Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H18N2O2S |
Molecular Weight | 242.338 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCC(C)C1(CC)C(=O)NC(=S)NC1=O
InChI
InChIKey=IUJDSEJGGMCXSG-UHFFFAOYSA-N
InChI=1S/C11H18N2O2S/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)
Sodium thiopental (also known as Sodium Pentothal, thiopental) was discovered in 1930s by investigators working for Abbott Laboratories. Thiopental sodium was used for the induction of general anesthesia and is used as an adjunct to provide hypnosis during balanced anesthesia with other anesthetic agents, including analgesics and muscle relaxants. Thiopental sodium was also used as an adjunct for control of convulsive disorders of various etiology, including those caused by local anesthetics. Finally, thiopental sodium had been used to reduce the intracranial pressure in patients with increased intracranial pressure, if controlled ventilation is provided. Nevertheless, these prescriptions of drug were discontinued. In addition, this drug was banned for use in US executions. Thiopental sodium acts through the CNS with particular activity in the mesencephalic reticular activating system. It was shown, that mechanism of action of sodium thiopental via GABAA receptor. Thiopental 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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18619475 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Palliative | PENTOTHAL Approved UsePentothal (Thiopental Sodium for Injection) is indicated (1) as the sole anesthetic agent for brief (15 minute) procedures, (2) for induction of anesthesia prior to administration of other anesthetic agents, (3) to supplement regional anesthesia, (4) to provide hypnosis during balanced anesthesia with other agents for analgesia or muscle relaxation, (5) for the control of convulsive states during or following inhalation anesthesia, local anesthesia, or other causes, (6) in neurosurgical patients with increased intracranial pressure, if adequate ventilation is provided, and (7) for narcoanalysis and narcosynthesis in psychiatric disorders. |
Doses
Dose | Population | Adverse events |
---|---|---|
500 mg multiple, intravenous Dose: 500 mg Route: intravenous Route: multiple Dose: 500 mg Sources: |
unhealthy, 31 years (range: 19 -44 years) Health Status: unhealthy Age Group: 31 years (range: 19 -44 years) Sex: M+F Sources: |
Other AEs: Hypothermia... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypothermia | 1 patient | 500 mg multiple, intravenous Dose: 500 mg Route: intravenous Route: multiple Dose: 500 mg Sources: |
unhealthy, 31 years (range: 19 -44 years) Health Status: unhealthy Age Group: 31 years (range: 19 -44 years) Sex: M+F Sources: |
PubMed
Title | Date | PubMed |
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Local anesthetic-induced convulsions in man--an electroencephalographic study. | 1966 Sep-Oct |
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Methohexitone and thiopentone. Response to stimuli and incidence of some side effects. | 1971 Oct |
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Abdominal-muscle rigidity induced by morphine and nitrous oxide. | 1973 Apr |
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Thiopentone anaphylaxis--case report. | 1975 Aug |
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Influence of tetrahydro-aminacrine on muscle pains after suxamethonium. | 1975 Jan 18 |
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A water-soluble benzodiazepine, RO21-3981, for induction of anesthesia. | 1978 Jul |
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Postischemic brain oxygenation with barbiturate therapy in rats. | 1979 Aug |
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Adverse reactions following fazadinium-thiopentone induction. | 1979 Jul-Aug |
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Brain blood flow and metabolism after global ischemia and post-insult thiopental therapy in monkeys. | 1979 Sep-Oct |
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Ketamine hypertension and the renin-angiotensin system. | 1983 |
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Domperidone--an acute dystonic reaction. | 1985 Feb |
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Thiopental-related immune hemolytic anemia and renal failure. Specific involvement of red-cell antigen I. | 1985 Feb 7 |
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[Phlebitis of the arm caused by pentothal infusion]. | 1985 Oct-Dec |
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Etomidate versus thiopental for induction of anesthesia. | 1985 Sep |
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[Mitral valve prolapse: a factor exacerbating peranesthetic anaphylactic shock]. | 1986 |
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[Use of thiopental in man. Determination of this drug and its metabolites in plasma and urine by liquid phase chromatography and mass spectrometry]. | 1986 |
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Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination. | 1986 Jul |
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Drug-induced arterial spasm relieved by lidocaine. Case report. | 1986 Nov |
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Drugs as allergens: the molecular basis of IgE binding to thiopentone. | 1987 |
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Comparison of the induction characteristics of thiopentone and propofol in children. | 1987 Nov |
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GABA involvement in naloxone induced reversal of respiratory paralysis produced by thiopental. | 1988 |
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Factors that influence cutaneous reactions following administration of thiopentone and atracurium. | 1988 Oct |
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Fatal haemopathological consequences of general anaesthesia. | 1989 Jan |
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[Muscular rigidity caused by alfentanil: prevention]. | 1989 Jun |
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Cardiovascular effects of and interaction between calcium blocking drugs and anesthetics in chronically instrumented dogs: VII. Verapamil and thiopental. | 1989 Oct |
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The molecular basis of IgE antibody binding to thiopentone. Binding of IgE from thiopentone-allergic and non-allergic subjects. | 1990 Sep |
