Phenylephrine

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Structural formula
Structure of phenylephrine
Structural formula of ( R ) -phenylephrine
General
Non-proprietary name Phenylephrine
other names
  • ( R ) -3- (1-Hydroxy-2-methylaminoethyl) phenol ( IUPAC )
  • ( R ) -1- (3-hydroxyphenyl) -2- (methylamino) ethanol
  • Latin: Phenylephrinum
Molecular formula C 9 H 13 NO 2
External identifiers / databases
CAS number
PubChem 6041
DrugBank DB00388
Wikidata Q421910
Drug information
ATC code
Drug class

Sympathomimetic

properties
Molar mass 167.21 g · mol -1
Melting point
pK s value

8.9; 10.1

solubility

Hydrochloride: soluble in water, ethanol and glycerin

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances

( R ) - (-) - Phenylephrine hydrochloride

07 - Warning

Caution

H and P phrases H: 302-315-319-335
P: 261-305 + 351 + 338
Toxicological data

350 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Phenylephrine is one of the direct acting sympathomimetics with partly indirect effects. It acts as an agonist on the α 1 adrenoceptor . Except for a missing 4- hydroxy group, phenylephrine has the same structure as adrenaline and is mainly used as a local vasoconstrictor in Europe , e.g. For example, as active ingredient of nose drops for decongesting the mucous membranes inside the nose. In eye drops it acts as a mydriatic , so it causes the pupils to dilate . Phenylephrine is also used internationally as a vasopressor , among other things in the context of obstetrics . In drugs which is hydrochloride and the tartrate used. The effect is most similar to that of norepinephrine .

Pharmacokinetics

After administration of tritium- labeled ( 3 H-phenylephrine) by infusion or orally in humans, analysis by means of ion exchange and thin-layer chromatography revealed an excretion of 86 (iv) and 80 (po) percent of the administered activity in the urine ; thus assuming complete enteral intake. The difference in the amount of free 3 H-phenylephrine in the serum of 16% of the amount administered in the iv application versus 2.6% in the oral application suggests a reduced bioavailability of the substance. The biological half-life of two to three hours, as well as the clearance of 2 L / h, is comparable to structurally related amines .

The metabolism to phenolic conjugates after oral intake or m -hydroxymandelic acid by intravenous injection to show that m -hydroxylated amines in the first pass are conjugated mainly metabolism.

Trade names

  • Nasal spray for children ® (CH)
  • Neosynephrin ® (A, D)
  • Rexophtal ® N UD (CH)
  • Thalia ® (A)
  • Vibrocil ® (A, CH)
  • Visadron ® (D, A)
  • Metaoxedrin ® (DK)
  • Mesatonum

Web links

Individual evidence

  1. ↑ a b c d e Entry on phenylephrine. In: Römpp Online . Georg Thieme Verlag, accessed on July 23, 2019.
  2. ↑ a b Data sheet (R) - (-) - Phenylephrine hydrochloride from Sigma-Aldrich , accessed on April 19, 2011 ( PDF ).
  3. ↑ Phenylephrine data sheet (PDF) at EDQM , accessed on June 21, 2008.
  4. ^ DW Cooper, P. Mowbray: Advantages of using a prophylactic phenylephrine infusion during spinal anaesthesia for caesarean section. In: International Journal of Obstetric Anesthesia. Vol. 13, No. 2, 2004, pp. 124-125, PMID 15321421 , doi : 10.1016 / j.ijoa.2003.11.001 .
  5. ^ WD Ngan Kee, KS Khaw, FF Ng: Comparison of phenylephrine infusion regimens for maintaining maternal blood pressure during spinal anesthesia for Caesarean section. In: British Journal of Anesthesia. Vol. 92, No. 4, April 2004, pp. 469-474, PMID 14977792 , doi : 10.1093 / bja / aeh088 .
  6. ↑ JH Hengstmann, J. Goronzy: Pharmacokinetics of 3H-phenylephrine in man. In: European Journal of Clinical Pharmacology . Vol. 21, No. 4, 1982, pp. 335-341, PMID 7056280 , doi : 10.1007 / BF00637623 .