関: demoxytocin

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/06/23 19:36:36」(JST)

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Demoxytocin (INN) (brand names Sandopart, Odeax, Sandopral), also known as desaminooxytocin or deaminooxytocin, as well as 1-(3-mercaptopropanoic acid)oxytocin ([Mpa¹]OT), is an oxytocic peptide drug and synthetic analogue of oxytocin that is marketed in several European countries, including Italy, Czechoslovakia, and Poland.^[1]^[2]^[3] It has the amino acid sequence Mpa-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH₂ (Mpa = β-mercaptopropionic acid),^[4] and is an analogue of oxytocin wherein the leading cysteine is replaced with β-mercaptopropionic acid.^[4] Demoxytocin has similar activities as oxytocin,^[5] but is more potent and has a longer half-life in comparison.^[3]^[4] Unlike oxytocin, which is given via intravenous injection, demoxytocin is administered as a buccal tablet formulation.^[3]^[6] It is used to induce labor,^[4] promote lactation,^[3] and to prevent and treat puerperal (postpartum) mastitis (breast inflammation).^[7] The drug was first synthesized in 1960 and was introduced into clinical practice in 1971 by Sandoz.^[2]^[8]

References

^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 301–. ISBN 978-3-88763-075-1.
^ ^a ^b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 349–. ISBN 978-1-4757-2085-3.
^ ^a ^b ^c ^d I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 93–. ISBN 978-94-011-4439-1.
^ ^a ^b ^c ^d Christine Bladon (3 April 2002). Pharmaceutical Chemistry: Therapeutic Aspects of Biomacromolecules. John Wiley & Sons. pp. 61–. ISBN 978-0-471-49637-3.
^ C.J. van Boxtel; B. Santoso; I.R. Edwards (6 August 2008). Drug Benefits and Risks: International Textbook of Clinical Pharmacology - Revised 2nd Edition. IOS Press. pp. 389–. ISBN 978-1-60750-345-3.
^ Tom K. A. B. Eskes; Mieczyslaw Finster (22 October 2013). Drug Therapy During Pregnancy. Elsevier. pp. 185–. ISBN 978-1-4831-6298-0.
^ Sternadel Z, Gerkowicz J (1979). "[Use of deaminooxytocin (Sandopart) in the prevention and treatment of puerperal mastitis]". Ginekol. Pol. (in Polish) 50 (5): 413–6. PMID 468056.
^ Erhard Gross; Johannes Meienhofer (10 May 2014). Major Methods of Peptide Bond Formation: The Peptides Analysis, Synthesis, Biology. Elsevier. pp. 53–. ISBN 978-1-4832-1796-3.

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English Journal

Time-resolved phosphorescence of tyrosine, tyrosine analogs, and tyrosyl residues in oxytocin and small peptides.

Rousslang KW1, Reid PJ, Holloway DM, Haynes DR, Dragavon J, Ross JB.
Journal of protein chemistry.J Protein Chem.2002 Nov;21(8):547-55.
We present the time-resolved phosphorescence of oxytocin, two oxytocin derivatives, vasopressin and a series of compounds that serve as models for free tyrosine. One of the oxytocin derivatives, desaminodicarbaoxytocin, has the disulfide bridge replaced by an ethylene bridge, and lacks the N-terminu
PMID 12638657

Synthesis and pharmacology of novel analogues of oxytocin and deaminooxytocin: directed methods for the construction of disulfide and trisulfide bridges in peptides.

Chen L1, Zoulíková I, Slaninová J, Barany G.
Journal of medicinal chemistry.J Med Chem.1997 Mar 14;40(6):864-76.
Using as models the neurohypophyseal nonapeptide hormone oxytocin and its analogue deaminooxytocin, several directed routes to formation of sulfur-sulfur bridges have been developed and evaluated. The linear sequences (through common octapeptide-resin intermediates) were assembled smoothly on tris(a
PMID 9083475

Syntheses and biological activities of parallel and antiparallel homo and hetero bis-cystine dimers of oxytocin and deamino-oxytocin.

