Phenylephrine

Phenylephrine
Clinical data
Pronunciation	/ˌfɛnəlˈɛfriːn, fiː-, -ɪn/
Trade names	Neo-synephrine, others
AHFS/Drugs.com	Monograph
License data	EU EMA: by INN; US DailyMed: Phenylephrine;
Routes of; administration	By mouth, in the nose, on the eye, intravenous, intramuscular
ATC code	C01CA06 (WHO) R01AA04 (WHO), R01AB01 (WHO) (combinations), R01BA03 (WHO), S01FB01 (WHO), S01GA05 (WHO), C05AX06 (WHO);
Legal status
Legal status	AU: S2 (Pharmacy medicine); UK: General sales list (GSL, OTC); US: OTC / Rx-only;
Pharmacokinetic data
Bioavailability	38% through GI tract
Protein binding	95%
Metabolism	Liver (oxidative deamination)
Onset of action	Very rapid (IV); within 20 min (by mouth)
Elimination half-life	2.1–3.4 h
Duration of action	Up to 20 min (IV); 4 hrs (by mouth)
Identifiers
	IUPAC name (R)-3-[-1-hydroxy-2-(methylamino)ethyl]phenol;
CAS Number	59-42-7 ; 61-76-7;
PubChem CID	6041;
IUPHAR/BPS	485;
DrugBank	DB00388 ;
ChemSpider	5818 ;
UNII	1WS297W6MV;
KEGG	D08365 ; D00511;
ChEBI	CHEBI:8093 ;
ChEMBL	ChEMBL1215 ;
CompTox Dashboard (EPA)	DTXSID9023465 ;
ECHA InfoCard	100.000.386
Chemical and physical data
Formula	C9H13NO2
Molar mass	167.208 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@H](c1cc(O)ccc1)CNC;
	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 ; Key:SONNWYBIRXJNDC-VIFPVBQESA-N ;
	(verify)

Phenylephrine is a medication used as a decongestant for uncomplicated nasal congestion, used to dilate the pupil, used to increase blood pressure (given intravenously in cases of low blood pressure), and used to relieve hemorrhoids. It can be taken by mouth, as a nasal spray, given by injection into a vein or muscle, or 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. It causes constriction of both arteries and veins.

Phenylephrine was patented in 1933 and came into medical use in 1938. It is available as a generic medication. Unlike pseudoephedrine, abuse of phenylephrine is very uncommon. Its effectiveness as a nasal decongestant has been questioned. In 2023, a Food and Drug Administration panel concluded that the drug was ineffective as a nasal decongestant when taken orally.

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