An antithrombin peptide
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Alternative(s)
37489PPACK (hydrochloride)
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PPACK (trifluoroacetate salt)

Item No. 15160

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
D-phenylalanyl-N-[(1S)-4-[(aminoiminomethyl)amino]-1-(2-chloroacetyl)butyl]-L-prolinamide, trifluoroacetate salt
Synonyms
  • Pebac
  • D-Phenylalanyl-prolyl-arginyl Chloromethyl Ketone
  • D-Phe-Pro-Arg-CH2Cl
Molecular Formula
C21H31ClN6O3 • XCF3COOH
Formula Weight
451.0
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 33 mg/mlDMSO: 33 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 5 mg/ml
SMILES
C[C@@H](C(N[C@@H](CS[H])C(N[C@@H](CCC(O)=O)C(N[C@@H](CCC(N[H])=O)C(N[C@@H](CC(N[H])=O)C(N1CCC[C@H]1C(N[C@@](C(N[C@@H](CC2=CC=C(O[H])C=C2)C(N[C@@H](CC3=CN([H])C4=C3C=CC=C4)C(N[C@H](C(N[C@@H](CCC/N=C(N[H])/N)C(N[C@@H](CC5=CC=C(O[H])C=C5)C(N[C@H](C(N[C@@H](CC(O)=O)C(N[C@@H](CC6=CN([H])C7=C6C=CC=C7)C(N[C@H](C(N[C@H](C(N[C@]([C@H](O[H])C)([H])C(N[C@]([C@H](O[H])C)([H])C(N8CCC[C@H]8C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](CC(O)=O)C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@@H](C(C)C)C(N[C@@H](CC(O)=O)C(N[C@H](C(N[C@@H](CC(O)=O)C(N[C@@H](CCC(O)=O)C(N[C@]([C@H](O[H])C)([H])C(O)=O)=O)=O)=O)C)=O)=O)=O)CC(C)C)=O)CC(C)C)=O)C)=O)CC(C)C)=O)=O)CC(C)C)=O)CC(C)C)=O)CC(C)C)=O)CC(C)C)=O)=O)=O)=O)CC9=CC=CC=C9)=O)CC(C)C)=O)=O)=O)C)=O)=O)=O)C)=O)=O)=O)([H])[C@@H](C)CC)=O)=O)=O)=O)=O)=O)N[H].OC(C(F)(F)F)=O
InChi Code
InChI=1S/C189H282N42O55S.C2HF3O2/c1-29-96(20)150(226-182(279)140-48-38-64-230(140)186(283)137(79-142(192)238)223-161(258)117(57-60-141(191)237)203-160(257)118(58-61-143(239)240)205-180(277)138(86-287)224-154(251)97(21)190)184(281)221-129(76-107-51-55-111(236)56-52-107)173(270)217-131(77-108-84-196-114-44-35-33-42-112(108)114)165(262)200-98(22)155(252)202-116(46-37-63-195-189(193)194)159(256)215-128(75-106-49-53-110(235)54-50-106)164(261)199-100(24)157(254)208-135(82-147(247)248)176(273)218-132(78-109-85-197-115-45-36-34-43-113(109)115)174(271)213-124(70-91(10)11)170(267)216-130(74-105-40-31-30-32-41-105)179(276)227-151(102(26)232)185(282)228-152(103(27)233)187(284)231-65-39-47-139(231)181(278)220-126(72-93(14)15)172(269)212-123(69-90(8)9)169(266)210-122(68-89(6)7)168(265)211-125(71-92(12)13)171(268)219-136(83-148(249)250)177(274)209-120(66-87(2)3)163(260)198-99(23)156(253)206-121(67-88(4)5)167(264)214-127(73-94(16)17)178(275)225-149(95(18)19)183(280)222-133(80-145(243)244)166(263)201-101(25)158(255)207-134(81-146(245)246)175(272)204-119(59-62-144(241)242)162(259)229-153(104(28)234)188(285)286;3-2(4,5)1(6)7/h30-36,40-45,49-56,84-85,87-104,116-140,149-153,196-197,232-236,287H,29,37-39,46-48,57-83,86,190H2,1-28H3,(H2,191,237)(H2,192,238)(H,198,260)(H,199,261)(H,200,262)(H,201,263)(H,202,252)(H,203,257)(H,204,272)(H,205,277)(H,206,253)(H,207,255)(H,208,254)(H,209,274)(H,210,266)(H,211,265)(H,212,269)(H,213,271)(H,214,264)(H,215,256)(H,216,267)(H,217,270)(H,218,273)(H,219,268)(H,220,278)(H,221,281)(H,222,280)(H,223,258)(H,224,251)(H,225,275)(H,226,279)(H,227,276)(H,228,282)(H,229,259)(H,239,240)(H,241,242)(H,243,244)(H,245,246)(H,247,248)(H,249,250)(H,285,286)(H4,193,194,195);(H,6,7)/t96-,97-,98-,99-,100-,101-,102+,103+,104+,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,149-,150-,151-,152-,153-;/m0./s1
InChi Key
IBJQTTAJGVGHFE-INDLMQKHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $167

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    10 mg

    $293

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    25 mg

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    Product Description

    PPACK 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).1,2,3 It has been used as an anticoagulant (100 μM) and to study thrombin-mediated fibrin deposition, angiogenesis, and proinflammatory processes.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kovach, I.M., Kelley, P., Eddy, C., et al. Proton bridging in the interactions of thrombin with small inhibitors. Biochemistry 48(30), 7296-7304 (2009).

    2. Bode, W., Turk, D., and Karshikov, A. The refined 1.9-Å x-ray crystal structure of D-Phe-Pro-Arg chloromethylketone-inhibited human α-thrombin: Structure analysis, overall structure, electrostatic properties, detailed active-site geometry, and structure-function relationships. Protein Sci. 1(4), 426-471 (1992).

    3. Hanson, S.R., and Harker, L.A. Interruption of acute platelet-dependent thrombosis by the synthetic antithrombin D-phenylalanyl-L-prolyl-L-arginyl chloromethyl ketone. Proc. Natl. Acad. Sci. USA 85(9), 3184-3488 (1988).

    4. Lyon, M.E., Fine, J.S., Henderson, P.J., et al. D-phenylalanyl-L-prolyl-L-arginine chloromethyl ketone (PPACK): Alternative anticoagulant to heparin salts for blood gas and electrolyte specimens. Clin. Chem. 41(7), 1038-1041 (1995).

    5. Liu, J.F., Hou, S.M., Tsai, C.H., et al. Thrombin induces heme oxygenase-1 expression in human synovial fibroblasts through protease-activated receptor signaling pathways. Arthritis Res. Ther. 14(2), R91 (2012).