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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H25BrN4O3
Molecular Weight 521.406
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZAURATEGRAST

SMILES

OC(=O)[C@H](CC1=CC=C(NC2=C3C=NC=CC3=CC=N2)C=C1)NC4=C(Br)C(=O)C45CCCCC5

InChI

InChIKey=KYHVWHYLKOHLKA-FQEVSTJZSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.ingentaconnect.com/content/ben/cir/2012/00000008/00000002/art00004?crawler=true | https://www.ncbi.nlm.nih.gov/pubmed/24179032

Zaurategrast (CDP323) is an ethyl ester prodrug of CT7758, a potent carboxylic acid antagonist of integrin alpha4-beta1 (α4β1) or very late antigen 4 (VLA4). CDP323 was under development with UCB and Biogen Idec for the treatment of multiple sclerosis. Its development was discontinued in 2009 based on inadequate interim efficacy data in a phase II clinical trial.

Approval Year

AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.5 μg × h/mL
500 mg/kg single, oral
dose: 500 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
ZAURATEGRAST plasma
Mus musculus
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1000 mg 2 times / day multiple, oral
Highest studied dose
Dose: 1000 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1000 mg, 2 times / day
Sources: Page: p.7, 8
unhealthy, ADULT
n = 14
Health Status: unhealthy
Condition: multiple sclerosis
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 14
Sources: Page: p.7, 8
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

PubMed

PubMed

TitleDatePubMed
Pharmacodynamic consequences of administration of VLA-4 antagonist CDP323 to multiple sclerosis subjects: a randomized, double-blind phase 1/2 study.
2013
In vitro hydrolysis and transesterification of CDP323, an α4β1/α4β7 integrin antagonist ester prodrug.
2014 Jan
Patents

Patents

Sample Use Guides

Multiple sclerosis subjects were randomized to 28-day treatment with Zaurategrast (CDP323) 100 mg twice daily (bid), 500 mg bid, 1000 mg once daily (qd), 1000 mg bid, or placebo. CDP323 at daily doses of 1000 or 2000 mg induced significant increases in total lymphocyte count and suppressed VCAM-1 binding by reducing unbound very late antigen-4 expression on lymphocytes.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
ZAURATEGRAST
INN   WHO-DD  
INN  
Official Name English
N-(2-BROMO-3-OXOSPIRO(3.5)NON-1-EN-1-YL)-4-(2,7-NAPHTHYRIDIN-1-YLAMINO)-L-PHENYLALANINE
Common Name English
CT-7758
Code English
CT7758
Code English
(2S)-2-((2-BROMO-3-OXOSPIRO(3.5)NON-1-EN-1-YL)AMINO)-3-(4-((2,7-NAPHTHYRIDIN-1-YL)AMINO)PHENYL)PROPANOIC ACID
Systematic Name English
Zaurategrast [WHO-DD]
Common Name English
zaurategrast [INN]
Common Name English
L-PHENYLALANINE, N-(2-BROMO-3-OXOSPIRO(3.5)NON-1-EN-1-YL)-4-(2,7-NAPHTHYRIDIN-1-YLAMINO)-
Common Name English
(S)-3-(4-((2,7-NAPHTHYRIDIN-1-YL)AMINO)PHENYL)-2-((2-BROMO-3-OXOSPIRO(3.5)NON-1-EN-1-YL)AMINO)PROPANOIC ACID
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29712
Created by admin on Sat Dec 16 17:33:37 GMT 2023 , Edited by admin on Sat Dec 16 17:33:37 GMT 2023
Code System Code Type Description
INN
9166
Created by admin on Sat Dec 16 17:33:37 GMT 2023 , Edited by admin on Sat Dec 16 17:33:37 GMT 2023
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EPA CompTox
DTXSID90196547
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SMS_ID
100000181230
Created by admin on Sat Dec 16 17:33:37 GMT 2023 , Edited by admin on Sat Dec 16 17:33:37 GMT 2023
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CAS
455264-31-0
Created by admin on Sat Dec 16 17:33:37 GMT 2023 , Edited by admin on Sat Dec 16 17:33:37 GMT 2023
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WIKIPEDIA
Zaurategrast
Created by admin on Sat Dec 16 17:33:37 GMT 2023 , Edited by admin on Sat Dec 16 17:33:37 GMT 2023
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NCI_THESAURUS
C90673
Created by admin on Sat Dec 16 17:33:37 GMT 2023 , Edited by admin on Sat Dec 16 17:33:37 GMT 2023
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PUBCHEM
10186367
Created by admin on Sat Dec 16 17:33:37 GMT 2023 , Edited by admin on Sat Dec 16 17:33:37 GMT 2023
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FDA UNII
06A0IC74I3
Created by admin on Sat Dec 16 17:33:37 GMT 2023 , Edited by admin on Sat Dec 16 17:33:37 GMT 2023
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