THIAMYLAL

Details

Stereochemistry	RACEMIC
Molecular Formula	C12H18N2O2S
Molecular Weight	254.349
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCC(C)C1(CC=C)C(=O)NC(=S)NC1=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

Molecular Formula	C12H18N2O2S
Molecular Weight	254.349
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.drugbank.ca/drugs/DB01154 | http://www.minclinic.ru/drugs/drugs_eng/S/Surital.html

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
GABA-A receptor; anion channel 203 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11900777 \| https://www.drugbank.ca/drugs/DB01154 \| http://drugcentral.org/drugcard/2626	Positive Allosteric Modulator 186
Sulfonylurea receptor 2, Kir6.2 11 Target ID: CHEMBL2095198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14739809	Inhibitor 8504	183.0 µM [EC50]
ATP-sensitive inward rectifier potassium channel 11 10 Target ID: Q14654 Gene ID: 3767.0 Gene Symbol: KCNJ11 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB01154	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.minclinic.ru/drugs/drugs_eng/S/Surital.html	Primary		Approved 8583	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 1951

F_unbound

Value	Dose	Analyte	Population
6.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10960410	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
7.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10960410	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
8.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10960410	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

Dose	Population	Adverse events
25 mg/kg single, rectal Dose: 25 mg/kg Route: rectal Route: single Dose: 25 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7900578	healthy, 3 months - 12 years Health Status: healthy Age Group: 3 months - 12 years Sources: https://pubmed.ncbi.nlm.nih.gov/7900578	Other AEs: Anal irritation, Discharge... Other AEs: Anal irritation (58%) Discharge (58%) Sleepiness (14%) Nausea (15%) Vomiting (15%) Stumbling (13%) Sources: https://pubmed.ncbi.nlm.nih.gov/7900578
10 mg/kg single, rectal Dose: 10 mg/kg Route: rectal Route: single Dose: 10 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/16368209	healthy, 3 years (range: 20 days–20 years) Health Status: healthy Age Group: 3 years (range: 20 days–20 years) Sources: https://pubmed.ncbi.nlm.nih.gov/16368209	Sources: https://pubmed.ncbi.nlm.nih.gov/16368209
9.3 mg/kg single, intravenous Highest studied dose Dose: 9.3 mg/kg Route: intravenous Route: single Dose: 9.3 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/32359890	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: https://pubmed.ncbi.nlm.nih.gov/32359890	Sources: https://pubmed.ncbi.nlm.nih.gov/32359890

AEs

AE	Significance	Dose	Population
Stumbling	13%	25 mg/kg single, rectal Dose: 25 mg/kg Route: rectal Route: single Dose: 25 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7900578	healthy, 3 months - 12 years Health Status: healthy Age Group: 3 months - 12 years Sources: https://pubmed.ncbi.nlm.nih.gov/7900578
Sleepiness	14%	25 mg/kg single, rectal Dose: 25 mg/kg Route: rectal Route: single Dose: 25 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7900578	healthy, 3 months - 12 years Health Status: healthy Age Group: 3 months - 12 years Sources: https://pubmed.ncbi.nlm.nih.gov/7900578
Nausea	15%	25 mg/kg single, rectal Dose: 25 mg/kg Route: rectal Route: single Dose: 25 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7900578	healthy, 3 months - 12 years Health Status: healthy Age Group: 3 months - 12 years Sources: https://pubmed.ncbi.nlm.nih.gov/7900578
Vomiting	15%	25 mg/kg single, rectal Dose: 25 mg/kg Route: rectal Route: single Dose: 25 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7900578	healthy, 3 months - 12 years Health Status: healthy Age Group: 3 months - 12 years Sources: https://pubmed.ncbi.nlm.nih.gov/7900578
Anal irritation	58%	25 mg/kg single, rectal Dose: 25 mg/kg Route: rectal Route: single Dose: 25 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7900578	healthy, 3 months - 12 years Health Status: healthy Age Group: 3 months - 12 years Sources: https://pubmed.ncbi.nlm.nih.gov/7900578
Discharge	58%	25 mg/kg single, rectal Dose: 25 mg/kg Route: rectal Route: single Dose: 25 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/7900578	healthy, 3 months - 12 years Health Status: healthy Age Group: 3 months - 12 years Sources: https://pubmed.ncbi.nlm.nih.gov/7900578

