Desmopressin

Title: Desmopressin
CAS Registry Number: 16679-58-6
CAS Name: 1-(3-Mercaptopropanoic acid)-8-D-arginine vasopressin
Additional Names: 8-D-arginine-1-(3-mercaptopropanoic acid) vasopressin; 1-desamino-8-D-arginine vasopressin
Molecular Formula: C46H64N14O12S2
Molecular Weight: 1069.22
Percent Composition: C 51.67%, H 6.03%, N 18.34%, O 17.96%, S 6.00%
Literature References: Synthetic analog of vasopressin, q.v., with antidiuretic activity and decreased pressor effects. Improves hemostasis by increasing plasma levels of von Willebrand factor, factor VIII and tissue plasminogen activator, q.q.v. Prepn: M. Zaoral et al., FR 1540536; eidem, US 3497491 (1968, 1970 both to Ceskoslovenska Akad. Ved). Syntheses: R. L. Huguenin, R. A. Boissonnas, Helv. Chim. Acta 49, 695 (1966); M. Zaoral et al., Collect. Czech. Chem. Commun. 32, 1250 (1967). Review of clinical experience in bleeding disorders: P. M. Mannucci, Blood 90, 2515-2521 (1997); in treatment of nocturnal enuresis: P. E. V. van Kerrebroeck, BJU Int. 89, 420-425 (2002); of mechanism of hemostatic effects: J. E. Kaufmann, U. M. Vischer, J. Thromb. Haemostasis 1, 682-689 (2003).
Properties: [a]D25 +85.5 ± 2° (calculated for the free peptide).
Optical Rotation: [a]D25 +85.5 ± 2° (calculated for the free peptide)
Derivative Type: Monoacetate
CAS Registry Number: 62288-83-9
Trademarks: Adiuretin SD (Ferring); DDAVP (Ferring); Desmospray (Ferring); Minirin (Ferring); Octim (Ferring); Octostim (Ferring); Presinex (Pliva); Stimate (ZLB Behring)
Molecular Formula: C46H64N14O12S2.C2H4O2
Molecular Weight: 1129.27
Percent Composition: C 51.05%, H 6.07%, N 17.36%, O 19.84%, S 5.68%
Literature References: Occurs as the trihydrate.
Therap-Cat: Antidiuretic; hemostatic.
Keywords: Antidiuretic; Hemostatic.
Desmosterol Desogestrel Desomorphine Desonide Desosamine

Desmopressin
Desmopressin.svg
Desmopressin ball-and-stick.png
Systematic (IUPAC) name
(2S)-N-[(2R)-1-[(2-amino-2-oxoethyl)amino]-5-
(diaminomethylideneamino)-1-oxopentan-2-yl]-1-
[(4R,7S,10S,13S,16S)-7-(2-amino-2-oxoethyl)-10-
(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-
6,9,12,15,18-pentaoxo-13-(phenylmethyl)1,2-dithia-
5,8,11,14,17-pentazacycloicosane-4-carbonyl]
pyrrolidine-2-carboxamide
Clinical data
Trade names Ddavp, Minirin, Minirin Melt, Octim, Stimate
AHFS/Drugs.com monograph
Pregnancy cat. B2 (AU) B (US)
Legal status POM (UK) -only (US)
Routes IV, IM, SC, intranasal, oral
Pharmacokinetic data
Bioavailability Variable; 0.08–0.16% (oral)
Protein binding 50%
Half-life 1.5–2.5 hours
Excretion Renal
Identifiers
CAS number 16679-58-6 YesY
ATC code H01BA02
PubChem CID 5311065
DrugBank DB00035
ChemSpider 10481973 YesY
UNII ENR1LLB0FP YesY
KEGG D00291 YesY
ChEMBL CHEMBL376685 YesY
Chemical data
Formula C46H64N14O12S2 
Mol. mass 1069.22 g/mol
 YesY (what is this?)  (verify)

Desmopressin (trade names: DDAVP, DesmoMelt, Minirin, Minirin Melt, Octim, Stimate) is a synthetic replacement for vasopressin, the hormone that reduces urine production. It may be taken nasally, intravenously, or as an oral or sublingual tablet. Physicians prescribe desmopressin most frequently for treatment of diabetes insipidus, bedwetting, or nocturia.