4-[(1R)-1-hydroxy-2-{[4-(4-hydroxyphenyl)butyl]amino}ethyl]benzene-1,2-diol

• ChemBase ID: 973
• Molecular Formular: C18H23NO4
• Molecular Mass: 317.37952
• Monoisotopic Mass: 317.16270822
• SMILES: O[C@@H](CNCCCCc1ccc(O)cc1)c1cc(O)c(O)cc1
• Canonical SMILES: Oc1ccc(cc1)CCCCNC[C@@H](c1ccc(c(c1)O)O)O
• InChI: InChI=1S/C18H23NO4/c20-15-7-4-13(5-8-15)3-1-2-10-19-12-18(23)14-6-9-16(21)17(22)11-14/h4-9,11,18-23H,1-3,10,12H2/t18-/m0/s1
• InChIKey: IIRWWTKISYTTBL-SFHVURJKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1R)-1-hydroxy-2-{[4-(4-hydroxyphenyl)butyl]amino}ethyl]benzene-1,2-diol
• IUPAC Traditional name: arbutamine
• Brand Name: GenESA
• Synonyms: Arbutamine

Database IDs

• CAS Number: 128470-16-6
• PubChem SID: 160964436; 46509010
• PubChem CID: 60789

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.966536
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -0.28557155
• LogD (pH = 7.4): 0.7714923
• Log P: 1.9953033
• Molar Refractivity: 89.7808 cm^3
• Polarizability: 34.847473 Å^3
• Polar Surface Area: 92.95 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.08
• LOG S: -3.58
• Solubility (Water): 8.42e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.9

DETAILS

DrugBank - DB01102

• Drug Groups: approved
• Description: Arbutamine, administered through a closed-loop, computer-controlled drug-delivery system, is indicated to elicit acute cardiovascular responses, similar to those produced by exercise, in order to aid in diagnosing the presence or absence of coronary artery disease in patients who cannot exercise adequately .
• Indication: Used to elicit acute cardiovascular responses (cardiac stumulant), similar to those produced by exercise, in order to aid in diagnosing the presence or absence of coronary artery disease (CAD) in patients who cannot exercise adequately.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily metabolized to methoxyarbutamine. Another possible metabolite is ketoarbutamine. The metabolites of arbutamine appear to have less pharmacological activity and a longer half-life and than the parental drug.
• Half Life: Elimination half-life is approximately 8 minutes.
• Protein Binding: 58%