Lypressin | CAS#50-57-7 | porcine antidiuretic hormone

MedKoo Cat#: 597500 | Name: Lypressin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lypressin is the porcine antidiuretic hormone (vasopressins). It is a cyclic nonapeptide that differs from arg-vasopressin by one amino acid, containing a lysine at residue 8 instead of an arginine. Lys-vasopressin is used to treat diabetes insipidus or to improve vasomotor tone and blood pressure.

Chemical Structure

Lypressin

CAS#50-57-7 (free base)

Theoretical Analysis

MedKoo Cat#: 597500

Name: Lypressin

CAS#: 50-57-7 (free base)

Chemical Formula: C46H65N13O12S2

Exact Mass: 1055.4317

Molecular Weight: 1056.23

Elemental Analysis: C, 52.31; H, 6.20; N, 17.24; O, 18.18; S, 6.07

Price and Availability

Size	Price	Availability
5mg	USD 320.00	2 weeks
10mg	USD 585.00	2 weeks
50mg	USD 950.00	2 weeks

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Related CAS #

22049-37-2 50-57-7 (free base)

Synonym

Lypressin; Diapid; L-8; L 8; L8; Lypressine; Vasopressin-8-lysine; Vasopressin;

IUPAC/Chemical Name

(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

InChi Key

BJFIDCADFRDPIO-DZCXQCEKSA-N

InChi Code

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

SMILES Code

NCCCC[C@@H](C(NCC(N)=O)=O)NC([C@@H]1CCCN1C([C@@H]2CSSC[C@@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N2)=O)CC(N)=O)=O)CCC(N)=O)=O)Cc3ccccc3)=O)Cc4ccc(O)cc4)=O)N)=O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

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.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lypressin is the porcine antidiuretic hormone (vasopressins).

In vitro activity:

When a hormonal ligand, [Lys8]vasopressin, was added to the elution buffer at the concentration of 0.1 mM so that a major portion of the immobilized BNPII was liganded, the affinity between the immobilized liganded BNPII and the precursor was enhanced 8-fold and approached the affinity for the liganded (bovine neurophysin I-immobilized BNPII) interaction. Reference: J Biol Chem. 1985 Jul 15;260(14):8474-82. https://pubmed.ncbi.nlm.nih.gov/4008499/

In vivo activity:

[Mca1,TyrMe2,Arg8]vasopressin, a vasopressin pressor (V1) receptor antagonist, was found to reduce dose dependently the extent of the lesions in all models, and to protect the deeper layer of the mucosa (assessed by histology). [Lys8]Vasopressin injected exogenously aggravated all types of lesions in normal rats. Reference: Eur J Pharmacol. 1994 Jun 2;258(1-2):15-22. https://pubmed.ncbi.nlm.nih.gov/7925594/

	Solvent	mg/mL	mM
Solubility
	Water	100.0	94.68

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 1,056.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kanmera T, Chaiken IM. Molecular properties of the oxytocin/bovine neurophysin biosynthetic precursor. Studies using a semisynthetic precursor. J Biol Chem. 1985 Jul 15;260(14):8474-82. PMID: 4008499. 2. Penit J, Faure M, Jard S. Vasopressin and angiotensin II receptors in rat aortic smooth muscle cells in culture. Am J Physiol. 1983 Jan;244(1):E72-82. doi: 10.1152/ajpendo.1983.244.1.E72. PMID: 6295182. 3. László F, Karácsony G, Pávó I, Varga C, Rojik I, László FA. Aggressive role of vasopressin in development of different gastric lesions in rats. Eur J Pharmacol. 1994 Jun 2;258(1-2):15-22. doi: 10.1016/0014-2999(94)90052-3. PMID: 7925594. 4. Schlicker E, Erkens K, Göthert M. Probable involvement of vascular angiotensin II formation in the beta 2-adrenoceptor-mediated facilitation of the neurogenic vasopressor response in the pithed rat. Naunyn Schmiedebergs Arch Pharmacol. 1988 Nov;338(5):536-42. doi: 10.1007/BF00179326. PMID: 2907610.

In vitro protocol:

In vivo protocol:

1. László F, Karácsony G, Pávó I, Varga C, Rojik I, László FA. Aggressive role of vasopressin in development of different gastric lesions in rats. Eur J Pharmacol. 1994 Jun 2;258(1-2):15-22. doi: 10.1016/0014-2999(94)90052-3. PMID: 7925594. 2. Schlicker E, Erkens K, Göthert M. Probable involvement of vascular angiotensin II formation in the beta 2-adrenoceptor-mediated facilitation of the neurogenic vasopressor response in the pithed rat. Naunyn Schmiedebergs Arch Pharmacol. 1988 Nov;338(5):536-42. doi: 10.1007/BF00179326. PMID: 2907610.

1: Belletti A, Musu M, Silvetti S, Saleh O, Pasin L, Monaco F, Hajjar LA, Fominskiy E, Finco G, Zangrillo A, Landoni G. Non-Adrenergic Vasopressors in Patients with or at Risk for Vasodilatory Shock. A Systematic Review and Meta-Analysis of Randomized Trials. PLoS One. 2015 Nov 11;10(11):e0142605. doi: 10.1371/journal.pone.0142605. eCollection 2015. Review. PubMed PMID: 26558621; PubMed Central PMCID: PMC4641698. 2: Cavallin M, Fasolato S, Marenco S, Piano S, Tonon M, Angeli P. The Treatment of Hepatorenal Syndrome. Dig Dis. 2015;33(4):548-54. doi: 10.1159/000375346. Epub 2015 Jul 6. Review. PubMed PMID: 26159272. 3: Nassar Junior AP, Farias AQ, D' Albuquerque LA, Carrilho FJ, Malbouisson LM. Terlipressin versus norepinephrine in the treatment of hepatorenal syndrome: a systematic review and meta-analysis. PLoS One. 2014 Sep 9;9(9):e107466. doi: 10.1371/journal.pone.0107466. eCollection 2014. PubMed PMID: 25203311; PubMed Central PMCID: PMC4159336. 4: Celis P, Rada G. Noradrenaline or terlipressin for hepatorenal syndrome? Medwave. 2015 Aug 27;15 Suppl 2:e6235. doi: 10.5867/medwave.2015.6235. English, Spanish. PubMed PMID: 26334297. 5: Lee WC. Pharmacotherapy of Small-for-Size of the Liver. Transplantation. 2014 May 15;97(9):890-1. doi: 10.1097/TP.0000000000000067. PubMed PMID: 24621540. 6: Ida KK, Otsuki DA, Sasaki AT, Borges ES, Castro LU, Sanches TR, Shimizu MH, Andrade LC, Auler JO Jr, Dyson A, Smith KJ, Rocha Filho JA, Malbouisson LM. Effects of terlipressin as early treatment for protection of brain in a model of haemorrhagic shock. Crit Care. 2015 Mar 13;19:107. doi: 10.1186/s13054-015-0825-9. PubMed PMID: 25888229; PubMed Central PMCID: PMC4373118. 7: Elia C, Solà Vergés E, Rodríguez E, Ginès P. Transient increase in urine protein excretion during treatment with terlipressin and albumin for type-1 hepatorenal syndrome. J Hepatol. 2015 Feb;62(2):493-5. doi: 10.1016/j.jhep.2014.09.030. Epub 2014 Oct 2. PubMed PMID: 25283143. 8: Mattos ÂZ, Mattos AA, Ribeiro RA. Terlipressin versus noradrenaline in the treatment of hepatorenal syndrome: systematic review with meta-analysis and full economic evaluation. Eur J Gastroenterol Hepatol. 2016 Mar;28(3):345-51. doi: 10.1097/MEG.0000000000000537. Review. PubMed PMID: 26649801. 9: Won YJ, Kim HJ, Lim BG, Ahn HS, Hwang MH, Lee IO. Effect of Perioperative Terlipressin on Postoperative Renal Function in Patients Who Have Undergone Living Donor Liver Transplantation: A Meta-Analysis of Randomized Controlled Trials. Transplant Proc. 2015 Jul-Aug;47(6):1917-25. doi: 10.1016/j.transproceed.2015.06.023. Review. PubMed PMID: 26293074. 