Cimetidin

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Achtung

• Gefahrenhinweise

  H303：May be harmfulif swallowed

  H360：Kann die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen.

• Sicherheit

  P201：Vor Gebrauch besondere Anweisungen einholen.

  P202：Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.

  P280：Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.

  P308+P313：BEI Exposition oder falls betroffen: Ärztlichen Rat einholen/ärztliche Hilfe hinzuziehen.

  P405：Unter Verschluss aufbewahren.

Cimetidine Chemische Eigenschaften,Einsatz,Produktion Methoden

• R-Sätze Betriebsanweisung:

  R60:Kann die Fortpflanzungsfähigkeit beeinträchtigen.
  R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
  R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
  R20/22:Gesundheitsschädlich beim Einatmen und Verschlucken.

• S-Sätze Betriebsanweisung:

  S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
  S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
  S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
  S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
  S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
  S22:Staub nicht einatmen.

• Beschreibung

  Cimetidine is a representative of first-generation antihistamine drugs that block H2 receptors.

• Chemische Eigenschaften

  White Solid

• Originator

  Tagamet,SKF,UK,1977

• Verwenden

  antibacterial

• Verwenden

  Competitive histamine H2-receptor antagonist which inhibits gastric acid secretion and reduces pepsin output

• Verwenden

  Cimetidine is used for treating ulcer problems of the stomach and duodenum and for other conditions accompanied by an elevation of acidity and excess secretion of gastric juice. It is used for preventing injuries and the blood flow of the upper regions of the gastrointestinal tract.

• Indications

  Cimetidine, the first released H2-blocker, like histamine, contains an imidazole ring structure. It is well absorbed following oral administration, with peak blood levels 45 to 90 minutes after drug ingestion. Blood levels remain within therapeutic concentrations for approximately 4 hours after a 300-mg dose. Following oral administration, 50 to 75% of the parent compound is excreted unchanged in the urine; the rest appears primarily as the sulfoxide metabolite.

• Definition

  ChEBI: A member of the class of guanidines that consists of guanidine carrying a methyl substituent at position 1, a cyano group at position 2 and a 2-{[(5-methyl-1H-imidazol-4-yl)methyl]sulfanyl}ethyl group at position 3. It is a H -receptor antagonist that inhibits the production of acid in stomach.

• Manufacturing Process

  In an initial step, 2-chloroacetic acid ethyl ester is reacted with formamide to give 5-methylimidazole-4-carboxylic acid ethyl ester. Then sodium in ammonia is used to convert that to 4-hydroxymethyl-5-methylimidazole-hydrochloride. Cysteamine HCl (HSCH2CH2NH2·HCl) is then reacted to give 4-(2- aminomethyl)-thiomethyl-5-methyl-imidazole dihydrochloride. Then Ncyanamido-5,5-dimethyl-dithio-carbonate (from cyanamid, KOH, CS2 and ((CH3)2SO4) is reacted to give a further intermediate which is finally reacted with methylamine to give cimetidine
  The preparation of the pyridyl analogs of the imidazolyl compounds of the
  type of cimetidine are discussed in the patent cited below.
  Further references are given by Kleeman and Engel in the reference below.

• Trademarks

  Tagamet (GlaxoSmithKline).

• Therapeutic Function

  Antiulcer

• Allgemeine Beschreibung

  White crystals with a slight sulfur-mercaptan odor.

• Air & Water Reaktionen

  Slightly water soluble.

• Brandgefahr

  Flash point data for Cimetidine are not available. Cimetidine is probably combustible.

• Biologische Aktivität

  Widely used H 2 histamine antagonist which has more recently been described as an inverse agonist. Also a potent I 1 imidazoline binding site ligand.

• Biochem/physiol Actions

  H2 histamine receptor antagonist; I1 imidazoline receptor agonist; anti-ulcer agent. Blocks cancer metastasis by inhibiting the expression of E-selectin on the surface of endothelial cells, thus blocking tumor cell adhesion.

• Pharmakologie

  The main pharmacological effect of cimetidine is the suppression of gastric juice secretion associated with H2 receptors of the stomach walls. It suppresses both basal and stimulated hydrochloric acid produced by food as well as histamine and gastrine, which simultaneously lower pepsin activity.

