Lysipressin

Lysipressin is a pressor peptide isolated from marsupials and pigs that binds to VP receptors, which are analogous to human Vasopressin 2 (V2) receptors. Lysipressin induces contractions in smooth muscle and potentiates effects of gastric lesioning in animal models.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Lysipressin(CAS 50-57-7)

CAT No: 10-101-23

CAS No:50-57-7

Synonyms/Alias:LYPRESSIN;Lysipressin;Lysine vasopressin;50-57-7;Syntopressin;8-L-Lysinevasopressin;Postacton;Diapid;Lysine pitressin;Lipresina;Lypressine;Vasopressin, 8-L-lysine-;Vasopressin pig;L-Lysine vasopressin;Vasopressin-8-lysine;Vasopressin, 8-L-lysine;[Lys8]-Vasopressin;DTXSID8048575;(8-Lysine)vasopressin;Vasopressin (lysine form);8-L-Lysine vasopressin;50-57-7 (free base);7CZF3L922Y;DTXCID8028501;(Lys8)-Vasopressin;L-Cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-lysylglycinamide cyclic (1->6)-disulfide;[8-Lysine]vasopressin;Lysine-vasopressin;(2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4R,7S,10S,13S,16S,19R)-19-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]pyrrolidine-2-carboxamide;LVP;Lipressina;Lypressinum;Lysopressin;Lysylvasopressin;Lys Vasopressin;Lysyl Vasopressin;CAS-50-57-7;Vasopressin, Lysyl;(S)-N-((S)-6-amino-1-((2-amino-2-oxoethyl)amino)-1-oxohexan-2-yl)-1-((4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)pyrrolidine-2-carboxamide;L-8;Vasopressin, Lysine;Lipressina [DCIT];8 Lysine Vasopressin;8-Lysine Vasopressin;Vasopressin, 8-Lysine;Lipresina [INN-Spanish];Lypressine [INN-French];Lypressinum [INN-Latin];UNII-7CZF3L922Y;Lysipressin?;3-(Phenylalanine)-8-lysine oxytocin;L-lysinamide,;Lysine-ADH;Lypressin [USAN:USP:INN:BAN];NCGC00181743-01;NCGC00181743-02;EINECS 200-050-5;MFCD00076754;BRN 4648365;[Lys8]AVP;LYPRESSIN (MART.);LYPRESSIN (USP-RS);SCHEMBL33287;GTPL2172;CHEMBL1200690;LYPRESSIN (USP IMPURITY);CHEBI:94802;H01BA03;Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2, cyclic 1-6 disulfide;HY-P0004;Tox21_112902;Tox21_113427;AKOS030529559;CCG-270620;CS-5838;DB14642;FL38924;NS00032082;Oxytocin, 3-(L-phenylalanine)-8-L-lysine-;Vasopressin, 8-L-lysine- (7CI,8CI,9CI);C75370;l]carbonyl]-L-prolyl-N-(2-amino-2-oxoethyl)-;BRD-K93331255-001-01-2;BRD-K93331255-001-02-0;Q27082434;1,2-Dithia-5,8,11,14,17-pentaazacycloeicosane-10-propionamide;Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Lys-Gly-NH2[Disulfide Bridge: 1-6];(2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;(2S)-N-[(2S)-6-amino-1-[(2-amino-2-oxoethyl)amino]-1-oxohexan-2-yl]-1-[[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)-1,2-dithia-5,8,11,14,17-pentazacycloeicos-4-yl]-oxomethyl]-2-pyrrolidinecarboxamide;1-[[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)-1,2-dithia-5,8,11,14,17-pentaazacycloeicos-4-y;19-amino-4-[2-[[5-amino-1-[(carbamoylmethyl)carbamoyl]pentyl]carbamoyl]-1-pyrrolidinylcarbonyl]-13-benzyl-7-(carbamoylmethyl)-16-p-hydroxybenzyl-6,9,12,15,18-pentaoxo- (6CI);200-050-5;Glycinamide, L-cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-lysyl-, cyclic (1>6)-disulfide;L 8;L-CYSTEINYL-L-TYROSYL-L-PHENYLALANYL-L-GLUTAMINYL-L-ASPARAGINYL-L-CYSTEINYL-L-PROLYL-L-LYSYLGLYCINAMIDE CYCLIC (1->6)-DISULPHIDE;L-Cysteinyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-lysylglycinamide cyclic (1-6)-disulfide;

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M.F/Formula
C46H65N13O12S2
M.W/Mr.
1056.2
Sequence
One Letter Code:CYFQNCPKG
Three Letter Code:H-Cys(1)-Tyr-Phe-Gln-Asn-Cys(1)-Pro-Lys-Gly-NH2
Labeling Target
Vasopressin receptor
Application
Lysipressin Acetate is a lysine vasopressin, which retains water in the body and constricts blood vessels, It is used to treat bleeding esophageal varices.
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Biological Activity
Lysipressin is Antidiuretic hormone that have been found in pigs and some marsupial families. Induces contraction of the rabbit urinary bladder smooth muscle, activate adenylate-cyclase.
Areas of Interest
Cardiovascular System & Diseases
Pituitary & Hypothalamic Hormones

Lysipressin, also known as lysine vasopressin or LVP, is a synthetic analogue of the naturally occurring antidiuretic hormone vasopressin. Structurally characterized by the substitution of a lysine residue at the eighth position, Lysipressin exhibits unique pharmacological properties that distinguish it from its arginine-based counterpart. Its potent vasoconstrictive and antidiuretic actions make it a valuable compound in laboratory research, particularly in studies exploring water balance, vascular tone, and receptor selectivity. The stability and specificity of Lysipressin enable researchers to dissect the physiological and molecular mechanisms underlying vasopressin-mediated pathways, offering insights into endocrine and renal regulation.

