Stimate

デスモプレシン

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/12/17 21:59:52」(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, 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, 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. 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 stimultate 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

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

• 1. 血友病A・血友病B：予防を含めた日常的なマネージメント hemophilia a and b routine management including prophylaxis
• 2. 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
• 3. 中枢性尿崩症の治療 treatment of central diabetes insipidus
• 4. Nocturnal enuresis in children: Management
• 5. 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

English Journal

• Integrated pipeline for inferring the evolutionary history of a gene family embedded in the species tree: a case study on the STIMATE gene family.

• Song J1, Zheng S2, Nguyen N3, Wang Y2, Zhou Y3, Lin K4.
• BMC bioinformatics.BMC Bioinformatics.2017 Oct 3;18(1):439. doi: 10.1186/s12859-017-1850-2.
• PMID 28974198

• STIM-TRP Pathways and Microdomain Organization: Auxiliary Proteins of the STIM/Orai Complex.

• Pacheco J1, Vaca L2.
• Advances in experimental medicine and biology.Adv Exp Med Biol.2017;993:189-210. doi: 10.1007/978-3-319-57732-6_10.
• PMID 28900915

• Molecular modulators of store-operated calcium entry.

• Lopez JJ1, Albarran L1, Gómez LJ1, Smani T2, Salido GM1, Rosado JA3.
• Biochimica et biophysica acta.Biochim Biophys Acta.2016 Aug;1863(8):2037-43. doi: 10.1016/j.bbamcr.2016.04.024. Epub 2016 Apr 27.
• PMID 27130253

Japanese Journal

• 出穂後葉色値からのコシヒカリ玄米タンパク質含有率の推定

• 北陸作物学会報 (49), 25-27, 2014-03-31
• NAID 110009984570

• Action of Thioglycolic Acid and L-Cysteine to Disulfide Cross-Links in Hair Fibers during Permanent Waving Treatment

• 繊維学会誌 64(6), 137-144, 2008
• NAID 130004434065

• ESRD in Sri Lanka-1998

• 日本透析医学会雑誌 = Journal of Japanese Society for Dialysis Therapy 32(6), 963-964, 1999-06-28
• NAID 10004921860

Related Links

• Stimate - FDA prescribing information, side effects and uses

Stimate - Clinical Pharmacology Stimate Nasal Spray contains as active substance, desmopressin acetate, which is a synthetic analogue of the natural hormone arginine vasopressin. One spray or 0.1 mL (150 mcg) of Stimate Nasal ...

• CSL Behring Stimate (desmopressin acetate) Nasal Spray, 1 ...

(desmopressin acetate) ® ® ® ® ® ® bleeding. ® Stimate® ® ® ® ® ® ® ® ® ® ® ® ® ® ® ® ®. ® ® ® ® ® ® ® ® ® ® ® desmopressin acetate

Related Pictures

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★リンクテーブル★

リンク元

「デスモプレシン」

「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?