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{{Short description|Chemical compound}}
{{drugbox | verifiedrevid = 381761475
{{cs1 config|name-list-style=vanc}}
|
{{Drugbox
| IUPAC_name = N-(2-phenoxy-5-fluorophenyl)-N-(2,5-dimethoxybenzyl)acetamide
| verifiedrevid = 438864385
| image = DAA-1106_structure.png
| drug_name =
| width = 200
| type =
| CAS_number = 220551-92-8
| IUPAC_name = ''N''-(2-Phenoxy-5-fluorophenyl)-''N''-(2,5-dimethoxybenzyl)acetamide
| ATC_prefix =
| image = DAA-1106_structure.png
| ATC_suffix =
| width = 200
| PubChem = 10430788

| DrugBank =
<!--Clinical data-->
| C = 23 | H = 22 | F = 1 | N = 1 | O = 4
| alt =
| molecular_weight = 395.423 ]/]
| caption =
| smiles = c3ccccc3Oc2ccc(F)cc2N(C(C)=O)Cc1cc(OC)ccc1OC
| bioavailability = | tradename =
| metabolism = | MedlinePlus =
| licence_EU =
| elimination_half-life =
| excretion = | licence_US =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category = | pregnancy_category =
| legal_status =
| routes_of_administration = | routes_of_administration = <!--Pharmacokinetic data-->
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion = <!--Identifiers-->
| CAS_number = 220551-92-8
| ATC_prefix =
| PubChem = 10430788
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID = 8606215
| StdInChI = 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
| StdInChIKey = DCRZYADKQRHHSF-UHFFFAOYSA-N
| StdInChI_Ref = https://drugs.ncats.io/drug/696AIN172A#
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 3A8IVT5Q3P

