Tiacrilast
[CAS# 78299-53-3]

Identification

• Name: Tiacrilast
• Synonyms: (E)-3-(6-Methylsulfanyl-4-Oxo-Quinazolin-3-Yl)Prop-2-Enoic Acid; (E)-3-[6-(Methylthio)-4-Oxo-3-Quinazolinyl]Prop-2-Enoic Acid; (E)-3-[4-Keto-6-(Methylthio)Quinazolin-3-Yl]Acrylic Acid
• Molecular Formula: C₁₂H₁₀N₂O₃S
• Molecular Weight: 262.28
• CAS Registry Number: 78299-53-3
• SMILES: C1=C(SC)C=CC2=C1C(N(\C=C\C(O)=O)C=N2)=O
• InChI: 1S/C12H10N2O3S/c1-18-8-2-3-10-9(6-8)12(17)14(7-13-10)5-4-11(15)16/h2-7H,1H3,(H,15,16)/b5-4+
• InChIKey: VHFPVEGFRVEDBK-SNAWJCMRSA-N

Properties

• Density: 1.382g/cm³ (Cal.)
• Boiling point: 499.291°C at 760 mmHg (Cal.)
• Flash point: 255.762°C (Cal.)

References

• (1): Manfred Kansy, Frank Senner, and Klaus Gubernator. Physicochemical High Throughput Screening: Parallel Artificial Membrane Permeation Assay in the Description of Passive Absorption Processes, J. Med. Chem., 1998, 41(7), 1007-101025 compounds and their % Absorption values (humans) are given in the paper. These have been provided here.
• (2): Tapan Sanghvi, Nina Ni, Michael Mayersohn, Samuel H. Yalkowsky. Predicting Passive Intestinal Absorption Using A Single Parameter, QSAR Comb. Sci. 2003, 22(2), 247-257131 compounds and their 'Fraction Absorbed' values have been obtained from the table given in the paper. Some compounds had multiple values reported (as obtained from various references). These have been averaged and provided by us in the SDF and AMP files. The "Sanghvi_values.txt" file contains all data (as reported in Table 1) and "Sanghvi_avg_values.txt" contains averaged data for compounds with multiple entries (as reported in Table 2). "Benserazide, HCl" was retrieved as "Benserazide", "Ceftriaxone, Na" as "Ceftriaxone", "Foscarnet, Na" as "Foscarnet", "L-Dopa" as "Levodopa", "L-Leucine" as "Leucine" and "Triacrilast" as "Tiacrilast". The last compound was found to be mispelt as checked from the original reference.
• (3): David E. Clark. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 1. Prediction of intestinal absorption, J. Pharm. Sci. 1999, 88 (8), 807-8143 tables with %FA values are given in this paper. One is from Palm et. al. (20 compounds, available on this web-page). Other is from Wessel et. al. (86 compounds, available on this web-page). The third dataset is from Kansy et. al. and is made available here. A total of 24 drugs and their oral drug absorption in humans (FA) values taken from the 3rd table given in the paper. Compound "acetylsalicylic acid" was retrieved as "aspirin" from ChemIDplus.