CPG-52364

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H36N6O3
Molecular Weight	492.6131
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

COC1=C(OC)C=C2C(NCCN3CCOCC3)=NC(=NC2=C1)C4=CC=C(C=C4)N5CCN(C)CC5

InChI

InChIKey=TUOZJWZCVIRDKO-UHFFFAOYSA-N

InChI=1S/C27H36N6O3/c1-31-10-12-33(13-11-31)21-6-4-20(5-7-21)26-29-23-19-25(35-3)24(34-2)18-22(23)27(30-26)28-8-9-32-14-16-36-17-15-32/h4-7,18-19H,8-17H2,1-3H3,(H,28,29,30)

HIDE SMILES / InChI

Molecular Formula	C27H36N6O3
Molecular Weight	492.6131
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

CPG-52364 is a potent antagonist of toll-like receptors TLR7, TLR8, TLR9. The drug was developed by Coley Pharmaceutical Group (later acquired by Pfizer) for the treatment of immune diseases and reached phase I of clinical trials presumably for systemic lupus erythematosus. However, the development of CPG-52364 was terminated by unknown reason.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Toll-like receptor 7 12	Antagonist 2,778	13.0 nM [IC50]
Toll-like receptor 9 4	Antagonist 2,778	18.0 nM [IC50]
Toll-like receptor 8 3	Antagonist 2,778	35.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Systemic lupus erythematosus 16	Primary		Phase I 428	Unknown

PubMed

Title	Date	PubMed
Toll-like receptors as therapeutic targets for autoimmune connective tissue diseases.	2013 Jun	23531543

Patents

Sample Use Guides

In Vivo Use Guide

Patienrs received 1, 3, 10, 30 or 100 mg of CPG-52364 orally as a single dose.

Route of Administration: Oral

In Vitro Use Guide

It has been shown that CPG-52364, at concentrations of less than 10 nM, effectively antagonizes TLR signaling in vitro in human cells that have been transfected with TLR9 or TLR8 expression vectors.

Substance Class	Chemical
Record UNII	5TVM84YK6F
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

CPG-52364

Common Name

English

6,7-DIMETHOXY-2-(4-(4-METHYLPIPERAZIN-1-YL)PHENYL)-N-(2-MORPHOLINOETHYL)QUINAZOLIN-4-AMINE

Systematic Name

English

4-QUINAZOLINAMINE, 6,7-DIMETHOXY-2-(4-(4-METHYL-1-PIPERAZINYL)PHENYL)-N-(2-(4-MORPHOLINYL)ETHYL)-

Systematic Name

English

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Code System

Code

Type

Description

FDA UNII

5TVM84YK6F

PRIMARY

MANUFACTURER PRODUCT INFORMATION

CPG-52364

PRIMARY

Description: CPG-52364 a small molecule TLR7/8/9 antagonist, has recently completed phase 1 clinical trial for SLE therapy. Toll-like receptors (TLRs) are a family of type I transmembrane receptors and the central components of the innate immune system. Human TLR3, TLR7, TLR8, and TLR9 are expressed on endosomal membranes in the cells and recognize pathogenderived nucleic acid molecular patterns.5 However, recognition of endogenous immune complexes containing self-nucleic acids as PAMPs or DAMPs contributes to certain autoimmune diseases, such as systemic lupus erythematosus (SLE), psoriasis,7 arthritis, and multiple sclerosis.8 Therefore, inhibition of these recognition signals is expected to have therapeutic value. (last updated: 11/11/2015).

PUBCHEM

25105690

PRIMARY

CAS

1093135-60-4

PRIMARY

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Related Record

Type

Details


					7GAF379J5J

TOLL-LIKE RECEPTOR 9

TARGET -> INHIBITOR

1873203CCC

TOLL-LIKE RECEPTOR 7

TARGET -> INHIBITOR


					3PDA6T8Q7J

TOLL-LIKE RECEPTOR 8

TARGET -> INHIBITOR

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Related Record

Type

Details


					5TVM84YK6F

CPG-52364

ACTIVE MOIETY

Comments:

Originator: Coley Pharmaceutical Group; Class: Small molecule; Mechanism of Action: Toll-like receptor 7 antagonist, Toll-like receptor 8 antagonist, Toll-like receptor 9 antagonist; Highest Development Phase: Discontinued for Systemic lupus erythematosus; Most Recent Events: 27 Jan 2010 Discontinued - Phase-I for Systemic lupus erythematosus in USA (PO), 27 Jan 2010 Discontinued - Phase-I for Systemic lupus erythematosus in USA (PO), 29 Oct 2007 Phase-I clinical trials in Systemic lupus erythematosus in USA (PO)

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