Roxatidine acetate
Chemical compound
From Wikipedia, the free encyclopedia
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.[1][2]
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| Routes of administration | Oral |
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| Bioavailability | 80–90% |
| Protein binding | 5–7% |
| Metabolism | Hepatic deacetylation Minor involvement of CYP2D6 and CYP2A6 |
| Elimination half-life | 5–7 hours |
| Excretion | Renal |
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| Chemical and physical data | |
| Formula | C19H28N2O4 |
| Molar mass | 348.443 g·mol−1 |
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Pharmacodynamic studies showed that 150 mg of roxatidine acetate were optimal in suppressing gastric acid 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.[1]
It was patented in 1979 and approved for medical use in 1986.[3] It is available in countries including China, Japan, Korea, Germany, Italy, the Netherlands, Greece, and South Africa.[2]
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 yields (3-(1-piperidinylmethyl)phenoxy)propylamine (6). Heating with glycolic acid (7) provides roxatidine (8) which is then converted to its acetate ester, roxatidine acetate (9), by acetylation with acetic anhydride.