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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 of THIOPENTAL

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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

Doses

DosePopulationAdverse events​
500 mg multiple, intravenous
Dose: 500 mg
Route: intravenous
Route: multiple
Dose: 500 mg
Sources:
unhealthy, 31 years (range: 19 -44 years)
Health Status: unhealthy
Age Group: 31 years (range: 19 -44 years)
Sex: M+F
Sources:
Other AEs: Hypothermia...
Other AEs:
Hypothermia (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypothermia 1 patient
500 mg multiple, intravenous
Dose: 500 mg
Route: intravenous
Route: multiple
Dose: 500 mg
Sources:
unhealthy, 31 years (range: 19 -44 years)
Health Status: unhealthy
Age Group: 31 years (range: 19 -44 years)
Sex: M+F
Sources:
PubMed

PubMed

TitleDatePubMed
Local anesthetic-induced convulsions in man--an electroencephalographic study.
1966 Sep-Oct
Methohexitone and thiopentone. Response to stimuli and incidence of some side effects.
1971 Oct
Abdominal-muscle rigidity induced by morphine and nitrous oxide.
1973 Apr
Thiopentone anaphylaxis--case report.
1975 Aug
Influence of tetrahydro-aminacrine on muscle pains after suxamethonium.
1975 Jan 18
A water-soluble benzodiazepine, RO21-3981, for induction of anesthesia.
1978 Jul
Postischemic brain oxygenation with barbiturate therapy in rats.
1979 Aug
Adverse reactions following fazadinium-thiopentone induction.
1979 Jul-Aug
Brain blood flow and metabolism after global ischemia and post-insult thiopental therapy in monkeys.
1979 Sep-Oct
Ketamine hypertension and the renin-angiotensin system.
1983
Domperidone--an acute dystonic reaction.
1985 Feb
Thiopental-related immune hemolytic anemia and renal failure. Specific involvement of red-cell antigen I.
1985 Feb 7
[Phlebitis of the arm caused by pentothal infusion].
1985 Oct-Dec
Etomidate versus thiopental for induction of anesthesia.
1985 Sep
[Mitral valve prolapse: a factor exacerbating peranesthetic anaphylactic shock].
1986
[Use of thiopental in man. Determination of this drug and its metabolites in plasma and urine by liquid phase chromatography and mass spectrometry].
1986
Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination.
1986 Jul
Drug-induced arterial spasm relieved by lidocaine. Case report.
1986 Nov
Drugs as allergens: the molecular basis of IgE binding to thiopentone.
1987
Comparison of the induction characteristics of thiopentone and propofol in children.
1987 Nov
GABA involvement in naloxone induced reversal of respiratory paralysis produced by thiopental.
1988
Factors that influence cutaneous reactions following administration of thiopentone and atracurium.
1988 Oct
Fatal haemopathological consequences of general anaesthesia.
1989 Jan
[Muscular rigidity caused by alfentanil: prevention].
1989 Jun
Cardiovascular effects of and interaction between calcium blocking drugs and anesthetics in chronically instrumented dogs: VII. Verapamil and thiopental.
1989 Oct
The molecular basis of IgE antibody binding to thiopentone. Binding of IgE from thiopentone-allergic and non-allergic subjects.
1990 Sep
The effects of thiopental sodium on fentanyl-induced muscle rigidity in a human model.
1991 Sep-Oct
Effect of some psychotropic drugs and a barbiturate on mycoplasmas.
2000 Apr
The influence of the timing of administration of thiopentone sodium on nitric oxide-mediated neurotoxicity in vitro.
2000 Mar 1
Intravenous midazolam significantly enhances the lethal effect of thiopental but not that of ketamine in mice.
2001 Dec
Effect of propofol at two injection rates or thiopentone on post-intubation apnoea in the dog.
2001 Feb
The use of thiopentone/propofol admixture for laryngeal mask airway insertion.
2001 Feb
Dual effects of melatonin on barbiturate-induced narcosis in rats.
2001 Mar 16
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Effect of thiopental, propofol, and etomidate on vincristine toxicity in PC12 cells.
2002
Interaction of intravenous anesthetics with recombinant human M1-M3 muscarinic receptors expressed in chinese hamster ovary cells.
2002 Dec
Inhibition of activator protein 1 by barbiturates is mediated by differential effects on mitogen-activated protein kinases and the small G proteins ras and rac-1.
2004 Dec
Effects of different anaesthetic agents on immune cell function in vitro.
2005 Aug
Is ketamine a safe anesthetic for percutaneous liver biopsy in a liver transplant recipient immunosuppressed with cyclosporine?
2005 Jan
Inhibitory effect of thiopental on ultra-rapid delayed rectifier K+ current in H9c2 cells.
2005 Oct
Pre- or postinsult administration of lidocaine or thiopental attenuates cell death in rat hippocampal slice cultures caused by oxygen-glucose deprivation.
2005 Oct
Painless injection of propofol: pretreatment with ketamine vs thiopental, meperidine, and lidocaine.
2007 Oct
Thiopental protects human T lymphocytes from apoptosis in vitro via the expression of heat shock protein 70.
2008 Apr
The effect of thiopentone on severity and duration of succinylcholine-induced fasciculation.
2009 Mar-Apr
Theophylline-associated status epilepticus in an infant: pharmacokinetics and the risk of suppository use.
2009 Nov
Thiopental exaggerates ischemic brain damage and neurological deficits after experimental stroke in spontaneously hypertensive rats.
2009 Oct 19
Anesthesia and arrhythmogenesis in the chronic atrioventricular block dog model.
2010 Jun
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
[Use of midazolam for refractory status epilepticus in children].
2010 Jun-Jul
Pretreatment with dexmedetomidine or thiopental decreases myoclonus after etomidate: a randomized, double-blind controlled trial.
2010 Mar
Patents