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252 inducer 1087 activator 150	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079 OATP1B3 961	CYP2E1 729

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	activator 342 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTIwMTA2NSJ9fQ%3D%3D	no [Activation >12.5893 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTIwMTA2NSJ9fQ%3D%3D	yes [Activation 12.5893 uM]
PXR 51	activator 342 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50103607, https://pubmed.ncbi.nlm.nih.gov/20966043/	yes [EC50 4.1 uM]
CYP3A4 2633	inducer 1966 Sources: https://go.drugbank.com/drugs/DB01154\| http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50103607\| https://pubmed.ncbi.nlm.nih.gov/20966043/	yes [EC50 6.4 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEwNjUifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEyMDEwNjUifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]

Drug as victim

Target	Modality	Activity
CYP2C9 1193	substrate 4014 Sources: https://go.drugbank.com/drugs/DB01154, https://pubmed.ncbi.nlm.nih.gov/10960410/	major
CYP2E1 729	substrate 4014 Sources: https://go.drugbank.com/drugs/DB01154, https://pubmed.ncbi.nlm.nih.gov/10960410/	minor
CYP3A4 1946	substrate 4014 Sources: https://go.drugbank.com/drugs/DB01154, https://pubmed.ncbi.nlm.nih.gov/10960410/	minor

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:9536	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9536
eMolecules	595235	https://www.emolecules.com/cgi-bin/more?vid=595235

