Structure via PubChem · Public domain (PubChem)
desmopressin
Sign in to saveAlso known as 1-(3-mercaptopropionic acid)-8-D-arginine-vasopressin, 1-deamino-8-D-arginine vasopressin, 1-desamino-8-D-arginine vasopressin, deamino arginine vasopressin, DDAVP
Desmopressin, sold under the trade name Ddavp among others, 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.
Key facts
- Drug.N
- 14
- Drug.O
- 12
- Drug.S
- 2
- Drug.SMILES
- 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
- Drug.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
- Drug.C
- 46
- Drug.H
- 64
- Drug.StdInChI
- 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
- Drug.StdInChIKey
- NFLWUMRGJYTJIN-PNIOQBSNSA-N
- Drug.image
- Desmopressin.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Desmopressin ball-and-stick.png
- Drug.image_class2
- bg-transparent
- Drug.tradename
- Ddavp, Desmoda, others
- Drug.MedlinePlus
- a608010
- Drug.DailyMedID
- Desmopressin
- Drug.pregnancy_AU
- B2
- Drug.routes_of_administration
- Intravenous, intramuscular, subcutaneous, intranasal, by mouth, sublingual
via Wikipedia infobox
Chemical data
- Formula
- C46H64N14O12S2
- Molecular weight
- 1069.2 g/mol
- 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)-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
- SMILES
- C1C[C@H](N(C1)C(=O)[C@@H]2CSSCCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)C(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N
- InChIKey
- NFLWUMRGJYTJIN-PNIOQBSNSA-N
- XLogP
- -4
- Polar surface area
- 489 Ų
- H-bond donors
- 13
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Research
6,716 papers- Desmopressin.Annals of internal medicine · 1985
- Desmopressin revisited in mild hemophilia A.Blood · 2022
- Desmopressin (Nocdurna and Noctiva) for nocturnal polyuria.The Medical letter on drugs and therapeutics · 2019
- Desmopressin acetate the first sublingual tablet to treat nocturia due to nocturnal polyuria.Expert review of clinical pharmacology · 2021
- Desmopressin acetate nasal spray for adults with nocturia.Expert review of clinical pharmacology · 2017
via PubMed
~6 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Bed wetting
- Nocturia
- Bleeding disorders
- Diabetes insipidus
- Side effects
- Mechanism of action
- Chemistry
- References
- Further reading
- External links
Desmopressin, sold under the trade name Ddavp among others, 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.
Common side effects include headaches, diarrhea, and low blood sodium. The low blood sodium that results may cause seizures. It should not be used in people with significant kidney problems or low blood sodium. It appears to be safe to use during pregnancy. It is a synthetic analogue of vasopressin, the hormone that plays roles in the control of the body's osmotic balance, blood pressure regulation, kidney function, and reduction of urine production.
Excerpted from Wikipedia’s “desmopressin” article, available under the CC BY-SA 4.0 licence.