Patents

Sample Use Guides

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 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
HSDB   VANDF   WHO-DD  
Common Name English
THIOPENTAL CIII
USP-RS  
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
Created by admin on Mon Mar 31 18:31:06 GMT 2025 , Edited by admin on Mon Mar 31 18:31:06 GMT 2025
DEA NO. 2100
Created by admin on Mon Mar 31 18:31:06 GMT 2025 , Edited by admin on Mon Mar 31 18:31:06 GMT 2025
WHO-ATC N05CA19
Created by admin on Mon Mar 31 18:31:06 GMT 2025 , Edited by admin on Mon Mar 31 18:31:06 GMT 2025
NCI_THESAURUS C245
Created by admin on Mon Mar 31 18:31:06 GMT 2025 , Edited by admin on Mon Mar 31 18:31:06 GMT 2025
WHO-VATC QN05CA19
Created by admin on Mon Mar 31 18:31:06 GMT 2025 , Edited by admin on Mon Mar 31 18:31:06 GMT 2025
WHO-ATC N01AF03
Created by admin on Mon Mar 31 18:31:06 GMT 2025 , Edited by admin on Mon Mar 31 18:31:06 GMT 2025
WHO-VATC QN01AF03
Created by admin on Mon Mar 31 18:31:06 GMT 2025 , Edited by admin on Mon Mar 31 18:31:06 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
200-984-3
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PRIMARY
PUBCHEM
3000715
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PRIMARY
ChEMBL
CHEMBL441
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PRIMARY
LACTMED
Thiopental
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PRIMARY
EVMPD
SUB04816MIG
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PRIMARY
EPA CompTox
DTXSID1023653
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PRIMARY
FDA UNII
JI8Z5M7NA3
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PRIMARY
RS_ITEM_NUM
1661002
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PRIMARY
DRUG BANK
DB00599
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PRIMARY
RXCUI
10493
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PRIMARY RxNorm
NCI_THESAURUS
C72166
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PRIMARY
CAS
76-75-5
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PRIMARY
MESH
D013874
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PRIMARY
CHEBI
102166
Created by admin on Mon Mar 31 18:31:06 GMT 2025 , Edited by admin on Mon Mar 31 18:31:06 GMT 2025
PRIMARY
DRUG CENTRAL
2633
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PRIMARY
HSDB
7791
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PRIMARY
SMS_ID
100000088041
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PRIMARY
IUPHAR
2579
Created by admin on Mon Mar 31 18:31:06 GMT 2025 , Edited by admin on Mon Mar 31 18:31:06 GMT 2025
PRIMARY