THIOBUTABARBITAL SODIUM

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H15N2O2S.Na
Molecular Weight	250.293
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=SLZHLQUFNFXTHB-UHFFFAOYSA-M

InChI=1S/C10H16N2O2S.Na/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14;/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15);/q;+1/p-1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13217426 | https://www.ncbi.nlm.nih.gov/pubmed/13500903 | https://www.ncbi.nlm.nih.gov/pubmed/13991716 | http://www.sciencedirect.com/topics/neuroscience/thiobarbiturates

Thiobutabarbital is a barbiturate derivative invented in the 1950s. It has sedative, anticonvulsant and hypnotic effects, it is used in veterinary medicine for induction in surgical anaesthesia. Thiobutabarbital was formerly used as anesthetic Inactin. ‘Inactin’ (sodium thiobutabarbital) produces smooth induction of anaesthesia after intravenous administration and has a prolonged duration of action. It has variable analgesic activity.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
hexose transport 2 Target ID: GO:0008645 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7819247	Inhibitor 8297		1.0 mM [IC50]
hexose transport 2 Target ID: GO:0008645 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7819247	Inhibitor 8297		1.0 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19881310 https://www.ncbi.nlm.nih.gov/pubmed/13283294 http://www.sciencedirect.com/topics/neuroscience/thiobarbiturates	Primary		Approved 8429	Inactin Approved Use Unknown

PubMed

Title	Date	PubMed
Peripheral melatonin mediates neural stimulation of duodenal mucosal bicarbonate secretion.	2001 Aug	11518737
c-Fos generation in the dorsal vagal complex after systemic endotoxin is not dependent on the vagus nerve.	2001 Jan	11124163
Enhanced intestinal motility influences absorption in anaesthetized rat.	2001 Jun	11442451
The influence of phosphodiesterase inhibitor, rolipram, on hemodynamics in lipopolysaccharide-treated rats.	2001 Mar	11325016
Role of endothelin ET(A)- and ET(B)-receptors in haemodynamic compensation following haemorrhage in anaesthetized rats.	2002 Feb	11861314
Renal interstitial fluid concentrations of angiotensins I and II in anesthetized rats.	2002 Jan	11799091
Chemoprophylaxis of transfusion-transmitted agents in labile blood components.	2002 Jul-Aug	12170320
Propofol anesthesia compared to awake reduces infarct size in rats.	2002 May	11981160
Oxytocin-induced renin secretion by denervated kidney in anaesthetized rat.	2002 Nov 15	12421653
Brevenal is a natural inhibitor of brevetoxin action in sodium channel receptor binding assays.	2004 Aug	15233378
Kidney function in mice: thiobutabarbital versus alpha-chloralose anesthesia.	2004 Oct	15549274
Cardiovascular activity of rasagiline, a selective and potent inhibitor of mitochondrial monoamine oxidase B: comparison with selegiline.	2004 Oct	15339864
AT(2) receptors mediate tonic renal medullary vasoconstriction in renovascular hypertension.	2005 Feb	15678096
Differential effects of isoflurane and ketamine/inactin anesthesia on cAMP and cardiac function in FVB/N mice during basal state and beta-adrenergic stimulation.	2005 Mar	15739124
Natural and derivative brevetoxins: historical background, multiplicity, and effects.	2005 May	15866774
Effects of BW245C, a prostaglandin dp receptor agonist, on systemic and regional haemodynamics in the anaesthetized rat.	2005 Nov	16405449
The effect of brevenal on brevetoxin-induced DNA damage in human lymphocytes.	2005 Nov	15986201
Carbon monoxide and pancreatic islet blood flow in the rat: inhibition of haem oxygenase does not affect islet blood perfusion.	2006	17101545
Total synthesis of the proposed structure of brevenal.	2006 Aug 2	16866516
Total synthesis, structure revision, and absolute configuration of (-)-brevenal.	2006 Dec 27	17177450
The inhibition of CHO-K1-BH4 cell proliferation and induction of chromosomal aberrations by brevetoxins in vitro.	2006 Jul	16487644
Hemodynamic effects of potent and selective JNK inhibitors in anesthetized rats: implication for targeting protein kinases in metabolic diseases.	2007 Jan 15	17055723
Vasodilator effect of nicorandil on retinal blood vessels in rats.	2007 Jul	17525845
Vasodilator effects of fasudil, a Rho-kinase inhibitor, on retinal arterioles in stroke-prone spontaneously hypertensive rats.	2007 Jun	17593003
Brevenal inhibits pacific ciguatoxin-1B-induced neurosecretion from bovine chromaffin cells.	2008	18941627
Glucose-induced time-dependent potentiation of insulin release, but not islet blood perfusion, in anesthetized rats.	2008	18521798
Convergent strategies for the total synthesis of polycyclic ether marine metabolites.	2008 Apr	18389143
Increased renal renin content in mice lacking the Na+/H+ exchanger NHE2.	2008 Apr	18287398
Low-dose candesartan improves renal blood flow and kidney oxygen tension in rats with endotoxin-induced acute kidney dysfunction.	2008 Aug	18091574
Brevisamide: an unprecedented monocyclic ether alkaloid from the dinoflagellate Karenia brevis that provides a potential model for ladder-frame initiation.	2008 Aug 21	18646771
Total synthesis of (-)-brevenal: a concise synthetic entry to the pentacyclic polyether core.	2008 Jun 5	18444658
Reversal of high pancreatic islet and white adipose tissue blood flow in type 2 diabetic GK rats by administration of the beta3-adrenoceptor inhibitor SR-59230A.	2009 Aug	19491297
Resistin increases islet blood flow and decreases subcutaneous adipose tissue blood flow in anaesthetized rats.	2009 Feb	18715288
Total synthesis of brevenal.	2009 Jun 18	19441795
Vasodilator effects of ibudilast on retinal blood vessels in anesthetized rats.	2009 Nov	19881310
Antenatal Corticosteroids and Postnatal Fluid Restriction Produce Differential Effects on AQP3 Expression, Water Handling, and Barrier Function in Perinatal Rat Epidermis.	2010	21234324
Gastric emptying of enterally administered liquid meal in conscious rats and during sustained anaesthesia.	2010 Feb	19735361
High-NaCl intake impairs dynamic autoregulation of renal blood flow in ANG II-infused rats.	2010 Nov	20720177

Patents

Sample Use Guides

In Vivo Use Guide

Male Wistar rats (8 to 10 weeks old) were anesthetized with thiobutabarbital (120 mg/kg, intraperitoneally (i.p.)).

Route of Administration: Intraperitoneal

In Vitro Use Guide

Thiobutabarbital inhibits hexose transport in cultured 3T3-C2 cells with IC50 value of 1.0 mM.

Name

Type

Language

THIOBUTABARBITAL SODIUM

Common Name

English

5-SEC-BUTYL-5-ETHYL-2-THIOBARBITURIC ACID, SODIUM SALT

Common Name

English

Thiobutabarbital sodium [WHO-DD]

Common Name

English

THIOBUTABARBITAL SODIUM SALT

Common Name

English

THIOBUTABARBITAL SODIUM SALT [MI]

Common Name

English

5-ETHYL-5-(1-METHYLPROPYL)-2-THIOBARBITURIC ACID, SODIUM SALT

Common Name

English

SODIUM THIOBUTABARBITAL

Common Name

English

THIBUTABARBITAL SODIUM

Common Name

English

THIOBUTABARBITAL SODIUM [VANDF]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67084