Terlipressin

Terlipressin is a synthetic vasopressin analog that supports vascular and renal research. Purchase Terlipressin peptide from a verified supplier for liver and hemodynamic studies.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Terlipressin(CAS 14636-12-5)

CAT No: 10-101-342

CAS No:14636-12-5

Synonyms/Alias:Terlipressin;14636-12-5;glypressin;Terlipressin acetate;glycylpressin;Terlipressine;Terlipressina;Terlipressinum;Lucassin;Terlipressine [INN-French];Terlipressinum [INN-Latin];Terlipressina [INN-Spanish];N-(N-(N-Glycylglycyl)glycyl)-8-L-lysinevasopressin;Terlipresina;Variquel;EINECS 238-680-8;UNII-7Z5X49W53P;DTXSID7048952;(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;DTXCID0028878;7Z5X49W53P;Terlivaz;NCGC00185754-01;Terlipressine (INN-French);Terlipressinum (INN-Latin);Terlipressina (INN-Spanish);glycyl-glycyl-glycyl-L-cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparagyl-L-cysteinyl-L-prolyl-L-lysyl-glycinamide (4->9)-disulfide;terlypressin;triglycylvasopressin;TGLVP;914453-96-6;triglycyl lysine vasopressin;Terlipressin?;Terlipressin [USAN:INN:BAN];Lucassin (TN);HS-2028;Terlipressin (USAN/INN);SCHEMBL22699;TERLIPRESSIN (MART.);CHEMBL2135460;GTPL11241;H01BA04;BENFXAYNYRLAIU-QSVFAHTRSA-N;CHEBI:135905;TERLIPRESSIN (EP MONOGRAPH);EX-A3116;Tox21_113374;AKOS015994637;CCG-270662;CS-5769;DB02638;DA-58411;HY-12554;CAS-14636-12-5;NS00024791;C72780;D06672;GLYCYLGLYCYLGLYCYL(8-L-LYSINE)VASOPRESSIN;N-(N-(N-glycylglycyl)glycyl)-L-lysinevasopressin;Q324147;BRD-K73451719-001-01-2;VASOPRESSIN, N-(GLYCYLGLYCYLGLYCYL)-8-L-LYSINE-;GLY-GLY-GLY-CYS-TYR-PHE-GLN-ASN-CYS-PRO-LYS-GLY-NH2 (4-9 DISULFIDE);(2S)-6-amino-2-{[(2S)-1-{[(4R,7S,10S,13S,16S,19R)-19-{2-[2-(2-aminoacetamido)acetamido]acetamido}-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)hexanamide;238-680-8;

Chemical 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

Custom Peptide Synthesis
cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C52H74N16O15S2
M.W/Mr.
1227.4
Sequence
One Letter Code:GGGCYFQNCPKG
Three Letter Code:H-Gly-Gly-Gly-Cys(1)-Tyr-Phe-Gln-Asn-Cys(1)-Pro-Lys-Gly-NH2
Activity
Agonist
Biological Activity
Terlipressin is an analogue of vasopressin used as a vasoactive drug in the management of hypotension which has been found to be effective when norepinephrine fails.
Target
Vasopressin Receptor

Terlipressin is a synthetic peptide analog of vasopressin, designed to mimic and extend the biological activity of the natural antidiuretic hormone. Structurally, it consists of a modified peptide sequence that confers increased stability and a prolonged duration of action compared to its endogenous counterpart. Its receptor selectivity and resistance to enzymatic degradation make it a valuable tool for exploring vasopressinergic signaling pathways and peptide pharmacodynamics. Due to its well-defined structure and predictable bioactivity, terlipressin is widely utilized in advanced biochemical and pharmacological research, particularly in studies investigating vascular tone regulation, receptor binding, and peptide-based drug development.

Receptor Pharmacology: Terlipressin serves as an important ligand for probing vasopressin receptor subtypes, especially V1 receptors, in both in vitro and ex vivo experimental models. By selectively activating these receptors, researchers can dissect downstream signaling cascades, assess receptor distribution, and evaluate the functional consequences of vasopressinergic modulation in various tissues. Its predictable receptor affinity and slower metabolic breakdown compared to native vasopressin facilitate more precise kinetic and mechanistic studies, supporting the elucidation of receptor-mediated physiological effects.

Vascular Biology Research: In the context of vascular tone and hemodynamic regulation, terlipressin is frequently employed to simulate vasoconstrictive responses in isolated vessel assays, tissue bath experiments, and organ perfusion setups. Its robust vasopressor activity enables the study of smooth muscle contractility, endothelial function, and the interplay between vasoconstrictive and vasodilatory mediators. Such investigations contribute to a deeper understanding of blood flow regulation, vascular pathophysiology, and the molecular underpinnings of circulatory homeostasis.

Peptide Drug Development: As a stable peptide analog, terlipressin provides a valuable template for the design and optimization of next-generation peptide therapeutics. It is often used in structure-activity relationship (SAR) studies, where modifications to its amino acid sequence yield insights into the determinants of receptor selectivity, metabolic stability, and bioactivity. These findings inform the rational development of novel peptide-based agents targeting vasopressin receptors or related pathways, supporting innovation in peptide medicinal chemistry and drug discovery.

Analytical Method Development: The defined chemical structure and robust bioactivity of terlipressin make it an ideal reference compound for the development and validation of analytical techniques such as high-performance liquid chromatography (HPLC), mass spectrometry, and immunoassays. Researchers utilize it as a standard for quantifying peptide concentrations, assessing peptide stability, and calibrating detection systems. This supports the generation of accurate, reproducible data in peptide analysis and quality control workflows.

Peptide Stability and Degradation Studies: Terlipressin's resistance to enzymatic degradation offers a unique model for investigating peptide stability in biological matrices and under various experimental conditions. By comparing its degradation kinetics to those of other peptides, scientists can elucidate factors influencing peptide half-life, identify key proteolytic enzymes, and characterize protective modifications. Such studies are instrumental in optimizing peptide formulations, improving delivery strategies, and advancing the field of peptide therapeutics research.

Long-term Storage Conditions
DMF: 20 mg/ml
DMSO: 25 mg/ml
Ethanol: Partially soluble
PBS (pH 7.2): 10 mg/ml
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
Isomeric SMILES
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

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