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
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)
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 |
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Target ID: CHEMBL2095198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14739809 |
183.0 µM [EC50] | ||
Target ID: Q14654 Gene ID: 3767.0 Gene Symbol: KCNJ11 Target Organism: Homo sapiens (Human) Sources: https://www.drugbank.ca/drugs/DB01154 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Surital Approved UseSurital 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
Value | Dose | Co-administered | Analyte | Population |
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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 |
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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 |
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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 (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%) Sources: Discharge (58%) Sleepiness (14%) Nausea (15%) Vomiting (15%) Stumbling (13%) |
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: |
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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
AE | Significance | Dose | Population |
---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | ||||
minor | ||||
minor |
PubMed
Title | Date | PubMed |
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Lack of compensatory increase in plasma free-norepinephrine during hypotension induced by intravenous thiamylal anesthesia. | 1973 Jul |
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Arrhythmias in dogs associated with epinephrine and thiamylal anesthesia. | 1975 Sep |
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Arrhythmogenic properties of thiamylal sodium in the dog. | 1976 Jan 15 |
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Hypertension in bulls and steers anesthetized with guaifenesin-thiobarbiturate-halothane combination. | 1986 Jul |
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Treatment of acute systemic toxicity after the rapid intravenous injection of ropivacaine and bupivacaine in the conscious dog. | 1991 Oct |
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Propofol versus thiamylal-enflurane anesthesia for outpatient laparoscopy. | 1992 May-Jun |
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Effects of thiamylal, sevoflurane and isoflurane on the cortically recorded somatosensory evoked potentials. | 2002 Dec |
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[Anesthetic management of a patient with Evans syndrome--benefit of perioperative hemodilutional autologous blood transfusion]. | 2002 Nov |
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Hemodynamic and bispectral index responses to tracheal intubation during isoflurane or sevoflurane anesthesia. | 2003 |
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[Propofol was useful for intractable convulsion in a patient with tetanus: a case report]. | 2003 Feb |
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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 |
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Effects of the intravenously administered anaesthetics ketamine, propofol, and thiamylal on the cortical renal blood flow in rats. | 2003 May |
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Thiamylal and pentobarbital have opposite effects on human platelet aggregation in vitro. | 2003 Nov |
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Effects of propofol on endotoxin-induced acute lung injury in rabbit. | 2004 Feb |
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Molecular mechanisms of the inhibitory effects of propofol and thiamylal on sarcolemmal adenosine triphosphate-sensitive potassium channels. | 2004 Feb |
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[Lockjaw caused by induction of anesthesia in a volunteer bone marrow donor]. | 2004 Mar |
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Premedication medicines do not cause drug metabolic interaction with propofol using human liver microsomes in vitro. | 2004 Oct |
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[Effects of propofol and thiamylal on nicorandil induced ATP-sensitive potassium channel activities in cultured rat aortic smooth muscle cells]. | 2005 Apr |
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A study of the in vitro interaction between lidocaine and premedications using human liver microsomes. | 2005 Apr |
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[Pressor responses to inhalation of isoflurane during induction of anesthesia and subsequent tracheal intubation]. | 2005 Aug |
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[Anesthetic management in a patient with Goldenhar's syndrome using a perilaryngeal airway and a videolaryngoscope]. | 2005 Dec |
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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 |
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Deep sedation with methohexital or thiamylal with midazolam for invasive procedures in children with acute lymphoblastic leukemia. | 2005 Sep-Oct |
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Efficacy and adverse effects of rectal thiamylal with oral triclofos for children undergoing magnetic resonance imaging. | 2006 Apr |
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Utility of the auditory evoked potentials index as an indicator for endotracheal intubation. | 2006 Dec |
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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 |
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[Reduction of the concentration of isoflurane prevents tachycardia and hypertension associated with tracheal intubation]. | 2006 May |
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Effect of prophylactic bronchodilator treatment with i.v. carperitide on airway resistance and lung compliance after tracheal intubation. | 2006 May |
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[Awareness during anesthesia with sevoflurane: a case report]. | 2006 Oct |
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[A boy with nystagmus, refractory dystonia and apneic attack due to alternating hemiplegia of childhood]. | 2007 Jul |
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[Clinical usefulness of remifentanil]. | 2007 Nov |
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Unilateral fixed dilated pupil during plastic surgery--a case report. | 2007 Sep |
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[Case of general anesthesia combined with epidural anesthesia in a pregnant woman undergoing thoracotomy for spontaneous pneumothorax]. | 2008 Feb |
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[Airway access using an endotracheal tube changer for safe extubation in an infant with a difficult airway]. | 2008 Feb |
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Immediate impact of electroconvulsive therapy on cardiac autonomic function in schizophrenia: a preliminary study. | 2008 Mar |
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[Anesthetic management of the ex-utero intrapartum treatment (EXIT) procedure for giant epignathus and of the tumor excision]. | 2008 Oct |
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[Grand mal convulsion after an interscalene block with ropivacaine]. | 2009 Apr |
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Anaesthesia for in vitro fertilisation. | 2009 Aug |
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[Anesthetic management for a patient with significant orthostatic hypotension probably due to pure autonomic failure]. | 2009 Aug |
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Thiamylal antagonizes the inhibitory effects of dorsal column stimulation on dorsal horn activities in humans. | 2009 Aug |
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[Case report of dentatorubral pallidoluysian atrophy in a patient on a ketogenic diet]. | 2009 Jun |
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Thiamylal and thiopental attenuate beta-adrenergic signaling pathway by suppressing adenylyl cyclase in rat ventricular myocytes. | 2009 Mar |
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[Hypertension with tachycardia caused by propofol during induction of general anesthesia]. | 2009 May |
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[General anesthesia for cesarean section in a patient with moyamoya disease]. | 2009 May |
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Novel inhibitors of the calcineurin/NFATc hub - alternatives to CsA and FK506? | 2009 Oct 27 |
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The intravenous anesthetics barbiturates inhibit hypoxia-inducible factor 1 activation. | 2009 Sep 1 |
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Effects of propofol on beta-adrenoceptor-mediated signal transduction in cardiac muscle; role of cAMP. | 2010 Apr |
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Intravenous thiamylal and local anesthetic infiltration for pediatric facial repair procedures performed in emergency departments. | 2010 Apr |
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Electromyographic study of differential sensitivity to succinylcholine of the diaphragm, laryngeal and somatic muscles: a swine model. | 2010 Dec |
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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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2751144
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).
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Code | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C67084
Created by
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WHO-VATC |
QN01AF90
Created by
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DEA NO. |
2100
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NCI_THESAURUS |
C245
Created by
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Code System | Code | Type | Description | ||
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DB01154
Created by
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PRIMARY | |||
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01T23W89FR
Created by
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PRIMARY | |||
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C66596
Created by
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PRIMARY | |||
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CHEMBL440
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PRIMARY | |||
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77-27-0
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PRIMARY | |||
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D013840
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PRIMARY | |||
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3032285
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PRIMARY | |||
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SUB15530MIG
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PRIMARY | |||
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THIAMYLAL
Created by
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PRIMARY | |||
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M10724
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PRIMARY | Merck Index | ||
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7305
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PRIMARY | |||
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2626
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PRIMARY | |||
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77-27-0
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PRIMARY | |||
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201-018-3
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PRIMARY | |||
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10464
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PRIMARY | RxNorm |
ACTIVE MOIETY