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.
Chemical Properties
White or almost white, fluffy powder.
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.
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)
Drug interactions
Potentially hazardous interactions with other drugs
None 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.
