Larazotide
Identification
- Generic Name
- Larazotide
- DrugBank Accession Number
- DB05645
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 725.845
Monoisotopic: 725.407189007 - Chemical Formula
- C32H55N9O10
- Synonyms
- Larazotide
- External IDs
- AT-2347
Pharmacology
- Indication
Investigated for use/treatment in autoimmune diseases, diabetes mellitus type 1, and gastrointestinal diseases and disorders (miscellaneous).
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- Pharmacodynamics
Not Available
- Mechanism of action
AT-1001 is an orally administered octapeptide zonulin receptor antagonist that appears to exert its inhibitory effect on gliadin-induced tight junction disassembly by blocking putative zonulin receptors on the luminal surface of the small intestine.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Larazotide acetate FO8S2IW40N 881851-50-9 NYGCNONRVCGHAT-UFIKZEAMSA-N
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- ZN3R5560ZV
- CAS number
- 258818-34-7
- InChI Key
- ORFLZNAGUTZRLQ-ZMBVWFSWSA-N
- 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
- IUPAC Name
- 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
- SMILES
- CC(C)C[C@H](NC(=O)[C@@H](NC(=O)CNC(=O)CN)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N1CCC[C@H]1C(=O)NCC(O)=O
References
- General References
- Not Available
- External Links
- ChemSpider
- 7986288
- ChEMBL
- CHEMBL2105646
- ZINC
- ZINC000068009799
- Wikipedia
- Larazotide
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Terminated Treatment Celiac Disease 1 2 Completed Treatment Celiac Disease 5 2 Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) / Multisystem Inflammatory Syndrome in Children 1 2 Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) / Post Acute Sequelae of COVID-19 / Post-acute COVID-19 (PACS), or "Long COVID" Syndrome 1 1 Completed Basic Science Healthy Volunteers (HV) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.218 mg/mL ALOGPS logP -2 ALOGPS logP -6.2 Chemaxon logS -3.5 ALOGPS pKa (Strongest Acidic) 3.43 Chemaxon pKa (Strongest Basic) 7.84 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 301.32 Å2 Chemaxon Rotatable Bond Count 21 Chemaxon Refractivity 180.06 m3·mol-1 Chemaxon Polarizability 75.32 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 282.0154672 predictedDarkChem Lite v0.1.0 [M+H]+ 275.2910672 predictedDarkChem Lite v0.1.0 [M+Na]+ 275.7250672 predictedDarkChem Lite v0.1.0
Drug created at November 18, 2007 18:26 / Updated at February 21, 2021 18:51