Chen L1, Bauerová H, Slaninová J, Barany G.
Peptide research.Pept Res.1996 May-Jun;9(3):114-21.
New methods have been developed for the synthesis of disulfide-bridged homo and hetero peptide dimers (both parallel and antiparallel), as exemplified in the oxytocin and deamino-oxytocin families. The linear sequences were assembled by 9-fluorenyl-methyloxycarbonyl (Fmoc) solid-phase synthesis tech
PMID 8875590

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★リンクテーブル★

リンク元	「デアミノオキシトシン」「demoxytocin」

「デアミノオキシトシン」

Demoxytocin
Systematic (IUPAC) name
	2-[(1-{[13-(butan-2-yl)-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}pyrrolidin-2-yl)formamido]-N-(carbamoylmethyl)-4-methylpentanamide
Clinical data
Routes of; administration	Buccal
Legal status
Legal status	℞ (Prescription only);
Identifiers
CAS Number	113-78-0
ATC code	H01BB01 (WHO)
PubChem	CID 449224
ChemSpider	395815
Synonyms	ODA-914;; 1-mercaptopropionate-; oxytoxin
Chemical data
Formula	C43H65N11O12S2
Molar mass	992.1727 g/mol
	SMILES CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSCCC(=O)N[C@H](C(=O)N1)Cc2ccc(cc2)O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N ;
	InChI InChI=1S/C43H65N11O12S2/c1-5-23(4)36-42(65)49-26(12-13-32(44)56)38(61)50-29(19-33(45)57)39(62)52-30(21-68-67-16-14-35(59)48-28(40(63)53-36)18-24-8-10-25(55)11-9-24)43(66)54-15-6-7-31(54)41(64)51-27(17-22(2)3)37(60)47-20-34(46)58/h8-11,22-23,26-31,36,55H,5-7,12-21H2,1-4H3,(H2,44,56)(H2,45,57)(H2,46,58)(H,47,60)(H,48,59)(H,49,65)(H,50,61)(H,51,64)(H,52,62)(H,53,63)/t23-,26-,27-,28-,29-,30-,31-,36-/m0/s1 ; Key:GTYWGUNQAMYZPF-QPLNMOKZSA-N ;

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英: deaminooxytocin
関: デモキシトシン

「demoxytocin」

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デモキシトシン

関: deaminooxytocin

[1] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 301–. ISBN 978-3-88763-075-1.

[Elks2014-2] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 349–. ISBN 978-1-4757-2085-3.

[MortonHall2012-3] I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 93–. ISBN 978-94-011-4439-1.

[Bladon2002-4] Christine Bladon (3 April 2002). Pharmaceutical Chemistry: Therapeutic Aspects of Biomacromolecules. John Wiley & Sons. pp. 61–. ISBN 978-0-471-49637-3.

[BoxtelSantoso2008-5] C.J. van Boxtel; B. Santoso; I.R. Edwards (6 August 2008). Drug Benefits and Risks: International Textbook of Clinical Pharmacology - Revised 2nd Edition. IOS Press. pp. 389–. ISBN 978-1-60750-345-3.

[EskesFinster2013-6] Tom K. A. B. Eskes; Mieczyslaw Finster (22 October 2013). Drug Therapy During Pregnancy. Elsevier. pp. 185–. ISBN 978-1-4831-6298-0.

[pmid468056-7] Sternadel Z, Gerkowicz J (1979). "[Use of deaminooxytocin (Sandopart) in the prevention and treatment of puerperal mastitis]". Ginekol. Pol. (in Polish) 50 (5): 413–6. PMID 468056.

[GrossMeienhofer2014-8] Erhard Gross; Johannes Meienhofer (10 May 2014). Major Methods of Peptide Bond Formation: The Peptides Analysis, Synthesis, Biology. Elsevier. pp. 53–. ISBN 978-1-4832-1796-3.

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案内

deaminooxytocin