Desmopressin

Hemostatic and anti-diuretic CAS# 16679-58-6

Desmopressin

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Chemical structure

Desmopressin

3D structure

Chemical Properties of Desmopressin

Cas No. 16679-58-6 SDF Download SDF
PubChem ID 64759 Appearance Powder
Formula C46H64N14O12S2 M.Wt 1069.22
Type of Compound N/A Storage Desiccate at -20°C
Synonyms DDAVP
Solubility Soluble to 4 mg/ml in water
Sequence XYFQNCPRG

(Modifications: X = Mpr, Arg-8 = D-Arg, Gly-9 = C-terminal amide, Cyclized = X-1 - Cys-6)

Chemical Name acetic acid;N-[1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-1-[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;trihydrate
SMILES CC(=O)O.C1CC(N(C1)C(=O)C2CSSCCC(=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)C(=O)NC(CCCN=C(N)N)C(=O)NCC(=O)N.O.O.O
Standard InChIKey YNKFCNRZZPFMEX-UHFFFAOYSA-N
Standard InChI InChI=1S/C46H64N14O12S2.C2H4O2.3H2O/c47-35(62)15-14-29-40(67)58-32(22-36(48)63)43(70)59-33(45(72)60-18-5-9-34(60)44(71)56-28(8-4-17-52-46(50)51)39(66)53-23-37(49)64)24-74-73-19-16-38(65)54-30(21-26-10-12-27(61)13-11-26)41(68)57-31(42(69)55-29)20-25-6-2-1-3-7-25;1-2(3)4;;;/h1-3,6-7,10-13,28-34,61H,4-5,8-9,14-24H2,(H2,47,62)(H2,48,63)(H2,49,64)(H,53,66)(H,54,65)(H,55,69)(H,56,71)(H,57,68)(H,58,67)(H,59,70)(H4,50,51,52);1H3,(H,3,4);3*1H2
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Desmopressin

DescriptionSynthetic vasopressin analog that acts as an agonist at V1B and V2 receptors (EC50 values are 11.4 and 23.9 nM and Ki values are 5.84 and 65.9 nM respectively). Prevents polycystic kidney disease formation and exhibits antidiuretic, antiproliferative, hemostatic and hypotensive activity in vivo.

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Background on Desmopressin

Desmopressin (dDAVP) is a synthetic peptide analog of natural pituitary hormone 8-arginine vasopressin (ADH) with hemostatic and anti-diuretic properties [1].
Desmopressin reduced the formation of lung nodules in F3II tumor cell injected BALB/c mice. In vitro, desmopressin blocked the F3II cell colony formation. Desmopressin could inhibit metastasis formation on V2 vasopressin receptors in both endothelial and cancer cells [1].
Desmopressin has been proved to increase the release of platelet adhesion promoting factors which is most likely von Willebrand factor (VWF), from endothelial cells (ECs). However, desmopressin had no direct effect on platelets [2].
The administration of desmopressin agglomerates in rats significantly reduced the urine production [3]. Apart from these, rats treated by desmopressin had demonstrated a stronger Pimonidazole staining in the outer and inner medulla compared to control. Desmopressin-treated rats revealed nuclear accumulation in the papilla, which was confirmed by HIF-1α immunostaining. Desmopressin-treated animals had shown a significant increase of HIF-target genes in the group of Desmopressin-regulated gene products including insulin-like growth factor binding proteins 1 and 3, fibronectin, hexokinase 2, angiopoietin 2, cathepsin D and cyclooxygenase 2. Desmopressin had been shown to cause the renal urine concentrating mechanism, leading to an upregulation of hypoxia-inducible gene expression and renal medullary hypoxia [4].
References:
1.Garona J1, Pifano M1, Scursoni AM2, Gomez DE1, Alonso DF3, Ripoll GV1.Insight into the effect of the vasopressin analog desmopressin on lung colonization by mammary carcinoma cells in BALB/c mice. Anticancer Res. 2014 Sep;34(9):4761-5.
2.Calmer S1, Ferkau A, Larmann J, Johanning K, Czaja E, Hagl C, Echtermeyer F, Goudeva L, Heuft HG, Theilmeier G. Desmopressin (DDAVP) improves recruitment of activated platelets to collagen but simultaneously increases platelet endothelial interactions in vitro. Platelets. 2014;25(1):8-15.
3.Balducci AG1, Ferraro L, Bortolotti F, Nastruzzi C, Colombo P, Sonvico F, Russo P, Colombo G. Antidiuretic effect of desmopressin chimera agglomerates by nasal administration in rats. Int J Pharm. 2013 Jan 20;440(2):154-60.
4.Dietrich A1, Mathia S, Kaminski H, Mutig K, Rosenberger C, Mrowka R, Bachmann S, Paliege A. Chronic activation of vasopressin V2 receptor signalling lowers renal medullary oxygen levels in rats. Acta Physiol (Oxf). 2013 Apr;207(4):721-31.

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References on Desmopressin

Effect of Desmopressin on the Amount of Bleeding and Transfusion Requirements in Patients Undergoing Heart Transplant Surgery.[Pubmed:28326680]

Basic Clin Pharmacol Toxicol. 2017 Sep;121(3):175-180.

One of the most common risks after a heart transplant is bleeding. In this study, the effect of Desmopressin administration on the amount of bleeding and transfusion requirements after heart transplant surgery was investigated. In a double-blind clinical trial, 48 patients who were candidates for heart transplant surgery were randomly assigned to two groups. In the intervention group, patients received Desmopressin of 0.3 mug/kg, 30 min. before surgery. Patients in the control group received normal saline at the same amount and time. Homeostasis was evaluated using activated clotting time (ACT), PT, PTT and PLT before, 12 and 24 hr after surgery, and also, chest tube drainage, blood products transfusion requirements during the first day in both groups. No significant differences were found between the groups in terms of ACT, PT, PTT and PLT at all times. Transfusion of packed red blood cells and the mean drainages of chest tube during the first 24 hr after surgery were significantly lower in the Desmopressin group compared to the saline group. Desmopressin may reduce post-operative bleeding in patients undergoing heart transplant surgery. Further studies are required to confirm the potential effect of Desmopressin on establishing haemostasis after heart transplantation.

Vasopressin antagonists in polycystic kidney disease.[Pubmed:18519091]

Semin Nephrol. 2008 May;28(3):306-17.

Increased cell proliferation and fluid secretion, probably driven by alterations in intracellular calcium homeostasis and cyclic adenosine 3,5-phosphate, play an important role in the development and progression of polycystic kidney disease. Hormone receptors that affect cyclic adenosine monophosphate and are preferentially expressed in affected tissues are logical treatment targets. There is a sound rationale for considering the arginine vasopressin V2 receptor as a target. The arginine vasopressin V2 receptor antagonists OPC-31260 and tolvaptan inhibit the development of polycystic kidney disease in cpk mice and in three animal orthologs to human autosomal recessive polycystic kidney disease (PCK rat), autosomal dominant polycystic kidney disease (Pkd2/WS25 mice), and nephronophthisis (pcy mouse). PCK rats that are homozygous for an arginine vasopressin mutation and lack circulating vasopressin are markedly protected. Administration of V2 receptor agonist 1-deamino-8-D-arginine vasopressin to these animals completely recovers the cystic phenotype. Administration of 1-deamino-8-D-arginine vasopressin to PCK rats with normal arginine vasopressin aggravates the disease. Suppression of arginine vasopressin release by high water intake is protective. V2 receptor antagonists may have additional beneficial effects on hypertension and chronic kidney disease progression. A number of clinical studies in polycystic kidney disease have been performed or are currently active. The results of phase 2 and phase 2-3 clinical trials suggest that tolvaptan is safe and well tolerated in autosomal dominant polycystic kidney disease. A phase 3, placebo-controlled, double-blind study in 18- to 50-yr-old patients with autosomal dominant polycystic kidney disease and preserved renal function but relatively rapid progression, as indicated by a total kidney volume >750 ml, has been initiated and will determine whether tolvaptan is effective in slowing down the progression of this disease.

Desmopressin and other synthetic vasopressin analogues in cancer treatment.[Pubmed:16517412]

Bull Cancer. 2006 Feb;93(2):E7-12.

Desmopressin (DDAVP) is a well tolerated and convenient haemostatic agent that can be used in a number of clinical conditions with bleeding diathesis. It has several effects on the haemostatic system, causing endogenous release of coagulation factor VIII, von Willebrand factor and tissue-type plasminogen activator, among others. In this review we present a growing body of evidence showing that DDAVP treatment may impair spread of cancer cells and contribute to encapsulation of tumour tissue. Our data in preclinical animal models suggest a potential application of DDAVP in the perioperative management of aggressive solid tumours. Novel vasopressin analogues with improved antitumor effects are currently in development.

1-desamino-8-D-arginine vasopressin (DDAVP) as an agonist on V1b vasopressin receptor.[Pubmed:9264324]

Biochem Pharmacol. 1997 Jun 1;53(11):1711-7.

1-desamino-8-D-arginine vasopressin (DDAVP) is considered a standard vasopressin V2 receptor-selective agonist with a potent antidiuretic effect through V2 receptor without the induction of vasoconstriction through V1a receptor. Furthermore, DDAVP was reported to act as an agonist on non-V1a, non-V2 receptor to cause the accumulation of intracellular Ca2+ in several tissues. However, the agonistic activity of DDAVP against the other vasopressin receptor, V1b (or V3), which can accumulate intracellular Ca2+ and which we recently cloned, has not been clarified. Hence, we compared the characteristics of DDAVP on V1b receptor with those on the other vasopressin receptors. In binding experiments, DDAVP more strongly inhibited [3H]arginine vasopressin binding to V1b than to V2 receptor (Ki: 5.84 nM vs 65.9 nM). In addition, DDAVP dose-dependently stimulated inositol turnover in human V1b receptor-expressing COS-1 cells. DDAVP acted as a full agonist on human V1b receptor (EC50: 11.4 nM) as well as on human V2 receptor (EC50: 23.9 nM). However, DDAVP behaved as a partial agonist toward rat V1b receptor (intrinsic activity: 0.7, EC50: 43.5 nM), while there was no significant difference in the agonistic properties of arginine vasopressin on human and rat V1b receptor. In conclusion, DDAVP acts as an agonist on V1b receptor, as it does on V2 receptor. These findings will allow us to better understand the physiological role of V1b receptor in pancreatic beta cells and in the renal inner medullary collecting duct, and help us to identify as yet unknown vasopressin receptors through which DDAVP cause the accumulation of intracellular Ca2+ in other tissues.

Description

Synthetic vasopressin analog; V1B and V2 agonist,Desmopressin(DDAVP) is the synthetic analogue of the antidiuretic hormone arginine vasopressin.

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