PubMed

Title	Date	PubMed
Electromyographic study of differential sensitivity to succinylcholine of the diaphragm, laryngeal and somatic muscles: a swine model.	2010-12	21186012
A comparison of the effect on QT interval between thiamylal and propofol during anaesthetic induction*.	2010-07	20528837
Effects of propofol on beta-adrenoceptor-mediated signal transduction in cardiac muscle; role of cAMP.	2010-04	20508795
Intravenous thiamylal and local anesthetic infiltration for pediatric facial repair procedures performed in emergency departments.	2010-04	20434100
Novel inhibitors of the calcineurin/NFATc hub - alternatives to CsA and FK506?	2009-10-27	19860902
The intravenous anesthetics barbiturates inhibit hypoxia-inducible factor 1 activation.	2009-09-01	19595685
Anaesthesia for in vitro fertilisation.	2009-08	20640202
[Anesthetic management for a patient with significant orthostatic hypotension probably due to pure autonomic failure].	2009-08	19702221
Thiamylal antagonizes the inhibitory effects of dorsal column stimulation on dorsal horn activities in humans.	2009-08	19393696
[Case report of dentatorubral pallidoluysian atrophy in a patient on a ketogenic diet].	2009-06	19522273
[Hypertension with tachycardia caused by propofol during induction of general anesthesia].	2009-05	19462811
[General anesthesia for cesarean section in a patient with moyamoya disease].	2009-05	19462810
[Grand mal convulsion after an interscalene block with ropivacaine].	2009-04	19364012
Thiamylal and thiopental attenuate beta-adrenergic signaling pathway by suppressing adenylyl cyclase in rat ventricular myocytes.	2009-03	19400552
[Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision].	2008-10	18975539
Immediate impact of electroconvulsive therapy on cardiac autonomic function in schizophrenia: a preliminary study.	2008-03	18060743
[Case of general anesthesia combined with epidural anesthesia in a pregnant woman undergoing thoracotomy for spontaneous pneumothorax].	2008-02	18277570
[Airway access using an endotracheal tube changer for safe extubation in an infant with a difficult airway].	2008-02	18277563
[Clinical usefulness of remifentanil].	2007-11	18027598
Unilateral fixed dilated pupil during plastic surgery--a case report.	2007-09	17972621
[A boy with nystagmus, refractory dystonia and apneic attack due to alternating hemiplegia of childhood].	2007-07	17633086
Lethal injection for execution: chemical asphyxiation?	2007-04	17455994
Utility of the auditory evoked potentials index as an indicator for endotracheal intubation.	2006-12	17233364
[Awareness during anesthesia with sevoflurane: a case report].	2006-10	17051987
[Reduction of the concentration of isoflurane prevents tachycardia and hypertension associated with tracheal intubation].	2006-05	16715914
Effect of prophylactic bronchodilator treatment with i.v. carperitide on airway resistance and lung compliance after tracheal intubation.	2006-05	16531446
Deep sedation with methohexital or thiamylal with midazolam for invasive procedures in children with acute lymphoblastic leukemia.	2006-04-28	16640004
Efficacy and adverse effects of rectal thiamylal with oral triclofos for children undergoing magnetic resonance imaging.	2006-04	16368209
Effects of premedication medicines on the formation of the CYP3A4-dependent metabolite of ropivacaine, 2', 6'-Pipecoloxylidide, on human liver microsomes in vitro.	2006-02	16445592
[Anesthetic management in a patient with Goldenhar's syndrome using a perilaryngeal airway and a videolaryngoscope].	2005-12	16370341
[Pressor responses to inhalation of isoflurane during induction of anesthesia and subsequent tracheal intubation].	2005-08	16104539
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.	2005-06	15880489
[Effects of propofol and thiamylal on nicorandil induced ATP-sensitive potassium channel activities in cultured rat aortic smooth muscle cells].	2005-04	15852621
A study of the in vitro interaction between lidocaine and premedications using human liver microsomes.	2005-04	15811173
[Nitroglycerin to relax the uterus during cesarean delivery for the low birthweight baby].	2005-03	15794106
[A survival case of tetanus complicated with disseminated intravascular coagulation syndrome in the elderly, rescued by mechanical ventilation and administration of thiamylal].	2005-01	15717480
[Case of premature ventricular contraction immediately after electroconvulsive therapy in a depressive patient].	2005-01	15717468
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.	2004-12	15263067
[Anesthetic management for cesarean section in a patient with corrected transposition of great arteries].	2004-11	15587180
Premedication medicines do not cause drug metabolic interaction with propofol using human liver microsomes in vitro.	2004-10	15351923
Extraction of thiamylal in serum using hydrophilic acetonitrile with subzero-temperature and salting-out methods.	2004-08-15	15307775
[Refractory generalized convulsions in a patient undergoing brain tumor resection during propofol anesthesia].	2004-06	15242047
[A case of adult Reye's syndrome with favorable outcome despite status epilepticus].	1996-11	9046859
Propofol versus thiamylal-enflurane anesthesia for outpatient laparoscopy.	1992-05-01	1535202
Treatment of acute systemic toxicity after the rapid intravenous injection of ropivacaine and bupivacaine in the conscious dog.	1991-10	1897763
Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination.	1986-07	3740628
Arrhythmogenic properties of thiamylal sodium in the dog.	1976-01-15	54351
Arrhythmias in dogs associated with epinephrine and thiamylal anesthesia.	1975-09	51600
Lack of compensatory increase in plasma free-norepinephrine during hypotension induced by intravenous thiamylal anesthesia.	1973-07	4730132
A hypotensive episode caused by amitriptyline?	1969-10-04	4186181

Patents

Sample Use Guides

In Vivo Use Guide

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).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:33:27 GMT 2025` Edited by `admin` on `Mon Mar 31 18:33:27 GMT 2025`
Record UNII	01T23W89FR
Record Status	`Validated (UNII)`
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Name

Type

Language

THIAMYLAL

Common Name

English

NSC-120815

Preferred Name

English

THIAMYLAL [MI]

Common Name

English

THIAMYLAL [VANDF]

Common Name

English

Thiamylal [WHO-DD]

Common Name

English

5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acid

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67084