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Details

Stereochemistry ACHIRAL
Molecular Formula C23H22FNO4
Molecular Weight 394.4242
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAA-1106 C-11

SMILES

COC1=CC=C(O[11CH3])C(CN(C(C)=O)C2=C(OC3=CC=CC=C3)C=CC(F)=C2)=C1

InChI

InChIKey=DCRZYADKQRHHSF-KTXUZGJCSA-N
InChI=1S/C23H22FNO4/c1-16(26)25(15-17-13-20(27-2)10-12-22(17)28-3)21-14-18(24)9-11-23(21)29-19-7-5-4-6-8-19/h4-14H,15H2,1-3H3/i3-1

HIDE SMILES / InChI
The radioligand N-(2,5-dimethoxybenzyl)-N-(5-fluoro- 2-phenoxyphenyl) acetamide labeled with carbon-11 (abbreviated as [11C]DAA1106) has emerged as a reliable radiotracer for examining neuroinflammation with positron emission tomography (PET) scanning in vivo. DAA-1106 is a selective agonist for the peripheral benzodiazepine receptor (also known as Translocator protein or TSPO). DAA-1106 exerts potent anxiolytic-like properties, in laboratory animals.

CNS Activity

Curator's Comment: DAA-1106 C-11 is CNS penetrant in humans. In animals, it exerts potent anxiolytic-like properties. https://www.ncbi.nlm.nih.gov/pubmed/10321725

Approval Year

PubMed

PubMed

TitleDatePubMed
Binding characteristics of [3H]DAA1106, a novel and selective ligand for peripheral benzodiazepine receptors.
1999 Apr 29
Design, synthesis and structure-affinity relationships of aryloxyanilide derivatives as novel peripheral benzodiazepine receptor ligands.
2004 Jan 15
Novel peripheral benzodiazepine receptor ligand [11C]DAA1106 for PET: an imaging tool for glial cells in the brain.
2004 Jun 15
Quantitative analysis for estimating binding potential of the peripheral benzodiazepine receptor with [(11)C]DAA1106.
2007 Jan
The positron emission tomography ligand DAA1106 binds with high affinity to activated microglia in human neurological disorders.
2008 Oct
A comparative autoradiography study in post mortem whole hemisphere human brain slices taken from Alzheimer patients and age-matched controls using two radiolabelled DAA1106 analogues with high affinity to the peripheral benzodiazepine receptor (PBR) system.
2009 Jan
Peripheral benzodiazepine receptors in patients with chronic schizophrenia: a PET study with [11C]DAA1106.
2010 Aug
Evaluation of [11C]-DAA1106 for imaging and quantification of neuroinflammation in a rat model of herpes encephalitis.
2010 Jan
Radiation dosimetry and biodistribution of the translocator protein radiotracer [(11)C]DAA1106 determined with PET/CT in healthy human volunteers.
2014 Nov-Dec
Patents

Sample Use Guides

Participants underwent full body dynamic [11C]DAA1106 PET scanning obtained with the Philips Gemini TruFlight PET Scanner (Koninklijke Philips Electronics N.V., Eindhoven, the Netherlands). Following intravenous bolus injection of 369 ± 70 MBq [11C]DAA1106 over 30 seconds, each participant had 8 sequential whole body scans (three 30-sec, three 1-min, and two-2 min at each bed position) with approximately 12 bed positions each (from the vertex to the mid-thigh).
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Name Type Language
DAA-1106 C-11
Common Name English
[11C]DAA1106
Common Name English
ACETAMIDE, N-(5-FLUORO-2-PHENOXYPHENYL)-N-((2-METHOXY-5-(METHOXY-11C)PHENYL)METHYL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
5458184
Created by admin on Sat Dec 16 08:39:56 GMT 2023 , Edited by admin on Sat Dec 16 08:39:56 GMT 2023
PRIMARY
CAS
505084-32-2
Created by admin on Sat Dec 16 08:39:56 GMT 2023 , Edited by admin on Sat Dec 16 08:39:56 GMT 2023
PRIMARY
FDA UNII
696AIN172A
Created by admin on Sat Dec 16 08:39:56 GMT 2023 , Edited by admin on Sat Dec 16 08:39:56 GMT 2023
PRIMARY