Amastatin

{{Short description|Chemical compound}}

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| IUPAC_name = (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-3-Amino-2-hydroxy-5-methylhexanoyl]amino]-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]butanedioic acid

| image = Amastatin.svg

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| CAS_number = 67655-94-1

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| ATC_prefix = None

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| PubChem = 439518

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| ChemSpiderID = 388612

| KEGG = C01552

| C=21 | H=38 | N=4 | O=8

| smiles = CC(C)CC(C(C(=O)NC(C(C)C)C(=O)NC(C(C)C)C(=O)NC(CC(=O)O)C(=O)O)O)N

| StdInChI = 1S/C21H38N4O8/c1-9(2)7-12(22)17(28)20(31)25-16(11(5)6)19(30)24-15(10(3)4)18(29)23-13(21(32)33)8-14(26)27/h9-13,15-17,28H,7-8,22H2,1-6H3,(H,23,29)(H,24,30)(H,25,31)(H,26,27)(H,32,33)/t12-,13+,15+,16+,17+/m1/s1

| StdInChIKey = QFAADIRHLBXJJS-ZAZJUGBXSA-N

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Amastatin, also known as 3-amino-2-hydroxy-5-methylhexanoyl-L-valyl-L-valyl-L-aspartic acid, is a naturally occurring, competitive and reversible aminopeptidase inhibitor that was isolated from Streptomyces sp. ME 98-M3.{{cite book| vauthors = Buckingham J | chapter = Amastatins |title=Dictionary of Natural Products| chapter-url = https://books.google.com/books?id=1W0NUD42fA4C&pg=PA197|date=2 December 1993|publisher=CRC Press|isbn=978-0-412-46620-5|pages=197–}} It specifically inhibits leucyl aminopeptidase, alanyl aminopeptidase (aminopeptidase M/N), bacterial leucyl aminopeptidase (Aeromonas proteolytica aminopeptidase), leucyl/cystinyl aminopeptidase (oxytocinase/vasopressinase),{{cite journal | vauthors = Nakanishi Y, Nomura S, Okada M, Ito T, Katsumata Y, Kikkawa F, Hattori A, Tsujimoto M, Mizutani S | display-authors = 6 | title = Immunoaffinity purification and characterization of native placental leucine aminopeptidase/oxytocinase from human placenta | journal = Placenta | volume = 21 | issue = 7 | pages = 628–634 | date = September 2000 | pmid = 10985965 | doi = 10.1053/plac.2000.0564 }} and, to a lesser extent, glutamyl aminopeptidase (aminopeptidase A),{{cite book| vauthors = Schloss JV | chapter = Modern Aspects of Enzyme Inhibition with Particular Emphasis on Reaction-Intermediate Analogs and Other Potent, Reversible Inhibitors | veditors = Boger P, Sandmann G |title=Target Sites of Herbicide Action| chapter-url = https://books.google.com/books?id=eRGpF10Yj10C&pg=PA203 |date=31 July 1989|publisher=CRC Press|isbn=978-0-8493-4985-0|pages=203–}} as well as other aminopeptidases.{{cite book| vauthors = Scott T, Mercer EI |title=Concise Encyclopedia Biochemistry and Molecular Biology |url=https://archive.org/details/conciseencyclope00scot_0|url-access=registration |year=1997 |publisher=Walter de Gruyter|isbn=978-3-11-014535-9|pages=[https://archive.org/details/conciseencyclope00scot_0/page/35 35]–}} It does not inhibit arginyl aminopeptidase (aminopeptidase B).{{cite book| vauthors = Umezawa H |title=Small Molecular Immunomodifiers of Microbial Origin: Fundamental and Clinical Studies of Bestatin |url= https://books.google.com/books?id=p4XiBQAAQBAJ&pg=PA10|date=9 May 2014|publisher=Elsevier Science|isbn=978-1-4831-9033-4|pages=10–}}{{cite book | vauthors = Drey CN | chapter = Beta and Higher Homologous Amino Acids| veditors = Barrett G |title=Chemistry and Biochemistry of the Amino Acids | chapter-url= https://books.google.com/books?id=gjLsCAAAQBAJ&pg=PA28 |date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-009-4832-7|pages=28– | doi = 10.1007/978-94-009-4832-7_3 }} Amastatin has been found to potentiate the central nervous system effects of oxytocin and vasopressin in vivo.{{cite journal | vauthors = Meisenberg G, Simmons WH | title = Amastatin potentiates the behavioral effects of vasopressin and oxytocin in mice | journal = Peptides | volume = 5 | issue = 3 | pages = 535–539 | year = 1984 | pmid = 6540873 | doi = 10.1016/0196-9781(84)90083-4 | s2cid = 3881661 }} It also inhibits the degradation of met-enkephalin, dynorphin A, and other endogenous peptides.{{cite journal | vauthors = Oka T, Hiranuma T, Liu XF, Ohgiya N, Iwao K, Matsumiya T | title = [Enkephalin-inactivating enzymes] | language = ja | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 101 | issue = 4 | pages = 197–207 | date = April 1993 | pmid = 8390390 | doi = 10.1254/fpj.101.4_197 | doi-access = free }}

It contains the unusual amino acid Statine.