Desmopressin acetateProduct ingredient for Desmopressin
- Name
- Desmopressin acetate
- 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
- DBSALT001154
- Structure
Structure for Desmopressin acetate (DBSALT001154)
- Synonyms
- Desmopressin acetate hydrate / Desmopressin acetate trihydrate / Desmopressin monoacetate trihydrate
- UNII
- XB13HYU18U
- CAS Number
- 62357-86-2
- Weight
- Average: 1183.32
Monoisotopic: 1182.479779327 - Chemical Formula
- C48H74N14O17S2
- InChI Key
- YNKFCNRZZPFMEX-XHPDKPNGSA-N
- InChI
- InChI=1S/C46H64N14O12S2.C2H4O2.3H2O/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);3*1H2/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 trihydrate
- SMILES
- O.O.O.CC(O)=O.NC(=O)CC[C@@H]1NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)CCSSC[C@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](CCCNC(N)=N)C(=O)NCC(N)=O
- External Links
- ChemSpider
- 26331715
- ChEBI
- 59728
- Wikipedia
- Desmopressin
- Predicted Properties
Property Value Source Water Solubility 0.11 mg/mL ALOGPS logP -1 ALOGPS logP -6.1 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 9.5 Chemaxon pKa (Strongest Basic) 11.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 15 Chemaxon Hydrogen Donor Count 14 Chemaxon Polar Surface Area 435.41 Å2 Chemaxon Rotatable Bond Count 19 Chemaxon Refractivity 279.78 m3·mol-1 Chemaxon Polarizability 104.78 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon