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Roxatidine acetate

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.

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Jul 24, 2026
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Wikipedia ↗
Roxatidine acetate
Clinical data
Routes of
administration		Oral
ATC code
Pharmacokinetic data
Bioavailability80–90%
Protein binding5–7%
MetabolismHepatic deacetylation
Minor involvement of CYP2D6 and CYP2A6
Elimination half-life5–7 hours
ExcretionRenal
Identifiers
  • 2-oxo-2-(3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino)ethyl acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H28N2O4
Molar mass348.443 g·mol−1
3D model (JSmol)
  • O=C(C)OCC(=O)NCCCOc1cccc(c1)CN2CCCCC2
  • InChI=1S/C19H28N2O4/c1-16(22)25-15-19(23)20-9-6-12-24-18-8-5-7-17(13-18)14-21-10-3-2-4-11-21/h5,7-8,13H,2-4,6,9-12,14-15H2,1H3,(H,20,23) checkY
  • Key:SMTZFNFIKUPEJC-UHFFFAOYSA-N checkY
 X markNcheckY (what is this?)  (verify)

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.12

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

ThiemeChemDrug Synthesis:4 Patent:5 Sino revised protocols:6789 source ↗

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.

References

References

  1. Murdoch D, McTavish D (August 1991). "Roxatidine acetate. A review of its pharmacodynamic and pharmacokinetic properties, and its therapeutic potential in peptic ulcer disease and related disorders". Drugs. 42 (2): 240–260. doi:10.2165/00003495-199142020-00006. PMID 1717223. S2CID 46973503.
  2. BioSpectrum Bureau 1 November 2012 Sinhuan's generic heart drug gets production approval
  3. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 444. ISBN 9783527607495.
  4. Castaer, J.; Serradell, MN; TZU-0460. Drugs Fut 1985, 10, 12, 995.
  5. Kenyu Shibata, 7 More », EP0024510 (1983 to Teikoku Hormone Mfg. Co., Ltd.).
  6. Zhang Yang, et al. WO2019075976 (to Beijing Xuansheng Pharmaceutical Co Ltd).
  7. Guo Rongyao & Wang Xiaofeng, CN107698538 (2018 to Inner Mongolia Jingdong Pharmaceutical Co Ltd).
  8. 刘占滨, et al. CN102993121 (2013 to HARBIN PHARMACEUTICAL GROUP SANJING PHARMACEUTICAL CO Ltd).
  9. He Minrong, CN101717363 (2012 to Jiangsu Baosheng Longcheng Pharmaceutical Co Ltd).