Desmopressin Chemical Properties

alpha 

D25 +85.5 ± 2° (calculated for the free peptide)

Density 

1.56±0.1 g/cm3(Predicted)

RTECS 

YW9000000

storage temp. 

Store at 0°C

solubility 

H2O: soluble20mg/mL, clear, colorless

pka

9.90±0.15(Predicted)

Water Solubility 

Soluble to 4 mg/ml in water

InChIKey

NFLWUMRGJYTJIN-PNIOQBSNSA-N

Safety Information

WGK Germany 

3

Desmopressin Usage And Synthesis

Description

Desmopressin (Brand name: DDAVP) is an artificial derivative of vasopressin, being similar to the antidiuretic hormone (ADH) that naturally produced in the body. It is used for the treatment of diabetes insipidus, bedwetting, hemophilia A, von Willebrand disease and high blood urea levels. It is capable of increasing the water permeability in the renal tubular cells, further increasing the urine concentration and decreasing the urine production. Therefore, it can be used to prevent and control severe thirst, urination and dehydration caused by various kinds of reasons including injury, surgery and certain medical condition. This help you sleep throughout the night without being awaken by urinate.

References

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

Chemical Properties

White or almost white, fluffy powder.

Originator

DAV,Ritter,Switz.,1974

Uses

Antidiuretic.

Uses

[deamino-Cys1, D-Arg8]-Vasopressin acetate salt hydrate was used to study the impact of vasopressin on pendrin abundance. E3 ubiquitin (Ub)-protein ligases (E3s) was administered in rat kidney and the changes in protein abundance of the selected E3s in response to [deamino-Cys1, D-Arg8]-Vasopressin acetate salt hydrate was examined.

Definition

ChEBI: A synthetic analogue of vasopressin in which 3-mercaptopropionic acid replaces the cysteine residue at position 1 and D-arginine replaces the residue at position 8. An antidiuretic, it increases urine concentration and decreases urine prod ction, and is used (usually as the trihydrate of the acetic acid salt) to prevent and control excessive thirst, urination, and dehydration caused by injury, surgery, and certain medical conditions. It is also used in the diagnosis and treatment of cranial iabetes insipidus and in tests of renal function.

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.

brand name

Concentraid (Ferring Pharmaceuticals); Ddavp (Sanofi Aventis); Stimate (ZLB Behring).

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 insipidus
Nocturnal enuresis
Nocturia due to idiopathic nocturnal polyuria
Post-biopsy bleeding (unlicensed indication)
Pre-biopsy prophylaxis (unlicensed indication)

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.

storage

Store at -20°C

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