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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/04/29 14:22:15」(JST)

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Desmopressin (trade names: DDAVP, DesmoMelt, Stimate, Minirin) 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. Doctors 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.

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. ^[1] ^[2] 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. ^[3]

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. ^[4]

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

^ Evans, JH (2001). "Evidence based management of nocturnal enuresis". BMJ (Clinical research ed.) 323 (7322): 1167–9. PMC 1121645. PMID 11711411.
^ "La prise en charge de l’énurésie nocturne primaire". Paediatr Child Health 10 (10): 616–620. 2005. PMC 2722621. PMID 19668677.
^ 2 Deaths Spur sleep apnea Drug Warning. Webmd.com (2007-12-04). Retrieved on 2011-04-18.
^ [1]^{[dead link]}

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. 尿毒症における血小板機能不全 platelet dysfunction in uremia
4. 小児における夜尿症のマネージメント management of nocturnal enuresis in children
5. 浸透圧性脱髄症候群と低ナトリウム血症の過度に急速な補正 osmotic demyelination syndrome and overly rapid correction of hyponatremia

English Journal

Use of objective efficacy criteria for evaluation of von willebrand factor/factor VIII concentrates.

Kessler CM, Windyga J, Schwartz BA, Knaub S.SourceaDivision of Coagulation, Hemophilia and Thrombosis Comprehensive Treatment Center, Georgetown University Medical Center, Washington, District of Columbia, USA bDepartment of Disorders of Haemostasis and Internal Medicine, Institute of Hematology and Transfusion Medicine, Warsaw, Poland cDepartment of Clinical Research and Development, Octapharma USA Inc., Hoboken, New Jersey, USA dDepartment of Hematology, Octapharma AG, Lachen, Switzerland.
Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis.Blood Coagul Fibrinolysis.2012 Jun;23(4):262-7.
von Willebrand disease (VWD) is the most common inherited coagulation disorder and is typically treated by restoring the deficient von Willebrand factor (VWF) with exogenous VWF or by stimulating release of endogenous VWF with desmopressin. Assessment of treatment efficacy is complex because there a
PMID 22322140

Unlike arginine vasopressin, the selective V1a receptor agonist FE 202158 does not cause procoagulant effects by releasing von Willebrand factor*.

Rehberg S, Enkhbaatar P, Rehberg J, La E, Ferdyan N, Qi S, Wisniewski K, Traber LD, Schteingart CD, Rivière PJ, Laporte R, Traber DL.SourceFrom the Department of Anesthesiology (SR, PE, JR, LDT, DLT), The University of Texas Medical Branch, Galveston, TX; Department of Anesthesiology, Intensive Care and Pain Medicine (SR), University of Muenster, Muenster, Germany; and Ferring Research Institute (EL, NF, SQ, KW, CDS, PJMR, RL), San Diego, CA.
Critical care medicine.Crit Care Med.2012 Jun;40(6):1957-60.
OBJECTIVE: : To compare the effects on von Willebrand factor release of the mixed vasopressin type 1a and type 2 receptor agonist arginine vasopressin and the selective vasopressin type 1a receptor agonist FE 202158, [Phe,Ile,Hgn,Orn(iPr)]vasopressin, at doses required for the treatment of septic sh
PMID 22488005

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

症例サルコイドーシスと中枢性尿崩症を合併した混合性結合組織病の1例

松田潤,伊藤大介,森大輔 [他]
日本腎臓学会誌 53(7), 1041-1045, 2011
NAID 40019047626

Related Pictures

★リンクテーブル★

リンク元	「デスモプレシン」「DDAVP」
拡張検索	「desmopressin acetate」

「デスモプレシン」

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, 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
ATC code	H01BA02
PubChem	CID 5311065
DrugBank	DB00035
ChemSpider	10481973
UNII	ENR1LLB0FP
KEGG	D00291
ChEMBL	CHEMBL376685
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 ; Key:NFLWUMRGJYTJIN-NXBWRCJVSA-N ;
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　　[★]

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?

「DDAVP」

　　[★] デスモプレシン desmopressin

「desmopressin acetate」

　　[★] 酢酸デスモプレシン

[1] Evans, JH (2001). "Evidence based management of nocturnal enuresis". BMJ (Clinical research ed.) 323 (7322): 1167–9. PMC 1121645. PMID 11711411.

[2] "La prise en charge de l’énurésie nocturne primaire". Paediatr Child Health 10 (10): 616–620. 2005. PMC 2722621. PMID 19668677.

[3] 2 Deaths Spur sleep apnea Drug Warning. Webmd.com (2007-12-04). Retrieved on 2011-04-18.

[4] [1]^{[dead link]}

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desmopressin