phenylephrine

Also known as PEF100, m-oxedrine, metasynephrine, (-)-m-hydroxy-alpha-(methylaminomethyl)benzyl alcohol, (R)-3-[-1-hydroxy-2-(methylamino)ethyl]phenol, (R)-3-hydroxy-alpha-[(methylamino)methyl]-benzenemethanol, l-(3-hydroxyphenyl)-N-methylethanolamine, R(-)-phenylephrine

Key facts

Drug.KEGG2: D00511
Drug.ChEBI: 8093
Drug.ChEMBL: 1215
Drug.KEGG: D08365
Drug.Watchedfields: changed
Drug.verifiedrevid: 464201108
Drug.image: Phenylephrine v2.svg
Drug.image_class: skin-invert-image
Drug.alt: Skeletal formula of phenylephrine
Drug.image2: (R)-Phenylephrine molecule ball.png
Drug.image_class2: bg-transparent
Drug.alt2: Ball-and-stick model of the phenylephrine molecule
Drug.tradename: Neosynephrine, Sudafed PE, others
Drug.licence_EU: yes
Drug.DailyMedID: Phenylephrine
Drug.routes_of_administration: By mouth, intranasal, ophthalmic, intravenous, intramuscular, rectal
Drug.class: α1-adrenergic receptor agonist; vasopressor
Drug.ATC_prefix: C01

via Wikipedia infobox

Chemical data

Formula: C9H13NO2
Molecular weight: 167.2 g/mol
IUPAC name: 3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
SMILES: CNC[C@@H](C1=CC(=CC=C1)O)O
InChIKey: SONNWYBIRXJNDC-VIFPVBQESA-N
XLogP: -0.3
Polar surface area: 52.5 Å²
H-bond donors: 3
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

24,567 papers

The safety of intracameral phenylephrine - A systematic review.Survey of ophthalmology · 2022
Effects of phenylephrine on systemic and cerebral circulations in humans: a systematic review with mechanistic explanations.Anaesthesia · 2024
Phenylephrine.Critical care nurse · 1989
Effect of phenylephrine on cerebral oxygen saturation and cardiac output in adults when used to treat intraoperative hypotension: a systematic review.JBI evidence synthesis · 2021
The haemodynamic effects of phenylephrine after cardiac surgery.Acta anaesthesiologica Scandinavica · 2023

via PubMed

Wikidata facts

Mass: 167.094629

Show 7 more facts

chemical formula: C₉H₁₃NO₂
defined daily dose: 4
canonical SMILES: CNCC(C1=CC(=CC=C1)O)O
isomeric SMILES: CNC[C@@H](C1=CC(=CC=C1)O)O
World Health Organisation international non-proprietary name: phenylephrine
melting point: 144
Commons category: Phenylephrine

Sources (5)

via Wikidata · CC0

~23 min read

Article

28 sections

Contents

Medical uses
Decongestant
Hemorrhoids
Pupil dilation
Intraocular bleeding
Low blood pressure
Other uses
Available forms
Contraindications
Side effects
Heart
Others
Interactions
Pharmacology
Pharmacodynamics
Pharmacokinetics
Absorption
Distribution
Metabolism
Elimination
Chemistry
History
Society and culture
Names
Availability
Research
Hair loss
References

Phenylephrine, sold under the brand names Neosynephrine and Sudafed PE among others, is a medication used as a decongestant for uncomplicated nasal congestion in the form of a nasal spray or oral tablet, intravenously in cases of low blood pressure, or as a suppository to relieve hemorrhoids. It can also be applied to the skin.

Common side effects when taken by mouth or injected include nausea, vomiting, headache, and anxiety. Use on hemorrhoids is generally well tolerated. Severe side effects may include a slow heart rate, intestinal ischemia, chest pain, kidney failure, and tissue death at the site of injection. It is unclear whether its use during pregnancy and breastfeeding is safe. Phenylephrine is a selective α1-adrenergic receptor agonist with minimal to no β-adrenergic receptor agonist activity or induction of norepinephrine release. It causes constriction of both arteries and veins.