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MedKoo Cat#: 597814 | Name: PPACK free base

Description:

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

PPACK free base is a synthetic peptide derivative that irreversibly and specifically inhibits thrombin-mediated platelet activation by binding with high affinity to the active site of thrombin (Ki = 0.24 nM). It has been used as an anticoagulant (100 μM) and to study thrombin-mediated fibrin deposition, angiogenesis, and proinflammatory processes.

Chemical Structure

PPACK free base
PPACK free base
CAS#71142-71-7 (free base)

Theoretical Analysis

MedKoo Cat#: 597814

Name: PPACK free base

CAS#: 71142-71-7 (free base)

Chemical Formula: C21H33Cl3N6O3

Exact Mass: 0.0000

Molecular Weight: 523.88

Elemental Analysis: C, 48.15; H, 6.35; Cl, 20.30; N, 16.04; O, 9.16

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 #
71142-71-7 (free base) 82188-90-7 (HCl)
Synonym
PPACK free base
IUPAC/Chemical Name
(S)-1-(D-phenylalanyl)-N-((S)-1-chloro-6-guanidino-2-oxohexan-3-yl)pyrrolidine-2-carboxamide
InChi Key
KWPACVJPAFGBEQ-IKGGRYGDSA-N
InChi Code
InChI=1S/C21H31ClN6O3/c22-13-18(29)16(8-4-10-26-21(24)25)27-19(30)17-9-5-11-28(17)20(31)15(23)12-14-6-2-1-3-7-14/h1-3,6-7,15-17H,4-5,8-13,23H2,(H,27,30)(H4,24,25,26)/t15-,16+,17+/m1/s1
SMILES Code
O=C([C@H]1N(C([C@@H](CC2=CC=CC=C2)N)=O)CCC1)N[C@@H](CCCNC(N)=N)C(CCl)=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 523.88 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: Palekar RU, Jallouk AP, Myerson JW, Pan H, Wickline SA. Inhibition of Thrombin With PPACK-Nanoparticles Restores Disrupted Endothelial Barriers and Attenuates Thrombotic Risk in Experimental Atherosclerosis. Arterioscler Thromb Vasc Biol. 2016 Mar;36(3):446-55. doi: 10.1161/ATVBAHA.115.306697. Epub 2016 Jan 14. PubMed PMID: 26769047; PubMed Central PMCID: PMC4767676. 2: Rahr HB, Sørensen JV, Danielsen D. Markers of coagulation and fibrinolysis in blood drawn into citrate with and without D-Phe-Pro-Arg-Chloromethylketone (PPACK). Thromb Res. 1994 Mar 1;73(5):279-84. PubMed PMID: 8016814. 3: Lyon ME, Drobot DW, Harding SR, Lyon AW. Evaluation of the thrombin inhibitor D-phenylalanyl-L-prolyl-L-arginine chloromethylketone (PPACK) with the factor Xa inhibitor 1,5-dansyl-L-glutamyl-L-glycyl-L-arginine chloromethylketone (GGACK) as anticoagulants for critical care clinical chemistry specimens. Clin Chim Acta. 1999 Feb;280(1-2):91-9. PubMed PMID: 10090527. 4: Yamashita T, Yamamoto J, Sasaki Y, Matsuoka A. The antithrombotic effect of low molecular weight synthetic thrombin inhibitors, argatroban and PPACK, on He-Ne laser-induced thrombosis in rat mesenteric microvessels. Thromb Res. 1993 Jan 1;69(1):93-100. PubMed PMID: 8465278. 5: Schmaier AH, Meloni FJ, Nawarawong W, Jiang YP. PPACK-thrombin is a noncompetitive inhibitor of alpha-thrombin binding to human platelets. Thromb Res. 1992 Sep 1;67(5):479-89. PubMed PMID: 1448784. 6: Voss R, Grebe M, Pralle H, Tillmanns H, Matzdorff A. Pharmacodynamics of two different dosing regimens of tirofiban in citrate or PPACK anticoagulated blood. Platelets. 2005 Dec;16(8):492-7. PubMed PMID: 16287616. 7: Palekar RU, Vemuri C, Marsh JN, Arif B, Wickline SA. Antithrombin nanoparticles inhibit stent thrombosis in ex vivo static and flow models. J Vasc Surg. 2016 Nov;64(5):1459-1467. doi: 10.1016/j.jvs.2015.08.086. Epub 2015 Oct 17. PubMed PMID: 26482989; PubMed Central PMCID: PMC4834274. 