TAK-779

Details

Stereochemistry	ACHIRAL
Molecular Formula	C33H39N2O2.Cl
Molecular Weight	531.128
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].CC1=CC=C(C=C1)C2=CC=C3CCCC(=CC3=C2)C(=O)NC4=CC=C(C[N+](C)(C)C5CCOCC5)C=C4

InChI

InChIKey=VDALIBWXVQVFGZ-UHFFFAOYSA-N

InChI=1S/C33H38N2O2.ClH/c1-24-7-11-27(12-8-24)28-14-13-26-5-4-6-29(22-30(26)21-28)33(36)34-31-15-9-25(10-16-31)23-35(2,3)32-17-19-37-20-18-32;/h7-16,21-22,32H,4-6,17-20,23H2,1-3H3;1H

HIDE SMILES / InChI

Molecular Formula	C33H39N2O2
Molecular Weight	495.675
Charge	1
Count

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12142563 | https://www.ncbi.nlm.nih.gov/pubmed/11575704

TAK-779 is a selective antagonist of CCR5 receptor, which was initially developed by Takeda for the treatment of HIV infection. However, the development was terminated due to poor oral bioavailability. Also, TAK-779 demonstrated the ability to protect the brain against focal cerebral ischemia in mice.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
C-C chemokine receptor type 5 19 Target ID: P51681\|\|\|O14700\|\|\|O14708 Gene ID: 1234.0 Gene Symbol: CCR5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/10318947	Antagonist 2778	1.1 nM [Ki]
C-C chemokine receptor type 5 19 Target ID: CHEMBL274 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10318947	Inhibitor 8297	1.4 nM [IC50]
C-C chemokine receptor type 2 17 Target ID: CHEMBL4015 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10318947	Inhibitor 8297	27.0 nM [IC50]
Human immunodeficiency virus 1 33 Target ID: CHEMBL378 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10318947	Inhibitor 8297	1.2 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV infection 21 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11575704	Primary		Preclinical	Unknown Approved Use Unknown
Focal cerebral ischemia 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12142563	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A small-molecule, nonpeptide CCR5 antagonist with highly potent and selective anti-HIV-1 activity.	1999 May 11	10318947
TAK-779 (Takeda).	2001 Mar	11575704
TAK-779, a nonpeptide CC chemokine receptor antagonist, protects the brain against focal cerebral ischemia in mice.	2002 Jul	12142563
Effects of a calcineurin inhibitor, FK506, and a CCR5/CXCR3 antagonist, TAK-779, in a rat small intestinal transplantation model.	2011 Jul	21515370
Diverse modifications of the 4-methylphenyl moiety of TAK-779 by late-stage Suzuki-Miyaura cross-coupling.	2014 Jan 7	24217712
CXCR3 antagonist VUF10085 binds to an intrahelical site distinct from that of the broad spectrum antagonist TAK-779.	2015 Apr	25425280

Sample Use Guides

In Vivo Use Guide

In a mouse model of ischemic brain injury, TAK-779 (25 or 250 ng in 5 uL) was administered by intracerebroventricular injection (1.0 mm lateral, 0.5 mm posterior, 3.0 mm ventral to bregma) at 10 minutes before MCA occlusion, or by intravenous injection (5 ug/100 uL per 20 g body weight).

Route of Administration: Other

In Vitro Use Guide

The effect of TAK-779 on virus replication in PBMC was assayed after incubation of cells for 30 min with a range of concentrations of the inhibitor (0.01 to 100 uM) prior to infection with the UK1-br and MACS2-br primary isolates. IC50 values were 70 and 4 uM, respectively.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:07:02 GMT 2023` Edited by `admin` on `Fri Dec 15 16:07:02 GMT 2023`
Record UNII	BQW1Y9KIIP
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TAK-779

Code

English

TAK-799

Code

English

N,N-DIMETHYL-N-(4-(((2-(4-METHYLPHENYL)-6,7-DIHYDRO-5H-BENZOCYCLOHEPTEN-8-YL)CARBONYL)AMINO)BENZYL)TETRAHYDRO-2H-PYRAN-4-AMINIUM CHLORIDE

Systematic Name

English

Code System Code Type Description

CAS

229005-80-5

Created by admin on Fri Dec 15 16:07:02 GMT 2023 , Edited by admin on Fri Dec 15 16:07:02 GMT 2023

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FDA UNII

BQW1Y9KIIP

Created by admin on Fri Dec 15 16:07:02 GMT 2023 , Edited by admin on Fri Dec 15 16:07:02 GMT 2023

PRIMARY

PUBCHEM

183789

Created by admin on Fri Dec 15 16:07:02 GMT 2023 , Edited by admin on Fri Dec 15 16:07:02 GMT 2023

PRIMARY

Related Record Type Details


					RN3X97C29H

TAK-779 CATION

PARENT -> SALT/SOLVATE

Related Record Type Details


					RN3X97C29H

TAK-779 CATION

ACTIVE MOIETY

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12142563 | https://www.ncbi.nlm.nih.gov/pubmed/11575704

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

PubMed

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12142563 | https://www.ncbi.nlm.nih.gov/pubmed/11575704