Tetryzoline

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Structural formula
Structure of the tetryzoline enantiomers
1: 1 stereoisomeric mixture of ( R ) -form (left) and ( S ) -form (right),
General
Non-proprietary name Tetryzoline
other names
  • Tetrahydrozoline
  • 2- (1,2,3,4-tetrahydronaphthalen-1-yl) -2-imidazole
  • 2-tetralin-1-yl-4,5-dihydro-1 H -imidazole
  • 2 - [(1 RS ) (1,2,3,4-tetrahydronaphthalen-1-yl)] -4,5-dihydro-1 H -imidazole
  • 2- (1,2,3,4-tetrahydro-1-naphthyl) imidazoline
  • 4,5-dihydro-2- (1,2,3,4-tetrahydro-1-naphthyl) -1 H -imidazoline
Molecular formula C 13 H 16 N 2
External identifiers / databases
CAS number
EC number 201-522-3
ECHA InfoCard 100.001.384
PubChem 5419
ChemSpider 5226
DrugBank DB06764
Wikidata Q425109
Drug information
ATC code

R01 AA06 , R01 AB03 , S01 GA02 , S01 GA52

Drug class

Sympathomimetic

Mechanism of action

α 1 -adrenoceptor - agonist

properties
Molar mass
Melting point
solubility

Hydrochloride :

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

Hydrochloride

07 - Warning

Caution

H and P phrases H: 302-315-319-335
P: 261-305 + 351 + 338
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tetryzoline is a chemical compound that has a decongestant effect and blood vessel constricting effect. It serves as a drug to reduce swelling of the mucous membrane of eye irritation and runny nose ( rhinitis ). Tetryzoline hydrochloride solution is applied topically in the form of eye drops , nasal drops or nasal spray .

pharmacology

Tetryzoline is a sympathomimetic and acts on α-adrenoceptors of the sympathetic nervous system . This results in vasoconstriction and decongestant. The effect on β-adrenoceptors is weak. The effect on the conjunctiva takes a few minutes and lasts for 4 to 8 hours. Tetryzoline is usually only slightly absorbed when used locally and properly and the epithelium is intact . In contrast to phenylephrine , no or only a slight dilation of the pupil was observed even after repeated use .

Clinical information

Application areas (indications)

Tetryzoline is indicated for decongesting the swelling of the mucous membrane in non-infectious conjunctivids (e.g. irritation from wind, smoke, chlorinated water or allergic irritation) as well as in rhinitis , hay fever and sinusitis . A transient improvement in sympathetic ptosis (hanging sore) was also observed.

Adverse effects (side effects)

Often (in 1–10% of those treated) undesirable effects may include increased blood flow to the mucous membrane at the site of application (full blood, reactive hyperemia ), burning mucous membrane and dry mucous membrane. Systemic effects can take the form of e.g. B. express heart palpitations, headache, tremors, weakness, sweating and increase in blood pressure . Long-term nasal congestion ( rhinitis medicamentosa , "drug snuff") has often been observed when using nasal drops and sprays over a longer period of time .

Especially with small children, even with the correct dosage, there is a risk that considerable effects on the central nervous system such as restlessness , cramps , respiratory depression or circulatory collapse can occur. These undesirable effects are, among other things, favored by the permeable blood-brain barrier at this age.

Overdose

When used as directed in the eye, symptoms of overdose are unlikely. However, if accidentally ingested, tetryzoline can cause serious adverse effects. Poisoning can manifest itself in various ways in the clinical picture:

  • Symptoms of central nervous system stimulation are anxiety, agitation, hallucinations, and convulsions
  • Symptoms due to the inhibition of the central nervous system include lowering of body temperature, lethargy, drowsiness, and coma.

Other symptoms may occur: dilation of pupils ( mydriasis ), fever, pallor, cyanosis , nausea, vomiting, increased heart rate ( tachycardia ), slow heart rate ( bradycardia ), cardiac arrhythmia (cardiac arrhythmia), cardiac arrest, high blood pressure ( hypertension ), shock-like hypotension , Pulmonary edema, breathing disorders and respiratory failure (apnea). The toxic dose is 0.01 mg of tetryzoline hydrochloride per kilogram of body weight.

abuse

With chronic use as a nasal spray, the hypoxemic damage to the tissue can lead to necrotic destruction of the nasal mucosa ( rhinitis sicca ).

In the journal Forensic Science International , the abuse of eye drops with alcohol to commit DFSA offenses (German: substance-supported sexual abuse) was described in case reports . One death (manslaughter with drugs) is also reported.

Chemical and pharmaceutical information

Tetryzoline is chiral and has an asymmetrically substituted carbon atom at the 1-position of the tetralin skeleton . It can therefore exist as the ( R ) or ( S ) enantiomer . The racemate is used medicinally , mostly in the form of the water-soluble tetryzoline hydrochloride , less often than tetryzoline phosphate .

