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{{Short description|Chemical compound}}
{{Chembox
{{Drugbox
| ImageFile = Abediterol.svg
| Watchedfields = changed
| ImageSize =200px
| verifiedrevid =
| ImageAlt =
| IUPACName = (''R'')-5-(2-((6-(2,2-difluoro-2-phenylethoxy)hexyl)amino)-1-hydroxyethyl)-8-hydroxyquinolin-2(1''H'')-one
| IUPAC_name = 5-[(1''R'')-2-{[6-(2,2-Difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl]-8-hydroxyquinolin-2(1''H'')-one
| image = Abediterol.svg
| OtherNames =
| width = 225
| Section1 = {{Chembox Identifiers

| CASNo = 915133-65-2
<!--Clinical data-->| tradename =
| CASNo_Ref = {{cascite|correct|}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| UNII = QXA167CM6F
| pregnancy_US = <!-- A / B / C / D / X -->
| PubChem = 11962616
| pregnancy_category =
| ChemSpiderID = 10136846
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| KEGG = D10219
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| SMILES = FC(F)(c1ccccc1)COCCCCCCNC[C@H](O)c3ccc(O)c2c3\C=C/C(=O)N2
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| InChI = 1/C25H30F2N2O4/c26-25(27,18-8-4-3-5-9-18)17-33-15-7-2-1-6-14-28-16-22(31)19-10-12-21(30)24-20(19)11-13-23(32)29-24/h3-5,8-13,22,28,30-31H,1-2,6-7,14-17H2,(H,29,32)/t22-/m0/s1
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| InChIKey = SFYAXIFVXBKRPK-QFIPXVFZBE
| routes_of_administration = Inhalation
| StdInChI = 1S/C25H30F2N2O4/c26-25(27,18-8-4-3-5-9-18)17-33-15-7-2-1-6-14-28-16-22(31)19-10-12-21(30)24-20(19)11-13-23(32)29-24/h3-5,8-13,22,28,30-31H,1-2,6-7,14-17H2,(H,29,32)/t22-/m0/s1
| legal_status = <!--Pharmacokinetic data-->
| StdInChIKey = SFYAXIFVXBKRPK-QFIPXVFZSA-N}}
| bioavailability =
| Section2 = {{Chembox Properties
| C=25 | H=30 | F=2 | N=2 | O=4
| protein_bound =
| metabolism =
| Appearance =
| elimination_half-life = 24.3 hours<ref>{{cite journal | vauthors = Timmer W, Massana E, Jimenez E, Seoane B, de Miquel G, Ruiz S | title = First-in-human study of the safety, tolerability, pharmacokinetics and pharmacodynamics of abediterol (LAS100977), a novel long-acting Β2 -agonist | journal = Journal of Clinical Pharmacology | volume = 54 | issue = 12 | pages = 1347–53 | date = December 2014 | pmid = 24989946 | doi = 10.1002/jcph.355 | s2cid = 20959248 }}</ref>
| Density =
| excretion = <!--Identifiers-->
| MeltingPt =
| CAS_number = 915133-65-2
| BoilingPt =
| ATC_prefix = None
| Solubility = }}
| ATC_suffix =
| Section3 = {{Chembox Hazards
| PubChem = 11962616
| MainHazards =
| IUPHAR_ligand = 9326
| FlashPt =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| Autoignition = }}
| DrugBank =
| Section5 = {{Chembox Pharmacology
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| AdminRoutes =
| ChemSpiderID = 10136846
| Bioavail =
| UNII_Ref = {{fdacite|correct|FDA}}
| Metabolism =
| UNII = QXA167CM6F
| HalfLife =
| KEGG_Ref = {{keggcite|correct|kegg}}
| ProteinBound =
| KEGG = D10219
| Excretion =
| ChEBI = 142077
| Legal_status =
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| Legal_US =
| ChEMBL = 3039530
| Legal_UK =

| Legal_AU =
<!--Chemical data-->| C = 25
| Legal_CA =
| H = 30
| PregCat =
| F = 2
| PregCat_AU =
| N = 2
| PregCat_US = }}
| O = 4
| smiles = FC(F)(c1ccccc1)COCCCCCCNC[C@H](O)c3ccc(O)c2c3\C=C/C(=O)N2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C25H30F2N2O4/c26-25(27,18-8-4-3-5-9-18)17-33-15-7-2-1-6-14-28-16-22(31)19-10-12-21(30)24-20(19)11-13-23(32)29-24/h3-5,8-13,22,28,30-31H,1-2,6-7,14-17H2,(H,29,32)/t22-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SFYAXIFVXBKRPK-QFIPXVFZSA-N
}}
}}


