U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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(CN(C(C)=O)C2=CC(F)=CC=C2OC3=CC=CC=C3)=C(O[11CH3])C=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

Molecular Formula C23H22FNO4
Molecular Weight 394.4242
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Radiation dosimetry and biodistribution of the translocator protein radiotracer [(11)C]DAA1106 determined with PET/CT in healthy human volunteers.
2014-06-05
Peripheral benzodiazepine receptors in patients with chronic schizophrenia: a PET study with [11C]DAA1106.
2010-08
Evaluation of [11C]-DAA1106 for imaging and quantification of neuroinflammation in a rat model of herpes encephalitis.
2010-01
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.
2009-01
The positron emission tomography ligand DAA1106 binds with high affinity to activated microglia in human neurological disorders.
2008-10
Quantitative analysis for estimating binding potential of the peripheral benzodiazepine receptor with [(11)C]DAA1106.
2007-01
Novel peripheral benzodiazepine receptor ligand [11C]DAA1106 for PET: an imaging tool for glial cells in the brain.
2004-06-15
Design, synthesis and structure-affinity relationships of aryloxyanilide derivatives as novel peripheral benzodiazepine receptor ligands.
2004-01-15
Binding characteristics of [3H]DAA1106, a novel and selective ligand for peripheral benzodiazepine receptors.
1999-04-29
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
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:14:58 GMT 2025
Edited
by admin
on Mon Mar 31 22:14:58 GMT 2025
Record UNII
696AIN172A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
[11C]DAA1106
Preferred Name English
DAA-1106 C-11
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 Mon Mar 31 22:14:58 GMT 2025 , Edited by admin on Mon Mar 31 22:14:58 GMT 2025
PRIMARY
CAS
505084-32-2
Created by admin on Mon Mar 31 22:14:58 GMT 2025 , Edited by admin on Mon Mar 31 22:14:58 GMT 2025
PRIMARY
FDA UNII
696AIN172A
Created by admin on Mon Mar 31 22:14:58 GMT 2025 , Edited by admin on Mon Mar 31 22:14:58 GMT 2025
PRIMARY
Related Record Type Details
NON-LABELED -> LABELED
TARGET->RADIOLIGAND
Related Record Type Details
ACTIVE MOIETY