An endogenous vasodilator
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Active Metabolite(s)
31136(Des-Arg9)-Bradykinin
Metabolite(s)
39723Bradykinin (2-9) (trifluoroacetate salt)
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Bradykinin (human, mouse, rat, bovine) (acetate)

Item No. 37408

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
6846-03-3
Synonyms
  • Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH
  • BK
  • RPPGFSPFR-OH
Molecular Formula
C50H73N15O11 • XC2H4O2
Formula Weight
1060.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 12 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 2 mg/ml
SMILES
CC(O)=O.O=C(N(CCC1)[C@@H]1C(NCC(N[C@H](C(N[C@@H](CO)C(N(CCC2)[C@@H]2C(N[C@H](C(N[C@H](C(O)=O)CCCNC(N)=N)=O)CC3=CC=CC=C3)=O)=O)=O)CC4=CC=CC=C4)=O)=O)[C@H](CCC5)N5C([C@@H](N)CCCNC(N)=N)=O
InChi Code
InChI=1S/C50H73N15O11.C2H4O2/c51-32(16-7-21-56-49(52)53)45(72)65-25-11-20-39(65)47(74)64-24-9-18-37(64)43(70)58-28-40(67)59-34(26-30-12-3-1-4-13-30)41(68)62-36(29-66)46(73)63-23-10-19-38(63)44(71)61-35(27-31-14-5-2-6-15-31)42(69)60-33(48(75)76)17-8-22-57-50(54)55;1-2(3)4/h1-6,12-15,32-39,66H,7-11,16-29,51H2,(H,58,70)(H,59,67)(H,60,69)(H,61,71)(H,62,68)(H,75,76)(H4,52,53,56)(H4,54,55,57);1H3,(H,3,4)/t32-,33-,34-,35-,36-,37-,38-,39-;/m0./s1
InChi Key
VIGBULRGBBKXHS-MIEKKPBHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $32

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    5 mg

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    10 mg

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    25 mg

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    Product Description

    Bradykinin is an endogenous vasodilator that is also involved in inflammation.1,2 It is formed from kininogen via cleavage of high molecular weight kininogen (HMWK) by kallikrein or prekallikrein in a Factor XIIa-dependent or -independent manner.3 Bradykinin binds to the bradykinin B2 receptor (IC50 = 0.54 nM in COS-7 cells expressing the human receptor) and acts as an agonist but does not bind the bradykinin B1 receptor (Ki = >10,000 nM in HEK293 cells expressing the human receptor).4,5 It stimulates arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) release in CHO cells expressing the human bradykinin B2 receptor (EC50 = 0.7 nM).4 Bradykinin (100 nM) induces relaxation of isolated porcine coronary arterial rings precontracted with acetylcholine (ACh; Item No. 23829) or phorbol 12,13-dibutyrate (PDBu; Item No. 27785).1 It induces hyperalgesia in mice when administered at a dose of 1 µg/paw, an effect that can be reversed by the bradykinin B2 antagonist icatibant (HOE 140; Item No. 24083).2 Plasma levels of bradykinin are increased in patients during an acute attack of angioedema.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Weintraub, N.L., Fang, X., Kaduce, T.L., et al. Potentiation of endothelium-dependent relaxation by epoxyeicosatrienoic acids. Circ. Res. 81, 258-267 (1997).

    2. Ferreira, S.H., Lorenzetti, B.B., and Poole, S. Bradykinin initiates cytokine-mediated inflammatory hyperalgesia. Br. J. Pharmacol. 110(3), 1227-1231 (1993).

    3. Joseph, K., Tholanikunnel, B.G., and Kaplan, A.P. Factor XII-independent cleavage of high-molecular-weight kininogen by prekallikrein and inhibition by C1 inhibitor. J. Allergy Clin. Immunol. 124(1), 143-149 (2009).

    4. Hess, J.F., Borkowski, J.A., Macneil, T., et al. Differential pharmacology of cloned human and mouse B2 bradykinin receptors. Mol. Pharmacol. 45(1), 1-8 (1994).

    5. Bastian, S., Loillier, B., Paquet, J.L., et al. Stable expression of human kinin B1 receptor in 293 cells: Pharmacological and functional characterization. Br. J. Pharmacol. 122(2), 393-399 (1997).

    6. Nussberger, J., Cugno, M., Amstutz, C., et al. Plasma bradykinin in angio-oedema. Lancet 351(9117), 1693-1697 (1998).