carmoterol

Also known as TA-2005, CHF-4226, 8-hydroxy-5-((R)-1-hydroxy-2-(((R)-1-(4-methoxyphenyl)propan-2-yl)amino)ethyl)quinolin-2(1H)-one

Carmoterol (INN; development codes TA-2005 and CHF-4226) is a non-catechol experimental ultra-long-acting β adrenoreceptor agonist (ultra-LABA) that was in clinical trials before 2010 when it has been withdrawn from further development based on evidence that the compound does not possess a competitive profile.

Chemical data

Formula: C21H24N2O4
Molecular weight: 368.4 g/mol
IUPAC name: 8-hydroxy-5-[(1R)-1-hydroxy-2-[[(2R)-1-(4-methoxyphenyl)propan-2-yl]amino]ethyl]-1H-quinolin-2-one
SMILES: C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=C3C=CC(=O)NC3=C(C=C2)O)O
InChIKey: IHOXNOQMRZISPV-YJYMSZOUSA-N
XLogP: 2.1
Polar surface area: 90.8 Å²
H-bond donors: 4
H-bond acceptors: 5
Formal charge: 0

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Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule
Indications: chronic obstructive pulmonary disease

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Wikidata facts

Subclass of: chemical compound
Mass: 368.174

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canonical SMILES: CC(CC1=CC=C(C=C1)OC)NCC(C2=C3C=CC(=O)NC3=C(C=C2)O)O
chemical formula: C₂₁H₂₄N₂O₄
isomeric SMILES: C[C@H](CC1=CC=C(C=C1)OC)NC[C@@H](C2=C3C=CC(=O)NC3=C(C=C2)O)O
physically interacts with: adrenoceptor beta 2

Sources (3)

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Encyclopedic overview

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Contents

References

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

Excerpted from Wikipedia’s “carmoterol” article, available under the CC BY-SA 4.0 licence.

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