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, a synthetic vasopressin analog, is a peptide compound widely recognized for its potent vasoconstrictive properties and prolonged duration of action compared to natural vasopressin. Its unique structure, featuring a triglycyl residue attached to the lysine at position eight, enables a slow enzymatic release of the active lysine-vasopressin, resulting in sustained physiological effects. This characteristic makes the compound particularly valuable in research settings where controlled modulation of vascular tone and hemodynamics is required. Terlipressin's stability and predictable pharmacological profile have facilitated its adoption in a variety of experimental models, allowing researchers to probe the mechanisms underlying vascular regulation and fluid homeostasis.

Vascular Physiology Research: In the field of vascular biology, terlipressin serves as a reliable tool for investigating the mechanisms of vasoconstriction and blood flow regulation. Researchers utilize this peptide to induce targeted vasoconstriction in isolated tissue preparations or in vivo models, enabling detailed studies of receptor-mediated signaling pathways and endothelial responses. By modulating vascular resistance, terlipressin helps elucidate the interplay between vasoactive peptides, nitric oxide, and other mediators that govern vascular tone, offering insights into the pathophysiology of hypertension and circulatory shock.

Liver Disease Modeling: The compound is extensively used in experimental models of portal hypertension and liver dysfunction, where it mimics the hemodynamic alterations observed in these conditions. Scientists employ terlipressin to elevate portal pressure and study its effects on splanchnic circulation, hepatic perfusion, and the development of complications such as ascites. This approach facilitates the evaluation of novel therapeutic strategies aimed at mitigating portal hypertension and improving liver microcirculation, thereby advancing our understanding of hepatic vascular disorders.

Renal Hemodynamics and Water Balance: Terlipressin is instrumental in research exploring the regulation of renal blood flow and water reabsorption. Its vasoconstrictive action on renal vasculature allows investigators to model conditions such as hepatorenal syndrome and acute kidney injury. By manipulating renal perfusion and glomerular filtration, researchers can assess the impact of altered hemodynamics on renal function, sodium handling, and the activity of antidiuretic hormone pathways, contributing to the development of interventions for fluid and electrolyte imbalances.

Pharmacological Screening and Drug Development: The peptide analog is a valuable reference compound in the screening of new vasoactive agents and antagonists. Its well-characterized mechanism of action provides a benchmark for evaluating the efficacy and selectivity of novel drug candidates targeting vasopressin receptors. By comparing the pharmacodynamic profiles of test compounds with those of terlipressin, pharmaceutical scientists can identify promising molecules for further development, optimize dosing regimens, and minimize off-target effects in preclinical studies.

Cardiovascular System Investigations: In cardiovascular research, terlipressin is utilized to model acute changes in systemic vascular resistance and cardiac output, offering a controlled means to study compensatory mechanisms such as baroreceptor reflexes and neurohormonal activation. Its application in animal models helps delineate the contributions of vasopressinergic signaling to blood pressure regulation, heart function, and the pathogenesis of cardiovascular diseases. By leveraging its potent vasoconstrictive properties, researchers gain valuable insights into the dynamic interactions between the heart, blood vessels, and neuroendocrine systems.

Endocrine and Neurohormonal Research: The use of terlipressin extends to studies investigating the broader roles of vasopressin analogs in endocrine and neurohormonal regulation. Scientists explore its effects on the hypothalamic-pituitary-adrenal axis, stress response, and the modulation of hormone release under various physiological and pathophysiological conditions. Through these investigations, the peptide aids in unraveling the complex network of hormonal interactions that maintain homeostasis, providing a foundation for future research into the treatment of endocrine disorders and stress-related diseases.

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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