Sulpiride

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Structural formula
Structural formula of sulpiride
( R ) shape (top) and ( S ) shape (bottom)
General
Non-proprietary name Sulpiride
other names
  • 3 - [(1-ethylpyrrolidin-2-yl) methylcarbamoyl] -4-methoxybenz-1-sulfonamide ( IUPAC )
  • Sulpiridum ( Latin )
Molecular formula C 15 H 23 N 3 O 4 S
Brief description

white to almost white, crystalline powder

External identifiers / databases
CAS number
  • 15676-16-1 [( RS ) sulpiride]
  • 23672-07-3 [( S ) -Sulpiride]
EC number 239-753-7
ECHA InfoCard 100.036.124
PubChem 5355
ChemSpider 5162
DrugBank DB00391
Wikidata Q422418
Drug information
ATC code
Drug class

Neuroleptics , Atypical Neuroleptics , Antidepressants

Mechanism of action

Blockade of the D 2 receptors

properties
Molar mass 341.43 g · mol -1
Melting point
  • 178-180 ° C [( RS ) sulpiride]
  • 185-187 ° C [( S ) sulpiride]
pK s value

9.12

solubility
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

170 mg kg −1 ( LD 50 ,  mouse ,  ip )

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

Sulpiride is a drug that is mainly used in psychiatry . It is one of the atypical neuroleptics (but is also treated as a typical neuroleptic in some texts ), but also has a certain antidepressant effect. In terms of its chemical structure , it is a substituted benzamide . Sulpiride was launched in 1972.

Action profile

Sulpiride has in mind a strong affinity for the D 2 - and D 3 - receptors . Other neurotransmitter systems are hardly affected.

The anti- psychotic effect only sets in at doses above 600 mg / day. The reason for this is probably the low level of barriers in sulpiride, which only allows the highly potent substance to act as a neuroleptic at higher doses . The higher permeability of the blood-brain barrier in the area of ​​the tubero-infundibular system means that even relatively small doses of sulpiride can cause an increased release of prolactin .

At lower doses, sulpiride has a mood-enhancing and activating effect .

indication

Sulpiride is approved for the treatment of depression when other antidepressants have failed or could not be used. In higher doses it can be used to treat schizophrenia .

Sulpiride is also approved for the symptomatic treatment of dizziness ( Menière's disease ). However, the application for this indication is controversial.

Although sulpiride was spared a setback as with clozapine , interest in the substance declined noticeably in the 1980s. Sulpiride was not introduced in the United States.

The enantiomerically pure levosulpiride [( S ) -sulpiride] is indicated for the treatment of dyspeptic disorders because of its prokinetic activity .

unwanted effects

The most important side effect of sulpiride is the increase in prolactin secretion, which in women e.g. B. to menstrual cycle disorders, feminization and breast enlargement ( gynecomastia ) in men . The activating effect of sulpiride can sometimes be perceived as very annoying and cause sleep disorders.

Especially in high doses, sulpiride can cause extrapyramidal motor disorders ( extrapyramidal syndrome ). The QTc time may be prolonged in the heart.

Dosage forms

Sulpiride is available in a wide variety of dosage forms for oral intake ( tablets , capsules, juice, etc.) and as an injection solution .

The daily dose depends on the respective area of ​​application; because of its activating effect, sulpiride should be taken in the morning , or the last single dose should be given by 4:00 p.m. at the latest. The dosage should be changed gradually or gradually, especially with a higher target dose.

synthesis

Synthesis pathways for the active ingredient sulpiride

A multistep synthesis for sulpiride is described in the literature. Many processes for activating 2-methoxy-5-sulfamoylbenzoic acid are used to produce sulpiride. The clearly differentiated reactivity of the acid chlorides in 2-methoxy-5-fluorosulfonylbenzoyl chloride towards amines and ammonia is useful in another process. An alternative way to do this is to chlorosulfonate a benzamide . (see scheme).

Related links

Amisulpride and Tiapride are analogues of sulpiride; Remoxiprid is also an analogue, but not available commercially.

Trade names

Monopreparations

Arminol (D), Dogmatil (D, A, CH), Meresa (D), Meresasul (D, A), Neogama (D), Sulpivert (D), Vertigo-Meresa (D), Vertige-Neogama (D), numerous generics (D)

See also

Individual evidence

  1. ↑ a b c European Pharmacopoeia Commission (Ed.): EUROPÄISCHE PHARMACOPÖE 5th EDITION . tape 5.0-5.8 , 2006.
  2. ↑ a b Joint Formulary Committee. British National Formulary (BNF) (65 ed.). London, UK: Pharmaceutical Press. ISBN 978-0-85711-084-8 .
  3. ↑ a b The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, pp. 1542-1543, ISBN 978-0-911910-00-1 .
  4. ↑ a b c Entry on sulpiride in the ChemIDplus database of the United States National Library of Medicine (NLM)
  5. ↑ a b data sheet (±) -Sulpiride, powder from Sigma-Aldrich , accessed on February 26, 2013 ( PDF ).
  6. ↑ Peter Riederer, Gerd Laux, Walter Pöldinger (eds.): Neuro-Psychopharmaka: A Therapy Manual, Volume 4: Neuroleptics. 2nd edition, Springer 1998, ISBN 3-211-82943-1 , p. 28.
  7. ^ Claus-Jürgen Estler, Harald Schmidt: Pharmacology and toxicology: for study and practice. 6th edition, Schattauer Verlag 2007, ISBN 3-7945-2295-8 , p. 231.
  8. ↑ ePsy.de: Psychopharmaka Zeittafel
  9. ↑ Perez N., Fernandez S., Legarda I., Garcia-Tapia R: Distonia aguda por neurolepticos en el tartamiento del vertigo: a proposito de dos casos. Acta Otorrinolaringol Esp. 1992 Jul-Aug; 43 (4): 287-9, PMID 1419163 .
  10. ↑ Hans Bangen: History of the drug therapy of schizophrenia. Berlin 1992, p. 93 ISBN 3-927408-82-4 .
  11. ↑ A. Madisch et al .: Diagnosis and therapy of functional dyspepsia , Dtsch Arztebl Int 2018; 115: 222-32; doi : 10.3238 / arztebl.2018.0222
  12. ↑ Levosulpiride Teva 25 mg compresse / Levosulpiride Teva 25 mg / ml gocce orali soluzione , technical information (Italian). Accessed December 10, 2019 (PDF).
  13. ↑ Torsten Kratz, Albert Diefenbacher: Psychopharmacotherapy in old age. Avoidance of drug interactions and polypharmacy. In: Deutsches Ärzteblatt. Volume 116, Issue 29 f. (July 22) 2019, pp. 508-517, p. 512.
  14. ^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances, 4th edition (2000), 2 volumes published by Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 ; online since 2003 with biannual additions and updates.
  15. ↑ FR 5 916 M (full text) (1968), Miller, Charles Stewart; Engelhardt, Edward L .; Thominet, Michel L .; Nouveux medicaments à base de benzamides hétérocycliques; Chem. Abstr. 1969: 470 484.
  16. ↑ Patent DE2901170 : Substituted heterocyclic benzamides, process for their preparation and pharmaceuticals containing them. Published July 26, 1979 , Applicant: ILE DE FRANCE, Inventor: Thominet, Michel; Acher, Jacques; Monier, Jean Claude. ‌
  17. ↑ Patent DE2414498 : Process for the preparation of [N, N-dialkylamino-alkyl] -2-alkoxy-5-sulfamoylbenzamides. Published on October 2, 1975 , applicant: LUDWIG HEUMANN & CO GMBH, inventor: Liebenow, Walter; Count, Ingomar. ‌
  18. ↑ Patent DE2331959 : Process for the production of heterocyclic benzamide compounds. Published January 10, 1974 , Applicant: DELMAR CHEM., Inventor: Podesva, Ctirad; Scott, William Thomas; Navratil, Milada M ..
  19. ↑ Patent DE2358267 : Process for the production of benzenesulfonamides. Published June 6, 1974 , applicant: ILE DE FRANCE, inventor: Morimoto, Akira. ‌