'''Abediterol''' ([[International Nonproprietary Name|INN]]<ref>[http://whqlibdoc.who.int/druginfo/24_4_2010_INN104.pdf WHO Drug Information, Vol. 24, No. 4, 2010]</ref>) is an experimental drug candidate for the treatment of [[asthma]] and [[chronic obstructive pulmonary disease]]. It is currently under [[drug development|development]] by the Spanish pharmaceutical company [[Almirall]] and is in Phase II clinical trials.<ref>[http://www.almirall.com/webcorp2/cda/ImD_03_02.jsp Product development pipeline], [[Almirall]]</ref> It acts as a [[Beta2-adrenergic agonist|β<sub>2</sub>-adrenergic agonist]].<ref>{{cite patent|WO|2006122788}}</ref><ref>{{cite patent|WO|2010094484}}</ref>
'''Abediterol''' ([[International Nonproprietary Name|INN]];<ref>{{cite journal|title=International Nonproprietary Names for Pharmaceutical Substances (INN). Proposed International Nonproprietary Names: List 104|journal=WHO Drug Information|date=2010|volume=24|issue=1|page=352|url=https://www.who.int/medicines/publications/druginformation/issues/PL-104.pdf|access-date=25 March 2016}}</ref> development codes AZD-0548 and LAS 100977) is a once-daily experimental drug candidate for the treatment of [[asthma]] and [[chronic obstructive pulmonary disease]] (COPD), but it has never been marketed.


==References==
==History==
Abediterol was under [[drug development|development]] by the Spanish pharmaceutical company [[Almirall]] and reached [[Phases of clinical research#Phase II|Phase II]] clinical trials,<ref>[http://www.almirall.com/webcorp2/cda/ImD_03_02.jsp Product development pipeline], [[Almirall]]</ref><ref>{{cite web|title=AdisInsight: Abediterol|url=http://adisinsight.springer.com/drugs/800026746|website=Adis Insight|publisher=Springer International Publishing AG|access-date=25 March 2016}}</ref> but was discontinued in 2021.<ref>{{cite web | url = https://adisinsight.springer.com/drugs/800026746 | title = Abediterol |website=Adis Insight |publisher=Springer International Publishing AG |access-date= 6 February 2024}}</ref> Its coformulation with [[mometasone furoate]] also progressed to Phase II clinical trials, but was discontinued in 2019.<ref>{{cite web|title=AdisInsight: Abediterol/mometasone|url=http://adisinsight.springer.com/drugs/800033847|website=Adis Insight|publisher=Springer International Publishing AG |access-date= 6 February 2024}}</ref>
{{reflist}}


==Mechanism of action==
Abediterol acts as a dual [[Beta2-adrenergic agonist|β<sub>2</sub> adrenergic agonist]]<ref>{{Cite web|title=Espacenet - Bibliographic data|url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=WO&NR=2006122788&KC=&FT=E&locale=en_EP|access-date=2021-05-07|website=worldwide.espacenet.com}}</ref><ref>{{Cite web|title=Espacenet - Bibliographic data|url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=WO&NR=2010094484&KC=&FT=E&locale=en_EP|access-date=2021-05-07|website=worldwide.espacenet.com}}</ref> and [[muscarinic antagonist]] and is classified as an [[Long-acting beta-adrenoceptor agonist|ultra-long-acting β<sub>2</sub> agonist]] (ultra-LABA).<ref>{{cite journal | vauthors = Beier J, Fuhr R, Massana E, Jiménez E, Seoane B, de Miquel G, Ruiz S | title = Abediterol (LAS100977), a novel long-acting β2-agonist: efficacy, safety and tolerability in persistent asthma | journal = Respiratory Medicine | volume = 108 | issue = 10 | pages = 1424–9 | date = October 2014 | pmid = 25256258 | doi = 10.1016/j.rmed.2014.08.005 | url = http://www.resmedjournal.com/article/S0954-6111(14)00287-X/pdf | doi-access = free }}</ref>


