A prodrug form of lysipressin
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Active Metabolite(s)
37430Lysipressin (acetate)
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Terlipressin (acetate)

Item No. 27027

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(glycylglycylglycyl)-8-L-lysine-vasopressin, acetate
CAS Number
914453-96-6
Synonyms
  • Glycylpressin
  • Remestyp
Molecular Formula
C52H74N16O15S2 • XC2H4O2
Formula Weight
1227.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 25 mg/mlEthanol: Partially solublePBS (pH 7.2): 10 mg/ml
SMILES
OC(C=C1)=CC=C1C[C@H](NC([C@@H](NC(CNC(CNC(CN)=O)=O)=O)CSSC[C@@H](C(N2CCC[C@H]2C(N[C@@H](CCCCN)C(NCC(N)=O)=O)=O)=O)NC([C@H](CC(N)=O)N3)=O)=O)C(N[C@@H](CC4=CC=CC=C4)C(N[C@@H](CCC(N)=O)C3=O)=O)=O.CC(O)=O
InChi Code
InChI=1S/C52H74N16O15S2.C2H4O2/c53-17-5-4-9-31(45(76)60-23-41(57)72)63-51(82)38-10-6-18-68(38)52(83)37-27-85-84-26-36(61-44(75)25-59-43(74)24-58-42(73)22-54)50(81)65-34(20-29-11-13-30(69)14-12-29)48(79)64-33(19-28-7-2-1-3-8-28)47(78)62-32(15-16-39(55)70)46(77)66-35(21-40(56)71)49(80)67-37;1-2(3)4/h1-3,7-8,11-14,31-38,69H,4-6,9-10,15-27,53-54H2,(H2,55,70)(H2,56,71)(H2,57,72)(H,58,73)(H,59,74)(H,60,76)(H,61,75)(H,62,78)(H,63,82)(H,64,79)(H,65,81)(H,66,77)(H,67,80);1H3,(H,3,4)/t31-,32-,33-,34-,35-,36-,37-,38-;/m0./s1
InChi Key
BYDVFOPTAIPAGA-LCGYVTRFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Terlipressin is a prodrug form of the vasopressin peptide lysipressin and a partial agonist of the vasopressin V1A receptor (Ki = 0.85 µM).1 It is also an agonist of vasopressin V1B and V2 receptors (Kis = 1.11 and 1.58 µM, respectively). It increases mean arterial pressure (MAP) and decreases mortality in a rat model of uncontrolled hemorrhagic shock when administered at a dose of 15 µg/kg.2 Terlipressin (2.6 µg/kg per hour), in combination with norepinephrine, improves vascular reactivity and increases survival time in a rat model of cecal ligation and puncture-induced septic shock and a rabbit model of LPS-induced septic shock.3 It also increases MAP in a rat model of liver cirrhosis with portal hypertension, arterial hypotension, high cardiac output, and low systemic vascular resistance.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Lee, C.C., Lee, M.T., Chang, S.S., et al. A comparison of vasopressin, terlipressin, and lactated ringers for resuscitation of uncontrolled hemorrhagic shock in an animal model. PLoS One 9(4), e95821 (2014).

    3. Xiao, X., Zhu, Y., Zhen, D., et al. Beneficial and side effects of arginine vasopressin and terlipressin for septic shock. J. Surg. Res. 195(2), 568-579 (2015).

    4. Fernández-Varo, G., Oró, D., Cable, E.E., et al. Vasopressin 1a receptor partial agonism increases sodium excretion and reduces portal hypertension and ascites in cirrhotic rats. Hepatology 63(1), 207-216 (2016).