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 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
Incidence of postoperative delirium is high even in a population without known risk factors.	2014-04	24068571
Anesthesia and arrhythmogenesis in the chronic atrioventricular block dog model.	2010-06	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.	2010-06	20456060
Pretreatment with dexmedetomidine or thiopental decreases myoclonus after etomidate: a randomized, double-blind controlled trial.	2010-03	20018300
Theophylline-associated status epilepticus in an infant: pharmacokinetics and the risk of suppository use.	2009-11	19911151
Thiopental exaggerates ischemic brain damage and neurological deficits after experimental stroke in spontaneously hypertensive rats.	2009-10-19	19646967
Thiopental pharmacokinetics in newborn infants: a case report of overdose.	2009-10	19583708
[Use of midazolam for refractory status epilepticus in children].	2009-05-09	20171707
[Comparative study of the efficacy and tolerance of propofol and thiopental in induction and in continuous perfusion with neuroleptanesthesia].	1991-05-01	1961959
[Comparative study between thiopental and propofol in short-duration anesthesia].	1991-05-01	1961958
The molecular basis of IgE antibody binding to thiopentone. Binding of IgE from thiopentone-allergic and non-allergic subjects.	1990-09	2215478
Cardiovascular effects of and interaction between calcium blocking drugs and anesthetics in chronically instrumented dogs: VII. Verapamil and thiopental.	1989-10	2802216
Thiopental infusion in the treatment of intracranial hypertension complicating fulminant hepatic failure.	1989-09	2759548
[Muscular rigidity caused by alfentanil: prevention].	1989-06	2575721
Fatal haemopathological consequences of general anaesthesia.	1989-01	2917103
Acute macular neuroretinopathy following intravenous sympathomimetics.	1989	2629043
Factors that influence cutaneous reactions following administration of thiopentone and atracurium.	1988-10	2974255
GABA involvement in naloxone induced reversal of respiratory paralysis produced by thiopental.	1988	2893236
Comparison of the induction characteristics of thiopentone and propofol in children.	1987-11	3500735
Drugs as allergens: the molecular basis of IgE binding to thiopentone.	1987	3654008
Drug-induced arterial spasm relieved by lidocaine. Case report.	1986-11	3564823
Asystole associated with vecuronium.	1986-08	2873831
Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination.	1986-07	3740628
[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
[Phlebitis of the arm caused by pentothal infusion].	1985-10-01	4095143
Etomidate versus thiopental for induction of anesthesia.	1985-09	4025853
Thiopental-related immune hemolytic anemia and renal failure. Specific involvement of red-cell antigen I.	1985-02-07	3969087
Domperidone--an acute dystonic reaction.	1985-02	3977040
Another case of grand mal seizure after fentanyl administration.	1984-04	6422799
The safety of etomidate: a new intravenous anaesthetic induction agent.	1983-06	6322557
Ketamine hypertension and the renin-angiotensin system.	1983	6349867
Venous complications after intravenous injection of diazepam, flunitrazepam, thiopentone and etomidate.	1980-06	6108669
Comparison of etomidate in combination with fentanyl or diazepam, with thiopentone as an induction agent for general anaesthesia.	1979-12	526382
Postischemic brain oxygenation with barbiturate therapy in rats.	1979-08	37043
Adverse reactions following fazadinium-thiopentone induction.	1979-07-01	42323
Survival following 1000 mg of amethocaine.	1979-05	444350
Cimetidine: does neurotoxicity occur? Report of three cases.	1979-03	552491
A water-soluble benzodiazepine, RO21-3981, for induction of anesthesia.	1978-07	352195
Abdominal-muscle rigidity induced by morphine and nitrous oxide.	1973-04	4350546
A comparison of althesin and thiopentone in induction of anaesthesia.	1973-01	4696413
Thrombophlebitis following thiopentone injection.	1972-11	4635835
Intramuscular ketamine in a developing country. Experience in the British Solomon Islands.	1972-10	4634748
Case reports: thiopentone anaphylaxis.	1972-08	4654818
Methohexitone and thiopentone. Response to stimuli and incidence of some side effects.	1971-10	5115033
Further investigation into local complications of thiopentone injection.	1971-05	5556860
Anaphylactoid response to thiopentone. Case report.	1971-02	5550850
Clinical studies on induction agents. 28. A further comparison of venous complications following thiopentone, methohexitone and propanidid.	1969-08	4897470
A comparison of propaniid and thiopentone as induction agents for electro-convulsive therapy.	1969-06	5792883
Local anesthetic-induced convulsions in man--an electroencephalographic study.	1966-09-01	5950380

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

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