y1-mediated mechanism. | 2001 Jun |
|
| Neurologic outcomes of pediatric epileptic patients with pentobarbital coma. | 2001 Sep |
|
| Corticotropin-releasing hormone (CRH) downregulates the function of its receptor (CRF1) and induces CRF1 expression in hippocampal and cortical regions of the immature rat brain. | 2002 Jul |
|
| Co-assembly of GABA rho subunits with the GABA(A) receptor gamma(2) subunit cloned from white perch retina. | 2002 Jun 30 |
|
| Spinal carbonic anhydrase contributes to nociceptive reflex enhancement by midazolam, pentobarbital, and propofol. | 2003 Apr |
|
| Pharmacological characterization of the homomeric and heteromeric UNC-49 GABA receptors in C. elegans. | 2003 Mar |
|
| Preprocedural fasting state and adverse events in children undergoing procedural sedation and analgesia in a pediatric emergency department. | 2003 Nov |
|
| A single M1 residue in the beta2 subunit alters channel gating of GABAA receptor in anesthetic modulation and direct activation. | 2003 Oct 31 |
|
| Key structural features of ligands for activation of human pregnane X receptor. | 2004 Apr |
|
| 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 |
|
| 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 |
|
| Influence of different anaesthetics on pro-inflammatory cytokine expression in rat spleen. | 2004 Jul |
|
| 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 |
|
| Discriminative stimulus effects of ethanol in mice lacking the gamma-aminobutyric acid type A receptor delta subunit. | 2004 Jun |
|
| Monitoring expression of cytochrome P450 genes during postischemic rat liver reperfusion using DNA microarrays. | 2005 Jan |
|
| Transgenic mice with a hypomorphic NADPH-cytochrome P450 reductase gene: effects on development, reproduction, and microsomal cytochrome P450. | 2005 Jan |
|
| 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 |
|
| 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 |
|
| The differential effect of cyclosporine on hypnotic response and pain reaction in mice. | 2007 Nov |
|
| 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 |
|
| 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 |
|
| Striatal FoxP2 is actively regulated during songbird sensorimotor learning. | 2010 Jan 6 |
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
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Edited
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| Record UNII |
66V4W08X7J
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| Record Status |
Validated (UNII)
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| Record Version |
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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 |