desmopressin acetate

酢酸デスモプレシン

WordNet

1. a salt or ester of acetic acid (同)ethanoate

PrepTutorEJDIC

1. 酢酸(さくさん)塩;アセテート(酢酸人造絹糸)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/04/16 18:05:12」(JST)

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Desmopressin

Systematic (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
Clinical data
Trade names	Ddavp, Minirin, Minirin Melt, Octim, Stimate
AHFS/Drugs.com	monograph
Pregnancy cat.	B2 (AU) B (US)
Legal status	POM (UK) ℞-only (US)
Routes	IV, IM, SC, intranasal, oral
Pharmacokinetic data
Bioavailability	Variable; 0.08–0.16% (oral)
Protein binding	50%
Half-life	1.5–2.5 hours
Excretion	Renal
Identifiers
CAS number	16679-58-6 Y
ATC code	H01BA02
PubChem	CID 5311065
DrugBank	DB00035
ChemSpider	10481973 Y
UNII	ENR1LLB0FP Y
KEGG	D00291 Y
ChEMBL	CHEMBL376685 Y
Chemical data
Formula	C46H64N14O12S2
Mol. mass	1069.22 g/mol
SMILES NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H]1CCCN1C(=O)[C@@H]4CSSCCC(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)N[C@@H](Cc3ccccc3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N4
InChI 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-/m0/s1 Y Key:NFLWUMRGJYTJIN-NXBWRCJVSA-N Y
Y (what is this?)  (verify)

Desmopressin (trade names: DDAVP, DesmoMelt, Minirin, Minirin Melt, Octim, Stimate) is a synthetic replacement for vasopressin, the hormone that reduces urine production. It may be taken nasally, intravenously, or as an oral or sublingual tablet. Physicians prescribe desmopressin most frequently for treatment of diabetes insipidus, bedwetting, or nocturia.

Chemistry

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 (see stereochemistry).

Mode of action

Desmopressin works by limiting the amount of water that is eliminated in the urine.

Desmopressin binds to V2 receptors in renal collecting ducts, increasing water reabsorption. It also stimulates release of von Willebrand factor from endothelial cells by acting on the V2 receptor.

Desmopressin is degraded more slowly than recombinant vasopressin, and requires less frequent administration. In addition, it has little effect on blood pressure, while vasopressin may cause arterial hypertension. Vasopressin stimulates the release of ACTH, which indirectly increases responsiveness of alpha-1 receptor in blood vessel smooth muscle, increasing vessel tone and blood pressure. Desmopressin does not stimulate ACTH release, and therefore does not directly raise blood pressure.

Clinical uses

Nocturnal Enuresis

Doctors prescribe desmopressin frequently for treatment. It is usually in the form of desmopressin acetate, DDAVP. Patients taking DDAVP are 4.5 times more likely to sleep without disruption than with placebo. Examples of these situations are overnight camp and sleepovers.

US drug regulators banned treating bedwetting with desmopressin nasal sprays after two patients died and 59 other patients suffered seizures. The patients were using desmopressin when they developed hyponatremia, an imbalance of the body's sodium levels.

FDA regulators said that desmopressin tablets could still be considered safe for nocturnal enuresis treatment, as long as the patient was otherwise healthy. Patients must stop taking desmopressin if they become sick and have severe vomiting and diarrhea, fever, the flu, or severe cold. They should also be very cautious during hot weather or following strenuous exercise that may make them thirsty.

A healthy body needs to maintain a balance of water and salt (sodium). If sodium levels become too low (hyponatremia) – either as a result of increased water take-up or reduced salt levels – a person may have seizures and, in extreme cases, may die.

Coagulation disorders

Desmopressin can be used to promote the release of von Willebrand factor (with subsequent increase in factor VIII survival secondary to vWF complexing) in patients with coagulation disorders such as von Willebrand disease, mild hemophilia A (factor VIII deficiency), and thrombocytopenia. It can be used with uremic induced platelet dysfunction. It is not effective in the treatment of hemophilia B (factor IX deficiency), severe hemophilia A, or von Willebrand 2B.

