Terlipressin acetate

Alias: Gly-Gly-Gly-8-Lys-vasopressin; TGLVP; triglycyl lysine vasopressin; Terlipressin; Terlipressin acetate; trade names: Glypressin; Teripress

Cat No.:V16096 Purity: = 99.58%

COA Product Data Instructions for use SDS

Terlipressin acetate Chemical Structure CAS No.: 914453-96-6
Product category: Vasopressin Receptor

This product is for research use only, not for human use. We do not sell to patients.

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Other Forms of Terlipressin acetate:

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Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: = 99.58%

COA

MSDS

HPLC

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Clinical Trial Information
Biological Data

Product Description

Terlipressin acetate is a tube-active vasopressin analog and a selective vasopressin V1 receptor agonist (activator) that reduces splanchnic blood flow and portal pressure and controls acute variceal bleeding. Terlipressin acetate has anti~inflammatory and antioxidant effects and may be utilized in study/research of hepatorenal syndrome and norepinephrine-resistant septic shock.

Biological Activity I Assay Protocols (From Reference)

Targets	vasopressin V1 receptor
References	[1]. Terlipressin Protects Intestinal Epithelial Cells Against Oxygen-Glucose Deprivation/Re-Oxygenation Injury via the Phosphatidylinositol 3-kinase Pathway. Exp Ther Med. 2017 Jul;14(1):260-266. [2]. Refractory Torsade De Pointes Induced by Terlipressin (Glypressin). Int J Cardiol. 2016 Nov 1;222:135-140. [3]. Signaling Through Hepatocyte Vasopressin Receptor 1 Protects Mouse Liver From Ischemia-Reperfusion Injury. Oncotarget. 2016 Oct 25;7(43):69276-69290. [4]. Terlipressin Protects Intestinal Epithelial Cells Against Oxygen-Glucose Deprivation/Re-Oxygenation Injury via the Phosphatidylinositol 3-kinase Pathway. Exp Ther Med. 2017 Jul;14(1):260-266. [5]. Terlipressin for the Treatment of Acute Variceal Bleeding: A Systematic Review and Meta-Analysis of Randomized Controlled Trials. Medicine (Baltimore). 2018 Nov;97(48):e13437.

Targets

vasopressin V1 receptor

References

[1]. Terlipressin Protects Intestinal Epithelial Cells Against Oxygen-Glucose Deprivation/Re-Oxygenation Injury via the Phosphatidylinositol 3-kinase Pathway. Exp Ther Med. 2017 Jul;14(1):260-266.

[2]. Refractory Torsade De Pointes Induced by Terlipressin (Glypressin). Int J Cardiol. 2016 Nov 1;222:135-140.

[3]. Signaling Through Hepatocyte Vasopressin Receptor 1 Protects Mouse Liver From Ischemia-Reperfusion Injury. Oncotarget. 2016 Oct 25;7(43):69276-69290.

[4]. Terlipressin Protects Intestinal Epithelial Cells Against Oxygen-Glucose Deprivation/Re-Oxygenation Injury via the Phosphatidylinositol 3-kinase Pathway. Exp Ther Med. 2017 Jul;14(1):260-266.

[5]. Terlipressin for the Treatment of Acute Variceal Bleeding: A Systematic Review and Meta-Analysis of Randomized Controlled Trials. Medicine (Baltimore). 2018 Nov;97(48):e13437.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula	C54H78N16O17S2
Molecular Weight	1287.433
Exact Mass	1286.52
Elemental Analysis	C, 50.38; H, 6.11; N, 17.41; O, 21.13; S, 4.98
CAS #	914453-96-6
Related CAS #	Terlipressin diacetate; 1884420-36-3; Terlipressin; 14636-12-5
Appearance	Solid powder
SMILES	CC(=O)O.C1C[C@H](N(C1)C(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](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)N[C@@H](CCCCN)C(=O)NCC(=O)N
InChi Key	BYDVFOPTAIPAGA-LCGYVTRFSA-N
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
Chemical Name	acetic acid;(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	Gly-Gly-Gly-8-Lys-vasopressin; TGLVP; triglycyl lysine vasopressin; Terlipressin; Terlipressin acetate; trade names: Glypressin; Teripress
HS Tariff Code	2934.99.9001
Storage	Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	0.7767 mL	3.8837 mL	7.7674 mL
	5 mM	0.1553 mL	0.7767 mL	1.5535 mL
	10 mM	0.0777 mL	0.3884 mL	0.7767 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

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Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
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The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
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The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

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Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
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Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

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Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

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Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Clinical Trial Information

NCT Number	Recruitment	interventions	Conditions	Sponsor/Collaborators	Start Date	Phases
NCT04460560	Active Recruiting	Drug: Terlipressin	Hepatorenal Syndrome	University of Pennsylvania	December 11, 2020	Phase 3
NCT05170230	Recruiting	Drug: Terlipressin	Myoma	Wael Elbanna Clinic	February 27, 2022	Not Applicable
NCT05242783	Recruiting	Drug: Terlipressin	Myoma	Wael Elbanna Clinic	February 1, 2022	Not Applicable
NCT05154279	Recruiting	Drug: Terlipressin	Laparoscopic Myomectomy	Wael Elbanna Clinic	February 27, 2022	Not Applicable
NCT04961528	Recruiting	Drug: Terlipressin Drug: Placebo Drug: Tranexamic Acid 500 MG	Hemoptysis	Assistance Publique - Hôpitaux de Paris	March 27, 2022	Phase 3

Biological Data

Forest plot showing the difference in the control of bleeding in patients treated with terlipressin compared with no vasoactive drugs. Medicine (Baltimore) . 2018 Nov;97(48):e13437.
Forest plot showing the difference in the rebleeding in patients treated with terlipressin compared with balloon tamponade. Medicine (Baltimore) . 2018 Nov;97(48):e13437.
The effect of Terlipressin on the overall mouse hepatic blood perfusion in vivo. Oncotarget . 2016 Oct 25;7(43):69276-69290.
Terlipressin treatment ameliorates hepatic injury and inflammation. Oncotarget . 2016 Oct 25;7(43):69276-69290.
Changes in IEC-6 cell viability following OGD/R. (A) Effect of different concentrations of terlipressin on IEC-6 cell viability following OGD/R. Exp Ther Med . 2017 Jul;14(1):260-266.