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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H16ClN5O2
Molecular Weight 381.8163
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZD-2066

SMILES

C[C@]([H])(c1cc(-c2cccc(c2)Cl)on1)Oc3nnc(-c4ccncc4)n3C

InChI

InChIKey=SXWHYTICXCLKDG-GFCCVEGCSA-N
InChI=1S/C19H16ClN5O2/c1-12(16-11-17(27-24-16)14-4-3-5-15(20)10-14)26-19-23-22-18(25(19)2)13-6-8-21-9-7-13/h3-12H,1-2H3/t12-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H16ClN5O2
Molecular Weight 381.8163
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

AstraZeneca was developing AZD-2066, a metabotropic glutamate receptor 5 (mGLUR5) antagonist, for the oral treatment of pain indications (e.g. chronic neuropathic pain and painful diabetic neuropathies), depressive disorders and gastro-oesophageal reflux disease. AZD-2066 had been in phase II clinical trials by AstraZeneca for the treatment of diabetic neuropathic pain and phase I for the treatment of gastrooesophageal reflux disease (GERD). However, this reasearch had being discontinued.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6 nM
13 mg single, oral
dose: 13 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AZD-2066 blood
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
The effects of a novel metabotropic glutamate receptor 5 antagonist (AZD2066) on transient lower oesophageal sphincter relaxations and reflux episodes in healthy volunteers.
2012 May
Glutamate modulators as potential therapeutic drugs in schizophrenia and affective disorders.
2013 Aug
A positron emission tomography study in healthy volunteers to estimate mGluR5 receptor occupancy of AZD2066 - estimating occupancy in the absence of a reference region.
2013 Nov 15
AZD9272 and AZD2066: selective and highly central nervous system penetrant mGluR5 antagonists characterized by their discriminative effects.
2014 Aug
Patents

Sample Use Guides

Treatment of pain: capsule, once daily, 12 mg AZD-2066 day 1-4 and 18 mg AZD2066 day 5-28.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment:: AZD-2066 (0–300 uM, 0–100 uM for CYP2C9) and specific probe substrates were pre-incubated with human liver microsomes for 10 min before the reactions were initiated by the addition of NADPH to give a final incubation volume of 100 uL.
In vitro inhibition by AZD-2066 was observed for the following CYP: CYP1A2 (IC50=14.3 uM), CYP2B6 (IC50=7.4 uM), CYP2C9 (IC50=4.9 μM), CYP2C19 (IC50=9.6 μM) and CYP2D6 (IC50=15 μM). Inhibition of CYP3A4 was also observed, with 60 and 80 % of inhibition at the highest tested concentration of AZD-2066 (300 uM) with midazolam and testosterone as the probe substrates, respectively.
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:56:52 UTC 2021
Edited
by admin
on Sat Jun 26 02:56:52 UTC 2021
Record UNII
MQ908Y1ZB2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZD-2066
Common Name English
AZD 2066 [WHO-DD]
Common Name English
AZD2066
Common Name English
PYRIDINE, 4-(5-((1R)-1-(5-(3-CHLOROPHENYL)-3-ISOXAZOLYL)ETHOXY)-4-METHYL-4H-1,2,4-TRIAZOL-3-YL)-
Systematic Name English
Code System Code Type Description
ChEMBL
CHEMBL3545164
Created by admin on Sat Jun 26 02:56:52 UTC 2021 , Edited by admin on Sat Jun 26 02:56:52 UTC 2021
PRIMARY
CAS
934282-55-0
Created by admin on Sat Jun 26 02:56:52 UTC 2021 , Edited by admin on Sat Jun 26 02:56:52 UTC 2021
PRIMARY
DRUG BANK
DB12644
Created by admin on Sat Jun 26 02:56:52 UTC 2021 , Edited by admin on Sat Jun 26 02:56:52 UTC 2021
PRIMARY
FDA UNII
MQ908Y1ZB2
Created by admin on Sat Jun 26 02:56:52 UTC 2021 , Edited by admin on Sat Jun 26 02:56:52 UTC 2021
PRIMARY
PUBCHEM
16041426
Created by admin on Sat Jun 26 02:56:52 UTC 2021 , Edited by admin on Sat Jun 26 02:56:52 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
ANTAGONIST
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY