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Details

Stereochemistry RACEMIC
Molecular Formula C12H18N2O2S
Molecular Weight 254.3501
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIAMYLAL

SMILES

CCCC(C)C1(CC=C)C(=NC(=S)N=C1O)O

InChI

InChIKey=XLOMZPUITCYLMJ-UHFFFAOYSA-N
InChI=1S/C12H18N2O2S/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)

HIDE SMILES / InChI
Thiamylal is a barbiturate that is administered intravenously for the production of complete anesthesia of short duration, for the induction of general anesthesia, or for inducing a hypnotic state. Thiamylal, a barbiturate, is used in combination with acetaminophen or aspirin and caffeine for its sedative and relaxant effects in the treatment of tension headaches, migraines, and pain. Barbiturates act as nonselective depressants of the central nervous system (CNS), capable of producing all levels of CNS mood alteration from excitation to mild sedation, hypnosis, and deep coma. In sufficiently high therapeutic doses, barbiturates induce anesthesia. Thiamylal 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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Surital

Approved Use

Surital Indication: Used for the production of complete anesthesia of short duration, for the induction of general anesthesia, and for inducing a hypnotic state.

Launch Date

-599616000000
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7.2%
18 μmol single, unknown
dose: 18 μmol
route of administration: UNKNOWN
experiment type: SINGLE
co-administered:
THIAMYLAL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
6.7%
9 μmol single, unknown
dose: 9 μmol
route of administration: UNKNOWN
experiment type: SINGLE
co-administered:
THIAMYLAL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8.2%
90 μmol single, unknown
dose: 90 μmol
route of administration: UNKNOWN
experiment type: SINGLE
co-administered:
THIAMYLAL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
25 mg/kg single, rectal
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
Health Status: healthy
Age Group: 3 months - 12 years
Sources:
Other AEs: Anal irritation, Discharge...
Other AEs:
Anal irritation (58%)
Discharge (58%)
Sleepiness (14%)
Nausea (15%)
Vomiting (15%)
Stumbling (13%)
Sources:
10 mg/kg single, rectal
Dose: 10 mg/kg
Route: rectal
Route: single
Dose: 10 mg/kg
Sources:
healthy, 3 years (range: 20 days–20 years)
Health Status: healthy
Age Group: 3 years (range: 20 days–20 years)
Sources:
9.3 mg/kg single, intravenous
Highest studied dose
Dose: 9.3 mg/kg
Route: intravenous
Route: single
Dose: 9.3 mg/kg
Sources:
healthy, 31.5 months (range: 14.0–56.8 months)
Health Status: healthy
Age Group: 31.5 months (range: 14.0–56.8 months)
Sources:
AEs