<!--Chemical data-->| C = 23
| H = 22
| F = 1
| N = 1
| O = 4
| smiles = COC1=CC(CN(C(C)=O)C2=CC(F)=CC=C2OC3=CC=CC=C3)=C(O)C=C1
}} }}
'''DAA-1106''' is a drug which acts as a potent and selective ] at the ], also known as the mitochondrial 18 kDa translocator protein or TSPO, but with no affinity at ]. It has ] effects in animal studies.<ref name="pmid10321725">{{cite journal |author=Okuyama S, Chaki S, Yoshikawa R, Ogawa S, Suzuki Y, Okubo T, Nakazato A, Nagamine M, Tomisawa K |title=Neuropharmacological profile of peripheral benzodiazepine receptor agonists, DAA1097 and DAA1106 |journal=Life Sciences |volume=64 |issue=16 |pages=1455–64 |year=1999 |pmid=10321725 |doi= 10.1016/S0024-3205(99)00079-X|url=}}</ref><ref name="pmid14723961">{{cite journal |author=Okubo T, Yoshikawa R, Chaki S, Okuyama S, Nakazato A |title=Design, synthesis and structure-affinity relationships of aryloxyanilide derivatives as novel peripheral benzodiazepine receptor ligands |journal=Bioorganic & Medicinal Chemistry |volume=12 |issue=2 |pages=423–38 |year=2004 |month=January |pmid=14723961 |doi= 10.1016/j.bmc.2003.10.050|url=}}</ref><ref name="pmid16842193">{{cite journal |author=James ML, Selleri S, Kassiou M |title=Development of ligands for the peripheral benzodiazepine receptor |journal=Current Medicinal Chemistry |volume=13 |issue=17 |pages=1991–2001 |year=2006 |pmid=16842193 |doi= 10.2174/092986706777584979|url=}}</ref> DAA-1106 has a sub-nanomolar ] of 0.28nM, and has been used extensively in its <sup>3</sup>H or <sup>11</sup>C ] form to map TSPO in the body and brain, which has proved especially helpful in monitoring the progress of neurodegenerative diseases such as ].<ref name="pmid17555551">{{cite journal |author=Venneti S, Lopresti BJ, Wang G, Slagel SL, Mason NS, Mathis CA, Fischer ML, Larsen NJ, Mortimer AD, Hastings TG, Smith AD, Zigmond MJ, Suhara T, Higuchi M, Wiley CA |title=A comparison of the high-affinity peripheral benzodiazepine receptor ligands DAA1106 and (R)-PK11195 in rat models of neuroinflammation: implications for PET imaging of microglial activation |journal=Journal of Neurochemistry |volume=102 |issue=6 |pages=2118–31 |year=2007 |month=September |pmid=17555551 |doi=10.1111/j.1471-4159.2007.04690.x |url=}}</ref><ref name="pmid18800007">{{cite journal |author=Venneti S, Wang G, Nguyen J, Wiley CA |title=The positron emission tomography ligand DAA1106 binds with high affinity to activated microglia in human neurological disorders |journal=Journal of Neuropathology and Experimental Neurology |volume=67 |issue=10 |pages=1001–10 |year=2008 |month=October |pmid=18800007 |pmc=2669281 |doi=10.1097/NEN.0b013e318188b204 |url=}}</ref><ref name="pmid19020019">{{cite journal |author=Ji B, Maeda J, Sawada M, Ono M, Okauchi T, Inaji M, Zhang MR, Suzuki K, Ando K, Staufenbiel M, Trojanowski JQ, Lee VM, Higuchi M, Suhara T |title=Imaging of peripheral benzodiazepine receptor expression as biomarkers of detrimental versus beneficial glial responses in mouse models of Alzheimer's and other CNS pathologies |journal=Journal of Neuroscience |volume=28 |issue=47 |pages=12255–67 |year=2008 |month=November |pmid=19020019 |doi=10.1523/JNEUROSCI.2312-08.2008 |url= |pmc=2755188}}</ref><ref name="pmid19075709">{{cite journal |author=Doorduin J, de Vries EF, Dierckx RA, Klein HC |title=PET imaging of the peripheral benzodiazepine receptor: monitoring disease progression and therapy response in neurodegenerative disorders |journal=Current Pharmaceutical Design |volume=14 |issue=31 |pages=3297–315 |year=2008 |pmid=19075709 |doi= 10.2174/138161208786549443|url=}}</ref><ref name="pmid18984021">{{cite journal |author=Gulyás B, Makkai B, Kása P, Gulya K, Bakota L, Várszegi S, Beliczai Z, Andersson J, Csiba L, Thiele A, Dyrks T, Suhara T, Suzuki K, Higuchi M, Halldin C |title=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 |journal=Neurochemistry International |volume=54 |issue=1 |pages=28–36 |year=2009 |month=January |pmid=18984021 |doi=10.1016/j.neuint.2008.10.001 |url=}}</ref><ref name="pmid18790550">{{cite journal |author=Wang M, Gao M, Hutchins GD, Zheng QH |title=Synthesis of FEDAA1106 as a new PET imaging probe of peripheral benzodiazepine receptor expression |journal=European Journal of Medicinal Chemistry |volume=44 |issue=6 |pages=2748–53 |year=2009 |month=June |pmid=18790550 |doi=10.1016/j.ejmech.2008.08.001 |url=}}</ref> '''DAA-1106''' is a drug which acts as a potent and selective ] at the ], also known as the mitochondrial 18 kDa translocator protein or TSPO, but with no affinity at the ]. It has ] effects in animal studies.