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Carmoterol

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Chemical compound

Pharmaceutical compound

Carmoterol
Clinical data

Other names	TA-2005; CHF-4226
Routes of administration	Inhalation
ATC code	None
Legal status
Legal status	Development terminated
Identifiers
IUPAC name 8-Hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]-1H-quinolin-2-one
CAS Number	147568-66-9
PubChemCID	63952
IUPHAR/BPS	7582
ChemSpider	57545^Y
UNII	9810NUL4D1
ChEMBL	ChEMBL1094785^Y
CompTox Dashboard(EPA)	DTXSID201046374
Chemical and physical data
Formula	C₂₁H₂₄N₂O₄
Molar mass	368.433 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=C3C=CC(=O)NC3=C(C=C2)O)O
InChI InChI=1S/C21H24N2O4/c1-13(11-14-3-5-15(27-2)6-4-14)22-12-19(25)16-7-9-18(24)21-17(16)8-10-20(26)23-21/h3-10,13,19,22,24-25H,11-12H2,1-2H3,(H,23,26)/t13-,19+/m1/s1 Key:IHOXNOQMRZISPV-YJYMSZOUSA-N

Carmoterol (INN;^[1] development codesTA-2005 andCHF-4226) is a non-catechol^[2] experimentalultra-long-acting β adrenoreceptor agonist (ultra-LABA)^[2]^[3] that was in clinical trials before 2010 when it has been withdrawn from further development based on evidence that the compound does not possess a competitive profile.^[4]

Preliminary studies indicated duration of its effect exceeding 24 hours after inhalation of 3μg.^[2] The pharmacologic profile of this medication included the fact its potency in isolated guinea pig trachea is greater than that offormoterol andsalmeterol. It is over 100 times more selective for bronchial muscle than myocardial tissue.^[5]

References

[edit]

^"International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 53"(PDF).WHO Drug Information.19 (1): 74. 2005. Retrieved25 March 2016.
^^a ^b ^cMario C, Monica K (2008). "27. Bronchodilators: Beta2-Agonists and Anticholingercs".Clinical Asthma. Philadelphia, PA: Mosby / Elsevier Health Sciences.ISBN 978-0-323-04289-5.
^Cazzola M, Calzetta L, Matera MG (May 2011)."β(2) -adrenoceptor agonists: current and future direction".British Journal of Pharmacology.163 (1):4–17.doi:10.1111/j.1476-5381.2011.01216.x.PMC 3085864.PMID 21232045.
^"Chiesi: Annual Report 2010"(PDF). Chiesi Farmaceutici S.p.A. p. 20. Retrieved27 March 2016.
^Donohue JF (2006)."New Options in COPD Therapy".Medscape. Retrieved27 March 2016.

Adrenergic receptor modulators

α₁

Agonists

Antagonists

α₂

Agonists

Antagonists

Agonists

Antagonists

See also:Receptor/signaling modulators
Dopaminergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

Drugs forobstructive airway diseases:asthma/COPD (R03)

Adrenergics,inhalants

Short-acting β₂ agonists	Bitolterol Carbuterol Fenoterol Isoetarine Pirbuterol Procaterol Reproterol Rimiterol Salbutamol (albuterol)^#/Levosalbutamol (levalbuterol) Terbutaline Tulobuterol
Long-acting β₂ agonists	Bambuterol Clenbuterol Formoterol/Arformoterol Salmeterol
Ultra-long-acting β₂ agonists	Abediterol Carmoterol Indacaterol Olodaterol Vilanterol
Other	Clorprenaline Ephedrine (+theophylline,+theophylline/phenobarbital,theophylline/hydroxyzine) Epinephrine^# Etafedrine Hexoprenaline Isoprenaline (isoproterenol) Methylephedrine Orciprenaline (metaproterenol) Racephedrine Tretoquinol

Glucocorticoids

Anticholinergics/
muscarinic antagonist

Mast cell stabilizers

Xanthines

Eicosanoid inhibition

Leukotriene antagonists	Montelukast Pranlukast Zafirlukast
Arachidonate 5-lipoxygenase inhibitors	Zileuton
Thromboxane receptor antagonists	Ramatroban Seratrodast
Non-xanthinePDE4 inhibitors	Ibudilast Roflumilast

Others/unknown

Combination products

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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