Larazotide

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Larazotide
Accession Number
DB05645
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
AT-2347
Product Ingredients
IngredientUNIICASInChI Key
Larazotide acetateFO8S2IW40N881851-50-9NYGCNONRVCGHAT-UFIKZEAMSA-N
Categories
UNII
ZN3R5560ZV
CAS number
258818-34-7
Weight
Average: 725.845
Monoisotopic: 725.407189007
Chemical Formula
C32H55N9O10
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

Pharmacology

Indication

Investigated for use/treatment in autoimmune diseases, diabetes mellitus type 1, and gastrointestinal diseases and disorders (miscellaneous).

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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
7986288
ChEMBL
CHEMBL2105646
Wikipedia
Larazotide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceHealthy Volunteers1
1CompletedTreatmentGluten Enteropathy1
2CompletedTreatmentGluten Enteropathy5
3RecruitingTreatmentGluten Enteropathy1

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
PropertyValueSource
Water Solubility0.218 mg/mLALOGPS
logP-2ALOGPS
logP-6.2ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)7.84ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area301.32 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity180.06 m3·mol-1ChemAxon
Polarizability75.32 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Classification
Not classified

Drug created on November 18, 2007 11:26 / Updated on August 02, 2019 07:46