Endocrine research: Lysipressin serves as a critical tool in endocrine studies focusing on the mechanisms of water reabsorption and osmoregulation. By mimicking the action of endogenous vasopressin on V2 receptors in the renal collecting ducts, it allows researchers to investigate the hormonal control of water homeostasis without interference from other vasopressin analogues. This specificity is particularly beneficial in experiments designed to differentiate the roles of various vasopressin isoforms in regulating antidiuretic activity and electrolyte balance. Utilizing Lysipressin in in vitro and in vivo models, scientists can elucidate the signaling pathways and feedback mechanisms that maintain fluid equilibrium, contributing to a deeper understanding of endocrine system dynamics.

Vascular studies: In vascular biology, LVP is frequently employed to examine its vasoconstrictive effects on smooth muscle tissues. Its ability to selectively activate V1a receptors on vascular smooth muscle cells makes it an ideal candidate for probing the molecular mechanisms of vasopressin-induced vasoconstriction. Researchers use Lysipressin to induce controlled changes in vascular tone, enabling the study of blood pressure regulation, vascular resistance, and the interplay between endothelial and smooth muscle signaling. These investigations are crucial for mapping the pathways involved in circulatory homeostasis and for testing hypotheses related to vascular responsiveness under various physiological and experimental conditions.

Receptor pharmacology: Lysipressin is instrumental in receptor binding and pharmacological profiling studies. Its structural distinction from arginine vasopressin allows for selective investigation of receptor subtype affinity and activation, particularly at V1a and V2 receptors. By employing Lysipressin in radioligand binding assays, signal transduction experiments, and competitive inhibition studies, scientists can delineate the specificity and efficacy of receptor-ligand interactions. This information is vital for the rational design of new receptor modulators and for understanding the nuances of vasopressin receptor pharmacology in different tissue types.

Renal physiology: In the context of renal research, Lysipressin is utilized to model and analyze the mechanisms of urine concentration and diuresis. Its antidiuretic activity provides a controllable means of modulating water reabsorption in nephron segments, making it valuable for studies on aquaporin channel regulation, medullary osmolarity, and the effects of hormonal manipulation on renal function. Researchers often use Lysipressin to simulate conditions of altered water balance, facilitating the exploration of compensatory mechanisms in the kidney and the identification of novel targets for modulating renal water handling.

Behavioral neuroscience: LVP is also applied in behavioral neuroscience to investigate the central effects of vasopressin analogues on social behavior, stress responses, and learning processes. By administering Lysipressin in animal models, researchers can assess its influence on neural circuits involved in aggression, social recognition, and memory consolidation. Such studies contribute to the broader understanding of neuropeptide signaling in the brain and its implications for behavior and neuroendocrine integration. The use of Lysipressin in these experimental paradigms underscores its versatility as a research tool for dissecting complex interactions between hormones and neural function.

Source#
Synthetic
Long-term Storage Conditions
Soluble in DMSO
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage Conditions
Dry, dark and at 0 - 4 °C
Solubility
-20 °C
InChI
InChI=1S/C46H65N13O12S2/c47-17-5-4-9-29(40(65)52-22-38(51)63)54-45(70)35-10-6-18-59(35)46(71)34-24-73-72-23-28(48)39(64)55-31(20-26-11-13-27(60)14-12-26)43(68)56-32(19-25-7-2-1-3-8-25)42(67)53-30(15-16-36(49)61)41(66)57-33(21-37(50)62)44(69)58-34/h1-3,7-8,11-14,28-35,60H,4-6,9-10,15-24,47-48H2,(H2,49,61)(H2,50,62)(H2,51,63)(H,52,65)(H,53,67)(H,54,70)(H,55,64)(H,56,68)(H,57,66)(H,58,69)/t28-,29-,30-,31-,32-,33-,34-,35-/m0/s1
InChI Key
BJFIDCADFRDPIO-DZCXQCEKSA-N
BoilingPoint
1610.4±65.0 °C at 760 mmHg
References

The neurohypophyseal hormones of the hippopotamus (Hippopotamus amphibius) and collared peccary (Tayassu angulatus) were isolated by molecular sieving and preparative high-pressure liquid chromatography (HPLC). Oxytocin and arginine vasopressin have been identified by their amino acid compositions and their retention times in HPLC. Lysipressin (lysine vasopressin) was not detected in posterior pituitaries of two hippopotami and nine peccaries (less than 2% of arginine vasopressin in molar ratios). Among the suborder Suiformes of Artiodactyla, the families Hippopotamidae and Tayassuidae do not seem to possess lysipressin, in contrast to the family Suidae in which the pig has lysipressin in place of arginine vasopressin.

Rouille, Y., Chauvet, M. T., Chauvet, J., Acher, R., & Hadley, M. E. (1988). The distribution of lysine vasopressin (lysipressin) in placental mammals: a reinvestigation of the Hippopotamidae (Hippopotamus amphibius) and Tayassuidae (Tayassu angulatus) families. General and comparative endocrinology, 71(3), 475-483.

Melting Point
N/A

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