Tramazoline

Structural formula
General
Non-proprietary name	Tramazoline
other names	2- (5,6,7,8-tetrahydro-1-naphthylamino) -2-imidazoline ( IUPAC )
Molecular formula	C 13 H 17 N 3
Brief description	Crystals
External identifiers / databases
EC number	214-105-6
ECHA InfoCard	100.012.823
PubChem	5524
ChemSpider	5323
DrugBank	DB13064
Wikidata	Q412102
Drug information
ATC code	R01 AA09 ; S01 GA ;
Drug class	α-sympathomimetics; Vasoconstrictors;
Mechanism of action	α 1 -adrenoceptor - agonist
properties
Molar mass	215.29 g · mol -1
Melting point	142-143 ° C (tramazoline) ; 172–174 ° C (tramazoline monohydrochloride monohydrate) ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 301 + 331-314-372
	P: 260-280-301 + 310-303 + 361 + 353-305 + 351 + 338-405-501
Toxicological data	190 mg kg −1 ( LD 50 , rat , oral , monohydrochloride) ; 130 mg kg −1 ( LD 50 , mouse , oral , monohydrochloride) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tramazoline is a drug that has a decongestant effect. It is used in medicines to treat runny nose, irritation and allergic diseases of the eye.

Chemically, it is a more cyclic compound from the class of aromatics , guanidines and imidazolines . Pharmacologically, tramazoline is one of the α-sympathomimetics .

Clinical information

Application areas (indications)

Use on the eye

Tramazolin is used in the form of eye drops for symptomatic therapy in non-infectious forms of conjunctivitis, for example allergic conjunctivitis .

Use in rhinitis

As a nasal spray or nasal drops to reduce the swelling of the nasal mucous membrane in the event of a cold with excessive secretion of thick or thin secretion ( runny nose , catarrh , snot ); to facilitate the discharge of secretions in the case of sinus infections and tube catarrh in connection with rhinitis. Tramazolin can be used in school children and adults; special formulations are available for small children under six years of age.

Contraindications (contraindications)

Absolute contraindications

Hypersensitivity to the active ingredient
- intranasal: use in rhinitis sicca
- intraocular: narrow-angle glaucoma

Relative contraindications

Careful risk-benefit assessment for:

Glaucoma patients, especially those with angle- closure glaucoma

severe cardiovascular disease , such as coronary artery disease or high blood pressure

Pheochromocytoma

Metabolic disorders ( e.g. hyperthyroidism , thyrotoxicosis , diabetes mellitus )

Patients treated with MAOIs and other drugs that may increase blood pressure

Drug interactions

Medicines containing tramazoline must not be used at the same time as MAO inhibitors and tricyclic antidepressants because of the risk of a hypertensive crisis (high pressure crisis ) . The use of such drugs must be stopped before using tramazoline.

Anesthetics , atropine sulfate , propranolol, and insulin preparations can increase the cardiovascular effects of sympathomimetics.

Simultaneous use with theophylline and its derivatives in high doses increase the side effects.

Guanethidine and reserpine can lead to arterial hypertension (increase in blood pressure).

Any dampening of functions of the central nervous system can be intensified by alcohol consumption , sleeping pills , tranquilizers and antipsychotics .

Pharmacological properties

Mechanism of action (pharmacodynamics)

Tramazoline is an imidazoline derivative; it is structurally and pharmacologically related to naphazoline , oxymetazoline , tetryzoline and xylometazoline . As an α-sympathomimetic , it selectively stimulates the α-adrenoceptors of the sympathetic nervous system, but has little or no effect on beta-adrenoceptors .

Use in ophthalmology

The use of tramazoline in the eye leads to the constriction of dilated arterioles and thus to the normalization of the increased blood flow to the mucous membranes. This results in a reduction in the symptoms of conjunctival irritation. Some reactive vasodilation is commonly observed with the above uses.

Use in ear, nose and throat medicine

The intranasal application of tramazoline leads to the constriction of dilated arterioles and thus to a reduction in blood flow to the mucous membranes, a reduction in edema formation and an improvement in nasal ventilation . Local vasoconstriction (vasoconstriction) usually occurs within five minutes and lasts for eight to ten hours after using tramazoline solution or spray .

Absorption and distribution in the body (pharmacokinetics)

No human pharmacokinetic studies are available. The pharmacokinetic behavior of tramazoline has been investigated in laboratory rats , rabbits and primates . It was found that the absorption of the active ingredient with oral and intranasal administration is between 50% and 80%. Tramazoline and its metabolites are distributed in all internal organs, with the liver always showing the highest concentrations. The elimination from the blood takes place with a terminal half-life of five to seven hours. Tramazoline is primarily renally excreted . Three main metabolites were detected in the urine after oral or local administration. Occasionally, with intranasal application, the amount absorbed can be sufficient to produce systemic effects - for example on the central nervous system and the cardiovascular system.

Chemical and pharmaceutical information

Tramazoline hydrochloride is used medicinally .

Chemical synthesis

5,6,7,8-Tetrahydro-1-naphthylamine reacts with ammonium thiocyanate to form thiourea , whose tautomeric form forms the S -methylisothiuronium derivative with methyl iodide . With ethylenediamine , methanethiol and ammonia are split off from tramazoline.

Trade names

Medicines containing tramazoline are no longer on the market in Switzerland. In Germany and Austria they are only available in pharmacies .

Monopreparations

Biciron eye drops (D), Ellatun ½ nasal spray / nasal drops for toddlers up to 6 years of age (D), Ellatun N nasal spray / nasal drops for adults and school children (D), rhinospray for runny nose nasal spray (D), rhinospray plus for runny nose nasal spray ( THERE)

Combination preparations

Dexa Biciron eye drops with dexamethasone isonicotinate (D) ( prescription only )

literature

Hermann J. Roth: Medicinal Chemistry: Targets and Drugs; 157 tables . German Apotheker-Verlag, Stuttgart 2005, ISBN 3-7692-3483-9 .

Individual evidence

↑ ^a ^b ^c Entry on Tramazolin. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.
↑ ^a ^b lgcstandards: Monohydrochloridmonohydrat ( Memento from November 1, 2016 in the Internet Archive )
↑ ^a ^b Entry on tramazoline in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Pharmaceutical Research . Vol. 30, p. 1760, 1980.
↑ Andersson KE, Bende M .: Adrenoceptors in the control of human nasal mucosal blood flow . In: The Annals of Otology, Rhinology, and Laryngology . 93, No. 2 Pt 1, 1984, pp. 179-182. PMID 6201119 .
↑ Roth, Hermann J .; Kleemann, Axel: Pharmaceutical Chemistry I. Drug Synthesis . Thieme, Stuttgart 1982, ISBN 3-13-632901-5 , p. 221 .

[RÖMPP_Online-1] Entry on Tramazolin. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.

[lgcstandards-2] standards: Monohydrochloridmonohydrat ( Memento from November 1, 2016 in the Internet Archive )

[chemid-3] Entry on tramazoline in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[arzmf-4] Pharmaceutical Research . Vol. 30, p. 1760, 1980.

[pmid6201119-5] Andersson KE, Bende M .: Adrenoceptors in the control of human nasal mucosal blood flow . In: The Annals of Otology, Rhinology, and Laryngology . 93, No. 2 Pt 1, 1984, pp. 179-182. PMID 6201119 .

[Synthese-6] Roth, Hermann J .; Kleemann, Axel: Pharmaceutical Chemistry I. Drug Synthesis . Thieme, Stuttgart 1982, ISBN 3-13-632901-5 , p. 221 .