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The effects of thiopental sodium on fentanyl-induced muscle rigidity in a human model. | 1991 Sep-Oct |
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Effect of some psychotropic drugs and a barbiturate on mycoplasmas. | 2000 Apr |
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The influence of the timing of administration of thiopentone sodium on nitric oxide-mediated neurotoxicity in vitro. | 2000 Mar 1 |
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Intravenous midazolam significantly enhances the lethal effect of thiopental but not that of ketamine in mice. | 2001 Dec |
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Effect of propofol at two injection rates or thiopentone on post-intubation apnoea in the dog. | 2001 Feb |
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The use of thiopentone/propofol admixture for laryngeal mask airway insertion. | 2001 Feb |
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Dual effects of melatonin on barbiturate-induced narcosis in rats. | 2001 Mar 16 |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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Effect of thiopental, propofol, and etomidate on vincristine toxicity in PC12 cells. | 2002 |
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Interaction of intravenous anesthetics with recombinant human M1-M3 muscarinic receptors expressed in chinese hamster ovary cells. | 2002 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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Effects of different anaesthetic agents on immune cell function in vitro. | 2005 Aug |
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Is ketamine a safe anesthetic for percutaneous liver biopsy in a liver transplant recipient immunosuppressed with cyclosporine? | 2005 Jan |
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Inhibitory effect of thiopental on ultra-rapid delayed rectifier K+ current in H9c2 cells. | 2005 Oct |
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Pre- or postinsult administration of lidocaine or thiopental attenuates cell death in rat hippocampal slice cultures caused by oxygen-glucose deprivation. | 2005 Oct |
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Painless injection of propofol: pretreatment with ketamine vs thiopental, meperidine, and lidocaine. | 2007 Oct |
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Thiopental protects human T lymphocytes from apoptosis in vitro via the expression of heat shock protein 70. | 2008 Apr |
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The effect of thiopentone on severity and duration of succinylcholine-induced fasciculation. | 2009 Mar-Apr |
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Theophylline-associated status epilepticus in an infant: pharmacokinetics and the risk of suppository use. | 2009 Nov |
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Thiopental exaggerates ischemic brain damage and neurological deficits after experimental stroke in spontaneously hypertensive rats. | 2009 Oct 19 |
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Anesthesia and arrhythmogenesis in the chronic atrioventricular block dog model. | 2010 Jun |
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The effect of a 3 : 1 volume mixture of propofol 1% and thiopental 2.5% in reducing the pain on injection of propofol in children. | 2010 Jun |
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[Use of midazolam for refractory status epilepticus in children]. | 2010 Jun-Jul |
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Pretreatment with dexmedetomidine or thiopental decreases myoclonus after etomidate: a randomized, double-blind controlled trial. | 2010 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/medicine/14338
Thiopental Sodium 500 mg Injection is administered intravenously normally as a 2.5% w/v (500 mg in 20 ml) solution. On occasions it may be administered as a 5% w/v solution (500 mg in 10 ml).
The intravenous injection preparation should be used after reconstitution of the sterile powder with Water for Injections, usually to produce a 2.5% w/v solution and this should be discarded after seven hours.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18619475
In cultured spinal cord slices from mice, thiopental reduced action potential activity with an EC50 of 16.6 ± 2.4 μM. Recordings of GABAA and glycine receptor-mediated inhibitory currents indicated that the effect was largely mediated by GABAA receptors and that glycine receptors were not relevant targets. Specifically, 20 μM thiopental prolonged the decay time of spontaneous GABAergic inhibitory postsynaptic currents (sIPSCs) more than twofold. Although this prolongation of decay time increased the inhibitory charge per sIPSC the concomitant strong reduction of sIPSC frequency resulted in less inhibitory current entering the neurons via this route. However, 20 μM thiopental also induced a tonic current of 30 ± 10 pA, mediated by GABAA receptors; 50 μM thiopental nearly abolished sIPSC activity but augmented tonic currents to 69 ± 14 pA.
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Classification Tree | Code System | Code | ||
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LIVERTOX |
953
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DEA NO. |
2100
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WHO-ATC |
N05CA19
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NCI_THESAURUS |
C245
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WHO-VATC |
QN05CA19
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N01AF03
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QN01AF03
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200-984-3
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3000715
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CHEMBL441
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Thiopental
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SUB04816MIG
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1661002
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10493
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C72166
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76-75-5
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2633
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7791
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100000088041
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2579
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)