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

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 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18619475	Positive Allosteric Modulator 179

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.medicines.org.uk/emc/medicine/14338	Palliative		Approved 8429	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 (starting) 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) n = 13 Health Status: unhealthy Age Group: 31 years (range: 19 -44 years) Sex: M+F Population Size: 13 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 (starting) 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) n = 13 Health Status: unhealthy Age Group: 31 years (range: 19 -44 years) Sex: M+F Population Size: 13 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
Case reports: thiopentone anaphylaxis.	1972 Aug	4654818
Abdominal-muscle rigidity induced by morphine and nitrous oxide.	1973 Apr	4350546
Postischemic brain oxygenation with barbiturate therapy in rats.	1979 Aug	37043
The safety of etomidate: a new intravenous anaesthetic induction agent.	1983 Jun	6322557
Domperidone--an acute dystonic reaction.	1985 Feb	3977040
Asystole associated with vecuronium.	1986 Aug	2873831
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
[Muscular rigidity caused by alfentanil: prevention].	1989 Jun	2575721
[Hemodynamic effects of the induction of general anesthesia after low thoracic epidural anesthesia].	1991	1854047
Protective effect of thiopental against cerebral ischemia during circulatory arrest.	1999 Aug	10522791
The influence of the timing of administration of thiopentone sodium on nitric oxide-mediated neurotoxicity in vitro.	2000 Mar 1	10704975
Effect of propofol at two injection rates or thiopentone on post-intubation apnoea in the dog.	2001 Feb	11263701
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Interaction of intravenous anesthetics with recombinant human M1-M3 muscarinic receptors expressed in chinese hamster ovary cells.	2002 Dec	12456425
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
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
The effect of pretreatment with thiopental on reducing pain induced by rocuronium injection.	2005 Dec 31	16385651
[Comparison of the effectiveness of pentobarbital and thiopental in patients with refractory intracranial hypertension. Preliminary report of 20 patients].	2005 Feb	15756405
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
Thiopental protects human T lymphocytes from apoptosis in vitro via the expression of heat shock protein 70.	2008 Apr	18218830
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.

Name

Type

Language

THIOPENTAL SODIUM

Official 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

PENTOTHAL

Brand 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