Desmopressin
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Hodoodo CAT#: H581617

CAS#: 16679-58-6 (free base)

Description: Desmopressin is a synthetic analog of the pituitary hormone, ARGININE VASOPRESSIN. Its action is mediated by the VASOPRESSIN receptor V2. It has prolonged antidiuretic activity, but little pressor effects. It also modulates levels of circulating FACTOR VIII and VON WILLEBRAND FACTOR. It is a medication used to treat diabetes insipidus, bedwetting, hemophilia A, von Willebrand disease, and high blood urea levels. In hemophilia A and von Willebrand disease, it should only be used for mild to moderate cases. It may be given in the nose, by injection into a vein, by mouth, or under the tongue.


Chemical Structure

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Desmopressin
CAS# 16679-58-6 (free base)

Theoretical Analysis

Hodoodo Cat#: H581617
Name: Desmopressin
CAS#: 16679-58-6 (free base)
Chemical Formula: C46H64N14O12S2
Exact Mass: 1,068.43
Molecular Weight: 1,069.220
Elemental Analysis: C, 51.67; H, 6.03; N, 18.34; O, 17.96; S, 6.00

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Related CAS #: 62357-86-2 (acetate trihydrate)   69-25-0 (free base)   62288-83-9 (acetate)   16679-58-6 (free base)   16679-58-6 (free base)    

Synonym: Desmopressin; Desmopresina; Desmopressinum.

IUPAC/Chemical Name: (S)-1-((4R,7S,10S,13S,16S)-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl)-N-((R)-1-((2-amino-2-oxoethyl)amino)-5-guanidino-1-oxopentan-2-yl)pyrrolidine-2-carboxamide

InChi Key: NFLWUMRGJYTJIN-PNIOQBSNSA-N

InChi Code: InChI=1S/C46H64N14O12S2/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/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)/t28-,29+,30+,31+,32+,33+,34+/m1/s1

SMILES Code: c1ccc(cc1)C[C@H]2C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSCCC(=O)N[C@H](C(=O)N2)Cc3ccc(cc3)O)C(=O)N4CCC[C@H]4C(=O)N[C@H](CCCNC(=N)N)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 1,069.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Weiss JP, van der Meulen EA, Juul KV. Low-dose Desmopressin Orally Disintegrating Tablet: Suggested Clinically Meaningful Benefit in Patients with Nocturia Due to Nocturnal Polyuria. Eur Urol Focus. 2018 Nov 20. pii: S2405-4569(18)30333-X. doi: 10.1016/j.euf.2018.11.001. [Epub ahead of print] PubMed PMID: 30470646.

2: Singh K, Kanodia AK, Ross P, Torgersen A, Maclean J, Leese G, Hossain-Ibrahim K. Xanthomatous hypophysitis causing hypogonadotropic hypogonadism resulting in delayed presentation of slipped capital femoral epiphysis. Br J Neurosurg. 2018 Nov 19:1-4. doi: 10.1080/02688697.2018.1525482. [Epub ahead of print] PubMed PMID: 30450996.

3: Chevalier MT, Garona J, Sobol NT, Farina HG, Alonso DF, Álvarez VA. In vitro and in vivo evaluation of desmopressin-loaded poly(D,L-lactic-co-glycolic acid) nanoparticles for its potential use in cancer treatment. Nanomedicine (Lond). 2018 Nov 15. doi: 10.2217/nnm-2018-0065. [Epub ahead of print] PubMed PMID: 30430901.

4: Peng CC, Yang SS, Austin PF, Chang SJ. Systematic Review and Meta-analysis of Alarm versus Desmopressin Therapy for Pediatric Monosymptomatic Enuresis. Sci Rep. 2018 Nov 13;8(1):16755. doi: 10.1038/s41598-018-34935-1. PubMed PMID: 30425276.

5: Chellen S, Whittaker E, Eisenhut M, Grandjean L. Cerebral tuberculomas in a 6-year-old girl causing central diabetes insipidus. BMJ Case Rep. 2018 Nov 12;2018. pii: bcr-2018-226590. doi: 10.1136/bcr-2018-226590. PubMed PMID: 30420562.

6: Préel M, Kamperis K, Rittig S. [Nocturnal enuresis in children]. Ugeskr Laeger. 2018 Nov 12;180(46). pii: V01180027. Danish. PubMed PMID: 30417818.

7: Nuovo S, Fuiano L, Micalizzi A, Battini R, Bertini E, Borgatti R, Caridi G, D'Arrigo S, Fazzi E, Fischetto R, Ghiggeri GM, Giordano L, Leuzzi V, Romaniello R, Signorini S, Stringini G, Zanni G, Romani M, Valente EM, Emma F. Impaired urinary concentration ability is a sensitive predictor of renal disease progression in Joubert syndrome. Nephrol Dial Transplant. 2018 Nov 6. doi: 10.1093/ndt/gfy333. [Epub ahead of print] PubMed PMID: 30403813.

