Details of the Drug

General Information of Drug (ID: DMHDF7B)

Drug Name
Thiamylal
Synonyms
Surital; Thioquinalbarbitone; Thioseconal; Thiamylal [USAN]; Surital (TN); Barbituric acid, 5-allyl-5-(1-methylbutyl)-2-thio-(VAN); Barbituric acid, 5-allyl-5-(1-methylbutyl)-2-thio-(VAN) (8CI); Dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-4,6(1H,5H)-pyrimidinedione; Dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-4,6-(1H,5H)-pyrimidinedione; 4,6(1H,5H)-Pyrimidinedione, dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-(9CI); 5-(pentan-2-yl)-5-(prop-2-en-1-yl)-2-sulfanylidenedihydropyrimidine-4,6(1H,5H)-dione; 5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acid; 5-Allyl-5-(1-methylbutyl)-2-thiobarbitursaeure; 5-Allyl-5-(1-methylbutyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione; 5-allyl-5-(1-methylbutyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione; 5-pentan-2-yl-5-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
Indication
Disease Entry ICD 11 Status REF
Anaesthesia 9A78.6 Approved [1]
Therapeutic Class
Hypnotics and Sedatives
Affected Organisms
Humans and other mammals
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 254.35
Logarithm of the Partition Coefficient (xlogp) 3.2
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
Absorption
The drug is rapidly absorbed []
Half-life
The concentration or amount of drug in body reduced by one-half in 14.3 hours [2]
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C12H18N2O2S
IUPAC Name
5-pentan-2-yl-5-prop-2-enyl-2-sulfanylidene-1,3-diazinane-4,6-dione
Canonical SMILES
CCCC(C)C1(C(=O)NC(=S)NC1=O)CC=C
InChI
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)
InChIKey
XLOMZPUITCYLMJ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3032285
ChEBI ID
CHEBI:9536
CAS Number
77-27-0
UNII
01T23W89FR
DrugBank ID
DB01154
TTD ID
D06NSA
INTEDE ID
DR1579

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
GABA(A) receptor gamma-3 (GABRG3) TTEX6LM GBRG3_HUMAN Modulator [3]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [4]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [5]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [4]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [6]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7305).
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
4 Protein binding and the metabolism of thiamylal enantiomers in vitro. Anesth Analg. 2000 Sep;91(3):736-40.
5 Effects of premedication medicines on the formation of the CYP3A4-dependent metabolite of ropivacaine, 2', 6'-Pipecoloxylidide, on human liver microsomes in vitro. Basic Clin Pharmacol Toxicol. 2006 Feb;98(2):181-3.
6 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. J Pharmacol Exp Ther. 2004 Dec;311(3):1232-40. doi: 10.1124/jpet.104.071332. Epub 2004 Jul 19.