Argipressin

• CAT Number: I000522
• CAS Number: 113-79-1
• Molecular Formula: C46H65N15O12S2
• Molecular Weight: 1084.23
• Purity: ≥95%
• Solubility: 0.50 mg/ml in H2O
• Storage: Store at -20°C
• IUPAC Name: (2S)-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]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
• InChI: InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
• InChIKey: KBZOIRJILGZLEJ-LGYYRGKSSA-N
• 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)N)C(=O)NC(CCCN=C(N)N)C(=O)NCC(=O)N

Argipressin(CAT: I000522), also known as vasopressin or antidiuretic hormone (ADH), is a peptide hormone that is naturally produced in the hypothalamus and released from the posterior pituitary gland. It plays a crucial role in regulating water balance and blood pressure in the body. Argipressin acts on specific receptors in the kidneys, causing water reabsorption and reducing urine output. This action helps maintain fluid balance and prevent excessive water loss. In addition to its role in water regulation, argipressin also has vasoconstrictive effects, meaning it can cause blood vessels to constrict, leading to increased blood pressure. Argipressin is used therapeutically for various medical conditions, such as diabetes insipidus, septic shock, and bleeding disorders.

Overview of Clinical Research

Originator: DelSite Biotechnologies
Class: Antidiuretics; Antihaemorrhagics; Vasoconstrictors; Vasopressins
Mechanism of Action: Vasopressin receptor agonists
Orphan Drug Status: No

Reference

[1]. Zhongguo Yao Li Xue Bao. 1991 Mar;12(2):164-6.
[Effect of argipressin and its related compounds on corticotropin releasing hormone contents in hypothalamus of rats].
[Article in Chinese]
You ZB(1), Du JZ.
Author information: (1)Northwest Plateau Institute of Biology, Chinese Academy of Sciences, Xining.
The paper mainly stresses on the effect of argipressin (Arg), 2-destyrosyl-3-desphenyl-alanyl-9-desglycyl-amide-Arg (Arg4-8), [1-deaminopenicillamine, 2-(o-methyl)tyrosine]-Arg (DPArg) and Arg antiserum on corticotropin releasing hormone (CRH) contents in median eminence (ME) and the level of plasma corticosterone after injected into the third ventricle of rats. The results show: 1) the CRH contents in ME significantly reduced with icv 100, 200, and 800 ng of Arg; 2) 100 ng of Arg4-8 and Arg antiserum (2 microliters, 1:1 diluted with 0.9% saline) increased CRH contents in ME and enhanced plasma corticosterone; 3) DPArg had no effect on CRH level but blocked the inhibitory role of Arg on central CRH. These results suggest that Arg acts as an inhibitory factor in regulating central CRH level and V1 receptor is involved.
PMID: 1776482

[2]. Drugs. 2003;63(3):237-56. doi: 10.2165/00003495-200363030-00001.
Management of vasodilatory shock: defining the role of arginine vasopressin.
Dunser MW(1), Wenzel V, Mayr AJ, Hasibeder WR.
Author information: (1)Division of General and Surgical Critical Care Medicine, Department of Anesthesiology and Critical Care Medicine, Leopold-Franzens-University, Innsbruck, Austria.
The rationale for an arginine vasopressin (argipressin) infusion was put forward after it was discovered that patients in shock states might have an endogenous arginine vasopressin deficiency. Subsequently, several investigations impressively demonstrated that arginine vasopressin can successfully stabilise haemodynamics even in advanced vasodilatory shock. We report on physiological and pharmacological aspects of arginine vasopressin, and summarise current clinical knowledge on employing a continuous arginine vasopressin infusion in critically ill patients with catecholamine-resistant vasodilatory shock of different aetiologies. In view of presented experimental evidence and current clinical experience, a continuous arginine vasopressin infusion of approximately 2 to approximately 6 IU/h can be considered as a supplemental strategy to vasopressor catecholamines in order to preserve cardiocirculatory homeostasis in patients with advanced vasodilatory shock. Because data on adverse effects are still limited, arginine vasopressin should be reserved for patients in whom adequate haemodynamic stabilisation cannot be achieved with conventional vasopressor therapy or who have obvious adverse effects of catecholamines that result in further significant haemodynamic deterioration. For the same reasons, arginine vasopressin should not be used as a single, alternative vasopressor agent instead of catecholamine vasopressors. Future prospective studies will be necessary to define the exact role of arginine vasopressin in the therapy of vasodilatory shock.
DOI: 10.2165/00003495-200363030-00001 PMID: 12534330

[3]. Rapid Commun Mass Spectrom. 2020 Jun 30;34(12):e8799. doi: 10.1002/rcm.8799.
Impurity identification and quantification for arginine vasopressin by liquid chromatography/high-resolution mass spectrometry.
Wu P(1), Ye S(2), Li M(1), Li H(1), Kan Y(1), Yang Z(3).
Author information: (1)Division of Chemical Metrology and Analytical Science, National Institute of Metrology, Beijing, China. (2)College of Chemistry, Jilin University, Changchun, China. (3)Department of Gastrointestinal Surgery, The Second Hospital of Jilin University, Changchun, China.
RATIONALE: For pharmaceutical quality control, impurities may have unexpected pharmacological or toxicological effects on quality, safety, and efficacy of drugs. Arginine vasopressin (AVP) is an important cyclic peptide drug that is mainly used for the treatment of diabetes insipidus and esophageal varices bleeding. With the advancement made in analytical techniques, liquid chromatography/high-resolution mass spectrometry (LC/HRMS) has emerged as a critical technique for the identification and quantification of structurally related peptide impurities in AVP. METHODS: An LC/HRMS/MS-based method using a quadrupole ion trap-Orbitrap mass spectrometer operated in the positive ion electrospray ionization mode was developed for the determination and quantification of structurally related peptide impurities in AVP. RESULTS: Under optimized experimental conditions, three deamidation products, ([Glu4 ]AVP, [Asp5 ]AVP, and AVP acid), two amino acid deletion impurities (des-Pro7 -AVP and des-Gly9 -AVP), one amino acid insertion impurity (endo-Gly10a -AVP), one end chain reaction product (N-acetyl-AVP), and one AVP isomer were detected. Subsequent quantification using an external standard method estimated the total mass fraction of all structurally related peptide impurities in the AVP study material to be 30.3 mg/g with an expanded uncertainty of 3.0 mg/g (k = 2). CONCLUSIONS: This study complements the AVP impurity profile and improves the separation and discovery of other potential impurities in vasopressin analogues.
DOI: 10.1002/rcm.8799 PMID: 32247289

[4]. Amino Acids. 2015 Nov;47(11):2245-53. doi: 10.1007/s00726-015-2026-x. Epub 2015 Jun 23.
Vasopressin signaling at brain level controls stress hormone release: the vasopressin-deficient Brattleboro rat as a model.
Zelena D(1), Pintér O(1), Balázsfi DG(2)(3), Langnaese K(4), Richter K(4), Landgraf R(5), Makara GB(1), Engelmann M(6)(7).
Author information: (1)Institute of Experimental Medicine, Hungarian Academy of Sciences, Budapest, Hungary. (2)Institute of Experimental Medicine, Hungarian Academy of Sciences, Budapest, Hungary. . (3)János Szentágothai School of Neurosciences, Semmelweis University, Budapest, Hungary. . (4)AG Neuroendokrinologie & Verhalten, Institut für Biochemie und Zellbiologie, Otto-von-Guericke-Universität, Leipziger Str. 44/Haus 1, 39120, Magdeburg, Germany. (5)Max-Planck-Institut für Psychiatrie, Munich, Germany. (6)AG Neuroendokrinologie & Verhalten, Institut für Biochemie und Zellbiologie, Otto-von-Guericke-Universität, Leipziger Str. 44/Haus 1, 39120, Magdeburg, Germany. . (7)Center for Behavioral Brain Sciences, Magdeburg, Germany. .
The nonapeptide arginine vasopressin (AVP) has long been suggested to play an important role as a secretagogue for triggering the activity of the endocrine stress response. Most recent studies employed mutant mice for analyzing the importance of AVP for endocrine regulation under stress. However, it is difficult to compare and draw overall conclusions from all these studies as mixing the genetic material from different mouse strains has consequences on the individual's stress response. Moreover, mice are not ideal subjects for several experimental procedures. Therefore, to get more insight, we used a rather old mutant rat model: the AVP-deficient Brattleboro rat. The present short review is aimed at providing the most interesting results of these studies within the last 8 years that allowed gaining new insights in the potential signal function of AVP in stress and endocrine regulation.
DOI: 10.1007/s00726-015-2026-x PMID: 26100541

[5]. Ann Intern Med. 1985 Aug;103(2):228-39. doi: 10.7326/0003-4819-103-2-228.
Desmopressin.
Richardson DW, Robinson AG.
Desmopressin (dDAVP), a synthetic analog of the neurohypophyseal nonapeptide arginine vasopressin, has enhanced antidiuretic potency, markedly diminished pressor activity, and a prolonged half-life and duration of action compared to the natural hormone. Desmopressin is the treatment of choice for central diabetes insipidus and can be administered either intranasally or parenterally. A newly approved indication is treatment of mild classical hemophilia and von Willebrand's disease, in which deficient concentrations of factor VIII and von Willebrand's factor are transiently increased to levels that allow minor surgery.
DOI: 10.7326/0003-4819-103-2-228 PMID: 3893256