Naphazoline

Structural formula
General
Non-proprietary name	Naphazoline
other names	2- (1-naphthylmethyl) -4,5-dihydroimidazole ( IUPAC ) 2- (1-naphthylmethyl) imidazoline
Molecular formula	C 14 H 14 N 2
External identifiers / databases
CAS number 835-31-4 550-99-2 ( hydrochloride ) 5144-52-5 ( nitrate ) EC number 212-641-5 ECHA InfoCard 100,011,492 PubChem 4436 ChemSpider 4283 DrugBank DB06711 Wikidata Q415433
Drug information
ATC code	R01 AA08 R01 AB02 S01 GA01
Drug class	Sympathomimetic
Mechanism of action	α 1 -adrenoceptor - agonist
properties
Molar mass	210.27 g mol −1 246.74 g mol −1 (hydrochloride) 273.29 g mol −1 (nitrate)
Physical state	firmly
Melting point	255–260 ° C (hydrochloride)
pK s value	Naphazoline hydrochloride : 10.35 (25 ° C) 10.13 (35 ° C) 9.92 (45 ° C)
solubility	Naphazoline hydrochloride : soluble in water (400 g l −1 at 25 ° C) soluble in ethanol slightly soluble in chloroform insoluble in benzene and ether
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances danger H and P phrases H: 300 P: 264-301 + 310
Toxicological data	62 mg kg −1 ( LD 50 ,  mouse ,  ip ) 170 mg kg −1 ( LD 50 ,  mouse ,  iv ) 270 mg kg −1 ( LD 50 ,  mouse ,  oral ) 514 mg kg −1 ( LD 50 ,  mouse ,  sc ) 0.8 mg kg −1 ( LD 50 ,  rabbit ,  iv ) 0.95 mg kg −1 ( LD 50 ,  rabbit ,  sc ) 385 mg kg −1 ( LD 50 ,  rat ,  sc ) 13.2 mg kg −1 ( LD 50 ,  mouse ,  iv , naphazoline hydrochloride) 265 mg kg −1 ( LD 50 ,  mouse ,  oral , naphazoline hydrochloride) 1260 mg kg −1 ( LD 50 ,  rat ,  oral , naphazoline hydrochloride)
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Naphazoline is a chemical compound that has a decongestant effect on the mucous membrane and constricts blood vessels. It is used as a medicinal substance to reduce swelling in the event of nonspecific or allergic inflammation of the conjunctiva or the nasal mucosa and to decrease the swelling of the mucous membranes for diagnostic purposes. Naphazoline is used topically.

pharmacology

Naphazoline is a sympathomimetic and acts on α-adrenoceptors of the sympathetic nervous system , whereby the vasoconstriction of the blood vessels with the resulting decongestion of the mucous membrane is primarily caused by α ₁ -agonism. The effect on β-adrenoceptors is weak. The decongestant effect occurs after a few minutes and lasts for 4 to 6 hours.

Clinical information

application areas

Naphazolin is indicated for the swelling of the mucous membranes in non-infectious and allergic conjunctivitis as well as in rhinitis and sinusitis . The use of naphazoline is also indicated to facilitate the performance of certain diagnostic techniques ( rhinoscopy , cystoscopy ).

Side effects

Frequently (in 1–10% of those treated) undesirable effects may include increased blood flow to the mucous membrane at the site of application (fullness of blood, reactive hyperemia ), burning mucous membranes and dry mucous membranes. With long-term use on the nasal mucosa or abuse, there is a risk of protracted nasal congestion ( rhinitis medicamentosa , "drug snuff", "privinism").

Overdose

Systemic effects can mainly occur in the event of an overdose and manifest themselves in the form of, for example, nausea, fever , convulsions, changes in pulse rate, changes in blood pressure ( hypertension , hypotension ) and breathing disorders . In children in particular, there is a risk of overdose with considerable effects on the central nervous system.

Chemical and pharmaceutical information

Naphazoline does not require a prescription in Germany. The readily water-soluble naphazoline hydrochloride or the moderately water-soluble naphazoline nitrate are used medicinally .

Trade names

• Monopreparations : AK-Con (USA), Clear Eyes (USA), Estivin II (USA), Nafazair (USA), Naphcon-A (USA), Privin (USA, D), Proculin (adH), Rhinex (D), Rhinon (A), Vasocon (USA)
• Combination preparations: Naphcon-A (USA), Coldistan-A (A)

Individual evidence

1. ↑ WHO INN recommendation: WHO Chronicle, Vol. 9 ( Memento of January 13, 2011 in the Internet Archive ) (PDF; 235 kB), 1955, p. 190.
2. ↑ ^{a b c d} Axel Kleemann, Jürgen Engel, Bernhard Kutscher, Dietmar Reichert: Pharmaceutical Substances: Systheses, Patents, Applications of the most relevant APIs . 5th edition. Thieme Verlag, Stuttgart 2008, ISBN 3-13-558405-4 . P. 1398.
3. ↑ ^{a b} Lewis, RJ: Sax's Dangerous Properties of Industrial Materials . 10th edition. Wiley-Interscience, New York 2000, ISBN 0-471-35407-4 , p. 2625.
4. ↑ ^{a b c d e f} The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station . Merck, 2001
5. ↑ ^{a b} Data sheet Naphazoline hydrochloride from Sigma-Aldrich , accessed on April 12, 2011 ( PDF ).
6. ↑ ^{a b} In: Arzneimittel-Forschung / Drug Research . No. 29, 1979, p. 729.
7. ↑ ^{a b c d} In: Federation Proceedings, Federation of American Societies for Experimental Biology . No. 9, 1950, p. 280.
8. ^ In: Russian Pharmacology and Toxicology . No. 37, 1974, p. 198.
9. ↑ E. Mutschler, G. Geisslinger, HK Kroemer, P. Ruth, M. Schäfer-Korting: drug effects. Textbook of pharmacology and toxicology. 9th edition. Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 2008, ISBN 3-8047-1952-X . P. 377.
10. ^ Specialist information Privin , as of April 2009.
11. ↑ Specialist information Rhinex nasal spray with naphazoline 0.05% , as of January 2010.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !