Roxatidine acetate is a specific and competitive histamine H₂ receptor antagonist drug that is used to treat gastric ulcers, Zollinger–Ellison syndrome, erosive esophagitis, gastro-oesophageal reflux disease, and gastritis.BioSpectrum Bureau 1 November 2012
Sinhuan's generic heart drug gets production approval
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Pharmacodynamic Pharmacodynamics (PD) is the study of the biochemistry, biochemical and physiology, physiologic effects of drugs (especially pharmaceutical drugs). The effects can include those manifested within animals (including humans), microorganisms, or comb ...

studies showed that 150 mg of roxatidine acetate were optimal in suppressing

gastric acid Gastric acid or stomach acid is the acidic component – hydrochloric acid – of gastric juice, produced by parietal cells in the gastric glands of the stomach lining. In humans, the pH is between one and three, much lower than most other a ...

secretion, and that a single bedtime dose of 150 mg was more effective than a dose of 75 mg twice daily in terms of inhibiting nocturnal acid secretion. It was patented in 1979 and approved for medical use in 1986. It is available in countries including China, Japan, Korea, Germany, Italy, the Netherlands, Greece, and South Africa.

Synthesis

The reductive amination between piperidine (1) and 3-hydroxybenzaldehyde (2) gives 3-(1-piperidinylmethyl)phenol (3). Williamson ether synthesis with ''N''-(3-bromopropyl)phthalimide (4) gives the intermediate 5. Deprotection with

hydrazine Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydraz ...

yields (3-(1-piperidinylmethyl)phenoxy)propylamine (6). Heating with

glycolic acid Glycolic acid (or hydroxyacetic acid; chemical formula ) is a colorless, odorless and hygroscopic crystal, crystalline solid, highly solubility, soluble in water. It is used in various skin care, skin-care products. Glycolic acid is widespread in ...

(7) provides roxatidine (8) which is then converted to its acetate ester, roxatidine acetate (9), by acetylation with

acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...

References

{{H2-receptor antagonist H2 receptor antagonists 1-Piperidinyl compounds Phenol ethers Acetamides Acetate esters