THIOPENTAL SODIUM

First marketed in 1934

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

Structure Search

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

HIDE SMILES / InChI

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	( + / - )

Description
Sources: https://www.medicines.org.uk/emc/medicine/14338 | http://www.spiegel.de/international/europe/death-penalty-opposition-eu-set-to-ban-export-of-drug-used-in-us-executions-a-803238.html |

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
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18619475	Positive Allosteric Modulator 186

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.medicines.org.uk/emc/medicine/14338	Palliative		Approved 8583	PENTOTHAL Approved Use Pentothal (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: https://pubmed.ncbi.nlm.nih.gov/2759548	unhealthy, 31 years (range: 19 -44 years) Health Status: unhealthy Age Group: 31 years (range: 19 -44 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2759548	Other AEs: Hypothermia... Other AEs: Hypothermia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2759548

AEs

AE	Significance	Dose	Population
Hypothermia	1 patient	500 mg multiple, intravenous Dose: 500 mg Route: intravenous Route: multiple Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/2759548	unhealthy, 31 years (range: 19 -44 years) Health Status: unhealthy Age Group: 31 years (range: 19 -44 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2759548

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:102166	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:102166
ChemicalBook	CB5265910	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5265910
eMolecules	594613	https://www.emolecules.com/cgi-bin/more?vid=594613

PubMed

Title	Date	PubMed
Metabolism of thiopental-S35 and thiopental-2-C14 by a rat liver mince and identification of pentobarbital as a major metabolite.	1955 Jul	13243246
Local anesthetic-induced convulsions in man--an electroencephalographic study.	1966 Sep-Oct	5950380
Clinical studies on induction agents. 28. A further comparison of venous complications following thiopentone, methohexitone and propanidid.	1969 Aug	4897470
A comparison of propaniid and thiopentone as induction agents for electro-convulsive therapy.	1969 Jun	5792883
Anaphylactoid response to thiopentone. Case report.	1971 Feb	5550850
Further investigation into local complications of thiopentone injection.	1971 May	5556860
Methohexitone and thiopentone. Response to stimuli and incidence of some side effects.	1971 Oct	5115033
A comparison of althesin and thiopentone in induction of anaesthesia.	1973 Jan	4696413
A water-soluble benzodiazepine, RO21-3981, for induction of anesthesia.	1978 Jul	352195
Postischemic brain oxygenation with barbiturate therapy in rats.	1979 Aug	37043
Comparison of etomidate in combination with fentanyl or diazepam, with thiopentone as an induction agent for general anaesthesia.	1979 Dec	526382
Cimetidine: does neurotoxicity occur? Report of three cases.	1979 Mar	552491
Venous complications after intravenous injection of diazepam, flunitrazepam, thiopentone and etomidate.	1980 Jun	6108669
Ketamine hypertension and the renin-angiotensin system.	1983	6349867
The safety of etomidate: a new intravenous anaesthetic induction agent.	1983 Jun	6322557
Another case of grand mal seizure after fentanyl administration.	1984 Apr	6422799
Domperidone--an acute dystonic reaction.	1985 Feb	3977040
[Use of thiopental in man. Determination of this drug and its metabolites in plasma and urine by liquid phase chromatography and mass spectrometry].	1986	3093002
Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination.	1986 Jul	3740628
Drug-induced arterial spasm relieved by lidocaine. Case report.	1986 Nov	3564823
Drugs as allergens: the molecular basis of IgE binding to thiopentone.	1987	3654008
Comparison of the induction characteristics of thiopentone and propofol in children.	1987 Nov	3500735
Factors that influence cutaneous reactions following administration of thiopentone and atracurium.	1988 Oct	2974255
Acute macular neuroretinopathy following intravenous sympathomimetics.	1989	2629043
Fatal haemopathological consequences of general anaesthesia.	1989 Jan	2917103
[Muscular rigidity caused by alfentanil: prevention].	1989 Jun	2575721
Cardiovascular effects of and interaction between calcium blocking drugs and anesthetics in chronically instrumented dogs: VII. Verapamil and thiopental.	1989 Oct	2802216
Thiopental infusion in the treatment of intracranial hypertension complicating fulminant hepatic failure.	1989 Sep	2759548
[Hemodynamic effects of the induction of general anesthesia after low thoracic epidural anesthesia].	1991	1854047
Evaluation of mast cell activation (tryptase) in two patients suffering from drug-induced hypotensoid reactions.	1991 May	1897443
The effects of thiopental sodium on fentanyl-induced muscle rigidity in a human model.	1991 Sep-Oct	1931065
Effect of sodium succinate on gas exchange in rats with barbiturate-induced coma.	2003 Apr	12910308
Thiopental inhibits tumor necrosis factor alpha-induced activation of nuclear factor kappaB through suppression of kappaB kinase activity.	2003 Aug	12883408
Comparative benefit of preemptively applied thiopental for propofol injection pain: the advantage over lidocaine.	2004 Mar	15274426
Intermediates of Krebs cycle correct the depression of the whole body oxygen consumption and lethal cooling in barbiturate poisoning in rat.	2004 Oct 1	15337580
Effects of different anaesthetic agents on immune cell function in vitro.	2005 Aug	16119599
Inhibitory effect of thiopental on ultra-rapid delayed rectifier K+ current in H9c2 cells.	2005 Oct	16217144
Pre- or postinsult administration of lidocaine or thiopental attenuates cell death in rat hippocampal slice cultures caused by oxygen-glucose deprivation.	2005 Oct	16192539
Intravenous propofol precipitates the hypotension induced by inadvertent epidural thiopental injection.	2006 Dec	17233371
Succinate and artificial maintenance of normal body temperature synergistically correct lethal disorders in thiopental coma rat.	2006 Jan 20	16242831
Synergism of isothermal regimen and sodium succinate in experimental therapy of barbiturate coma.	2006 Jul	17369903
Hyperammoniemia in rats with barbiturate coma.	2007 Mar	18225757
Painless injection of propofol: pretreatment with ketamine vs thiopental, meperidine, and lidocaine.	2007 Oct	18044291
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	17721245
Thiopental protects human T lymphocytes from apoptosis in vitro via the expression of heat shock protein 70.	2008 Apr	18218830
Polymyoclonus seizure resulting from accidental injection of tranexamic acid in spinal anesthesia.	2009 Jun	19448237
The effect of thiopentone on severity and duration of succinylcholine-induced fasciculation.	2009 Mar-Apr	18978493
Theophylline-associated status epilepticus in an infant: pharmacokinetics and the risk of suppository use.	2009 Nov	19911151
Thiopental exaggerates ischemic brain damage and neurological deficits after experimental stroke in spontaneously hypertensive rats.	2009 Oct 19	19646967
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	20456060

