U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C11H18N2O2S
Molecular Weight 242.3393
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIOPENTAL

SMILES

CCCC(C)C1(CC)C(=NC(=S)N=C1O)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 (starting)
Dose: 500 mg
Route: intravenous
Route: multiple
Dose: 500 mg
Sources:
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:
Other AEs: Hypothermia...
Other AEs:
Hypothermia (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypothermia 1 patient
500 mg multiple, intravenous (starting)
Dose: 500 mg
Route: intravenous
Route: multiple
Dose: 500 mg
Sources:
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:
PubMed

PubMed

TitleDatePubMed
Local anesthetic-induced convulsions in man--an electroencephalographic study.
1966 Sep-Oct
Clinical studies on induction agents. 28. A further comparison of venous complications following thiopentone, methohexitone and propanidid.
1969 Aug
A comparison of propaniid and thiopentone as induction agents for electro-convulsive therapy.
1969 Jun
Anaphylactoid response to thiopentone. Case report.
1971 Feb
Further investigation into local complications of thiopentone injection.
1971 May
Methohexitone and thiopentone. Response to stimuli and incidence of some side effects.
1971 Oct
Case reports: thiopentone anaphylaxis.
1972 Aug
Thrombophlebitis following thiopentone injection.
1972 Nov
Intramuscular ketamine in a developing country. Experience in the British Solomon Islands.
1972 Oct
Abdominal-muscle rigidity induced by morphine and nitrous oxide.
1973 Apr
A comparison of althesin and thiopentone in induction of anaesthesia.
1973 Jan
A water-soluble benzodiazepine, RO21-3981, for induction of anesthesia.
1978 Jul
Comparison of etomidate in combination with fentanyl or diazepam, with thiopentone as an induction agent for general anaesthesia.
1979 Dec
Adverse reactions following fazadinium-thiopentone induction.
1979 Jul-Aug
Cimetidine: does neurotoxicity occur? Report of three cases.
1979 Mar
Survival following 1000 mg of amethocaine.
1979 May
Venous complications after intravenous injection of diazepam, flunitrazepam, thiopentone and etomidate.
1980 Jun
Ketamine hypertension and the renin-angiotensin system.
1983
The safety of etomidate: a new intravenous anaesthetic induction agent.
1983 Jun
Another case of grand mal seizure after fentanyl administration.
1984 Apr
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
Asystole associated with vecuronium.
1986 Aug
Drugs as allergens: the molecular basis of IgE binding to thiopentone.
1987
GABA involvement in naloxone induced reversal of respiratory paralysis produced by thiopental.
1988
Acute macular neuroretinopathy following intravenous sympathomimetics.
1989
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
Thiopental infusion in the treatment of intracranial hypertension complicating fulminant hepatic failure.
1989 Sep
The molecular basis of IgE antibody binding to thiopentone. Binding of IgE from thiopentone-allergic and non-allergic subjects.
1990 Sep
[Hemodynamic effects of the induction of general anesthesia after low thoracic epidural anesthesia].
1991
Evaluation of mast cell activation (tryptase) in two patients suffering from drug-induced hypotensoid reactions.
1991 May
[Comparative study of the efficacy and tolerance of propofol and thiopental in induction and in continuous perfusion with neuroleptanesthesia].
1991 May-Jun
[Comparative study between thiopental and propofol in short-duration anesthesia].
1991 May-Jun
The effects of thiopental sodium on fentanyl-induced muscle rigidity in a human model.
1991 Sep-Oct
Glutamate binding is altered in hippocampus and cortex of Wistar rats after pilocarpine-induced Status Epilepticus.
2007 Aug 31
Hyperammoniemia in rats with barbiturate coma.
2007 Mar
Painless injection of propofol: pretreatment with ketamine vs thiopental, meperidine, and lidocaine.
2007 Oct
Neonatal exposure to a combination of N-methyl-D-aspartate and gamma-aminobutyric acid type A receptor anesthetic agents potentiates apoptotic neurodegeneration and persistent behavioral deficits.
2007 Sep
Thiopental protects human T lymphocytes from apoptosis in vitro via the expression of heat shock protein 70.
2008 Apr
Polymyoclonus seizure resulting from accidental injection of tranexamic acid in spinal anesthesia.
2009 Jun
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 pharmacokinetics in newborn infants: a case report of overdose.
2009 Oct
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
[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
Incidence of postoperative delirium is high even in a population without known risk factors.
2014 Apr
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 [VANDF]
Common Name English
THIOPENTAL CIII
USP-RS  
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 Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
DEA NO. 2100
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
WHO-ATC N05CA19
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
NCI_THESAURUS C245
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
WHO-VATC QN05CA19
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
WHO-ATC N01AF03
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
WHO-VATC QN01AF03
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
200-984-3
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
PUBCHEM
3000715
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
ChEMBL
CHEMBL441
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
LACTMED
Thiopental
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
EVMPD
SUB04816MIG
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
EPA CompTox
76-75-5
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
USP_CATALOG
1661002
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY USP-RS
FDA UNII
JI8Z5M7NA3
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
DRUG BANK
DB00599
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
RXCUI
10493
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C72166
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
CAS
76-75-5
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
MESH
D013874
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
DRUG CENTRAL
2633
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
HSDB
7791
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY
IUPHAR
2579
Created by admin on Sat Jun 26 10:51:28 UTC 2021 , Edited by admin on Sat Jun 26 10:51:28 UTC 2021
PRIMARY