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Details

Stereochemistry RACEMIC
Molecular Formula C11H17N2O2S.Na
Molecular Weight 264.3212
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIOPENTAL SODIUM

SMILES

CCCC(C)C1(CC)C(=NC(=S)N=C1[O-])O.[Na+]

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 242.3393
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

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
Case reports: thiopentone anaphylaxis.
1972 Aug
Thrombophlebitis following thiopentone injection.
1972 Nov
Abdominal-muscle rigidity induced by morphine and nitrous oxide.
1973 Apr
A water-soluble benzodiazepine, RO21-3981, for induction of anesthesia.
1978 Jul
Postischemic brain oxygenation with barbiturate therapy in rats.
1979 Aug
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
[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
Asystole associated with vecuronium.
1986 Aug
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
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
Hyperammoniemia in rats with barbiturate coma.
2007 Mar
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
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
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:00:37 UTC 2021
Edited
by admin
on Fri Jun 25 21:00:37 UTC 2021
Record UNII
49Y44QZL70
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIOPENTAL SODIUM
GREEN BOOK   INN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
TRAPANAL
Brand Name English
THIOPENTAL SODIUM [WHO-DD]
Common 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
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
LEOPENTAL
Common Name English
HYPNOSTAN
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67084
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
NCI_THESAURUS C245
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
CFR 21 CFR 522.2444
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
DEA NO. 2100
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
CFR 21 CFR 522.2444A
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
CFR 21 CFR 522.2444B
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
THIOPENTAL SODIUM
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
PRIMARY Description: A yellowish white powder; odour, characteristic. Solubility: Freely soluble in water and ethanol (~750 g/l) TS; practically insoluble in ether R. Category: General anaesthetic. Storage: Thiopental sodium should be kept in a tightly closed container, protected from light. Additional information: Thiopental sodium is hygroscopic. Even in the absence of light, it is gradually degraded on exposure to a humid atmosphere, the decomposition being faster at higher temperatures. Requirements: Thiopental sodium contains not less than 97.0% and not more than the equivalent of 102.0% of C11H17N2NaO2S, calculated with reference to the dried substance.
CAS
71-73-8
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
PRIMARY
EPA CompTox
71-73-8
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-763-1
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
PRIMARY
MERCK INDEX
M10773
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
PRIMARY Merck Index
PUBCHEM
12832575
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
PRIMARY
INN
433
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
PRIMARY
EVMPD
SUB10981MIG
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
PRIMARY
RXCUI
282416
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
PRIMARY RxNorm
DRUG BANK
DBSALT001409
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
PRIMARY
EVMPD
SUB04816MIG
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
PRIMARY
ChEMBL
CHEMBL441
Created by admin on Fri Jun 25 21:00:37 UTC 2021 , Edited by admin on Fri Jun 25 21:00:37 UTC 2021
PRIMARY
WIKIPEDIA
Sodium thiopental
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
PRIMARY
FDA UNII
49Y44QZL70
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
PRIMARY
NCI_THESAURUS
C66599
Created by admin on Fri Jun 25 21:00:38 UTC 2021 , Edited by admin on Fri Jun 25 21:00:38 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY