16679-58-6

Basic information

• Product Name: Desmopressin
• Synonyms: MPR-TYR-PHE-GLN-ASN-CYS-PRO-D-ARG-GLY-NH2;MINIRIN;[DEAMINO1, DARG8] VASOPRESSIN;[DEAMINO-CYS1, D-ARG8]-VASOPRESSIN;DDAVP, HUMAN;DESMOPRESSIN;DESMOPRESSIN, HUMAN;DESAMINO-[D-ARG8]VASOPRESSIN
• CAS NO: 16679-58-6
• Molecular Formula: C₄₆H₆₄N₁₄O₁₂S₂
• Molecular Weight: 1069.22
• EINECS: 240-726-7
• Product Categories: Amino Acid Derivatives;Peptide;Vasopressin and Oxytocin receptor
• Mol File: 16679-58-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.563 g/cm³
• Refractive Index: 1.713
• Storage Temp.: Store at 0°C
• Solubility: H2O: soluble20mg/mL, clear, colorless
• PKA: 9.90±0.15(Predicted)
• CAS DataBase Reference: Desmopressin(CAS DataBase Reference)
• NIST Chemistry Reference: Desmopressin(16679-58-6)
• EPA Substance Registry System: Desmopressin(16679-58-6)

Safety Data

• WGK Germany: 3
• RTECS: YW9000000
• Hazardous Substances Data: 16679-58-6(Hazardous Substances Data)

Usage

Description

Desmopressin, also known as DDAVP, is an artificial derivative of the antidiuretic hormone (ADH) naturally produced in the body. It is a synthetic analogue of vasopressin, where 3-mercaptopropionic acid replaces the cysteine residue at position 1 and D-arginine replaces the residue at position 8. Desmopressin is a white or almost white, fluffy powder that increases urine concentration and decreases urine production.

Uses

1. Used in Antidiuretic Applications:
Desmopressin is used as an antidiuretic to prevent and control excessive thirst, urination, and dehydration caused by injury, surgery, and certain medical conditions. It increases the water permeability in the renal tubular cells, further increasing urine concentration and decreasing urine production.
2. Used in Diabetes Insipidus Treatment:
Desmopressin is used for the treatment of diabetes insipidus, a condition characterized by excessive urination and thirst due to insufficient ADH production or function.
3. Used in Bedwetting Treatment:
Desmopressin is used to treat bedwetting (nocturnal enuresis) in children and adults, helping to reduce the frequency of nighttime urination.
4. Used in Hemophilia A Treatment:
Desmopressin is used to manage and treat Hemophilia A, a genetic disorder that impairs the body's ability to form blood clots, by increasing the levels of clotting factors in the blood.
5. Used in von Willebrand Disease Treatment:
Desmopressin is used to treat von Willebrand disease, a bleeding disorder caused by a deficiency or dysfunction of von Willebrand factor, a protein that helps blood clot.
6. Used in High Blood Urea Levels:
Desmopressin is used to manage high blood urea levels, which can be caused by various medical conditions, by improving urine concentration and reducing urine production.
7. Used in Medical Research:
Desmopressin, specifically [deamino-Cys1, D-Arg8]-Vasopressin acetate salt hydrate, is used in research to study the impact of vasopressin on pendrin abundance and the changes in protein abundance of selected E3 ubiquitin (Ub)-protein ligases in response to the hormone.
Brand Names:
Some of the brand names for Desmopressin include Concentraid (Ferring Pharmaceuticals), DDAVP (Sanofi Aventis), and Stimate (ZLB Behring).

References

https://www.drugbank.ca/drugs/DB00035 http://www.medicinenet.com/desmopressin_tabs/article.htm https://en.wikipedia.org/wiki/Desmopressin

Originator

DAV,Ritter,Switz.,1974

Manufacturing Process

β-Benzylmercaptopropionyl-L-tyrosyl-L-phenylalanyl-L-glutaminyl-Lasparaginyl-S-benzyl-L-cysteinyl-L-prolyl-NG-tosyl-D-arginyl-glycinamide (0.5 g) is reduced with sodium in liquid ammonia. The liquid ammonia is then evaporated and the residue dissolved in 5% aqueous acetic acid (800 ml). The solution is filtered to remove the undissolved portion and the filtrate is adjusted to a pH of 6.5 to 7 by addition of aqueous sodium hydroxide and it is then oxidized by known procedure, cf. Kimbrough, R.D., Jr.; Cash, W.D.; Branda, L.A.; Chan, W.Y.; and Du Vigneaud, V.; J. Biol. Chem. 238,1411 (1963). The reaction mixture is thereupon adjusted to a pH of 4 to 4.5 by addition of acetic acid. The peptide is applied to a column of a carboxylate ion exchange resin, is eluted with 50% aqueous acetic acid and isolated by lyophilization (freeze-drying). The crude product is purified by known procedure using a carrier-free high-voltage electrophoresis, cf. Zaoral, M.; Sorm, F.; Collection Czechoslov. Chem Communs, 31, 310 (1966). Yield, 100 to 200 mg of 1-deamino-8-D-argine-vasopressin.

Therapeutic Function

Antidiuretic

Biochem/physiol Actions

[deamino-Cys1, D-Arg8]-Vasopressin acetate salt hydrate also known as DDAVP, Desmopressin is a selective and potent vasopressor agent that stabilizes the cardiocirculatory function in normal human as well as in patients suffering from catecholamine-resistant vasodilatory shock. It also stimulate three acid-base transporters and hence increases the capability of the cell to regulate pH.

Clinical Use

Diabetes insipidusNocturnal enuresisNocturia due to idiopathic nocturnal polyuriaPost-biopsy bleeding (unlicensed indication)Pre-biopsy prophylaxis (unlicensed indication)

Drug interactions

Potentially hazardous interactions with other drugsNone known

Metabolism

Metabolic fate of desmopressin is unknown. It is not affected by liver microsomal cytochrome P450 enzymes. As a peptide, desmopressin is expected to undergo catabolism to its constituent amino acids, with subsequent recycling of the amino acid in the body pool.

InChI:InChI=1/C46H64N14O12S2/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/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)/t28-,29+,30+,31+,32+,33+,34+/m1/s1

Upstream product

• 58928-35-1 Mpa(Bzl)-Tyr(Bzl)-Phe-Gln-Asn-Cys(Bzl)-Pro-D-Arg(TOS)-Gly-NH₂ 

Related news

Neuro-urologyLow-dose Desmopressin (cas 16679-58-6) Orally Disintegrating Tablet: Suggested Clinically Meaningful Benefit in Patients with Nocturia Due to Nocturnal Polyuria09/27/2019

BackgroundClinical benefit has not been evaluated much in patients with nocturia.detailed

Clinical studyCohort analysis of Desmopressin (cas 16679-58-6) effect on hematoma expansion in patients with spontaneous intracerebral hemorrhage and documented pre-ictus antiplatelet use09/26/2019

Antiplatelet therapy at the time of spontaneous intracerebral hemorrhage (sICH) may increase risk for hemorrhage expansion and mortality. Current guidelines recommend considering a single dose of desmopressin in sICH associated with cyclooxygenase-1 inhibitors or adenosine diphosphate receptor i...detailed

‘Frequently recurring’ nocturnal polyuria is predictive of response to Desmopressin (cas 16679-58-6) in monosymptomatic nocturnal enuresis in childhood09/25/2019

SummaryIntroductionThe nocturnal polyuria is considered a significant predictive value for response to desmopressin. The cutoff value useful to define nocturnal polyuria is still a matter of debate. Moreover, it is current notion that maximal voided volume (MVV) could be used as a predictor for ...detailed

ReviewOral Desmopressin (cas 16679-58-6) in nocturia with benign prostatic hyperplasia: A systematic review of the literature09/24/2019

ObjectiveTo evaluate the effect of oral desmopressin in patients with nocturia associated with benign prostatic hyperplasia (BPH).detailed

62 - Desmopressin (cas 16679-58-6) (DDAVP)09/09/2019

Desmopressin (1-deamino-8-D-arginine vasopressin, DDAVP) is a synthetic analogue of the antidiuretic hormone vasopressin, which increases the plasma levels of factor VIII and von Willebrand factor, without inducing clinically relevant side effects, like its parent compound vasopressin. It is use...detailed

Constipation in nocturnal enuresis may interfere Desmopressin (cas 16679-58-6) management success09/07/2019

SummaryBackgroundPrevious studies indicated that the prevalence of constipation in enuretic patients is higher than that in the general population. Several studies have revealed that successful treatment of constipation may be helpful in resolving enuresis. However, constipation affecting the ef...detailed

ReviewUse of Desmopressin (cas 16679-58-6) in Hyponatremia: Foe and Friend09/06/2019

Use of desmopressin (1-deamino-8-d-arginine vasopressin; DDAVP), a synthetic vasopressin receptor agonist, has expanded in recent years. Desmopressin leads to renal water retention, and iatrogenic hyponatremia may result if fluid intake is not appropriately restricted. It is common practice to s...detailed

Relevant articles and documents

Cyclic Peptide Formation in Reduced Solvent Volumes via In-Line Solvent Recycling by Organic Solvent Nanofiltration

Cyclic peptides have found numerous and wide ranging applications that include drug molecules, nanomaterials, and chiral chromatography stationary phases. However, in the crucial cyclization step, high dilution conditions are often required, resulting in large volumes of solvent being consumed to prepare relatively small quantities of product. This paper demonstrates the synthesis of a cyclic nonapeptide with in-line solvent recycling via organic solvent nanofiltration (OSN) resulting in a significant reduction in the solvent load of the reaction and concomitant improvement in process mass intensification (PMI). The membrane was used to remove the reaction product from the reaction vessel, as the cyclic peptide product shows limited stability in the presence of an excess of reaction reagent. In comparison to the standard batch reaction, no loss in yield or product purity was observed for the OSN process tested. The proof-of-concept study outlined in this paper was performed on a real active pharmaceutical ingredient (API), and the technique used is widely applicable and flexible.