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: CHEMBL2095198 |
183 µM [EC50] | ||
Target ID: Q14654 Gene ID: 3767 Gene Symbol: KCNJ11 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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-599616000000 |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
|
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: |
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%) 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 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
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
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 |
|---|---|---|
| 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 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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NCI_THESAURUS |
C67084
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WHO-VATC |
QN01AF90
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DEA NO. |
2100
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NCI_THESAURUS |
C245
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DB01154
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01T23W89FR
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C66596
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CHEMBL440
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77-27-0
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D013840
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3032285
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SUB15530MIG
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THIAMYLAL
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M10724
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7305
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2626
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77-27-0
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201-018-3
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10464
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PRIMARY | RxNorm |
ACTIVE MOIETY
