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	C11H18N2O2S
Molecular Weight	242.338
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Thrombophlebitis following thiopentone injection.	1972 Nov	4635835
Thiopentone anaphylaxis--case report.	1975 Aug	1166949
Venous complications after intravenous injection of diazepam, flunitrazepam, thiopentone and etomidate.	1980 Jun	6108669
Ketamine hypertension and the renin-angiotensin system.	1983	6349867
Another case of grand mal seizure after fentanyl administration.	1984 Apr	6422799
Fatal haemopathological consequences of general anaesthesia.	1989 Jan	2917103
Complications and side effects during thiopentone therapy in patients with severe head injuries.	1992 May	1595344
Protective effect of thiopental against cerebral ischemia during circulatory arrest.	1999 Aug	10522791
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
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
Torsade de pointes and sudden death induced by thiopental and isoflurane anesthesia in dogs with cardiac electrical remodeling.	2002 Jan	12000977
Seventy-four defibrillations for sotalol-induced torsades de pointes.	2004 Jul-Aug	15586745
Comparative benefit of preemptively applied thiopental for propofol injection pain: the advantage over lidocaine.	2004 Mar	15274426
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
Thiopental protects human T lymphocytes from apoptosis in vitro via the expression of heat shock protein 70.	2008 Apr	18218830
Theophylline-associated status epilepticus in an infant: pharmacokinetics and the risk of suppository use.	2009 Nov	19911151
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
[Use of midazolam for refractory status epilepticus in children].	2010 Jun-Jul	20171707
Pretreatment with dexmedetomidine or thiopental decreases myoclonus after etomidate: a randomized, double-blind controlled trial.	2010 Mar	20018300
Incidence of postoperative delirium is high even in a population without known risk factors.	2014 Apr	24068571

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 `Fri Dec 15 16:04:43 GMT 2023` Edited by `admin` on `Fri Dec 15 16:04:43 GMT 2023`
Record UNII	49Y44QZL70
Record Status	`Validated (UNII)`
Record Version

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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