THIOPENTAL

First marketed in 1934

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

Structure Search

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)

HIDE SMILES / InChI

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
Thiopentone anaphylaxis--case report.	1975 Aug	1166949
Influence of tetrahydro-aminacrine on muscle pains after suxamethonium.	1975 Jan 18	1090014
Postischemic brain oxygenation with barbiturate therapy in rats.	1979 Aug	37043
Cimetidine: does neurotoxicity occur? Report of three cases.	1979 Mar	552491
Brain blood flow and metabolism after global ischemia and post-insult thiopental therapy in monkeys.	1979 Sep-Oct	116395
Venous complications after intravenous injection of diazepam, flunitrazepam, thiopentone and etomidate.	1980 Jun	6108669
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
Thiopental-related immune hemolytic anemia and renal failure. Specific involvement of red-cell antigen I.	1985 Feb 7	3969087
[Phlebitis of the arm caused by pentothal infusion].	1985 Oct-Dec	4095143
Etomidate versus thiopental for induction of anesthesia.	1985 Sep	4025853
[Mitral valve prolapse: a factor exacerbating peranesthetic anaphylactic shock].	1986	3777555
Asystole associated with vecuronium.	1986 Aug	2873831
Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination.	1986 Jul	3740628
Factors that influence cutaneous reactions following administration of thiopentone and atracurium.	1988 Oct	2974255
Acute macular neuroretinopathy following intravenous sympathomimetics.	1989	2629043
[Muscular rigidity caused by alfentanil: prevention].	1989 Jun	2575721
[Hemodynamic effects of the induction of general anesthesia after low thoracic epidural anesthesia].	1991	1854047
Effect of some psychotropic drugs and a barbiturate on mycoplasmas.	2000 Apr	10773494
The influence of the timing of administration of thiopentone sodium on nitric oxide-mediated neurotoxicity in vitro.	2000 Mar 1	10704975
Intravenous midazolam significantly enhances the lethal effect of thiopental but not that of ketamine in mice.	2001 Dec	11735358
Effect of propofol at two injection rates or thiopentone on post-intubation apnoea in the dog.	2001 Feb	11263701
The use of thiopentone/propofol admixture for laryngeal mask airway insertion.	2001 Feb	11261909
Dual effects of melatonin on barbiturate-induced narcosis in rats.	2001 Mar 16	11226639
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Effect of thiopental, propofol, and etomidate on vincristine toxicity in PC12 cells.	2002	11991087
Interaction of intravenous anesthetics with recombinant human M1-M3 muscarinic receptors expressed in chinese hamster ovary cells.	2002 Dec	12456425
Torsade de pointes and sudden death induced by thiopental and isoflurane anesthesia in dogs with cardiac electrical remodeling.	2002 Jan	12000977
Life-threatening hyperkalaemia following therapeutic barbiturate coma.	2002 Sep	12209290
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
Central nervous system toxicity following the administration of levobupivacaine for lumbar plexus block: A report of two cases.	2003 Mar-Apr	12677626
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
The effect of pretreatment with thiopental on reducing pain induced by rocuronium injection.	2005 Dec 31	16385651
Contrasting anesthetic sensitivities of T-type Ca2+ channels of reticular thalamic neurons and recombinant Ca(v)3.3 channels.	2005 Jan	15644869
Is ketamine a safe anesthetic for percutaneous liver biopsy in a liver transplant recipient immunosuppressed with cyclosporine?	2005 Jan	15616057
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
Thiopental-induced apoptosis in lymphocytes is independent of CD95 activation.	2005 Sep	16129983
Intravenous propofol precipitates the hypotension induced by inadvertent epidural thiopental injection.	2006 Dec	17233371
Synergism of isothermal regimen and sodium succinate in experimental therapy of barbiturate coma.	2006 Jul	17369903
Fulminant hyperammonaemia induced by thiopental coma in rats.	2006 Jul 25	16704891
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
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
Pretreatment with dexmedetomidine or thiopental decreases myoclonus after etomidate: a randomized, double-blind controlled trial.	2010 Mar	20018300

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 18:31:06 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:06 GMT 2025`
Record UNII	JI8Z5M7NA3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIOPENTAL

Common Name

English

THIOPENTAL CIII

Preferred Name

English

THIOPENTAL [VANDF]

Common Name

English

Thiopental [WHO-DD]

Common Name

English

THIOPENTAL CIII [USP-RS]

Common Name

English

THIOPENTAL [HSDB]

Common Name

English

Classification Tree Code System Code

LIVERTOX

953