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Details

Stereochemistry ACHIRAL
Molecular Formula C14H6F2N4O
Molecular Weight 284.221
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZD-9272

SMILES

c1cc(-c2nc(-c3cc(cc(c3)F)C#N)on2)ncc1F

InChI

InChIKey=RBSPCALDSNXWEP-UHFFFAOYSA-N
InChI=1S/C14H6F2N4O/c15-10-1-2-12(18-7-10)13-19-14(21-20-13)9-3-8(6-17)4-11(16)5-9/h1-5,7H

HIDE SMILES / InChI

Molecular Formula C14H6F2N4O
Molecular Weight 284.221
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

AZD-9272 is an orally bioavailable and brain-penetrant potent and selective mGluR5 negative allosteric modulator. It exhibits high selectivity for mGluR5 over other mGlu receptors. It had been in phase I clinical trials for the treatment of gastroesophageal reflux disease and neuropathic pain. Single doses of the centrally acting mGluR5-antagonist AZD-9272 did not reduce C-fibre evoked pain, central sensitization or flare reaction in the study aimed to investigate its effect on electrically induced pain, central sensitization and axon reflex flare.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.6 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
24 mg single, oral (unknown)
MTD
Dose: 24 mg
Route: oral
Route: single
Dose: 24 mg
Sources:
healthy
n = 6
Health Status: healthy
Sex: unknown
Food Status: UNKNOWN
Population Size: 6
Sources:
PubMed

PubMed

TitleDatePubMed
Discovery and characterization of AZD9272 and AZD6538-Two novel mGluR5 negative allosteric modulators selected for clinical development.
2012 Nov 15
Palladium mediated ¹¹C-cyanation and characterization in the non-human primate brain of the novel mGluR5 radioligand [¹¹C]AZD9272.
2013 May
Evaluation of the effects of a metabotropic glutamate receptor 5-antagonist on electrically induced pain and central sensitization in healthy human volunteers.
2013 Nov
AZD9272 and AZD2066: selective and highly central nervous system penetrant mGluR5 antagonists characterized by their discriminative effects.
2014 Aug
Patents

Sample Use Guides

3-24 mg single dose (the maximum tolerated dose is 24 mg)
Route of Administration: Oral
[3H]AZD9272 binding in rat striatum was of high affinity and finite capacity (Kd = 9.4 ± 1.9 nM; Bmax = 1553 ± 474 fmol/mg T.E.; ±SD, n = 5) and could be inhibited by MPEP, MTEP and AZD6538 (IC50 AZD6538, 14.5 ± 4.7 nM; MTEP, 24 ± 6.1; n = 2, confirming that these compounds bind to a common site also at the native mGluR5 in rat brain sections.
Substance Class Chemical
Created
by admin
on Sat Jun 26 04:24:16 UTC 2021
Edited
by admin
on Sat Jun 26 04:24:16 UTC 2021
Record UNII
54SQ9B412I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZD-9272
Common Name English
BENZONITRILE, 3-FLUORO-5-(3-(5-FLUORO-2-PYRIDINYL)-1,2,4-OXADIAZOL-5-YL)-
Systematic Name English
3-FLUORO-5-(3-(5-FLUOROPYRIDIN-2-YL)-1,2,4-OXADIAZOL-5-YL)BENZONITRILE
Systematic Name English
AZD 9272 [WHO-DD]
Common Name English
3-(5-FLUOROPYRIDYL-2-YL)-5-(3-CYANO-5-FLUOROPHENYL)-1,2,4-OXADIAZOLE
Common Name English
AZD9272
Code English
Code System Code Type Description
FDA UNII
54SQ9B412I
Created by admin on Sat Jun 26 04:24:16 UTC 2021 , Edited by admin on Sat Jun 26 04:24:16 UTC 2021
PRIMARY
PUBCHEM
9838729
Created by admin on Sat Jun 26 04:24:16 UTC 2021 , Edited by admin on Sat Jun 26 04:24:16 UTC 2021
PRIMARY
CAS
327056-26-8
Created by admin on Sat Jun 26 04:24:16 UTC 2021 , Edited by admin on Sat Jun 26 04:24:16 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
ANTAGONIST
IC50
Related Record Type Details
ACTIVE MOIETY