Diabetes insipidus

Desmopressin is used in the treatment of central diabetes insipidus (DI), to replace endogenous ADH that is missing in the central nervous system type of this disorder (decreased production of ADH from the posterior pituitary). It is also used in the diagnostic workup for diabetes insipidus, in order to distinguish central from nephrogenic DI.

Side effects

• headaches
• facial flushing
• nausea
• hyponatremia
• seizures

References

Further reading

• Leissinger C, Becton D, Cornell C Jr, Cox Gill J. High-dose DDAVP intranasal spray (Stimate) for the prevention and treatment of bleeding in patients with mild haemophilia A, mild or moderate type 1 von Willebrand disease and symptomatic carriers of haemophilia A. Haemophilia 2001;7:258-66. PMID 11380629.

UpToDate Contents

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• 1. バソプレシンおよびデスモプレシン刺激試験 vasopressin and desmopressin stimulation test
• 2. 中枢性尿崩症の治療 treatment of central diabetes insipidus
• 3. 成人における低ナトリウム血症の治療の概要 overview of the treatment of hyponatremia in adults
• 4. 尿毒症における血小板機能不全 platelet dysfunction in uremia
• 5. 小児における夜尿症：マネージメント nocturnal enuresis in children management

English Journal

• Desmopressin treatment improves platelet function under flow in patients with postoperative bleeding.

• Swieringa F1, Lancé MD2, Fuchs B3, Feijge MA1, Solecka BA3, Verheijen LP4, Hughes KR1, van Oerle R1, Deckmyn H5, Kannicht C3, Heemskerk JW1, van der Meijden PE1.
• Journal of thrombosis and haemostasis : JTH.J Thromb Haemost.2015 Aug;13(8):1503-13. doi: 10.1111/jth.13007. Epub 2015 Jun 11.
• BACKGROUND: Patients undergoing major cardiothoracic surgery are subjected to dilution, owing to massive fluid infusion and blood component transfusion. These patients may experience bleeding perioperatively, and are frequently treated with the endothelium-activating agent desmopressin.OBJECTIVES: T
• PMID 25988848

• Episodic ventriculomegaly due to hypernatremia mimicking shunt malfunction: case report.

• Jernigan SC1, Stone SS1, Aronson JP2, Putman M3, Proctor MR1.
• Journal of neurosurgery. Pediatrics.J Neurosurg Pediatr.2015 Jul 17:1-4. [Epub ahead of print]
• Patients with shunted hydrocephalus presenting with altered mental status and ventriculomegaly are generally considered to be in shunt failure requiring surgical treatment. The authors describe a case of shunted hydrocephalus secondary to a disseminated neuroectodermal tumor in a pediatric patient i
• PMID 26186358

• Tandem inversion duplication within F8 Intron 1 associated with mild haemophilia A.

• Lannoy N1,2, Bandelier C1, Grisart B3, Reginster M4, Ronge-Collard E5, Vikkula M6, Hermans C2,7.
• Haemophilia : the official journal of the World Federation of Hemophilia.Haemophilia.2015 Jul;21(4):516-22. doi: 10.1111/hae.12675. Epub 2015 May 11.
• In approximately 90% of mild haemophilia A (HA) patients, a missense mutation can be identified using complete gene sequencing. In this study, multiplex ligation-dependent probe amplification analysis was performed as a second step in 10 French-speaking Belgian with mild HA presenting no detectable
• PMID 25962585

Japanese Journal

• 下垂体転移による中枢性尿崩症を合併した肺扁平上皮癌の1例

• 宮崎 健二,柴田 雅彦,酒井 俊彦,戸島 洋一
• 気管支学 : 日本気管支研究会雑誌 33(6), 452-457, 2011-11-25
• 背景.肺癌の剖検例での下垂体転移の頻度は8%とする報告があり,下垂体転移は必ずしも稀ではないが,下垂体転移の多くは無症候性であり尿崩症を発症する症例は稀である.症例.59歳,男性.2010年4月食欲低下,口渇,腰痛を主訴に救急外来を受診した.脱水,肝酵素の上昇,高Ca血症などの所見を認め入院となった.入院後の胸部CTで左下葉に腫瘤および無気肺を認めたため気管支内視鏡を施行し,肺扁平上皮癌と診断した …
• NAID 110008896962

• Transient Polyuria Related to Central Diabetes Insipidus Caused by Lymphocytic Infundibulo-neurohypophysitis in a Patient Treated for Graves Disease

• Yamazaki Masanori,Sato Ai,Nishio Shin-ichi,Uehara Takeshi,Komatsu Mitsuhisa
• Internal Medicine 49(17), 1885-1890, 2010
• … He received treatment with thiamazole (MMI) for GD and desmopressin acetate (DDAVP) for CDI. …
• NAID 130000336870

Related Links

• Desmopressin Acetate Monograph | Drugs.com

Desmopressin Acetate reference guide from the American Society of Health- System Pharmacists. Desmopressin Acetate guidance for safe and effective use.

Related Pictures

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★リンクテーブル★

リンク元	「デスモプレシン」
関連記事	「desmopressin」

「デスモプレシン」

　　[★]

英

desmopressin

同

1-desamino-8-D-arginine vasopressin, DDAVP, 1-deamino-8-D-arginine vasopressin、デアミノアルギニンバソプレッシン デアミノアルギニンバソプレシン deamino arginine vasopressin

化

酢酸デスモプレシン desmopressin acetate

商

Stimate、デスモプレシン点鼻薬、デスモプレシン注、ミニリンメルト

関

バソプレシン。脳下垂体ホルモン剤

• アルギニンバソプレシン誘導体;尿崩症治療薬
• 副作用の発現がバソプレシンより少ないが、水中毒にはやはり注意する必要がある。(QB.D-257)

I. NATURALLY OCCURRING VASOPRESSIN-LIKE PEPTIDES?
??A. Vertebrates?	A?	W?	X?	Y?	Z?
????1. Mammals
??????? Arginine? vasopressin* (AVP) (human beings and other mammals)	NH2	Tyr	Phe	Gln	Arg
???????Lypressin* (pigs, marsupials)	NH2	Tyr	Phe	Gln	Lys
???????Phenypressin (macropodids)	NH2	Phe	Phe	Gln	Arg
????2. Nonmammalian vertebrates
Vasotocin	NH2	Tyr	Ile	Gln	Arg
??B. Invertebrates?
????1. Arginine conopressin (Conus striatus)?	NH2	Ile	Ile	Arg	Arg
????2. Lysine conopressin (Conus geographicus)?	NH2	Phe	Ile	Arg	Lys
????3. Locust subesophageal ganglia peptide	NH2	Leu	Ile	Thr	Arg
II. SYNTHETIC VASOPRESSIN PEPTIDES?
??A. V1-selective agonists?
????1. V1a-Selective Agonist [Phe2, Ile3, Orn8]AVP	NH2	Phe	Ile	Gln	Orn
????2. V1b-Selective Agonist Deamino [D-3-(3'-pyridyl)-Ala2]AVP	H	D-3-(3'-pyridyl)-Ala2	Phe	Gln	Arg
??B. V2-selective agonists?
????1. Desmopressin* (DDAVP)	H	Tyr	Phe	Gln	D-Arg?
????2. Deamino[Val4, D-Arg8]AVP	H	Tyr	Phe	Val	D-Arg?
III. NONPEPTIDE AGONIST?
A. OPC-51803?

「desmopressin」

　　[★] デスモプレシン DDAVP