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Desmopressin acetate trihydrate

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Desmopressin acetate (trade names: DDAVP, Stimate, Minirin) is a synthetic replacement for vasopressin, the hormone that reduces urine production. It may be taken nasally, intravenously, or as a tablet. Doctors prescribe Desmopressin most frequently for treatment of diabetes insipidus or nocturnal enuresis. Desmopressin (1-desamino-8-D-arginine vasopressin) is a modified form of the normal human hormone arginine vasopressin, a peptide containing nine amino acids. Compared to vasopressin, desmopressin's first amino acid has been deaminated, and the arginine at the eighth position is in the dextro rather than the levo form.

Category

Peptide Inhibitors

Catalog number

BAT-010781

CAS number

62357-86-2

Molecular Formula

C48H74N14O17S2

Molecular Weight

1183.31

Specification
Reference Reading

IUPAC Name

acetic acid;(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)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;trihydrate

Synonyms

DDAVP; Noctiva; KW-8008; 1-(3-Mercaptopropionic acid)-8-D-arginine-vasopressin monoacetate (salt) trihydrate; 1-deamino-8-D-arginine vasopressin acetate trihydrate

Related CAS

16789-98-3 (diacetate) 16679-58-6 (free base)

Appearance

white to light yellow crystal

Sequence

CYFQNCPRG

Storage

Store at -20°C

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

InChI Key

YNKFCNRZZPFMEX-XHPDKPNGSA-N

Canonical SMILES

CC(=O)O.C1CC(N(C1)C(=O)C2CSSCCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)C(=O)NC(CCCN=C(N)N)C(=O)NCC(=O)N.O.O.O

1.Desmopressin acetate as a haemostatic elevator in individuals with combined deficiency of factors V and VIII: a clinical trial.

Mansouritorghabeh H1, Shirdel A2. J Thromb Haemost. 2016 Feb;14(2):336-9. doi: 10.1111/jth.13207. Epub 2016 Jan 30.

Essentials Combined factor V (FV) and factor VIII (FVIII) deficiency (CF5F8D) is an autosomal recessive coagulation disorder. Desmopressin acetate (DDAVP) was intravenously infused in 20 adult patients with CF5F8D. DDAVP can enhance FVIII levels but has no effect on FV levels in patients with CF5F8D. DDAVP can be substituted for FVIII concentrates in patients with CF5F8D.

2.Buccally Administered Intranasal Desmopressin Acetate for the Treatment of Neurogenic Diabetes Insipidus in Infancy.

Smego AR1, Backeljauw P1, Gutmark-Little I1. J Clin Endocrinol Metab. 2016 Mar 24:jc20161157. [Epub ahead of print]

CONTEXT: The treatment of neurogenic diabetes insipidus (DI) in infancy is challenging and complicated by fluid overload and dehydration. Therapy with subcutaneous, intranasal (IN), or oral tablet desmopressin acetate (DDAVP) remains difficult to titrate in infants.