THIOBUTABARBITAL

Possibly Marketed Outside US

Details

Stereochemistry	UNKNOWN
Molecular Formula	C10H16N2O2S
Molecular Weight	228.311
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IDELNEDBPWKHGK-UHFFFAOYSA-N

InChI=1S/C10H16N2O2S/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)

HIDE SMILES / InChI

Molecular Formula	C10H16N2O2S
Molecular Weight	228.311
Charge	0
Count

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

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 8504		1.0 mM [IC50]
hexose transport 2 Target ID: GO:0008645 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7819247	Inhibitor 8504		1.0 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 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 8583	Inactin Approved Use Unknown

PubMed

Title	Date	PubMed
High-NaCl intake impairs dynamic autoregulation of renal blood flow in ANG II-infused rats.	2010-11	20720177
Gastric emptying of enterally administered liquid meal in conscious rats and during sustained anaesthesia.	2010-02	19735361
Antenatal Corticosteroids and Postnatal Fluid Restriction Produce Differential Effects on AQP3 Expression, Water Handling, and Barrier Function in Perinatal Rat Epidermis.	2010	21234324
Vasodilator effects of ibudilast on retinal blood vessels in anesthetized rats.	2009-11	19881310
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.	2009-08	19491297
Total synthesis of brevenal.	2009-06-18	19441795
Resistin increases islet blood flow and decreases subcutaneous adipose tissue blood flow in anaesthetized rats.	2009-02	18715288
Brevisamide: an unprecedented monocyclic ether alkaloid from the dinoflagellate Karenia brevis that provides a potential model for ladder-frame initiation.	2008-08-21	18646771
Low-dose candesartan improves renal blood flow and kidney oxygen tension in rats with endotoxin-induced acute kidney dysfunction.	2008-08	18091574
Total synthesis of (-)-brevenal: a concise synthetic entry to the pentacyclic polyether core.	2008-06-05	18444658
Convergent strategies for the total synthesis of polycyclic ether marine metabolites.	2008-04	18389143
Increased renal renin content in mice lacking the Na+/H+ exchanger NHE2.	2008-04	18287398
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
Vasodilator effect of nicorandil on retinal blood vessels in rats.	2007-07	17525845
Vasodilator effects of fasudil, a Rho-kinase inhibitor, on retinal arterioles in stroke-prone spontaneously hypertensive rats.	2007-06	17593003
Hemodynamic effects of potent and selective JNK inhibitors in anesthetized rats: implication for targeting protein kinases in metabolic diseases.	2007-01-15	17055723
Total synthesis, structure revision, and absolute configuration of (-)-brevenal.	2006-12-27	17177450
Total synthesis of the proposed structure of brevenal.	2006-08-02	16866516
The inhibition of CHO-K1-BH4 cell proliferation and induction of chromosomal aberrations by brevetoxins in vitro.	2006-07	16487644
Carbon monoxide and pancreatic islet blood flow in the rat: inhibition of haem oxygenase does not affect islet blood perfusion.	2006	17101545
Effects of BW245C, a prostaglandin dp receptor agonist, on systemic and regional haemodynamics in the anaesthetized rat.	2005-11	16405449
The effect of brevenal on brevetoxin-induced DNA damage in human lymphocytes.	2005-11	15986201
Natural and derivative brevetoxins: historical background, multiplicity, and effects.	2005-05	15866774
Differential effects of isoflurane and ketamine/inactin anesthesia on cAMP and cardiac function in FVB/N mice during basal state and beta-adrenergic stimulation.	2005-03	15739124
AT(2) receptors mediate tonic renal medullary vasoconstriction in renovascular hypertension.	2005-02	15678096
Kidney function in mice: thiobutabarbital versus alpha-chloralose anesthesia.	2004-10	15549274
Cardiovascular activity of rasagiline, a selective and potent inhibitor of mitochondrial monoamine oxidase B: comparison with selegiline.	2004-10	15339864
Brevenal is a natural inhibitor of brevetoxin action in sodium channel receptor binding assays.	2004-08	15233378
Oxytocin-induced renin secretion by denervated kidney in anaesthetized rat.	2002-11-15	12421653
Chemoprophylaxis of transfusion-transmitted agents in labile blood components.	2002-08-10	12170320
Propofol anesthesia compared to awake reduces infarct size in rats.	2002-05	11981160
Role of endothelin ET(A)- and ET(B)-receptors in haemodynamic compensation following haemorrhage in anaesthetized rats.	2002-02	11861314
Renal interstitial fluid concentrations of angiotensins I and II in anesthetized rats.	2002-01	11799091
Peripheral melatonin mediates neural stimulation of duodenal mucosal bicarbonate secretion.	2001-08	11518737
Enhanced intestinal motility influences absorption in anaesthetized rat.	2001-06	11442451
The influence of phosphodiesterase inhibitor, rolipram, on hemodynamics in lipopolysaccharide-treated rats.	2001-03	11325016
c-Fos generation in the dorsal vagal complex after systemic endotoxin is not dependent on the vagus nerve.	2001-01	11124163

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:31:48 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:48 GMT 2025`
Record UNII	2N0251U7JH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIOBUTABARBITAL

Common Name

English

NSC-27685

Preferred Name

English

5-ETHYL-5-(1-METHYLPROPYL)-2-THIOBARBITURIC ACID

Systematic Name

English

Thiobutabarbital [WHO-DD]

Common Name

English

5-SEC-BUTYL-5-ETHYL-2-THIOXODIHYDROPYRIMIDINE-4,6(1H,5H)-DIONE

Systematic Name

English

THIOBUTABARBITAL [MI]

Common Name

English

NSC-32372

Code

English

5-ETHYLDIHYDRO-5-(1-METHYLPROPYL)-2-THIOXO-4,6(1H,5H)-PYRIMIDINEDIONE

Systematic Name

English

5-SEC-BUTYL-5-ETHYL-2-THIOBARBITURIC ACID

Systematic Name

English

THIOBUTABARBITAL [VANDF]

Common Name

English

THIBUTABARBITAL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67084