Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H17N2O2S.Na |
Molecular Weight | 264.32 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CCCC(C)C1(CC)C(=O)NC(=S)[N-]C1=O
InChI
InChIKey=AWLILQARPMWUHA-UHFFFAOYSA-M
InChI=1S/C11H18N2O2S.Na/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);/q;+1/p-1
Molecular Formula | Na |
Molecular Weight | 22.98976928 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C11H18N2O2S |
Molecular Weight | 242.338 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
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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Metabolism of thiopental-S35 and thiopental-2-C14 by a rat liver mince and identification of pentobarbital as a major metabolite. | 1955 Jul |
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Local anesthetic-induced convulsions in man--an electroencephalographic study. | 1966 Sep-Oct |
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Clinical studies on induction agents. 28. A further comparison of venous complications following thiopentone, methohexitone and propanidid. | 1969 Aug |
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A comparison of propaniid and thiopentone as induction agents for electro-convulsive therapy. | 1969 Jun |
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Anaphylactoid response to thiopentone. Case report. | 1971 Feb |
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Further investigation into local complications of thiopentone injection. | 1971 May |
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Methohexitone and thiopentone. Response to stimuli and incidence of some side effects. | 1971 Oct |
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A comparison of althesin and thiopentone in induction of anaesthesia. | 1973 Jan |
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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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Comparison of etomidate in combination with fentanyl or diazepam, with thiopentone as an induction agent for general anaesthesia. | 1979 Dec |
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Cimetidine: does neurotoxicity occur? Report of three cases. | 1979 Mar |
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Venous complications after intravenous injection of diazepam, flunitrazepam, thiopentone and etomidate. | 1980 Jun |
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Ketamine hypertension and the renin-angiotensin system. | 1983 |
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The safety of etomidate: a new intravenous anaesthetic induction agent. | 1983 Jun |
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Another case of grand mal seizure after fentanyl administration. | 1984 Apr |
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Domperidone--an acute dystonic reaction. | 1985 Feb |
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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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Factors that influence cutaneous reactions following administration of thiopentone and atracurium. | 1988 Oct |
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Acute macular neuroretinopathy following intravenous sympathomimetics. | 1989 |
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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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Thiopental infusion in the treatment of intracranial hypertension complicating fulminant hepatic failure. | 1989 Sep |
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[Hemodynamic effects of the induction of general anesthesia after low thoracic epidural anesthesia]. | 1991 |
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Evaluation of mast cell activation (tryptase) in two patients suffering from drug-induced hypotensoid reactions. | 1991 May |
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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 sodium succinate on gas exchange in rats with barbiturate-induced coma. | 2003 Apr |
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Thiopental inhibits tumor necrosis factor alpha-induced activation of nuclear factor kappaB through suppression of kappaB kinase activity. | 2003 Aug |
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Comparative benefit of preemptively applied thiopental for propofol injection pain: the advantage over lidocaine. | 2004 Mar |
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Intermediates of Krebs cycle correct the depression of the whole body oxygen consumption and lethal cooling in barbiturate poisoning in rat. | 2004 Oct 1 |
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Effects of different anaesthetic agents on immune cell function in vitro. | 2005 Aug |
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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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Intravenous propofol precipitates the hypotension induced by inadvertent epidural thiopental injection. | 2006 Dec |
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Succinate and artificial maintenance of normal body temperature synergistically correct lethal disorders in thiopental coma rat. | 2006 Jan 20 |
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Synergism of isothermal regimen and sodium succinate in experimental therapy of barbiturate coma. | 2006 Jul |
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Hyperammoniemia in rats with barbiturate coma. | 2007 Mar |
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Painless injection of propofol: pretreatment with ketamine vs thiopental, meperidine, and lidocaine. | 2007 Oct |
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Neonatal exposure to a combination of N-methyl-D-aspartate and gamma-aminobutyric acid type A receptor anesthetic agents potentiates apoptotic neurodegeneration and persistent behavioral deficits. | 2007 Sep |
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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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Polymyoclonus seizure resulting from accidental injection of tranexamic acid in spinal anesthesia. | 2009 Jun |
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The effect of thiopentone on severity and duration of succinylcholine-induced fasciculation. | 2009 Mar-Apr |
|
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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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 |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:18:23 GMT 2025
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Record UNII |
49Y44QZL70
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C67084
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NCI_THESAURUS |
C245
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CFR |
21 CFR 522.2444
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DEA NO. |
2100
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CFR |
21 CFR 522.2444A
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CFR |
21 CFR 522.2444B
Created by
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Code System | Code | Type | Description | ||
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102166
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THIOPENTAL SODIUM
Created by
admin on Mon Mar 31 18:18:23 GMT 2025 , Edited by admin on Mon Mar 31 18:18:23 GMT 2025
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PRIMARY | Description: A yellowish white powder; odour, characteristic. Solubility: Freely soluble in water and ethanol (~750 g/l) TS; practically insoluble in ether R. Category: General anaesthetic. Storage: Thiopental sodium should be kept in a tightly closed container, protected from light. Additional information: Thiopental sodium is hygroscopic. Even in the absence of light, it is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Requirements: Thiopental sodium contains not less than 97.0% and not more than the equivalent of 102.0% of C11H17N2NaO2S, calculated with reference to the dried substance. | ||
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71-73-8
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DTXSID1021744
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200-763-1
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m10773
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12832575
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433
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SUB10981MIG
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282416
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DBSALT001409
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100000091816
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SUB04816MIG
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CHEMBL441
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Sodium thiopental
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9561
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759557
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49Y44QZL70
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C66599
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |