Promazine

Structural formula
General
Non-proprietary name	Promazine
other names	N , N -dimethyl-3- (10 H -phenothiazin-10-yl) propan-1-amine
Molecular formula	C 17 H 20 N 2 S
External identifiers / databases
ECHA InfoCard	100,000,347
PubChem	4926
DrugBank	DB00420
Wikidata	Q419822
Drug information
ATC code	N05 AA03
Drug class	Antipsychotic
properties
Molar mass	284.42 g mol −1
Physical state	firmly
Melting point	155-158 ° C ; 177-181 ° C (hydrochloride);
boiling point	203-210 ° C (40 Pa )
pK s value	9.4
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; Caution
H and P phrases	H: 302-317
	P: 280-301 + 312 + 330
Toxicological data	401 mg kg −1 ( LD 50 , mouse , oral ) ; 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 .

Promazine is a heterocyclic , aromatic compound from the group of thiazines and the basic substance of Promazine . It is a weakly potent, classic neuroleptic from the group of phenothiazines . It was patented by Rhône-Poulenc in 1950 . As a medicinal substance , it was previously marketed in Germany under the names Protactyl and Sinophenin . It is one of the oldest drugs used to treat schizophrenia , but has been largely supplanted by newer drugs.

indication

Psychotic states. Manic phase in bipolar disorder . Psychomotor restlessness and tension, e.g. B. during alcohol withdrawal. Specific forms of nausea and nausea where first-line drugs are contraindicated or do not produce the expected effect.

Mechanism of action

Like all phenothiazines, promazine blocks a whole range of receptors for neurotransmitters , such as D ₂ -, α ₁ -, 5-HT ₂ -, H ₁ - and M ₁ receptors, causing an antipsychotic , sedative , anti- adrenergic , antihistaminic , anticholinergic , ganglion-blocking , antiemetic and local anesthetic effects can arise. Promazin also acts as a FIASMA (functional inhibitor of acid sphingomyelinase ).

unwanted effects

As with all classic neuroleptics, extrapyramidal motor effects can occur during treatment with promazine .

Daytime sleepiness, dry mouth and blood pressure fluctuations as well as micturition disorders , constipation and tachycardia often occur . These undesirable effects ( side effects ) disappear in the course of treatment with Promazine or can be reduced by reducing the dose .

Haematopoiesis , cholestasis , endocrine disorders, eczema and photosensitization are less common, and seizures or glaucoma formation have also been observed in individual cases . Also dyskinesia after prolonged treatment and tardive dyskinesia can occur.

A neuroleptic malignant syndrome with fever , muscle stiffness and decreased consciousness develop very rarely .

Long-term treatment and / or high doses of promazine can cause deposits in the cornea and lens of the eye .

Trade names

Prazine (CH), Protactyl (D, there are no longer any promazine preparations in Germany and Austria). Is still prescribed by doctors in Switzerland (Promazine HCI).

Individual evidence

^ Brockhaus ABC Chemie , VEB FA Brockhaus Verlag. Leipzig 1965, p. 1135.
↑ ^a ^b ^c ^d ^e ^f Entry on Promazin. In: Römpp Online . Georg Thieme Verlag, accessed on July 25, 2019.
↑ ^a ^b Data sheet Promazine hydrochloride from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
↑ compendium.ch , see under Prazine®.
↑ Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .
↑ Walter Schunack: Medicines. Springer-Verlag, 2013, ISBN 978-3-322-83553-6 , p. 139 ( limited preview in the Google book search).

[ABC_Chemie-1] Brockhaus ABC Chemie , VEB FA Brockhaus Verlag. Leipzig 1965, p. 1135.

[römpp-2] ↑ ^a ^b ^c ^d ^e ^f Entry on Promazin. In: Römpp Online . Georg Thieme Verlag, accessed on July 25, 2019.

[Sigma-3] Data sheet Promazine hydrochloride from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).

[4] um.ch , see under Prazine®.

[pmid18504571-5] Kornhuber J, Muehlbacher M, Trapp S, Pechmann S, Friedl A, Reichel M, Mühle C, Terfloth L, Groemer T, Spitzer G, Liedl K, Gulbins E, Tripal P: Identification of novel functional inhibitors of acid sphingomyelinase . In: PLoS ONE . 6, No. 8, 2011, p. E23852. doi : 10.1371 / journal.pone.0023852 .

[books-sm2eBgAAQBAJ-139-6] Walter Schunack: Medicines. Springer-Verlag, 2013, ISBN 978-3-322-83553-6 , p. 139 ( limited preview in the Google book search).