Larazotide

Larazotide is an octapeptide inhibitor of paracellular permeability whose structure is derived from a protein (zonula occludens toxin) secreted by Vibrio cholerae for treatment of Coeliac disease.

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CAT No: R1967

CAS No: 258818-34-7

Synonyms/Alias: Larazotide;258818-34-7;Larazotida;Larazotide [USAN:INN];AT 2347;AT-2347;ZN3R5560ZV;2-[[(2S)-1-[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]acetic acid;DTXSID30180526;258818-34-7 (free base);glycylglycyl-L-valyl-L-leucyl-L-valyl-L-glutaminyl-L-prolylglycine;larazotidum;UNII-ZN3R5560ZV;larazotide-acetate;2-(((2S)-1-((2S)-2-((2S)-2-((2S)-2-((2S)-2-(2-(2-aminoacetamido)acetamido)-3-methylbutanamido)-4-methylpentanamido)-3-methylbutanamido)-4-carbamoylbutanoyl)pyrrolidin-2-yl)formamido)acetic acid;2-{[(2S)-1-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[2-(2-aminoacetamido)acetamido]-3-methylbutanamido]-4-methylpentanamido]-3-methylbutanamido]-4-carbamoylbutanoyl]pyrrolidin-2-yl]formamido}acetic acid;Larazotide [INN];Larazotide (USAN/INN);LARAZOTIDE [USAN];LARAZOTIDE [WHO-DD];CHEMBL2105646;SCHEMBL23668120;DTXCID70103017;CHEBI:177799;ORFLZNAGUTZRLQ-ZMBVWFSWSA-N;AKOS040741937;DB05645;H-Gly-Gly-Val-Leu-Val-Gln-Pro-Gly-OH;DA-54793;HY-106268;CS-0025478;NS00072884;D09351;Q27295752;Glycine, glycylglycyl-L-valyl-L-leucyl-L-valyl-L-glutaminyl-L-prolyl-;2-((S)-1-((2S,5S,8S,11S)-17-Amino-2-(3-amino-3-oxopropyl)-8-isobutyl-5,11-diisopropyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazaheptadecan-1-oyl)pyrrolidine-2-carboxamido)acetic acid;

Chemical Name: 2-[[(2S)-1-[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]acetic acid

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Specification Technical Data Publications Customer reviews and Q&A

M.F/Formula	C32H55N9O10
M.W/Mr.	725.8
Sequence	One Letter Code:GGVLVQPG Three Letter Code:H-Gly-Gly-Val-Leu-Val-Gln-Pro-Gly-OH
Appearance	Solid powder
Biological Activity	Larazotide is an octapeptide inhibitor of paracellular permeability whose structure is derived from a protein (zonula occludens toxin) secreted by Vibrio cholerae for treatment of Coeliac disease.

InChI	InChI=1S/C32H55N9O10/c1-16(2)12-20(38-30(49)26(17(3)4)39-24(44)14-35-23(43)13-33)28(47)40-27(18(5)6)31(50)37-19(9-10-22(34)42)32(51)41-11-7-8-21(41)29(48)36-15-25(45)46/h16-21,26-27H,7-15,33H2,1-6H3,(H2,34,42)(H,35,43)(H,36,48)(H,37,50)(H,38,49)(H,39,44)(H,40,47)(H,45,46)/t19-,20-,21-,26-,27-/m0/s1
InChI Key	ORFLZNAGUTZRLQ-ZMBVWFSWSA-N
Canonical SMILES	CC(C)CC(C(=O)NC(C(C)C)C(=O)NC(CCC(=O)N)C(=O)N1CCCC1C(=O)NCC(=O)O)NC(=O)C(C(C)C)NC(=O)CNC(=O)CN
Isomeric SMILES	CC(C)C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)CN

1. C-peptide and its C-terminal fragments improve erythrocyte deformability in type 1 diabetes patients

2. Glucagonlike peptide 2 analogue teduglutide: stimulation of proliferation but reduction of differentiation in human Caco-2 intestinal epithelial cells

3. Implications of ligand-receptor binding kinetics on GLP-1R signalling

4. Extended exenatide administration enhances lipid metabolism and exacerbates pancreatic injury in mice on a high fat, high carbohydrate diet

5. Cationic cell-penetrating peptides are potent furin inhibitors

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Larazotide

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