Details of the Drug

General Information of Drug (ID: DM0SCDB)

Drug Name
TIAPAFANT
Synonyms PCA-4248; 2,4,6-Trimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl 5-(2-phenylthio)ethyl diester
Indication
Disease Entry ICD 11 Status REF
Sepsis 1G40-1G41 Terminated [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 361.5
Topological Polar Surface Area (xlogp) 3.6
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C19H23NO4S
IUPAC Name
3-O-methyl 5-O-(2-phenylsulfanylethyl) 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate
Canonical SMILES
CC1C(=C(NC(=C1C(=O)OCCSC2=CC=CC=C2)C)C)C(=O)OC
InChI
InChI=1S/C19H23NO4S/c1-12-16(18(21)23-4)13(2)20-14(3)17(12)19(22)24-10-11-25-15-8-6-5-7-9-15/h5-9,12,20H,10-11H2,1-4H3
InChIKey
DHCNAWNKZMNTIS-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4698
ChEBI ID
CHEBI:91615
CAS Number
123875-01-4
TTD ID
D0Q1UR

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Platelet-activating factor receptor (PTAFR) TTQL5VC PTAFR_HUMAN Antagonist [3], [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Sepsis
ICD Disease Classification 1G40-1G41
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Platelet-activating factor receptor (PTAFR) DTT PTAFR 3.53E-02 0.33 2.12
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression 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: 6080).
2 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800001989)
3 PCA-4248, a PAF receptor antagonist, inhibits PAF-induced phosphoinositide turnover. Eur J Pharmacol. 1995 Aug 15;290(3):183-8.
4 Therapeutic target database update 2012: a resource for facilitating target-oriented drug discovery. Nucleic Acids Res. 2012 Jan;40(Database issue):D1128-36.
5 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
6 Designed multiple ligands. An emerging drug discovery paradigm. J Med Chem. 2005 Oct 20;48(21):6523-43.
7 Amino acid residues critical for endoplasmic reticulum export and trafficking of platelet-activating factor receptor. J Biol Chem. 2010 Feb 19;285(8):5931-40.
8 Anti-inflammatory activities of LDP-392, a dual PAF receptor antagonist and 5-lipoxygenase inhibitor. Pharmacol Res. 2001 Sep;44(3):213-20.
9 Lexipafant and acute pancreatitis: a critical appraisal of the clinical trials.Eur J Surg.2002;168(4):215-9.
10 Effects of YM264, a novel PAF antagonist, on puromycin aminonucleoside-induced nephropathy in the rat. Biochem Biophys Res Commun. 1991 Apr 30;176(2):781-5.
11 The intestinal anti-inflammatory effect of dersalazine sodium is related to a down-regulation in IL-17 production in experimental models of rodent colitis. Br J Pharmacol. 2012 February; 165(3): 729-740.
12 Clinical pipeline report, company report or official report of 60 Degrees Pharmaceuticals.
13 Sch 37370: a new drug combining antagonism of platelet-activating factor (PAF) with antagonism of histamine. Agents Actions Suppl. 1991;34:313-21.
14 Biochemical and pharmacological activities of SR 27417, a highly potent, long-acting platelet-activating factor receptor antagonist. J Pharmacol Exp Ther. 1991 Oct;259(1):44-51.