An antithrombin peptide
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Alternative(s)
15160PPACK (trifluoroacetate salt)
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PPACK (hydrochloride)

Item No. 37489

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
D-phenylalanyl-N-[(1S)-4-[(aminoiminomethyl)amino]-1-(chloroacetyl)butyl]-L-prolinamide, dihydrochloride
CAS Number
82188-90-7
Synonyms
  • Pebac
  • D-Phenylalanyl-prolyl-arginyl Chloromethyl Ketone
  • D-Phe-Pro-Arg-CH2Cl
Molecular Formula
C21H31ClN6O3 • 2HCl
Formula Weight
523.9
Purity
≥95%
Formulation (Request formulation change)
A solid
Peptide Sequence
fPR-CH2Cl
Solubility(Learn about Variance in Solubility)
DMSO: SolubleWater: Soluble
SMILES
O=C([C@H](N)CC1=CC=CC=C1)N2[C@H](C(N[C@H](C(CCl)=O)CCCNC(N)=N)=O)CCC2.Cl.Cl
InChi Code
InChI=1S/C21H31ClN6O3.2ClH/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);2*1H/t15-,16+,17+;;/m1../s1
InChi Key
XKDCRQWZLPWLFG-LKLBIAKRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $40

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    5 mg

    $168

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    10 mg

    $315

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    25 mg

    $640

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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. 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).

    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. 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).

    4. 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).

    5. 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).