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
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
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.