<ref name="pmid10321725">{{cite journal |vauthors=Okuyama S, Chaki S, Yoshikawa R, Ogawa S, Suzuki Y, Okubo T, Nakazato A, Nagamine M, Tomisawa K |title=Neuropharmacological profile of peripheral benzodiazepine receptor agonists, DAA1097 and DAA1106 |journal=Life Sciences |volume=64 |issue=16 |pages=1455–64 |year=1999 |pmid=10321725 |doi= 10.1016/S0024-3205(99)00079-X}}</ref><ref name="pmid14723961">{{cite journal |vauthors=Okubo T, Yoshikawa R, Chaki S, Okuyama S, Nakazato A |title=Design, synthesis and structure-affinity relationships of aryloxyanilide derivatives as novel peripheral benzodiazepine receptor ligands |journal=Bioorganic & Medicinal Chemistry |volume=12 |issue=2 |pages=423–38 |date=January 2004 |pmid=14723961 |doi= 10.1016/j.bmc.2003.10.050}}</ref><ref name="pmid16842193">{{cite journal |vauthors=James ML, Selleri S, Kassiou M |title=Development of ligands for the peripheral benzodiazepine receptor |journal=Current Medicinal Chemistry |volume=13 |issue=17 |pages=1991–2001 |year=2006 |pmid=16842193 |doi= 10.2174/092986706777584979|url=https://flore.unifi.it/bitstream/2158/222808/1/id%20222808.pdf|hdl=2158/222808 |hdl-access=free }}</ref> DAA-1106 has a sub-nanomolar ] (K<sub>i</sub>) of 0.28 nM, and has been used extensively in its <sup>3</sup>H or <sup>11</sup>C ] form to map TSPO in the body and brain, which has proved especially helpful in monitoring the progress of neurodegenerative diseases such as ].<ref name="pmid17555551">{{cite journal |vauthors=Venneti S, Lopresti BJ, Wang G, Slagel SL, Mason NS, Mathis CA, Fischer ML, Larsen NJ, Mortimer AD, Hastings TG, Smith AD, Zigmond MJ, Suhara T, Higuchi M, Wiley CA |author-link12=Michael J. Zigmond |title=A comparison of the high-affinity peripheral benzodiazepine receptor ligands DAA1106 and (R)-PK11195 in rat models of neuroinflammation: implications for PET imaging of microglial activation |journal=Journal of Neurochemistry |volume=102 |issue=6 |pages=2118–31 |date=September 2007 |pmid=17555551 |doi=10.1111/j.1471-4159.2007.04690.x |doi-access= |s2cid=3788208 }}</ref><ref name="pmid18800007">{{cite journal |vauthors=Venneti S, Wang G, Nguyen J, Wiley CA |title=The positron emission tomography ligand DAA1106 binds with high affinity to activated microglia in human neurological disorders |journal=Journal of Neuropathology and Experimental Neurology |volume=67 |issue=10 |pages=1001–10 |date=October 2008 |pmid=18800007 |pmc=2669281 |doi=10.1097/NEN.0b013e318188b204 }}</ref><ref name="pmid19020019">{{cite journal |vauthors=Ji B, Maeda J, Sawada M, Ono M, Okauchi T, Inaji M, Zhang MR, Suzuki K, Ando K, Staufenbiel M, Trojanowski JQ, Lee VM, Higuchi M, Suhara T |title=Imaging of peripheral benzodiazepine receptor expression as biomarkers of detrimental versus beneficial glial responses in mouse models of Alzheimer's and other CNS pathologies |journal=Journal of Neuroscience |volume=28 |issue=47 |pages=12255–67 |date=November 2008 |pmid=19020019 |doi=10.1523/JNEUROSCI.2312-08.2008 |pmc=2755188}}</ref><ref name="pmid19075709">{{cite journal |vauthors=Doorduin J, de Vries EF, Dierckx RA, Klein HC |title=PET imaging of the peripheral benzodiazepine receptor: monitoring disease progression and therapy response in neurodegenerative disorders |journal=Current Pharmaceutical Design |volume=14 |issue=31 |pages=3297–315 |year=2008 |pmid=19075709 |doi= 10.2174/138161208786549443}}</ref><ref name="pmid18984021">{{cite journal |vauthors=Gulyás B, Makkai B, Kása P, Gulya K, Bakota L, Várszegi S, Beliczai Z, Andersson J, Csiba L, Thiele A, Dyrks T, Suhara T, Suzuki K, Higuchi M, Halldin C |title=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 |journal=Neurochemistry International |volume=54 |issue=1 |pages=28–36 |date=January 2009 |pmid=18984021 |doi=10.1016/j.neuint.2008.10.001 |s2cid=21033494 }}</ref><ref name="pmid18790550">{{cite journal |vauthors=Wang M, Gao M, Hutchins GD, Zheng QH |title=Synthesis of FEDAA1106 as a new PET imaging probe of peripheral benzodiazepine receptor expression |journal=European Journal of Medicinal Chemistry |volume=44 |issue=6 |pages=2748–53 |date=June 2009 |pmid=18790550 |doi=10.1016/j.ejmech.2008.08.001 }}</ref>

DAA-1106 is used in combination with ] (PET) scanning to examine ] '']''.<ref>{{Cite web|title=NCATS Inxight: Drugs — DAA-1106 C-11|url=https://drugs.ncats.io/drug/696AIN172A|access-date=2020-11-17|website=drugs.ncats.io|language=en}}</ref>


== References == == References ==
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{{Anxiolytics}} {{Anxiolytics}}
{{Translocator protein modulators}}


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{{nervous-system-drug-stub}} {{Anxiolytic-stub}}
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