Desmopressin acetate anhydrousProduct ingredient for Desmopressin

Name
Desmopressin acetate anhydrous
Drug Entry
Desmopressin

Desmopressin (dDAVP), a synthetic analogue of 8-arginine vasopressin (ADH), is an antidiuretic peptide drug modified by deamination of 1-cysteine and substitution of 8-L-arginine by 8-D-arginine. ADH is an endogenous pituitary hormone that has a crucial role in the control of the water content in the body. Upon release from the stimulation of increased plasma osmolarity or decreased circulating blood volume, ADH mainly acts on the cells of the distal part of the nephron and the collecting tubules in the kidney 6. The hormone interacts with V1, V2 or V3 receptors with differing signal cascade systems.

Desmopressin displays enhanced antidiuretic potency, fewer pressor effects due to V2-selective actions, and a prolonged half-life and duration of action compared to endogenous ADH 2. It has been employed clinically since 1972 and is available in various formulations including intranasal solution, intravenous solution, oral tablet and oral lyophilisate 3. Desmopressin is indicated for the treatment of polyuric conditions including primary nocturnal enuresis, nocturia, and diabetes insipidus. It was also newly approved for the treatment of mild classical hemophilia and von Willebrand's disease for minor surgeries. The active ingredient in most formulations is desmopressin acetate. Nocdurna, or desmopressin acetate, was approved by the FDA on June 21st, 2018 for the treatment of nocturia due to nocturnal polyuria in adults. It is available as a sublingual tablet.

Accession Number
DBSALT000044
Structure
Synonyms
Anhydrous desmopressin acetate / Desmopressin monoacetate anhydrous
UNII
1K12647SFC
CAS Number
62288-83-9
Weight
Average: 1129.269
Monoisotopic: 1128.448084334
Chemical Formula
C48H68N14O14S2
InChI Key
MLSVJHOYXJGGTR-IFHOVBQLSA-N
InChI
InChI=1S/C46H64N14O12S2.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t28-,29+,30+,31+,32+,33+,34+;/m1./s1
IUPAC Name
(2R)-2-{[(2S)-1-[(4R,7S,10S,13S,16S)-13-benzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-5-carbamimidamido-N-(carbamoylmethyl)pentanamide; acetic acid
SMILES
CC(O)=O.[H][C@]1(CCCN1C(=O)[C@@H]1CSSCCC(=O)N[C@@H](CC2=CC=C(O)C=C2)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)N[C@H](CCCNC(N)=N)C(=O)NCC(N)=O
PubChem Compound
9833407
ChemSpider
8009131
BindingDB
50247923
ChEMBL
CHEMBL1200556
Wikipedia
Desmopressin
Predicted Properties
PropertyValueSource
Water Solubility0.11 mg/mLALOGPS
logP-1ALOGPS
logP-6.1Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)9.5Chemaxon
pKa (Strongest Basic)11.77Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count15Chemaxon
Hydrogen Donor Count14Chemaxon
Polar Surface Area435.41 Å2Chemaxon
Rotatable Bond Count19Chemaxon
Refractivity279.78 m3·mol-1Chemaxon
Polarizability104.78 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon