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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 (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
A comparison of propaniid and thiopentone as induction agents for electro-convulsive therapy.
1969 Jun
Case reports: thiopentone anaphylaxis.
1972 Aug
Thrombophlebitis following thiopentone injection.
1972 Nov
Adverse reactions following fazadinium-thiopentone induction.
1979 Jul-Aug
Venous complications after intravenous injection of diazepam, flunitrazepam, thiopentone and etomidate.
1980 Jun
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
[Use of thiopental in man. Determination of this drug and its metabolites in plasma and urine by liquid phase chromatography and mass spectrometry].
1986
Asystole associated with vecuronium.
1986 Aug
Drug-induced arterial spasm relieved by lidocaine. Case report.
1986 Nov
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
Thiopental infusion in the treatment of intracranial hypertension complicating fulminant hepatic failure.
1989 Sep
Evaluation of mast cell activation (tryptase) in two patients suffering from drug-induced hypotensoid reactions.
1991 May
The effects of thiopental sodium on fentanyl-induced muscle rigidity in a human model.
1991 Sep-Oct
Complications and side effects during thiopentone therapy in patients with severe head injuries.
1992 May
The influence of the timing of administration of thiopentone sodium on nitric oxide-mediated neurotoxicity in vitro.
2000 Mar 1
Effect of propofol at two injection rates or thiopentone on post-intubation apnoea in the dog.
2001 Feb
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Interaction of intravenous anesthetics with recombinant human M1-M3 muscarinic receptors expressed in chinese hamster ovary cells.
2002 Dec
Torsade de pointes and sudden death induced by thiopental and isoflurane anesthesia in dogs with cardiac electrical remodeling.
2002 Jan
Thiopental inhibits tumor necrosis factor alpha-induced activation of nuclear factor kappaB through suppression of kappaB kinase activity.
2003 Aug
Central nervous system toxicity following the administration of levobupivacaine for lumbar plexus block: A report of two cases.
2003 Mar-Apr
Seventy-four defibrillations for sotalol-induced torsades de pointes.
2004 Jul-Aug
Intermediates of Krebs cycle correct the depression of the whole body oxygen consumption and lethal cooling in barbiturate poisoning in rat.
2004 Oct 1
The effect of pretreatment with thiopental on reducing pain induced by rocuronium injection.
2005 Dec 31
Severe refractory status epilepticus owing to presumed encephalitis.
2005 Mar
Inhibitory effect of thiopental on ultra-rapid delayed rectifier K+ current in H9c2 cells.
2005 Oct
Intravenous propofol precipitates the hypotension induced by inadvertent epidural thiopental injection.
2006 Dec
Succinate and artificial maintenance of normal body temperature synergistically correct lethal disorders in thiopental coma rat.
2006 Jan 20
Synergism of isothermal regimen and sodium succinate in experimental therapy of barbiturate coma.
2006 Jul
Fulminant hyperammonaemia induced by thiopental coma in rats.
2006 Jul 25
Glutamate binding is altered in hippocampus and cortex of Wistar rats after pilocarpine-induced Status Epilepticus.
2007 Aug 31
Thiopental pharmacokinetics in newborn infants: a case report of overdose.
2009 Oct
[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 [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 Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
DEA NO. 2100
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
WHO-ATC N05CA19
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
NCI_THESAURUS C245
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
WHO-VATC QN05CA19
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
WHO-ATC N01AF03
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
WHO-VATC QN01AF03
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
Code System Code Type Description
ECHA (EC/EINECS)
200-984-3
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
PUBCHEM
3000715
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
ChEMBL
CHEMBL441
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
LACTMED
Thiopental
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
EVMPD
SUB04816MIG
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
EPA CompTox
DTXSID1023653
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
FDA UNII
JI8Z5M7NA3
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
RS_ITEM_NUM
1661002
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
DRUG BANK
DB00599
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
RXCUI
10493
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY RxNorm
NCI_THESAURUS
C72166
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
CAS
76-75-5
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
MESH
D013874
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
CHEBI
102166
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
DRUG CENTRAL
2633
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
HSDB
7791
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY
IUPHAR
2579
Created by admin on Fri Dec 16 20:27:58 UTC 2022 , Edited by admin on Fri Dec 16 20:27:58 UTC 2022
PRIMARY