zaurategrast   Click here for help

GtoPdb Ligand ID: 11488

Synonyms: CDP-323 | CDP323
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Zaurategrast (CDP-323) is a small molecule inhibitor of α4-containing integrin complexes that was developed by Celltech [3]. It was intended as a new oral drug treatment for multiple sclerosis [2]. Zaurategrast has the same mechanism of action as the approved MS therapeutic natalizumab. Zaurategrast is an ester prodrug whose active entity is CT7758 [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 104.21
Molecular weight 520.11
XLogP 2.64
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC(=O)[C@@H](NC1=C(Br)C(=O)C21CCCCC2)Cc1ccc(cc1)Nc1nccc2c1cncc2
Isomeric SMILES OC(=O)[C@@H](NC1=C(Br)C(=O)C21CCCCC2)Cc1ccc(cc1)Nc1nccc2c1cncc2
InChI InChI=1S/C26H25BrN4O3/c27-21-22(26(23(21)32)10-2-1-3-11-26)31-20(25(33)34)14-16-4-6-18(7-5-16)30-24-19-15-28-12-8-17(19)9-13-29-24/h4-9,12-13,15,20,31H,1-3,10-11,14H2,(H,29,30)(H,33,34)/t20-/m0/s1
InChI Key KYHVWHYLKOHLKA-FQEVSTJZSA-N
References
1. Chanteux H, Staelens L, Mancel V, Gerin B, Boucaut D, Prakash C, Nicolas JM. (2015)
Cross-Species Differences in the Preclinical Pharmacokinetics of CT7758, an α4β1/α4β7 Integrin Antagonist.
Drug Metab Dispos, 43 (9): 1381-91. [PMID:26153275]
2. Davenport RJ, Munday JR. (2007)
Alpha4-integrin antagonism--an effective approach for the treatment of inflammatory diseases?.
Drug Discov Today, 12 (13-14): 569-76. [PMID:17631252]
3. Li H, Huang SY, Shi FH, Gu ZC, Zhang SG, Wei JF. (2018)
α4β7 integrin inhibitors: a patent review.
Expert Opin Ther Pat, 28 (12): 903-917. [PMID:30444683]
4. Wolf C, Sidhu J, Otoul C, Morris DL, Cnops J, Taubel J, Bennett B. (2013)
Pharmacodynamic consequences of administration of VLA-4 antagonist CDP323 to multiple sclerosis subjects: a randomized, double-blind phase 1/2 study.
PLoS One, 8 (3): e58438. [PMID:23472197]