1-hydroxynaphthalene-2-carboxylic acid; 4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol

• ChemBase ID: 154176
• Molecular Formular: C36H45NO7
• Molecular Mass: 603.745
• Monoisotopic Mass: 603.31960279
• SMILES: c1ccc(cc1)CCCCOCCCCCCNCC(c1ccc(c(c1)CO)O)O.c1ccc2c(c1)ccc(c2O)C(=O)O
• Canonical SMILES: OC(=O)c1ccc2c(c1O)cccc2.OCc1cc(ccc1O)C(CNCCCCCCOCCCCc1ccccc1)O
• InChI: InChI=1S/C25H37NO4.C11H8O3/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21;12-10-8-4-2-1-3-7(8)5-6-9(10)11(13)14/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2;1-6,12H,(H,13,14)
• InChIKey: XTZNCVSCVHTPAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-hydroxynaphthalene-2-carboxylic acid; 4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol
• IUPAC Traditional name: 1-hydroxy-2-naphthoic acid; salmeterol; 1-hydroxynaphthalene-2-carboxylic acid; 4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol
• Synonyms: (±) 4-Hydroxy-a1-[[[6-(4-phenylbutoxy)hexyl]amino]m-ethyl]-1,3-benzenedimethanol xinafoate; GR 33343X xinafoate; Salmeterol xinafoate; Aeromax; Beglan; Betamican; Inaspir; 4-Hydroxy-α1-[[[6-(4-phenylbutoxy)hexyl]amino]methyl]-1,3-benzenedimethanol 1-Hydroxy-2-naphthalenecarboxylic Acid; Salmeterol 1-Hydroxy-2-naphthoate; Arial; GR 33343G; GR 3343G; SN 408; Salmetedur; Salmeterol Hydroxynaphthoate; Salmeterol Xinafoate; Serevent; Serevent Diskus; Siduomi; Salmeterol Xinafoate; 4-(1-Hydroxy-2-((6-(4-phenylbutoxy)hexyl)amino)ethyl)-2-(hydroxymethyl)phenol 1-hydroxy-2-naphthoate

Database IDs

• CAS Number: 94749-08-3
• MDL Number: MFCD00897708
• PubChem SID: 162248315; 24278713
• PubChem CID: 56801

CALCULATED PROPERTIES

• Acid pKa: 10.116024
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.96173096
• LogD (pH = 7.4): 1.94889
• Log P: 3.6146963
• Molar Refractivity: 122.3904 cm^3
• Polarizability: 47.842678 Å^3
• Polar Surface Area: 81.95 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; ethanol: slightly soluble; H2O: slightly soluble; Methanol; methanol: freely soluble; Water
• Apperance: white solid; White to Off-White Solid
• Melting Point: 126-128°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ADRB2(154)
• Mechanism of Action: Beta-Adrenoceptor agonist; Sympathomimetic

Product Information

• Purity: ≥98% (HPLC); 95+%
• Salt Data: Xinafoate
• Application(s): Used in the treatment of asthma
• Empirical Formula (Hill Notation): C25H37NO4 · C11H8O3

DETAILS

Sigma Aldrich - S5068

Biochem/physiol Actions
β2-adrenoceptor agonist.

Toronto Research Chemicals - S090100

A β2-Adrenergic agonist. Structural analog of Albuterol (A514500).

REFERENCES

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