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Mon Mar 31 18:18:23 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:23 GMT 2025`
Record UNII	49Y44QZL70
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIOPENTAL SODIUM

Official Name

English

PENTOTHAL

Preferred Name

English

TRAPANAL

Brand Name

English

4,6(1H,5H)-PYRIMIDINEDIONE, 5-ETHYLDIHYDRO-5-(1-METHYLBUTYL)-2-THIOXO-, MONOSODIUM SALT, (±)-

Common Name

English

RAVONAL

Common Name

English

NESDONAL

Common Name

English

NSC-759557

Code

English

THIOPENTOBARBITONE SODIUM

Common Name

English

THIOPENTONE

Common Name

English

THIOPENTAL SODIUM [VANDF]

Common Name

English

THIOPENTAL SODIUM [MART.]

Common Name

English

PENTHIOBARBITAL SODIUM

Common Name

English

THIOPENTAL SODIUM [MI]

Common Name

English

THIOPENTAL SODIUM [ORANGE BOOK]

Common Name

English

Thiopental sodium [WHO-DD]

Common Name

English

SODIUM THIOPENTAL

Common Name

English

THIOPENTONE SODIUM

Common Name

English

THIOPENTAL SODIUM [GREEN BOOK]

Common Name

English

SODIUM (±)-5-ETHYL-5-(1-METHYLBUTYL)-2-THIOBARBITURATE

Systematic Name

English

SODIUM PENTOTHAL

Brand Name

English

FARMOTAL

Common Name

English

thiopental sodium [INN]

Common Name

English

THIOPENTALUM NATRICUM [WHO-IP LATIN]

Common Name

English

THIOMEBUMAL SODIUM

Common Name

English

THIOPENTAL SODIUM [WHO-IP]

Common Name

English

THIOPENTAL SODIUM [USP MONOGRAPH]

Common Name

English

THIOPENTAL SODIUM [JAN]

Common Name

English

LEOPENTAL

Common Name

English

HYPNOSTAN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67084