3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol

• ChemBase ID: 271
• Molecular Formular: C9H13NO2
• Molecular Mass: 167.20502
• Monoisotopic Mass: 167.09462866
• SMILES: O[C@@H](CNC)c1cc(O)ccc1
• Canonical SMILES: CNC[C@@H](c1cccc(c1)O)O
• InChI: InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1
• InChIKey: SONNWYBIRXJNDC-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
• IUPAC Traditional name: phenylephrine
• Brand Name: Adrianol; AK-Dilate; AK-Nefrin; Alcon Efrin; Alconefrin Nasal Drops 12; Alconefrin Nasal Drops 25; Alconefrin Nasal Drops 50; Alconefrin Nasal Spray 25; Biomydrin; Dilatair; Dimetane; Dionephrine; Doktors; Duration; I-Phrine; Isophrim; Isophrin; Isopto Frin; M-Sympathol; M-Sympatol; M-Synephrine; Mesaton; Mesatone; Mesatonum; Metasympatol; Metsatonum; Mezaton; Minims Phenylephrine; Mydfrin; Neo-Synephrine; Neo-Synephrine Nasal Drops; Neo-Synephrine Nasal Jelly; Neo-Synephrine Nasal Spray; Neofrin; Neophryn; Neosynephrine; Nostril; Nostril Spray Pump; Nostril Spray Pump Mild; Ocu-Phrin Sterile Eye Drops; Ocugestrin; Phenoptic; Prefrin; Prefrin Liquifilm; Pyracort D; Relief Eye Drops for Red Eyes; Rhinall; Spersaphrine; Vicks Sinex; Visadron
• Synonyms: Fenilefrina [INN-Spanish]; L-Phenylephedrine; L-Phenylephrine; M-Methylaminoethanolphenol; M-Oxedrine; Metaoxedrinum; Metaoxedrine; Metaoxedrin; Metasynephrine; Phenylephrinum [INN-Latin]; Phenylephrine

Database IDs

• CAS Number: 59-42-7
• PubChem SID: 160963734; 46506961
• PubChem CID: 6041

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.067801
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -2.5509999
• LogD (pH = 7.4): -1.3510551
• Log P: -0.070160724
• Molar Refractivity: 47.2494 cm^3
• Polarizability: 18.594257 Å^3
• Polar Surface Area: 52.49 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.69
• LOG S: -0.88
• Solubility (Water): 2.20e+01 g/l

PROPERTIES

Physical Property

• Solubility: Freely soluble in water
• Hydrophobicity(logP): 0.5

DETAILS

DrugBank - DB00388

• Drug Groups: approved
• Description: Phenylephrine is a sympathomimetic amine that acts predominantly on α-adrenergic receptors. It is mainly used to treat nasal congestion, but may also be useful in treating hypotension and shock, hypotension during spinal anaesthesia, prolongation of spinal anaesthesia, paroxysmal supraventricular tachycardia, symptomatic relief of external or internal hemorrhoids, and to increase blood pressure as an aid in the diagnosis of heart murmurs.
• Indication: Phenylephrine is mainly used to treat nasal congestion, but may also be useful in treating hypotension and shock, hypotension during spinal anaesthesia, prolongation of spinal anaesthesia, paroxysmal supraventricular tachycardia, symptomatic relief of external or internal hemorrhoids, and to increase blood pressure as an aid in the diagnosis of heart murmurs.
• Pharmacology: Phenylephrine is a powerful vasoconstrictor. It is used as a nasal decongestant and cardiotonic agent. Phenylephrine is a postsynaptic α₁-receptor agonist with little effect on β-receptors of the heart. Parenteral administration of phenylephrine causes a rise in systolic and diastolic pressures, a slight decrease in cardiac output, and a considerable increase in peripheral resistance; most vascular beds are constricted, and renal, splanchnic, cutaneous, and limb blood flows are reduced while coronary blood flow is increased. Phenelephrine also causes pulmonary vessel constriction and subsequent increase in pulmonary arterial pressure. Vasoconstriction in the mucosa of the respiratory tract leads to decreased edema and increased drainage of sinus cavities.
• Affected Organisms: Humans and other mammals
• Biotransformation: Undergoes extensive first-pass metabolism in the intestinal wall and extensive metabolism in the liver. Sulfate conjugation, primarily in the intestinal wall, and oxidative metabolism by monoamine oxidase (MAO) represent the principle routes of metabolism. Glucuronidation occurs to a lesser extent. Phenylephrine and its metabolites are mainly excreted in urine/; .
• Absorption: Completely absorbed after oral administration. It has a reduced bioavailability (compared to pseudoephedrine) following oral administration due to significant first-pass metabolism in the intestinal wall. Compared to IV administration, bioavailability is approximately 38%. Peak serum concentrations are achieved approximately 0.75-2 hours following oral administration. Phenylephrine should be administered parenterally to achieve cardiovascular effects. Occasionally, systemic effects are observed following oral inhalation.
• Half Life: 2.1 to 3.4 hours
• Protein Binding: 95% binding-plasma proteins
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com