(-)-adrenaline   

GtoPdb Ligand ID: 479

Synonyms: adrenalin | Auvi-Q® | Epipen® | l-adrenaline | L-epinephrine | levoepinephrine
(-)-adrenaline is an approved drug (FDA (no history prior to 1951))
Comment: Agonist at alpha and beta adrenoceptors. In addition to being assigned the INN epinephrine in its own right, (-)-adrenaline is also one of the enantiomers found in the INN-assigned compound (±)-adrenaline.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 4
Rotatable bonds 3
Topological polar surface area 72.72
Molecular weight 183.09
XLogP 0.28
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CNCC(c1ccc(c(c1)O)O)O
Isomeric SMILES CNC[C@@H](c1ccc(c(c1)O)O)O
InChI InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
InChI Key UCTWMZQNUQWSLP-VIFPVBQESA-N
References
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Distinct pharmacological properties and distribution in neurons and endocrine cells of two isoforms of the human vesicular monoamine transporter.
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2. Frielle T, Daniel KW, Caron MG, Lefkowitz RJ. (1988)
Structural basis of beta-adrenergic receptor subtype specificity studied with chimeric beta 1/beta 2-adrenergic receptors.
Proc. Natl. Acad. Sci. U.S.A., 85 (24): 9494-8. [PMID:2849109]
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Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells.
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Selectivity of the imidazoline alpha-adrenoceptor agonists (oxymetazoline and cirazoline) for human cloned alpha 1-adrenoceptor subtypes.
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beta2-adrenergic receptor desensitization, internalization, and phosphorylation in response to full and partial agonists.
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Selectivity of agonists for cloned alpha 1-adrenergic receptor subtypes.
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8. Pihlavisto M, Sjöholm B, Scheinin M, Wurster S. (1998)
Modulation of agonist binding to recombinant human alpha2-adrenoceptors by sodium ions.
Biochim. Biophys. Acta, 1448 (1): 135-46. [PMID:9824686]
9. Shibata K, Foglar R, Horie K, Obika K, Sakamoto A, Ogawa S, Tsujimoto G. (1995)
KMD-3213, a novel, potent, alpha 1a-adrenoceptor-selective antagonist: characterization using recombinant human alpha 1-adrenoceptors and native tissues.
Mol. Pharmacol., 48 (2): 250-8. [PMID:7651358]
10. Temperini C, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. (2007)
Carbonic anhydrase activators: L-Adrenaline plugs the active site entrance of isozyme II, activating better isoforms I, IV, VA, VII, and XIV.
Bioorg. Med. Chem. Lett., 17 (3): 628-35. [PMID:17127057]