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MedKoo Cat#: 561466 | Name: Larazotide Acetate
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

AT-1001, also known as Larazotide Acetate, is a tight junction regulator and reverses leaky junctions to their normally closed state. It is being studied in people with celiac disease.

Chemical Structure

Larazotide Acetate
Larazotide Acetate
CAS#881851-50-9 (acetate)

Theoretical Analysis

MedKoo Cat#: 561466

Name: Larazotide Acetate

CAS#: 881851-50-9 (acetate)

Chemical Formula: C34H59N9O12

Exact Mass: 785.4283

Molecular Weight: 785.90

Elemental Analysis: C, 51.96; H, 7.57; N, 16.04; O, 24.43

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 2 Weeks
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Related CAS #
258818-34-7 (free base) 881851-50-9 (acetate)
Synonym
Larazotide Acetate; AT-1001; AT 1001; AT1001;
IUPAC/Chemical Name
Glycine, glycylglycyl-L-valyl-L-leucyl-L-valyl-L-glutaminyl-L-prolyl-, monoacetate
InChi Key
NYGCNONRVCGHAT-UFIKZEAMSA-N
InChi Code
InChI=1S/C32H55N9O10.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t19-,20-,21-,26-,27-;/m0./s1
SMILES Code
O=C(O)CNC([C@H]1N(C([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC(CNC(CN)=O)=O)C(C)C)=O)CC(C)C)=O)C(C)C)=O)CCC(N)=O)=O)CCC1)=O.CC(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Larazotide acetate acts as a tight junction regulator and reverses leaky junctions to their normally closed state.
In vitro activity:
In this study, larazotide acetate inhibited the redistribution and rearrangement of zonula occludens-1 (ZO-1) and actin caused by AT-1002 and gliadin fragments in Caco-2 and IEC6 cells. Functionally, larazotide acetate inhibited the AT-1002-induced TEER reduction and TJ opening in Caco-2 cells. Additionally, larazotide acetate inhibited the translocation of a gliadin 13-mer peptide, which has been implicated in celiac disease, across Caco-2 cell monolayers. Reference: Peptides. 2012 May;35(1):86-94. https://pubmed.ncbi.nlm.nih.gov/22401908/
In vivo activity:
The α3β4 nAChR partial agonist AT-1001 selectively decreases nicotine self-administration in rats without affecting food responding. In the present experiments, this study examined the efficacy of AT-1001 in attenuating reinstatement of nicotine-seeking behavior in a model of stress-induced relapse. AT-1001 dose-dependently reduced yohimbine stress-induced reinstatement of nicotine seeking. Reference: Behav Brain Res. 2017 Aug 30;333:251-257. https://pubmed.ncbi.nlm.nih.gov/28693859/
Solvent mg/mL mM
Solubility
DMSO 3.2 4.07
Water 16.7 21.21
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 785.90 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Tuan EW, Horti AG, Olson TT, Gao Y, Stockmeier CA, Al-Muhtasib N, Bowman Dalley C, Lewin AE, Wolfe BB, Sahibzada N, Xiao Y, Kellar KJ. AT-1001 Is a Partial Agonist with High Affinity and Selectivity at Human and Rat α3β4 Nicotinic Cholinergic Receptors. Mol Pharmacol. 2015 Oct;88(4):640-9. doi: 10.1124/mol.115.099978. Epub 2015 Jul 10. PMID: 26162864; PMCID: PMC4576681. 2. Gopalakrishnan S, Durai M, Kitchens K, Tamiz AP, Somerville R, Ginski M, Paterson BM, Murray JA, Verdu EF, Alkan SS, Pandey NB. Larazotide acetate regulates epithelial tight junctions in vitro and in vivo. Peptides. 2012 May;35(1):86-94. doi: 10.1016/j.peptides.2012.02.015. Epub 2012 Feb 27. PMID: 22401908. 3. Yuan M, Malagon AM, Yasuda D, Belluzzi JD, Leslie FM, Zaveri NT. The α3β4 nAChR partial agonist AT-1001 attenuates stress-induced reinstatement of nicotine seeking in a rat model of relapse and induces minimal withdrawal in dependent rats. Behav Brain Res. 2017 Aug 30;333:251-257. doi: 10.1016/j.bbr.2017.07.004. Epub 2017 Jul 8. PMID: 28693859; PMCID: PMC5557392. 4. Cippitelli A, Wu J, Gaiolini KA, Mercatelli D, Schoch J, Gorman M, Ramirez A, Ciccocioppo R, Khroyan TV, Yasuda D, Zaveri NT, Pascual C, Xie XS, Toll L. AT-1001: a high-affinity α3β4 nAChR ligand with novel nicotine-suppressive pharmacology. Br J Pharmacol. 2015 Apr;172(7):1834-45. doi: 10.1111/bph.13034. Epub 2015 Jan 23. PMID: 25440006; PMCID: PMC4376460.
In vitro protocol:
1. Tuan EW, Horti AG, Olson TT, Gao Y, Stockmeier CA, Al-Muhtasib N, Bowman Dalley C, Lewin AE, Wolfe BB, Sahibzada N, Xiao Y, Kellar KJ. AT-1001 Is a Partial Agonist with High Affinity and Selectivity at Human and Rat α3β4 Nicotinic Cholinergic Receptors. Mol Pharmacol. 2015 Oct;88(4):640-9. doi: 10.1124/mol.115.099978. Epub 2015 Jul 10. PMID: 26162864; PMCID: PMC4576681. 2. Gopalakrishnan S, Durai M, Kitchens K, Tamiz AP, Somerville R, Ginski M, Paterson BM, Murray JA, Verdu EF, Alkan SS, Pandey NB. Larazotide acetate regulates epithelial tight junctions in vitro and in vivo. Peptides. 2012 May;35(1):86-94. doi: 10.1016/j.peptides.2012.02.015. Epub 2012 Feb 27. PMID: 22401908.
In vivo protocol:
1. Yuan M, Malagon AM, Yasuda D, Belluzzi JD, Leslie FM, Zaveri NT. The α3β4 nAChR partial agonist AT-1001 attenuates stress-induced reinstatement of nicotine seeking in a rat model of relapse and induces minimal withdrawal in dependent rats. Behav Brain Res. 2017 Aug 30;333:251-257. doi: 10.1016/j.bbr.2017.07.004. Epub 2017 Jul 8. PMID: 28693859; PMCID: PMC5557392. 2. Cippitelli A, Wu J, Gaiolini KA, Mercatelli D, Schoch J, Gorman M, Ramirez A, Ciccocioppo R, Khroyan TV, Yasuda D, Zaveri NT, Pascual C, Xie XS, Toll L. AT-1001: a high-affinity α3β4 nAChR ligand with novel nicotine-suppressive pharmacology. Br J Pharmacol. 2015 Apr;172(7):1834-45. doi: 10.1111/bph.13034. Epub 2015 Jan 23. PMID: 25440006; PMCID: PMC4376460.
1: Khaleghi S, Ju JM, Lamba A, Murray JA. The potential utility of tight junction regulation in celiac disease: focus on larazotide acetate. Therap Adv Gastroenterol. 2016 Jan;9(1):37-49. doi: 10.1177/1756283X15616576. Review. PubMed PMID: 26770266; PubMed Central PMCID: PMC4699279. 2: Szaflarska-Popławska A. Non-dietary methods in the treatment of celiac disease. Prz Gastroenterol. 2015;10(1):12-7. doi: 10.5114/pg.2014.47503. Epub 2015 Jan 14. Review. PubMed PMID: 25960809; PubMed Central PMCID: PMC4411409. 3: Veeraraghavan G, Leffler DA, Kaswala DH, Mukherjee R. Celiac disease 2015 update: new therapies. Expert Rev Gastroenterol Hepatol. 2015 Jul;9(7):913-27. doi: 10.1586/17474124.2015.1033399. Epub 2015 Apr 12. Review. PubMed PMID: 25864708. 4: Zofková I. [Celiac disease and its relation to bone metabolism]. Cas Lek Cesk. 2009;148(6):246-8. Review. Czech. PubMed PMID: 19642305. 5: Baldassarre M, Laneve AM, Grosso R, Laforgia N. Celiac disease: pathogenesis and novel therapeutic strategies. Endocr Metab Immune Disord Drug Targets. 2008 Sep;8(3):152-8. Review. PubMed PMID: 18782011.