• Clinical Use

  H2 antagonist:
  Conditions associated with hyperacidity
  
  Refractory uraemic pruritus (unlicensed use)

• Nebenwirkungen

  Cimetidine may infrequently cause diarrhea, nausea, vomiting, or mental confusion. A rare association with granulocytopenia, thrombocytopenia, and pancytopenia has been reported. Gynecomastia has been demonstrated in patients receiving either high-dose or long-term therapy.

• Synthese

  Cimetidine, 1-cyano-2-methyl-3-[2-[[5-[[methylimidazol-4-yl)methyl]thio] ethyl] guanidine (16.2.5), is synthesized in the following manner. Reacting 2-chloroacetoacetic ether with two moles of formamide gives 4-carbethoxy-5-methylimidazol (16.2.1). Reduction of the carbethoxy group of this produced with sodium in liquid ammonia gives 4- hydroxymethyl-5-methylimidazol (16.2.2). The hydrochloride of the resulting alcohol is reacted with 2-mercaptoethylamine hydrochloride to produce 4-(2-aminomethyl)-thiomethyl- 5-methylimidazol dihydrochloride (16.2.3). This is reacted with N-cyanimido-S,Sdimethyldithiocarbonate to give a thiourea derivative (16.2.4), which upon reaction with methylamine turns into cimetidine (16.2.5).

  

• Veterinary Drugs and Treatments

  In veterinary medicine, cimetidine has been used for the treatment and/or prophylaxis of gastric, abomasal and duodenal ulcers, uremic gastritis, stress-related or drug-induced erosive gastritis, esophagitis, duodenal gastric reflux, and esophageal reflux. It has also been employed to treat hypersecretory conditions associated with gastrinomas and systemic mastocytosis. Cimetidine has also been used investigationally as a immunomodulating agent (see doses) in dogs. Cimetidine has been used for the treatment of melanomas in horses, but the drug’s poor bioavailability and subsequent high doses (48 mg/kg/day) in adult horses makes it a very expensive, unproven treatment.

• Arzneimittelwechselwirkung

  Potentially hazardous interactions with other drugs
  Alpha-blockers: effects of tolazoline antagonised.
  Aminophylline and theophylline: metabolism of aminophylline and theophylline inhibited.
  Anti-arrhythmics: increased concentration of amiodarone, flecainide, lidocaine, procainamide and propafenone.
  Anticoagulants: enhanced effect of coumarins.
  Antiepileptics: metabolism of carbamazepine, fosphenytoin, phenytoin and valproate inhibited.
  Antifungals: absorption of itraconazole and ketoconazole reduced; posaconazole concentration reduced - avoid; terbinafine concentration increased.
  Antimalarials: avoid with artemether/lumefantrine; metabolism of chloroquine, hydroxychloroquine and quinine inhibited.
  Antipsychotics: possibly enhanced effect of antipsychotics, chlorpromazine and clozapine.
  Antivirals: concentration of atazanavir reduced; concentration of raltegravir and saquinavir possibly increased - avoid; avoid for 12 hours before and 4 hours after rilpivirine.
  Ciclosporin: possibly increased ciclosporin levels.
  Clopidogrel: possibly reduces antiplatelet effect.
  Cytotoxics: possibly enhances myelosuppressive effects of carmustine and lomustine; concentration of epirubicin and fluorouracil increased; avoid with dasatinib and erlotinib; possibly reduced absorption of lapatinib; possibly reduced absorption of pazopanib - give at least 2 hours before or 10 hours after cimetidine.
  Ergot alkaloids: increased risk of ergotism - avoid.
  Fampridine: avoid concomitant use.
  Ulipristal: contraceptive effect possibly reduced - avoid with high dose ulipristal.

• Stoffwechsel

  The bioavailability of cimetidine after oral doses is about 60-70%, due to hepatic first-pass metabolism. Cimetidine is partially metabolised in the liver to the sulfoxide and to hydroxymethylcimetidine. About 50% of an oral dose, and 75% of an intravenous dose, is excreted unchanged in the urine in 24 hours. After an oral or parenteral dose of 300 mg, blood concentrations remain above that required to provide 80% inhibition of basal gastric acid secretion for 4-5 hours.

• Lager

  Store at RT

• Dosage forms

  300 mg PO q.i.d. or 800 mg at bedtime.

Cimetidine Upstream-Materialien And Downstream Produkte

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