8: Ranucci M, Pistuddi V, Di Dedda U, Menicanti L, De Vincentiis C, Baryshnikova E; Surgical and Clinical Outcome REsearch (SCORE) group. Platelet function after cardiac surgery and its association with severe postoperative bleeding: the PLATFORM study. Platelets. 2018 Oct 26:1-7. doi: 10.1080/09537104.2018.1535706. [Epub ahead of print] PubMed PMID: 30365338.

9: Bowyer AE, Goodfellow KJ, Seidel H, Westhofen P, Stufano F, Goodeve A, Kitchen S, Makris M. Evaluation of a semi-automated von Willebrand factor multimer assay, the Hydragel 5 von Willebrand multimer, by two European Centers. Res Pract Thromb Haemost. 2018 Aug 12;2(4):790-799. doi: 10.1002/rth2.12141. eCollection 2018 Oct. PubMed PMID: 30349898; PubMed Central PMCID: PMC6178608.

10: Nguyen AL, Kamal M, Raghavan R, Nagaraj G. Acquired factor VII deficiency causing severe bleeding disorder secondary to AL amyloidosis of the liver. Hematol Rep. 2018 Sep 24;10(3):7235. doi: 10.4081/hr.2018.7235. eCollection 2018 Sep 5. PubMed PMID: 30344985; PubMed Central PMCID: PMC6176396.

11: Monmany J, Granell E, López L, Domingo P. Resolved heart tamponade and controlled exophthalmos, facial pain and diabetes insipidus due to Erdheim-Chester disease. BMJ Case Rep. 2018 Oct 17;2018. pii: bcr-2018-225224. doi: 10.1136/bcr-2018-225224. PubMed PMID: 30337283.

12: Candy V, Whitworth H, Grabell J, Thibeault L, Harpell L, Bowman M, Good D, Hopman WM, Sidonio RF Jr, James PD. A decreased and less sustained desmopressin response in hemophilia A carriers contributes to bleeding. Blood Adv. 2018 Oct 23;2(20):2629-2636. doi: 10.1182/bloodadvances.2018023713. PubMed PMID: 30327371; PubMed Central PMCID: PMC6199650.

13: Birder LA, Wolf-Johnston AS, Jackson EK, Wein AJ, Dmochowski R. Aging increases the expression of vasopressin receptors in both the kidney and urinary bladder. Neurourol Urodyn. 2018 Oct 12. doi: 10.1002/nau.23830. [Epub ahead of print] PubMed PMID: 30311671.

14: Chen S, Chen K, Lu L, Zhang X, Tong A, Pan H, Zhu H, Lu Z. The effects of sampling lateralization on bilateral inferior petrosal sinus sampling and desmopressin stimulation test for pediatric Cushing's disease. Endocrine. 2018 Oct 11. doi: 10.1007/s12020-018-1779-x. [Epub ahead of print] PubMed PMID: 30311170.

15: Higasa S, Tokugawa T, Sawada A. [Diagnosis and management of von Willebrand disease]. Rinsho Ketsueki. 2018;59(10):2222-2232. doi: 10.11406/rinketsu.59.2222. Japanese. PubMed PMID: 30305529.

16: Lees JS, McQuarrie EP, Mackinnon B. Renal biopsy: it is time for pragmatism and consensus. Clin Kidney J. 2018 Oct;11(5):605-609. doi: 10.1093/ckj/sfy075. Epub 2018 Sep 20. PubMed PMID: 30289128; PubMed Central PMCID: PMC6165764.

17: Drangsholt S, Ruiz MJA, Peyronnet B, Rosenblum N, Nitti V, Brucker B. Diagnosis and management of nocturia in current clinical practice: who are nocturia patients, and how do we treat them? World J Urol. 2018 Oct 4. doi: 10.1007/s00345-018-2511-4. [Epub ahead of print] PubMed PMID: 30288596.

18: Calmette L, Clauser S. [Von Willebrand disease]. Rev Med Interne. 2018 Dec;39(12):918-924. doi: 10.1016/j.revmed.2018.08.005. Epub 2018 Sep 29. French. PubMed PMID: 30279008.

19: Akhavizadegan H, Locke JA, Stothers L, Kavanagh A. A comprehensive review of adult enuresis. Can Urol Assoc J. 2018 Sep 27. doi: 10.5489/cuaj.5485. [Epub ahead of print] Review. PubMed PMID: 30273117.

20: Robert G, De La Taille A, Descazeaud A. [Impact of medical and surgical treatments of LUTS on nocturia]. Prog Urol. 2018 Nov;28(15):848-855. doi: 10.1016/j.purol.2018.08.004. Epub 2018 Sep 26. French. PubMed PMID: 30268350.