Terlipressin
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Terlipressin

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Terlipressin is an analog of vasopressin and a partial agonist of the vasopressin V1A receptor (Ki = 0.85 µM). It has been used as a vasoactive drug in the management of low blood pressure.

Category
Peptide Inhibitors
Catalog number
BAT-010058
CAS number
14636-12-5
Molecular Formula
C52H74N16O15S2
Molecular Weight
1227.4
Terlipressin
Size Price Stock Quantity
100 mg $299 In stock
IUPAC Name
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-[[2-[[2-[(2-aminoacetyl)amino]acetyl]amino]acetyl]amino]-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]pyrrolidine-2-carboxamide
Synonyms
glipressin; glycylpressin; glypressin; Remestyp; terlypressin; TGLVP; triglycylvasopressin; triglycyl lysine vasopressin; Terlipressine; Terlipressinum; Terlipressina; Terlipressina; EINECS 238-680-8; LS-161411
Related CAS
1884420-36-3 (diacetate)
Appearance
White Solid
Purity
≥95%
Density
1.46 g/cm3
Boiling Point
1824°C at 760 mmHg
Sequence
GGGC(1)YFQNC(1)PKG
Storage
Store at -20°C
InChI
InChI=1S/C52H74N16O15S2/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/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)/t31-,32-,33-,34-,35-,36-,37-,38-/m0/s1
InChI Key
BENFXAYNYRLAIU-QSVFAHTRSA-N
Canonical SMILES
C1CC(N(C1)C(=O)C2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)NC(=O)CNC(=O)CNC(=O)CN)C(=O)NC(CCCCN)C(=O)NCC(=O)N
1.[MODERN VIEW ON INTENSIVE THERAPY OF GASTRO-INTESTINAL HEMORRHAGE].
Tutchenko MI, Rudyk DV, Iskra NI, Trofimenko SP, Shchur IV. Klin Khir. 2015 Oct;(10):11-4.
Basing on analysis of the treatment results in 47 patients for gastro-intestinal hemorrhage, the experience of application of a tranexamic acid in a content of infusion therapy and hemaxam per os was adduced. The data obtained witness the expediency of hemaxam application in a content of therapy on the stage of a hemorrhage letup and for the recurrence prevention.
2.Terlipressin and albumin for type 1 hepatorenal syndrome: does bacterial infection affect the response?
Altun R1, Korkmaz M1, Yıldırım E1, Öcal S1, Akbaş E1, Selçuk H1. Springerplus. 2015 Dec 23;4:806. doi: 10.1186/s40064-015-1625-z. eCollection 2015.
Vasoconstrictor therapy with terlipressin and concomitant albumin can improve renal function in patients with hepatorenal syndrome (HRS) type 1, but the efficacy of therapy in patients with active infection is controversial. The aim of this study was to investigate the efficacy, adverse effects, and predictors of terlipressin therapy and to find out whether there was a difference in response rates between the patients with or without active infections. Data of 58 patients with type 1 HRS treated with terlipressin and albumin were retrospectively evaluated. Twenty-six patients (44.8 %) showed complete response to treatment. Response rates of patients with or without active bacterial infection were 47 and 43.9 %, respectively (p > 0.05). Only baseline serum creatinine level was significantly related to response in univariate/multivariate analyses (p < 0.05). Twenty-three patients (39.6 %) developed adverse effects probably related to treatment.
3.Current approaches to the management of patients with liver cirrhosis who have acute esophageal variceal bleeding.
Garbuzenko DV1. Curr Med Res Opin. 2016 Mar;32(3):467-75. doi: 10.1185/03007995.2015.1124846. Epub 2016 Jan 25.
OBJECTIVE: Esophageal variceal bleeding is the most dangerous complication in patients with liver cirrhosis, and it is accompanied by high mortality. Their treatment can be complex, and requires a multidisciplinary approach. This review examines current approaches to the management of patients with liver cirrhosis who have acute esophageal variceal bleeding.
4.Terlipressin plus albumin is more effective than albumin alone in improving renal function in patients with cirrhosis and hepatorenal syndrome type 1.
Boyer TD1, Sanyal AJ2, Wong F3, Frederick RT4, Lake JR5, O'Leary JG6, Ganger D7, Jamil K8, Pappas SC9; REVERSE Study Investigators. Gastroenterology. 2016 Feb 16. pii: S0016-5085(16)00217-1. doi: 10.1053/j.gastro.2016.02.026. [Epub ahead of print]
BACKGROUND & AIMS: Hepatorenal syndrome type 1 (HRS-1) in patients with cirrhosis and ascites is a functional, potentially reversible form of acute kidney injury characterized by rapid (<2 weeks) and progressive deterioration of renal function. Terlipressin is a synthetic vasopressin analogue that acts, via vascular vasopressin V1 receptors, as a systemic vasoconstrictor. We performed a phase 3 study to evaluate the efficacy and safety of intravenous terlipressin plus albumin vs placebo plus albumin in patients with HRS-1.
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