== References ==
{{pharma-stub}}
{{reflist|2}}


{{Asthma and copd rx}}
[[Category:Organofluorides]]
{{Adrenergic receptor modulators}}
[[Category:Quinolones]]
{{Muscarinic acetylcholine receptor modulators}}

[[Category:Long-acting beta2-adrenergic agonists]]
[[Category:Muscarinic antagonists]]
[[Category:Muscarinic antagonists]]
[[Category:Beta-adrenergic agonists]]
[[Category:Organofluorides]]
[[Category:2-Quinolones]]
[[Category:Hydroxyarenes]]
[[Category:Phenylethanolamines]]
[[Category:Abandoned drugs]]


{{respiratory-system-drug-stub}}

Latest revision as of 10:25, 21 October 2024

Abediterol
Clinical data
Routes of
administration		Inhalation
ATC code
  • None
Pharmacokinetic data
Elimination half-life24.3 hours[1]
Identifiers
  • 5-[(1R)-2-{[6-(2,2-Difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl]-8-hydroxyquinolin-2(1H)-one
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H30F2N2O4
Molar mass460.522 g·mol−1
3D model (JSmol)
  • FC(F)(c1ccccc1)COCCCCCCNC[C@H](O)c3ccc(O)c2c3\C=C/C(=O)N2
  • InChI=1S/C25H30F2N2O4/c26-25(27,18-8-4-3-5-9-18)17-33-15-7-2-1-6-14-28-16-22(31)19-10-12-21(30)24-20(19)11-13-23(32)29-24/h3-5,8-13,22,28,30-31H,1-2,6-7,14-17H2,(H,29,32)/t22-/m0/s1 checkY
  • Key:SFYAXIFVXBKRPK-QFIPXVFZSA-N checkY

Abediterol (INN;[2] development codes AZD-0548 and LAS 100977) is a once-daily experimental drug candidate for the treatment of asthma and chronic obstructive pulmonary disease (COPD), but it has never been marketed.

History

[edit]

Abediterol was under development by the Spanish pharmaceutical company Almirall and reached Phase II clinical trials,[3][4] but was discontinued in 2021.[5] Its coformulation with mometasone furoate also progressed to Phase II clinical trials, but was discontinued in 2019.[6]

Mechanism of action

[edit]

Abediterol acts as a dual β2 adrenergic agonist[7][8] and muscarinic antagonist and is classified as an ultra-long-acting β2 agonist (ultra-LABA).[9]

References

[edit]
  1. ^ Timmer W, Massana E, Jimenez E, Seoane B, de Miquel G, Ruiz S (December 2014). "First-in-human study of the safety, tolerability, pharmacokinetics and pharmacodynamics of abediterol (LAS100977), a novel long-acting Β2 -agonist". Journal of Clinical Pharmacology. 54 (12): 1347–53. doi:10.1002/jcph.355. PMID 24989946. S2CID 20959248.
  2. ^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Proposed International Nonproprietary Names: List 104" (PDF). WHO Drug Information. 24 (1): 352. 2010. Retrieved 25 March 2016.
  3. ^ Product development pipeline, Almirall
  4. ^ "AdisInsight: Abediterol". Adis Insight. Springer International Publishing AG. Retrieved 25 March 2016.
  5. ^ "Abediterol". Adis Insight. Springer International Publishing AG. Retrieved 6 February 2024.
  6. ^ "AdisInsight: Abediterol/mometasone". Adis Insight. Springer International Publishing AG. Retrieved 6 February 2024.
  7. ^ "Espacenet - Bibliographic data". worldwide.espacenet.com. Retrieved 2021-05-07.
  8. ^ "Espacenet - Bibliographic data". worldwide.espacenet.com. Retrieved 2021-05-07.
  9. ^ Beier J, Fuhr R, Massana E, Jiménez E, Seoane B, de Miquel G, Ruiz S (October 2014). "Abediterol (LAS100977), a novel long-acting β2-agonist: efficacy, safety and tolerability in persistent asthma". Respiratory Medicine. 108 (10): 1424–9. doi:10.1016/j.rmed.2014.08.005. PMID 25256258.


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