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
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
Case reports: thiopentone anaphylaxis.	1972 Aug	4654818
Thrombophlebitis following thiopentone injection.	1972 Nov	4635835
Intramuscular ketamine in a developing country. Experience in the British Solomon Islands.	1972 Oct	4634748
Abdominal-muscle rigidity induced by morphine and nitrous oxide.	1973 Apr	4350546
A comparison of althesin and thiopentone in induction of anaesthesia.	1973 Jan	4696413
Comparison of etomidate in combination with fentanyl or diazepam, with thiopentone as an induction agent for general anaesthesia.	1979 Dec	526382
Adverse reactions following fazadinium-thiopentone induction.	1979 Jul-Aug	42323
Cimetidine: does neurotoxicity occur? Report of three cases.	1979 Mar	552491
Survival following 1000 mg of amethocaine.	1979 May	444350
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
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
[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
Asystole associated with vecuronium.	1986 Aug	2873831
Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination.	1986 Jul	3740628
Comparison of the induction characteristics of thiopentone and propofol in children.	1987 Nov	3500735
GABA involvement in naloxone induced reversal of respiratory paralysis produced by thiopental.	1988	2893236
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
The molecular basis of IgE antibody binding to thiopentone. Binding of IgE from thiopentone-allergic and non-allergic subjects.	1990 Sep	2215478
[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
[Comparative study of the efficacy and tolerance of propofol and thiopental in induction and in continuous perfusion with neuroleptanesthesia].	1991 May-Jun	1961959
[Comparative study between thiopental and propofol in short-duration anesthesia].	1991 May-Jun	1961958
The effects of thiopental sodium on fentanyl-induced muscle rigidity in a human model.	1991 Sep-Oct	1931065
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 pharmacokinetics in newborn infants: a case report of overdose.	2009 Oct	19583708
Thiopental exaggerates ischemic brain damage and neurological deficits after experimental stroke in spontaneously hypertensive rats.	2009 Oct 19	19646967
Anesthesia and arrhythmogenesis in the chronic atrioventricular block dog model.	2010 Jun	20555233
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
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