10: Cavallin M, Piano S, Romano A, Fasolato S, Frigo AC, Benetti G, Gola E, Morando F, Stanco M, Rosi S, Sticca A, Cillo U, Angeli P. Terlipressin given by continuous intravenous infusion versus intravenous boluses in the treatment of hepatorenal syndrome: A randomized controlled study. Hepatology. 2016 Mar;63(3):983-92. doi: 10.1002/hep.28396. Epub 2016 Feb 3. PubMed PMID: 26659927. 11: Tutchenko MI, Rudyk DV, Iskra NI, Trofimenko SP, Shchur IV. [MODERN VIEW ON INTENSIVE THERAPY OF GASTRO-INTESTINAL HEMORRHAGE]. Klin Khir. 2015 Oct;(10):11-4. Ukrainian. PubMed PMID: 26946650. 12: Urbano J, González R, López J, Solana MJ, Bellón JM, Botrán M, García A, Fernández SN, López-Herce J. Comparison of normal saline, hypertonic saline albumin and terlipressin plus hypertonic saline albumin in an infant animal model of hypovolemic shock. PLoS One. 2015 Mar 20;10(3):e0121678. doi: 10.1371/journal.pone.0121678. eCollection 2015. PubMed PMID: 25794276; PubMed Central PMCID: PMC4368553. 13: Hrabovský V, Mendlová A, Vavříčková T. [Hepatorenal syndrome - pathophysiology, diagnosis and treatment]. Vnitr Lek. 2015 Jul-Aug;61(7-8):649-54. Review. Czech. PubMed PMID: 26375691. 14: Berg RA, Meaney PA, Nadkarni VM. Does a resuscitation pharmacologic bundle of epinephrine, terlipressin, and corticosteroids improve outcome from asphyxial cardiac arrest? Pediatr Crit Care Med. 2014 Jul;15(6):573-4. doi: 10.1097/PCC.0000000000000166. PubMed PMID: 25000425. 15: Francoz C, Durand F. Type-1 hepatorenal syndrome in patients with cirrhosis and infection vs. sepsis-induced acute kidney injury: what matters? J Hepatol. 2014 May;60(5):907-9. doi: 10.1016/j.jhep.2014.02.001. Epub 2014 Feb 6. PubMed PMID: 24508549. 16: Qiu X, Huang Y, Xu J, Qiu H, Yang Y. Effects of terlipressin on microcirculation of small bowel mesentery in rats with endotoxic shock. J Surg Res. 2014 May 15;188(2):503-9. doi: 10.1016/j.jss.2014.01.053. Epub 2014 Feb 3. PubMed PMID: 24582066. 17: Fortune BE, Groszmann RJ. Combination of splanchnic vasoconstrictors and endoscopic band ligation is an effective treatment strategy for acute variceal hemorrhage; but how do we get those drugs approved by the FDA? Hepatology. 2014 Sep;60(3):789-91. doi: 10.1002/hep.27080. Epub 2014 Jul 28. PubMed PMID: 24700393; PubMed Central PMCID: PMC4532375. 18: Kutina AV, Marina AS, Natochin YV. The involvement of V1b-subtype vasopressin receptors in regulation of potassium ions excretion in the rat kidneys. Dokl Biol Sci. 2014 Nov;459:338-40. doi: 10.1134/S001249661406009X. Epub 2015 Jan 6. PubMed PMID: 25560210. 19: Xiao X, Zhang J, Wang Y, Zhou J, Zhu Y, Jiang D, Liu L, Li T. Effects of terlipressin on patients with sepsis via improving tissue blood flow. J Surg Res. 2016 Jan;200(1):274-82. doi: 10.1016/j.jss.2015.07.016. Epub 2015 Jul 14. PubMed PMID: 26253455. 20: Biban P, Gaffuri M. Vasopressin and terlipressin in neonates and children with refractory septic shock. Curr Drug Metab. 2013 Feb;14(2):186-92. Review. PubMed PMID: 23439212.

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