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MedKoo Cat#: 585026 | Name: PSI-697

Description:

WARNING: This product is for research use only, not for human or veterinary use.

PSI-697 is an inhibitor of P selectin that decreases vein wall injury in a rat stenosis model of venous thrombosis.

Chemical Structure

PSI-697
PSI-697
CAS#851546-61-7

Theoretical Analysis

MedKoo Cat#: 585026

Name: PSI-697

CAS#: 851546-61-7

Chemical Formula: C21H18ClNO3

Exact Mass: 367.0975

Molecular Weight: 367.83

Elemental Analysis: C, 68.57; H, 4.93; Cl, 9.64; N, 3.81; O, 13.05

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
PSI-697; PSI697; PSI 697
IUPAC/Chemical Name
2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo(H)quinoline-4-carboxylic acid
InChi Key
DIEPFYNZGUUVHD-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H18ClNO3/c22-14-8-5-12(6-9-14)11-17-20(24)18(21(25)26)16-10-7-13-3-1-2-4-15(13)19(16)23-17/h5-10,24H,1-4,11H2,(H,25,26)
SMILES Code
O=C(C1=C(O)C(CC2=CC=C(Cl)C=C2)=NC3=C(CCCC4)C4=CC=C13)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 367.83 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Japp AG, Chelliah R, Tattersall L, Lang NN, Meng X, Weisel K, Katz A, Burt D, Fox KA, Feuerstein GZ, Connolly TM, Newby DE. Effect of PSI-697, a novel P-selectin inhibitor, on platelet-monocyte aggregate formation in humans. J Am Heart Assoc. 2013 Jan 28;2(1):e006007. doi: 10.1161/JAHA.112.006007. PubMed PMID: 23525448; PubMed Central PMCID: PMC3603266. 2: Bedard PW, Clerin V, Sushkova N, Tchernychev B, Antrilli T, Resmini C, Keith JC Jr, Hennan JK, Kaila N, Debernardo S, Janz K, Wang Q, Crandall DL, Schaub RG, Shaw GD, Carter LL. Characterization of the novel P-selectin inhibitor PSI-697 [2-(4-chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[h] quinoline-4-carboxylic acid] in vitro and in rodent models of vascular inflammation and thrombosis. J Pharmacol Exp Ther. 2008 Feb;324(2):497-506. Epub 2007 Nov 16. PubMed PMID: 18024786. 3: Myers DD Jr, Henke PK, Bedard PW, Wrobleski SK, Kaila N, Shaw G, Meier TR, Hawley AE, Schaub RG, Wakefield TW. Treatment with an oral small molecule inhibitor of P selectin (PSI-697) decreases vein wall injury in a rat stenosis model of venous thrombosis. J Vasc Surg. 2006 Sep;44(3):625-32. PubMed PMID: 16950445. 4: Myers DD Jr, Wrobleski SK, Longo C, Bedard PW, Kaila N, Shaw GD, Londy FJ, Rohrer SE, Fex BA, Zajkowski PJ, Meier TR, Hawley AE, Farris DM, Ballard NE, Henke PK, Schaub RG, Wakefield TW. Resolution of venous thrombosis using a novel oral small-molecule inhibitor of P-selectin (PSI-697) without anticoagulation. Thromb Haemost. 2007 Mar;97(3):400-7. PubMed PMID: 17334507. 5: Kutlar A, Embury SH. Cellular adhesion and the endothelium: P-selectin. Hematol Oncol Clin North Am. 2014 Apr;28(2):323-39. doi: 10.1016/j.hoc.2013.11.007. Epub 2014 Jan 17. Review. PubMed PMID: 24589269. 6: Kaila N, Janz K, Huang A, Moretto A, DeBernardo S, Bedard PW, Tam S, Clerin V, Keith JC Jr, Tsao DH, Sushkova N, Shaw GD, Camphausen RT, Schaub RG, Wang Q. 2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H]quinoline-4-carboxylic acid (PSI-697): identification of a clinical candidate from the quinoline salicylic acid series of P-selectin antagonists. J Med Chem. 2007 Jan 11;50(1):40-64. PubMed PMID: 17201409. 7: Chelliah R, Lucking AJ, Tattersall L, Daga S, Beresford-Cleary NJ, Cortas K, Fox KA, Feuerstein GZ, Connolly TM, Newby DE. P-selectin antagonism reduces thrombus formation in humans. J Thromb Haemost. 2009 Nov;7(11):1915-9. doi: 10.1111/j.1538-7836.2009.03587.x. Epub 2009 Aug 19. PubMed PMID: 19691482. 8: Huang A, Moretto A, Janz K, Lowe M, Bedard PW, Tam S, Di L, Clerin V, Sushkova N, Tchernychev B, Tsao DH, Keith JC, Shaw GD, Schaub RG, Wang Q, Kaila N. Discovery of 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carbox ylic acid (PSI-421), a P-selectin inhibitor with improved pharmacokinetic properties and oral efficacy in models of vascular injury. J Med Chem. 2010 Aug 26;53(16):6003-17. doi: 10.1021/jm9013696. PubMed PMID: 20718494. 9: Myers DD Jr, Rectenwald JE, Bedard PW, Kaila N, Shaw GD, Schaub RG, Farris DM, Hawley AE, Wrobleski SK, Henke PK, Wakefield TW. Decreased venous thrombosis with an oral inhibitor of P selectin. J Vasc Surg. 2005 Aug;42(2):329-36. PubMed PMID: 16102635. 10: Becker RC. A thought experiment in contemporary drug development: informed bench-to-bedside strategies. J Am Heart Assoc. 2013 Feb 12;2(1):e000031. doi: 10.1161/JAHA.112.000031. PubMed PMID: 23525416; PubMed Central PMCID: PMC3603250.

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