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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 of THIOBUTABARBITAL

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

Description

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 1.0 mM [IC50]
Inhibitor
8297
 1.0 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Inactin

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Peripheral melatonin mediates neural stimulation of duodenal mucosal bicarbonate secretion.
2001 Aug
c-Fos generation in the dorsal vagal complex after systemic endotoxin is not dependent on the vagus nerve.
2001 Jan
Enhanced intestinal motility influences absorption in anaesthetized rat.
2001 Jun
The influence of phosphodiesterase inhibitor, rolipram, on hemodynamics in lipopolysaccharide-treated rats.
2001 Mar
Role of endothelin ET(A)- and ET(B)-receptors in haemodynamic compensation following haemorrhage in anaesthetized rats.
2002 Feb
Chemoprophylaxis of transfusion-transmitted agents in labile blood components.
2002 Jul-Aug
Propofol anesthesia compared to awake reduces infarct size in rats.
2002 May
Oxytocin-induced renin secretion by denervated kidney in anaesthetized rat.
2002 Nov 15
Brevenal is a natural inhibitor of brevetoxin action in sodium channel receptor binding assays.
2004 Aug
Kidney function in mice: thiobutabarbital versus alpha-chloralose anesthesia.
2004 Oct
Cardiovascular activity of rasagiline, a selective and potent inhibitor of mitochondrial monoamine oxidase B: comparison with selegiline.
2004 Oct
AT(2) receptors mediate tonic renal medullary vasoconstriction in renovascular hypertension.
2005 Feb
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
Natural and derivative brevetoxins: historical background, multiplicity, and effects.
2005 May
Effects of BW245C, a prostaglandin dp receptor agonist, on systemic and regional haemodynamics in the anaesthetized rat.
2005 Nov
The effect of brevenal on brevetoxin-induced DNA damage in human lymphocytes.
2005 Nov
Carbon monoxide and pancreatic islet blood flow in the rat: inhibition of haem oxygenase does not affect islet blood perfusion.
2006
Total synthesis of the proposed structure of brevenal.
2006 Aug 2
Total synthesis, structure revision, and absolute configuration of (-)-brevenal.
2006 Dec 27
The inhibition of CHO-K1-BH4 cell proliferation and induction of chromosomal aberrations by brevetoxins in vitro.
2006 Jul
Hemodynamic effects of potent and selective JNK inhibitors in anesthetized rats: implication for targeting protein kinases in metabolic diseases.
2007 Jan 15
Vasodilator effect of nicorandil on retinal blood vessels in rats.
2007 Jul
Vasodilator effects of fasudil, a Rho-kinase inhibitor, on retinal arterioles in stroke-prone spontaneously hypertensive rats.
2007 Jun
Glucose-induced time-dependent potentiation of insulin release, but not islet blood perfusion, in anesthetized rats.
2008
Convergent strategies for the total synthesis of polycyclic ether marine metabolites.
2008 Apr
Increased renal renin content in mice lacking the Na+/H+ exchanger NHE2.
2008 Apr
Low-dose candesartan improves renal blood flow and kidney oxygen tension in rats with endotoxin-induced acute kidney dysfunction.
2008 Aug
Brevisamide: an unprecedented monocyclic ether alkaloid from the dinoflagellate Karenia brevis that provides a potential model for ladder-frame initiation.
2008 Aug 21
Total synthesis of (-)-brevenal: a concise synthetic entry to the pentacyclic polyether core.
2008 Jun 5
Vasodilator effects of ibudilast on retinal blood vessels in anesthetized rats.
2009 Nov
Antenatal Corticosteroids and Postnatal Fluid Restriction Produce Differential Effects on AQP3 Expression, Water Handling, and Barrier Function in Perinatal Rat Epidermis.
2010
High-NaCl intake impairs dynamic autoregulation of renal blood flow in ANG II-infused rats.
2010 Nov
Patents

Patents

US6562363
4
US6638528
14
WO2009151744A1
2

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
MI   VANDF   WHO-DD  
Common 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
NSC-27685
Code English
Classification Tree Code System Code
NCI_THESAURUS C67084
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
Code System Code Type Description
NSC
32372
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
EPA CompTox
DTXSID90871862
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
EVMPD
SUB15533MIG
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
ECHA (EC/EINECS)
218-260-0
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
NCI_THESAURUS
C87670
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
WIKIPEDIA
Thiobutabarbital
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
FDA UNII
2N0251U7JH
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
PUBCHEM
3032373
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
RXCUI
38077
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY RxNorm
CAS
2095-57-0
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
MERCK INDEX
m10746
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY Merck Index
SMS_ID
100000077014
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
NSC
27685
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
MESH
C004316
Created by admin on Fri Dec 15 16:34:46 GMT 2023 , Edited by admin on Fri Dec 15 16:34:46 GMT 2023
PRIMARY
SUBSTANCE RECORD
Structure of THIOBUTABARBITAL
NIH
NCATS
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