8: Lyon ME, Fine JS, Henderson PJ, Lyon AW. D-phenylalanyl-L-prolyl-L-arginine chloromethyl ketone (PPACK): alternative anticoagulant to heparin salts for blood gas and electrolyte specimens. Clin Chem. 1995 Jul;41(7):1038-41. PubMed PMID: 7600685. 9: Greco NJ, Tenner TE Jr, Tandon NN, Jamieson GA. PPACK-thrombin inhibits thrombin-induced platelet aggregation and cytoplasmic acidification but does not inhibit platelet shape change. Blood. 1990 May 15;75(10):1989-90. PubMed PMID: 2337670. 10: Vijayalakshmi J, Padmanabhan KP, Mann KG, Tulinsky A. The isomorphous structures of prethrombin2, hirugen-, and PPACK-thrombin: changes accompanying activation and exosite binding to thrombin. Protein Sci. 1994 Dec;3(12):2254-71. PubMed PMID: 7756983; PubMed Central PMCID: PMC2142772. 11: Kereiakes DJ, Lorenz T, Young JJ, Kukielka G, Mueller MN, Nanniazzi-Alaimo L, Phillips DR. Differential effects of citrate versus PPACK anticoagulation on measured platelet inhibition by abciximab, eptifibatide and tirofiban. J Thromb Thrombolysis. 2001 Oct;12(2):123-7. PubMed PMID: 11729363. 12: Myerson J, He L, Lanza G, Tollefsen D, Wickline S. Thrombin-inhibiting perfluorocarbon nanoparticles provide a novel strategy for the treatment and magnetic resonance imaging of acute thrombosis. J Thromb Haemost. 2011 Jul;9(7):1292-300. doi: 10.1111/j.1538-7836.2011.04339.x. PubMed PMID: 21605330; PubMed Central PMCID: PMC3686484. 13: McLellan I. Letter: A ppack for the emergency treatment of malignant hyperpyrexia. Anaesthesia. 1975 Jan;30(1):99-100. PubMed PMID: 1115352. 14: Rabbani LE, Johnstone MT, Rudd MA, Devine P, George D, Loscalzo J. PPACK attenuates plasmin-induced changes in endothelial integrity. Thromb Res. 1993 Jun 15;70(6):425-36. PubMed PMID: 8362368. 15: Chen J, Vemuri C, Palekar RU, Gaut JP, Goette M, Hu L, Cui G, Zhang H, Wickline SA. Antithrombin nanoparticles improve kidney reperfusion and protect kidney function after ischemia-reperfusion injury. Am J Physiol Renal Physiol. 2015 Apr 1;308(7):F765-73. doi: 10.1152/ajprenal.00457.2014. Epub 2015 Jan 28. PubMed PMID: 25651565; PubMed Central PMCID: PMC4385886. 16: Roussel BD, Hommet Y, Macrez R, Schulz T, Petersen KU, Berezowski V, Cecchelli R, Ali C, Vivien D. PPACK-Desmodus rotundus salivary plasminogen activator (cDSPAalpha1) prevents the passage of tissue-type plasminogen activator (rt-PA) across the blood-brain barrier and neurotoxicity. Thromb Haemost. 2009 Sep;102(3):606-8. doi: 10.1160/TH09-02-0114. PubMed PMID: 19718485. 17: Martin PD, Malkowski MG, Box J, Esmon CT, Edwards BF. New insights into the regulation of the blood clotting cascade derived from the X-ray crystal structure of bovine meizothrombin des F1 in complex with PPACK. Structure. 1997 Dec 15;5(12):1681-93. PubMed PMID: 9438869. 18: Handley LD, Treuheit NA, Venkatesh VJ, Komives EA. Thrombomodulin Binding Selects the Catalytically Active Form of Thrombin. Biochemistry. 2015 Nov 3;54(43):6650-8. doi: 10.1021/acs.biochem.5b00825. Epub 2015 Oct 26. PubMed PMID: 26468766; PubMed Central PMCID: PMC4697735. 19: Nunes GL, Hanson SR, King SB 3rd, Sahatjian RA, Scott NA. Local delivery of a synthetic antithrombin with a hydrogel-coated angioplasty balloon catheter inhibits platelet-dependent thrombosis. J Am Coll Cardiol. 1994 Jun;23(7):1578-83. PubMed PMID: 8195517. 20: Lyon AW, Harding SR, Drobot D, Lyon ME. Use of thrombin inhibitors ex vivo allows critical care clinical chemistry and hematology testing on common specimens. Clin Biochem. 1997 Mar;30(2):121-7. PubMed PMID: 9127693.