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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

-5.99616E11
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 (starting)
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
n = 462
Health Status: healthy
Age Group: 3 months - 12 years
Population Size: 462
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
Co-administed with::
triclofos(80–100 mg/kg, orally)
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 (starting)
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
n = 462
Health Status: healthy
Age Group: 3 months - 12 years
Population Size: 462
Sources:
Sleepiness 14%
25 mg/kg single, rectal (starting)
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
n = 462
Health Status: healthy
Age Group: 3 months - 12 years
Population Size: 462
Sources:
Nausea 15%
25 mg/kg single, rectal (starting)
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
n = 462
Health Status: healthy
Age Group: 3 months - 12 years
Population Size: 462
Sources:
Vomiting 15%
25 mg/kg single, rectal (starting)
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
n = 462
Health Status: healthy
Age Group: 3 months - 12 years
Population Size: 462
Sources:
Anal irritation 58%
25 mg/kg single, rectal (starting)
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
n = 462
Health Status: healthy
Age Group: 3 months - 12 years
Population Size: 462
Sources:
Discharge 58%
25 mg/kg single, rectal (starting)
Dose: 25 mg/kg
Route: rectal
Route: single
Dose: 25 mg/kg
Sources:
healthy, 3 months - 12 years
n = 462
Health Status: healthy
Age Group: 3 months - 12 years
Population Size: 462
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
Lack of compensatory increase in plasma free-norepinephrine during hypotension induced by intravenous thiamylal anesthesia.
1973 Jul
Arrhythmias in dogs associated with epinephrine and thiamylal anesthesia.
1975 Sep
Arrhythmogenic properties of thiamylal sodium in the dog.
1976 Jan 15
Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination.
1986 Jul
Treatment of acute systemic toxicity after the rapid intravenous injection of ropivacaine and bupivacaine in the conscious dog.
1991 Oct
Propofol versus thiamylal-enflurane anesthesia for outpatient laparoscopy.
1992 May-Jun
Effects of thiamylal, sevoflurane and isoflurane on the cortically recorded somatosensory evoked potentials.
2002 Dec
[Anesthetic management of a patient with Evans syndrome--benefit of perioperative hemodilutional autologous blood transfusion].
2002 Nov
Hemodynamic and bispectral index responses to tracheal intubation during isoflurane or sevoflurane anesthesia.
2003
[Propofol was useful for intractable convulsion in a patient with tetanus: a case report].
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
Effects of the intravenously administered anaesthetics ketamine, propofol, and thiamylal on the cortical renal blood flow in rats.
2003 May
Thiamylal and pentobarbital have opposite effects on human platelet aggregation in vitro.
2003 Nov
Effects of propofol on endotoxin-induced acute lung injury in rabbit.
2004 Feb
Molecular mechanisms of the inhibitory effects of propofol and thiamylal on sarcolemmal adenosine triphosphate-sensitive potassium channels.
2004 Feb
[Lockjaw caused by induction of anesthesia in a volunteer bone marrow donor].
2004 Mar
Premedication medicines do not cause drug metabolic interaction with propofol using human liver microsomes in vitro.
2004 Oct
[Effects of propofol and thiamylal on nicorandil induced ATP-sensitive potassium channel activities in cultured rat aortic smooth muscle cells].
2005 Apr
A study of the in vitro interaction between lidocaine and premedications using human liver microsomes.
2005 Apr
[Pressor responses to inhalation of isoflurane during induction of anesthesia and subsequent tracheal intubation].
2005 Aug
[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
Deep sedation with methohexital or thiamylal with midazolam for invasive procedures in children with acute lymphoblastic leukemia.
2005 Sep-Oct
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
Effects of premedication medicines on the formation of the CYP3A4-dependent metabolite of ropivacaine, 2', 6'-Pipecoloxylidide, on human liver microsomes in vitro.
2006 Feb
[Reduction of the concentration of isoflurane prevents tachycardia and hypertension associated with tracheal intubation].
2006 May
Effect of prophylactic bronchodilator treatment with i.v. carperitide on airway resistance and lung compliance after tracheal intubation.
2006 May
[Awareness during anesthesia with sevoflurane: a case report].
2006 Oct
[A boy with nystagmus, refractory dystonia and apneic attack due to alternating hemiplegia of childhood].
2007 Jul
[Clinical usefulness of remifentanil].
2007 Nov
Unilateral fixed dilated pupil during plastic surgery--a case report.
2007 Sep
[Case of general anesthesia combined with epidural anesthesia in a pregnant woman undergoing thoracotomy for spontaneous pneumothorax].
2008 Feb
[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
[Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision].
2008 Oct
[Grand mal convulsion after an interscalene block with ropivacaine].
2009 Apr
Anaesthesia for in vitro fertilisation.
2009 Aug
[Anesthetic management for a patient with significant orthostatic hypotension probably due to pure autonomic failure].
2009 Aug
Thiamylal antagonizes the inhibitory effects of dorsal column stimulation on dorsal horn activities in humans.
2009 Aug
[Case report of dentatorubral pallidoluysian atrophy in a patient on a ketogenic diet].
2009 Jun
Thiamylal and thiopental attenuate beta-adrenergic signaling pathway by suppressing adenylyl cyclase in rat ventricular myocytes.
2009 Mar
[Hypertension with tachycardia caused by propofol during induction of general anesthesia].
2009 May
[General anesthesia for cesarean section in a patient with moyamoya disease].
2009 May
Novel inhibitors of the calcineurin/NFATc hub - alternatives to CsA and FK506?
2009 Oct 27
The intravenous anesthetics barbiturates inhibit hypoxia-inducible factor 1 activation.
2009 Sep 1
Effects of propofol on beta-adrenoceptor-mediated signal transduction in cardiac muscle; role of cAMP.
2010 Apr
Intravenous thiamylal and local anesthetic infiltration for pediatric facial repair procedures performed in emergency departments.
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