Tetryzoline does not require a prescription.

Trade names

Monopreparations

Azolin (IL), Berberil N, Burnil (TR) Caltheon (D), Constrillia (F) Diabenyl T, Exrhinin, Eyesine (USA), Ischemol (I), Murine Tears Plus (USA), Narbel (J), Nasin ( IL), Oftan-Starine (FIN), Ophtalmin-N, Rhinopront Top (D), Stilla (IL), Tetrilin, Tinarhinin (D), Vasopos N, Typinal (IL), Tyzine (USA), Vidiseptal EDO Sine, Visine (USA), Visine Yxin (D)

Combination preparations

AllergoConjunct, Collypan (CH), Collyrium (USA), Efemolin (D, CH), Spersallerg (CH)

right

On January 7, 1956, Sahyun Labs secured several synthesis routes for imidazoline derivatives in US Pat. No. 2,731,471, including tetryzoline (column 3, example 2 ) and tetryzoline hydrochloride (column 2, example 1 ). The use as a sedative in veterinary medicine was protected on July 8, 1958 by Pfizer Inc. by US Pat. No. 2,842,478.

Individual evidence

  1. WHO INN proposal: WHO Chronicle, Vol. 12, No. 3 ( Memento of the original from June 14, 2007 in the Internet Archive ) Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 219 kB), March 1958, p. 109. @1@ 2Template: Webachiv / IABot / whqlibdoc.who.int
  2. WHO INN recommendation: WHO Chronicle, Vol. 13, No. 12 ( Memento of the original from December 19, 2010 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 285 kB), December 1959, p. 474. @1@ 2Template: Webachiv / IABot / whqlibdoc.who.int
  3. a b c d US Patent 2,731,471
  4. ^ A b c d e Axel Kleemann , Jürgen Engel, Bernhard Kutscher, Dietmar Reichert: Pharmaceutical Substances. Systheses, Patents, Applications of the most relevant APIs. 5th edition, completely revised. Thieme, Stuttgart 2009, ISBN 978-3-13-558405-8 , p. 1358.
  5. a b Data sheet Tetryzoline Hydrochloride CRS (PDF) at EDQM , accessed on February 15, 2011.
  6. ^ A b Ann Smith, Susan Budavari, Patricia E. Heckelman, Maryadele J. O'Neil (Eds.): The Merck Index. An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th edition. Merck, Whitehouse Station NJ 2001, ISBN 0-911910-13-1 .
  7. a b Datasheet Tetrahydrozoline hydrochloride from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
  8. a b Pharmaceutical Research. = Drug Research. Vol. 12, 1962, p. 971.
  9. ^ Drugs in Japan. 1990, p. 699.
  10. Ernst Mutschler, Gerd Geisslinger, Heyo K. Kroemer, Peter Ruth, Monika Schäfer-Korting: drug effects. Textbook of pharmacology and toxicology. = Mutschler drug effects. 9th, completely revised and expanded edition. Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 2008, ISBN 978-3-8047-1952-1 , p. 377.
  11. ^ EE Grossmann, RH Lehman: Ophthalmic use of Tyzine. A Clinical Study of this new Vasoconstrictor. In: American Journal of Ophthalmology. Vol. 42, No. 1, 1956, pp. 121-123, PMID 13339915 .
  12. Harold C. Menger: New ophthalmic decongestant, Tetrahydrozoline hydrochloride. In: The Journal of the American Medical Association. Vol. 170, No. 2, 1959, pp. 178-179, doi : 10.1001 / jama.1959.03010020036011 .
  13. W. Neuhann: Experiences with Tetryzoline eye drops in adhesive shell carriers. In: Therapy of the Present. Vol. 104, 1965, p. 1506.
  14. G. Duncker, KF Manthey: Tetryzoline eye drops for sympathetic ptosis. In: Clinical monthly sheets for ophthalmology. Vol. 182, No. 2, 1983, pp. 164-165, doi : 10.1055 / s-2008-1054738 .
  15. a b Johnson & Johnson GmbH: Specialist information Visine Yxin , as of June 2019.
  16. a b Claus-Jürgen Estler (founder), Harald Schmidt (ed.): Pharmacology and Toxicology. For study and practice. 6th, completely revised and expanded edition. Schattauer, Stuttgart et al. 2007, ISBN 978-3-7945-2295-8 , p. 130.
  17. Cornelius Courts: Eye drops as a rape drug , July 31, 2014.
  18. Welt Online: Wife poisons husband with eye drops. In: Welt Online. January 17, 2020, accessed January 17, 2020 .
  19. U.S. Patent 2,842,478 .

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