5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol

• ChemBase ID: 695
• Molecular Formular: C11H17NO3
• Molecular Mass: 211.25758
• Monoisotopic Mass: 211.12084341
• SMILES: OC(CNC(C)C)c1cc(O)cc(O)c1
• Canonical SMILES: OC(c1cc(O)cc(c1)O)CNC(C)C
• InChI: InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3
• InChIKey: LMOINURANNBYCM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol
• IUPAC Traditional name: orciprenaline
• Brand Name: Alotec; Alupent; Metaprel; Metaproterenol Polistirex; Novasmasol; Prometa
• Synonyms: 5-[1-Hydroxy-2-[(1-methylethyl)amino]ethyl]-1,3-benzenediol Sulfate; 3,5-Dihydroxy-α-[(isopropylamino)methyl]benzyl Alcohol Sulfate; (±)-Orciprenaline Sulfate; 1-(3,5-Dihydroxyphenyl)-1-hydroxy-2-isopropylaminoethane Sulfate; Alotec; Alupent; Astmopent; Metaprel; Novasmasol; Th 152; dl-Metaproterenol Sulfate; dl-Orciprenaline Sulfate; Metaproterenol Hemisulfate Salt; Metaproterenol Sulfate; Orciprenalina [INN-Spanish]; Orciprenalinum [INN-Latin]; Metaproterenol; Orciprenaline Sulfate; Orciprenaline

Database IDs

• CAS Number: 5874-97-5; 586-06-1
• PubChem SID: 46504464; 160964158
• PubChem CID: 4086

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.841109
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.091526
• LogD (pH = 7.4): -0.94034237
• Log P: 0.21496195
• Molar Refractivity: 58.3977 cm^3
• Polarizability: 22.886492 Å^3
• Polar Surface Area: 72.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.32
• LOG S: -1.48
• Solubility (Water): 6.92e+00 g/l

PROPERTIES

Physical Property

• Solubility: 9.7mg/L
• Hydrophobicity(logP): 1

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB00816

• Drug Groups: approved
• Description: A beta-adrenergic agonist used in the treatment of asthma and bronchospasms. [PubChem]
• Indication: For the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema.
• Pharmacology: Orciprenaline (also known as metaproterenol), a synthetic amine, is structurally and pharmacologically similar to isoproterenol. Orciprenaline is used exclusively as a bronchodilator. The pharmacologic effects of beta adrenergic agonist drugs, such as orciprenaline, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic- 3',5'- adenosine monophosphate (c-AMP). Increased c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
• Toxicity: Symptoms of overdose include angina, hypertension or hypotension, arrhythmias, nervousness, headache, tremor, dry mouth, palpitation, nausea, dizziness, fatigue, malaise and insomnia. LD₅₀=42 mg/kg (orally in rat).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic and gastric. The major metabolite, orciprenaline-3-0-sulfate, is produced in the gastrointestinal tract. Orciprenaline is not metabolized by catechol-0-methyltransferase nor have glucuronide conjugates been isolated to date.
• Absorption: 3% (oral bioavailability of 40%)
• Half Life: 6 hours
• External Links: Wikipedia; RxList

Toronto Research Chemicals - M225835

Bronchodilator.

REFERENCES

• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1971)