A peptide hormone
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Pro-drug Form(s)
27027Terlipressin (acetate)
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Lysipressin (acetate)

Item No. 37430

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-L-lysine-vasopressin, monoacetate
CAS Number
83968-49-4
Molecular Formula
C46H65N13O12S2 • C2H4O2
Formula Weight
1116.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 10 mM
SMILES
N[C@@H](CSSC[C@@H](C(N1CCC[C@H]1C(N[C@H](C(NCC(N)=O)=O)CCCCN)=O)=O)NC([C@H](CC(N)=O)N2)=O)C(N[C@@H](CC3=CC=C(O)C=C3)C(N[C@@H](CC4=CC=CC=C4)C(N[C@@H](CCC(N)=O)C2=O)=O)=O)=O.CC(O)=O
InChi Code
InChI=1S/C46H65N13O12S2.C2H4O2/c47-17-5-4-9-29(40(65)52-22-38(51)63)54-45(70)35-10-6-18-59(35)46(71)34-24-73-72-23-28(48)39(64)55-31(20-26-11-13-27(60)14-12-26)43(68)56-32(19-25-7-2-1-3-8-25)42(67)53-30(15-16-36(49)61)41(66)57-33(21-37(50)62)44(69)58-34;1-2(3)4/h1-3,7-8,11-14,28-35,60H,4-6,9-10,15-24,47-48H2,(H2,49,61)(H2,50,62)(H2,51,63)(H,52,65)(H,53,67)(H,54,70)(H,55,64)(H,56,68)(H,57,66)(H,58,69);1H3,(H,3,4)/t28-,29-,30-,31-,32-,33-,34-,35-;/m0./s1
InChi Key
NKWAIKZITYLOMT-DHSVNZEYSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    Product Description

    Lysipressin is a peptide hormone found in pigs and marsupials that corresponds to amino acids 20-28 of the vasoconstrictor peptide vasopressin with lysine in place of arginine at position 27.1,2 It is an arginine vasopressin receptor 1A (V1A) receptor agonist that binds to rat and human V1A receptors (Kis = 1.2 and 10.1 nM, respectively) and increases intracellular calcium levels in cultured rat and human aortic cells with half-maximal activation (Kact) values of 12 and 20.8 nM, respectively.3 Lysipressin induces vasoconstriction in isolated mesenteric arteries from normotensive and spontaneously hypertensive rats.4 It also has antidiuretic effects in non-anesthetized dwarf pigs, decreasing urine volume and increasing urinary solutes without affecting the glomerular filtration rate.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Munsick, R.A., Sawyer, W.H., and Van Dyke, H.B. The antidiuretic potency of arginine and lysine vasopressins in the pig with observations on porcine renal function. Endocrinology 63(5), 688-693 (1958).

    2. Chauvet, J., Hurpet, D., Michel, G., et al. Two multigene families for marsupial neurohypophysial hormones? Identification of oxytocin, mesotocin, lysipressin and arginine vasopressin in the North American opossum (Didelphis virginiana). Biochem. Biophys. Res. Commun. 123(1), 306-311 (1984).

    3. Colson, P.H., Virsolvy, A., Gaudard, P., et al. Terlipressin, a vasoactive prodrug recommended in hepatorenal syndrome, is an agonist of human V1, V2 and V1B receptors: Implications for its safety profile. Pharmacol. Res. 113(Pt A), 257-264 (2016).

    4. Schlegel, P.A., Monney, M., and Brunner, H.R. Isolated perfused mesenteric arteries of hypertensive and normotensive rats; response to norepinephrine, lysine vasopressin and angiotensin II. Clin. Exp. Hypertens. A. 7(11), 1583-1596 (1985).