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Details

Stereochemistry RACEMIC
Molecular Formula C12H17N2O2S.Na
Molecular Weight 276.33
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIAMYLAL SODIUM

SMILES

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

InChI

InChIKey=LYZGJWXNOGIVQA-UHFFFAOYSA-M
InChI=1S/C12H18N2O2S.Na/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);/q;+1/p-1

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
Functional imaging of the brain in sedated newborn infants using near infrared topography during passive knee movement.
2001 Feb 23
EEG-bispectral index changes with ketamine versus thiamylal induction of anesthesia.
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
Values of the bispectral index do not parallel the hemodynamic response to the rapid increase in isoflurane concentration.
2001 Nov
Tracheal lidocaine attenuates the cardiovascular response to endotracheal intubation.
2001 Sep
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
Perioperative factors associated with puppy vigor after delivery by cesarean section.
2002 Jan-Feb
[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
[Propofol was useful for intractable convulsion in a patient with tetanus: a case report].
2003 Feb
Intravenous nicorandil prevents thiamylal-fentanyl-induced bronchoconstriction in humans.
2003 Feb
Effect of prophylactic bronchodilator treatment with intravenous colforsin daropate, a water-soluble forskolin derivative, on airway resistance after tracheal intubation.
2003 Jul
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
[Anesthetic management for cesarean section in a patient with corrected transposition of great arteries].
2004 Nov
[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
[Case of premature ventricular contraction immediately after electroconvulsive therapy in a depressive patient].
2005 Jan
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
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
[Case of general anesthesia combined with epidural anesthesia in a pregnant woman undergoing thoracotomy for spontaneous pneumothorax].
2008 Feb
[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
[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
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
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 SODIUM
GREEN BOOK   MART.   ORANGE BOOK   VANDF   WHO-DD  
Common Name English
4,6-(1H,5H)-PYRIMIDINEDIONE, DIHYDRO-5-(1-METHYLBUTYL)-5-(2-PROPENYL)-2-THIOXO-, MONOSODIUM SALT
Common Name English
THIAMYLAL SODIUM [MART.]
Common Name English
SURITAL
Brand Name English
THIAMYLAL SODIUM [GREEN BOOK]
Common Name English
NSC-759558
Code English
SODIUM THIAMYLAL
Common Name English
THIAMYLAL SODIUM [ORANGE BOOK]
Common Name English
Sodium 5-allyl-5-(1-methylbutyl)-2-thiobarbiturate
Systematic Name English
THIAMYLAL SODIUM SALT [MI]
Common Name English
THIAMYLAL SODIUM [VANDF]
Common Name English
THIAMYLAL SODIUM SALT
MI  
Common Name English
Thiamylal sodium [WHO-DD]
Common Name English
THIAMYLAL SODIUM [JAN]
Common Name English
Classification Tree Code System Code
DEA NO. 2100
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
CFR 21 CFR 522.2424
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
NCI_THESAURUS C67084
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
NCI_THESAURUS C245
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
Code System Code Type Description
SMS_ID
100000077013
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
RXCUI
203201
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY RxNorm
NSC
759558
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
CAS
337-47-3
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL440
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
MERCK INDEX
M10724
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID3045988
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
FDA UNII
T4L2P3KH7K
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-415-5
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
PUBCHEM
23677058
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
DRUG BANK
DBSALT001404
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
EVMPD
SUB15531MIG
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY
NCI_THESAURUS
C66597
Created by admin on Wed Jul 05 23:47:37 UTC 2023 , Edited by admin on Wed Jul 05 23:47:37 UTC 2023
PRIMARY