| Identification | Back Directory | [Name]
Desmopressin acetate | [CAS]
16789-98-3 | [Synonyms]
DDAVP
DDAVP ACETATE
LKT Desmopressin
Desmopressin (ADH)
DESMORESSIN ACETATE
DESMOPRESSIN ACETATE
DDAVP, Desmopressin
DESMOPRESSIN MONOACETATE
DesMopressin (diacetate)
DESMOPRESSIN ACETATE SALT
1-Deamino-8-D-arginine-vasopressin diacetate
[DEAMINO-CYS1,D-ARG8]-VASOPRESSIN ACETATE SALT
Mpr-Tyr-Phe-Gln-Asn-Cys-Pro-D-Arg-Gly-NH2(S-S:1-5)
Mpr-Tyr-Phe-Gln-Asn-Cys-Pro-D-Arg-Gly-NH2(S-S:1-6)
[deamino-Cys1, D-Arg8]-Vasopressin hydrate acetate salt
1-(3-Mercaptopropionic acid)-8-D-arginine-vasopressin diacetate
3-MERCAPTOPROPIONYL-TYR-PHE-GLN-ASN-CYS-PRO-D-ARG-GLY-NH2 ACETATE SALT
1-[4-(2-amino-2-keto-ethyl)-7-(3-amino-3-keto-propyl)-10-(benzyl)-13-(4-hydroxybenzyl)-3,6,9,12,15-pentaketo-18,19-dithia-2,5,8,11,14-pentazacycloicosane-1-carbonyl]-N-[1-[(2-amino-2-keto-ethyl)carbamoyl]-4-guanidino-butyl]pyrrolidine-2-carboxamide
N-[1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-1-[4-(2-amino-2-oxoethyl)-7-(3-amino-3-oxopropyl)-13-[(4-hydroxyphenyl)methyl]-3,6,9,12,15-pentaoxo-10-(phenylmethyl)-18,19-dithia-2,5,8,11,14-pentazacycloicosane-1-carbonyl]pyrrolidine-2-carboxamide
N-[1-[(2-azanyl-2-oxo-ethyl)amino]-5-[bis(azanyl)methylideneamino]-1-oxo-pentan-2-yl]-1-[[4-(2-azanyl-2-oxo-ethyl)-7-(3-azanyl-3-oxo-propyl)-13-[(4-hydroxyphenyl)methyl]-3,6,9,12,15-pentaoxo-10-(phenylmethyl)-18,19-dithia-2,5,8,11,14-pentazacycloicos-1-yl]carbonyl]pyrrolidine-2-carboxamide | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C48H68N14O14S2 | [MDL Number]
MFCD00133962 | [MOL File]
16789-98-3.mol | [Molecular Weight]
1129.27 |
| Chemical Properties | Back Directory | [Melting point ]
170-172°C (dec.) | [storage temp. ]
−20°C
| [solubility ]
Acetic Acid (Slightly), Methanol (Slightly), Water (Slightly) | [form ]
Solid | [color ]
White to Off-White | [InChIKey]
MLSVJHOYXJGGTR-OZEDRGHLNA-N |
| Hazard Information | Back Directory | [Chemical Properties]
A recently synthesized vasopressin-like substance replaces the cysteine at position 1 and the L-arginine at position 8 of vasopressin with β-mercaptopropionic acid and D-arginine, respectively. This product has a 2,000-fold lower pressor effect than vasopressin, while its antidiuretic effect is stronger and more sustained than that of natural vasopressin, with a half-life three times longer. | [Originator]
DAV,Ritter,Switz.,1974 | [Uses]
Antidiuretic. | [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 | [General Description]
Desmopressin acetate(DDAVP, Stimate) is synthetic 1-desamino-8-D-argininevasopressin. Its efficacy, ease of administration (intranasal),long duration of action, and lack of side effects make itthe drug of choice for the treatment of central diabetesinsipidus. It may also be administered intramuscularly orintravenously. It is preferred to vasopressin injectionand oral antidiuretics for use in children. It is indicatedin the management of temporary polydipsia and polyuriaassociated with trauma to, or surgery in, the pituitary region. | [Clinical Use]
Desmopressin, as its acetate salt, is a synthetic analogue of vasopressin in which the Nterminal Cys is devoid of its α-amino function (1-Deamino) and where Arg8 is present as its D-isomer (D-Arg8), thus the commercial acronym DDAVP. The presence of D-Arg and
the absence of the N-terminal amine in the desmopressin structure have increased its half-life
such that it is available for oral, parenteral, or nasal use. It is used by all three of these routes
of administration to prevent or control polydipsia (excessive thirst), polyuria, and dehydration of
patients with diabetes insipidus caused by a deficiency of vasopressin. It also has been
approved for the treatment of nocturnal enuresis (bed-wetting), which is believed to be caused
by an absence of the normal night time rise in vasopressin levels.
Desmopressin is known to cause an increase in both plasma factor VIII (antihemophilic factor)
and plasminogen activator. It therefore is approved by the U.S. FDA for use, parenterally and
nasally, in reducing spontaneous or trauma-induced bleeding episodes in patients with
hemophilia A and type I Von Willebrand's disease, provided that their plasma factor VIII activity is greater than 5%. Stimate, the nasal spray used in treating patients with hemophilia A and
type I Von Willebrand's disease, is 15-fold the concentration of DDAVP nasal spray; the latter is
used in treating diabetes insipidus. | [Safety]
Desmopressin is generally well-tolerated in most patients. There are a few instances where patients require monitoring for adverse effects of the drug. Patients receiving desmopressin need monitoring for the occurrence of hyponatremia. Symptoms of hyponatremia include nausea, confusion, or altered mental status. As patients age, they should also be continually monitored for declining renal function, as the therapeutic index and clearance of the drug will change according to the renal function. There is no known antidote to an overdose of desmopressin. The most worrisome complication to result from an overdose is water intoxication. This condition would result in a delayed loss of consciousness and seizures in some instances. Patients require immediate admission to the intensive care unit to be monitored and have electrolyte correction. | [Veterinary Drugs and Treatments]
Desmopressin has been found to be useful in the treatment of central
diabetes insipidus
in small animals. It may be useful in treating
Von Willebrand’s disease, but its short duration of activity (2 – 4
hours) in this condition, resistance development, and expense limit
its usefulness for this disorder. Desmopressin may be useful perioperatively
to reduce lymph node involvement and metastatic disease
in canine mammary gland cancer. |
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