AEs

AESignificanceDosePopulation
Stumbling 13%
25 mg/kg single, rectal
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
Health Status: healthy
Age Group: 3 months - 12 years
Sources:
Sleepiness 14%
25 mg/kg single, rectal
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
Health Status: healthy
Age Group: 3 months - 12 years
Sources:
Nausea 15%
25 mg/kg single, rectal
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
Health Status: healthy
Age Group: 3 months - 12 years
Sources:
Vomiting 15%
25 mg/kg single, rectal
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
Health Status: healthy
Age Group: 3 months - 12 years
Sources:
Anal irritation 58%
25 mg/kg single, rectal
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
Health Status: healthy
Age Group: 3 months - 12 years
Sources:
Discharge 58%
25 mg/kg single, rectal
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
Health Status: healthy
Age Group: 3 months - 12 years
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [Activation >12.5893 uM]
yes [Activation 12.5893 uM]
yes [EC50 4.1 uM]
yes [EC50 6.4 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
A hypotensive episode caused by amitriptyline?
1969 Oct 4
Lack of compensatory increase in plasma free-norepinephrine during hypotension induced by intravenous thiamylal anesthesia.
1973 Jul
Intravenous anesthetics differentially reduce neurotransmission damage caused by oxygen-glucose deprivation in rat hippocampal slices in correlation with N-methyl-D-aspartate receptor inhibition.
2001 Apr
Effects of volatile and intravenous anesthetics on the uptake of GABA, glutamate and dopamine by their transporters heterologously expressed in COS cells and in rat brain synaptosomes.
2001 Aug 6
[Stump pain relieved by continuous intravenous ketamine infusion therapy].
2001 Jul
[Whole body heat production as a quantitative marker of anesthetic management under general anesthesia].
2001 Jun
Effects of propofol on ischemia and reperfusion in the isolated rat heart compared with thiamylal.
2001 Mar
Cesarean section in a patient with syringomyelia.
2001 May
A huge frontal meningioma associated with intraoperative massive bleeding and severe brain swelling--case report.
2001 May
Increased sensitivity to vecuronium and prolonged duration of its action in patients with end-stage renal failure.
2001 May
Values of the bispectral index do not parallel the hemodynamic response to the rapid increase in isoflurane concentration.
2001 Nov
[Anesthetic management of a patient with Dyggve-Melchior-Clausen syndrome].
2001 Oct
[Anesthesia for electroconvulsive therapy during pregnancy--a case report].
2001 Sep
Tracheal lidocaine attenuates the cardiovascular response to endotracheal intubation.
2001 Sep
Intravenous colforsin daropate, a water-soluble forskolin derivative, prevents thiamylal-fentanyl-induced bronchoconstriction in humans.
2002 Apr
A study of the in vitro clinical interaction between lidocaine and premedications using rat liver microsomes.
2002 Aug
[Anesthetic management of a patient with dentato-rubro-pallido-luysian atrophy].
2002 Aug
[Anesthetic management for elective cesarean section due to placenta previa in a patient with moyamoya disease].
2002 Dec
Effects of thiamylal, sevoflurane and isoflurane on the cortically recorded somatosensory evoked potentials.
2002 Dec
Anesthetic management for a patient with Jansky-Bielschowsky disease.
2002 Jan
Perioperative factors associated with puppy vigor after delivery by cesarean section.
2002 Jan-Feb
["Cannot-ventilate" after anesthetic induction in a patient with rapidly increased laryngeal tumor].
2002 Jul
[Quantitative analysis of plasma concentration of barbiturate for diagnosis of brain death].
2002 Jun
Electroconvulsive therapy with thiamylal or propofol during pregnancy.
2002 Mar
[Anesthetic management of a patient with Evans syndrome--benefit of perioperative hemodilutional autologous blood transfusion].
2002 Nov
Barbiturates induce mitochondrial depolarization and potentiate excitotoxic neuronal death.
2002 Nov 1
Hemodynamic and bispectral index responses to tracheal intubation during isoflurane or sevoflurane anesthesia.
2003
Intravenous nicorandil prevents thiamylal-fentanyl-induced bronchoconstriction in humans.
2003 Feb
The ED(95) of end-tidal sevoflurane concentration for the smooth exchange of the tracheal tube for a laryngeal mask airway is 2.97%.
2003 Feb
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 propofol on endotoxin-induced acute lung injury in rabbit.
2004 Feb
[Refractory generalized convulsions in a patient undergoing brain tumor resection during propofol anesthesia].
2004 Jun
[Lockjaw caused by induction of anesthesia in a volunteer bone marrow donor].
2004 Mar
[Complete neurological recovery in a patient with decerebrate rigidity following cardiac arrest from acute airway obstruction by advanced laryngeal cancer].
2004 Mar
Premedication medicines do not cause drug metabolic interaction with propofol using human liver microsomes in vitro.
2004 Oct
A study of the in vitro interaction between lidocaine and premedications using human liver microsomes.
2005 Apr
[Anesthetic management in a patient with Goldenhar's syndrome using a perilaryngeal airway and a videolaryngoscope].
2005 Dec
In vivo interaction of pulmonary intravascular macrophages with activated platelets in microvessels of equine lung after multiple exposures to halothane, isoflurane, and thiamylal: a comparative ultrastructural and cytochemical study.
2005 Jun
[Nitroglycerin to relax the uterus during cesarean delivery for the low birthweight baby].
2005 Mar
Efficacy and adverse effects of rectal thiamylal with oral triclofos for children undergoing magnetic resonance imaging.
2006 Apr
Utility of the auditory evoked potentials index as an indicator for endotracheal intubation.
2006 Dec
[Awareness during anesthesia with sevoflurane: a case report].
2006 Oct
Lethal injection for execution: chemical asphyxiation?
2007 Apr
[A boy with nystagmus, refractory dystonia and apneic attack due to alternating hemiplegia of childhood].
2007 Jul
[Airway access using an endotracheal tube changer for safe extubation in an infant with a difficult airway].
2008 Feb
Immediate impact of electroconvulsive therapy on cardiac autonomic function in schizophrenia: a preliminary study.
2008 Mar
Anaesthesia for in vitro fertilisation.
2009 Aug
Effects of propofol on beta-adrenoceptor-mediated signal transduction in cardiac muscle; role of cAMP.
2010 Apr
Electromyographic study of differential sensitivity to succinylcholine of the diaphragm, laryngeal and somatic muscles: a swine model.
2010 Dec
A comparison of the effect on QT interval between thiamylal and propofol during anaesthetic induction*.
2010 Jul
Patents

Sample Use Guides

In human medicine, thiamylal is used by the intravenous route as a 2.5% solution at an average dose ranging from 1 to 10 mg/kg bw.
Route of Administration: Intravenous
In Vitro Use Guide
In helical strips of dog cerebral, coronary, mesenteric, renal, and femoral arteries, the addition of thiamylal and thiopental, 10(-5) to 10(-3) M, caused a dose-related contraction.The persistent contraction was potentiated by 10(-4) M thiamylal but abolished at 10(-3) M. In the mesenteric artery soaked in Ca++-free media, the addition of Ca++ produced only a slight contraction, which was potentiated by thiamylal (10(-4) and 10(-3) M).
Name Type Language
THIAMYLAL
MI   VANDF   WHO-DD  
Common Name English
THIAMYLAL [MI]
Common Name English
THIAMYLAL [VANDF]
Common Name English
NSC-120815
Code English
THIAMYLAL [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67084
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
WHO-VATC QN01AF90
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
DEA NO. 2100
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
NCI_THESAURUS C245
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
Code System Code Type Description
DRUG BANK
DB01154
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
FDA UNII
01T23W89FR
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
NCI_THESAURUS
C66596
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
ChEMBL
CHEMBL440
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
EPA CompTox
77-27-0
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
MESH
D013840
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
PUBCHEM
3032285
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
EVMPD
SUB15530MIG
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
WIKIPEDIA
THIAMYLAL
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
MERCK INDEX
M10724
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY Merck Index
IUPHAR
7305
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
DRUG CENTRAL
2626
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
CAS
77-27-0
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-018-3
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY
RXCUI
10464
Created by admin on Sat Jun 26 00:06:50 UTC 2021 , Edited by admin on Sat Jun 26 00:06:50 UTC 2021
PRIMARY RxNorm