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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
Structure of PENTOBARBITAL

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)

HIDE SMILES / InChI

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

Curator's Comment: # Volwiler and Tabern (Abbott Laboratories)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PENTOBARBITAL SODIUM

Approved Use

Parenteral 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 Date

2016
Primary
PENTOBARBITAL SODIUM

Approved Use

Parenteral 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 Date

2016
Primary
PENTOBARBITAL SODIUM

Approved Use

Parenteral 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 Date

2016
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.15 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
8.2 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
50 h
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
The combined effect of halothane-induced hypotension and hypocapnia on canine myocardial blood-flow and oxygen consumption.
1975 Aug
Prolonged vertical nystagmus after pentobarbital sodium administration.
1975 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
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
The effect of pentobarbital anesthesia on the autonomic nervous system control of heart rate during baroreceptor activation.
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
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
GLUT1-deficiency: barbiturates potentiate haploinsufficiency in vitro.
1999 Dec
Anticonvulsants for soman-induced seizure activity.
1999 Mar-Apr
Role of hypotension in brain-death associated impairment of liver microcirculation and viability.
2000
Anxiety and sensitivity to ethanol and pentobarbital in alcohol withdrawal seizure-prone and withdrawal seizure-resistant mice.
2000 Dec
Pentobarbital induces nocifensive yhyperreflexia, not hyperalgesia in rats.
2000 Jul
Anaesthetic agents inhibit gastrin-stimulated but not basal histamine release from rat stomach ECL cells.
2000 Jun
Pentobarbital, but not propofol, suppresses vasopressin-stimulated heat shock protein 27 induction in aortic smooth muscle cells.
2000 Jun
Neurologic outcomes of pediatric epileptic patients with pentobarbital coma.
2001 Sep
Inhibition of cardiac potassium currents by pentobarbital.
2002 Jan
Antidepressant effects of the methanol extract of several Hypericum species from the Canary Islands.
2002 Jan
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
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
Preprocedural fasting state and adverse events in children undergoing procedural sedation and analgesia in a pediatric emergency department.
2003 Nov
Myoclonus and urinary retention following subarachnoid morphine injection in a dog.
2003 Oct
A single M1 residue in the beta2 subunit alters channel gating of GABAA receptor in anesthetic modulation and direct activation.
2003 Oct 31
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
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
Influence of different anaesthetics on pro-inflammatory cytokine expression in rat spleen.
2004 Jul
[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
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
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
Effects of isoflurane, pentobarbital, and urethane on apoptosis and apoptotic signal transduction in rat kidney.
2006 Nov
Modulation of neuronal activity in CNS pain pathways following propofol administration in rats: Fos and EEG analysis.
2007 May
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
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
The use of barbiturate coma as salvage therapy in a postoperative Jehovah's Witness patient with life-threatening anemia.
2009 Dec
Pentobarbital coma for refractory intra-cranial hypertension after severe traumatic brain injury: mortality predictions and one-year outcomes in 55 patients.
2010 Aug
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
by admin
on Fri Dec 15 18:59:38 GMT 2023
Edited
by admin
on Fri Dec 15 18:59:38 GMT 2023
Record UNII
I4744080IR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENTOBARBITAL
EP   GREEN BOOK   HSDB   INN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN  
Official Name English
MEBUMAL
Common Name English
MEBUBARBITAL
Common Name English
PENTOBARBITAL [EP MONOGRAPH]
Common Name English
Pentobarbital [WHO-DD]
Common Name English
NEMBUTAL
Brand Name English
PENTOBARBITAL [GREEN BOOK]
Common Name English
THIOPENTAL SODIUM IMPURITY B [EP IMPURITY]
Common Name English
PENTOBARBITAL CII [USP-RS]
Common Name English
PENTOBARBITAL [USP MONOGRAPH]
Common Name English
PENTOBARBITONE
Common Name English
(±)-5-ETHYL-5-(1-METHYLBUTYL)BARBITURIC ACID
Systematic Name English
PENTOBARBITAL [VANDF]
Common Name English
2,4,6(1H,3H,5H)-PYRIMIDINETRIONE, 5-ETHYL-5-(1-METHYLBUTYL)-, (±)-
Systematic Name English
NSC-28708
Code English
pentobarbital [INN]
Common Name English
PENTOBARBITAL CII
USP-RS  
Common Name English
PENTOBARBITAL [MI]
Common Name English
PENTOBARBITAL [HSDB]
Common Name English
PENTOBARBITAL [MART.]
Common Name English
PENTOBARBITAL [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.380
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
WHO-ATC N05CA01
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
WHO-VATC QN51AA01
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
LIVERTOX 757
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
WHO-VATC QN05CA01
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
WHO-VATC QN51AA51
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
DEA NO. 2270
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
Code System Code Type Description
MERCK INDEX
m8513
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
PRIMARY Merck Index
SMS_ID
100000088686
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PRIMARY
EVMPD
SUB09699MIG
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PRIMARY
DAILYMED
I4744080IR
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
PRIMARY
FDA UNII
I4744080IR
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PRIMARY
ChEMBL
CHEMBL448
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PRIMARY
RS_ITEM_NUM
1507002
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PRIMARY
LACTMED
Pentobarbital
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
PRIMARY
DRUG CENTRAL
2095
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PRIMARY
CHEBI
7983
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PRIMARY
NCI_THESAURUS
C61885
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PRIMARY
MESH
D010424
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
PRIMARY
WIKIPEDIA
PENTOBARBITAL
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
PRIMARY
DRUG BANK
DB00312
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
PRIMARY
PUBCHEM
4737
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PRIMARY
NSC
28708
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PRIMARY
IUPHAR
5480
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PRIMARY
INN
703
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PRIMARY
EPA CompTox
DTXSID7023435
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PRIMARY
CAS
76-74-4
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
PRIMARY
RXCUI
8004
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
200-983-8
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PRIMARY
HSDB
3151
Created by admin on Fri Dec 15 18:59:38 GMT 2023 , Edited by admin on Fri Dec 15 18:59:38 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
LABELED -> NON-LABELED
SALT/SOLVATE -> PARENT
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY