Roxatidine acetate
- A02BA06 (WHO)
Minor involvement of CYP2D6 and CYP2A6
- 2-oxo-2-(3-[3-(piperidin-1-ylmethyl)phenoxy]propylamino)ethyl acetate
- 78628-28-1
Y
- roxatidine: 78273-80-0
Y
- 5105
- DB08806
Y
- 4926
Y
- ZUP3LSD0DO
- roxatidine: IV9VHT3YUM
Y
- D08495
Y
- ChEMBL46102
Y
- DTXSID2048325
- Interactive image
- 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)
Y
- Key:SMTZFNFIKUPEJC-UHFFFAOYSA-N
Y
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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]
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
![](http://upload.wikimedia.org/wikipedia/commons/thumb/3/3c/Roxatidine_synthesis.svg/500px-Roxatidine_synthesis.svg.png)
The reductive amination between piperidine [110-89-4] (1) and 3-hydroxybenzaldehyde [100-83-4] (2) gives 3-(1-Piperidinylmethyl)phenol [73279-04-6] (3). William ether synthesis with N-(3-Bromopropyl)phthalimide [5460-29-7] (4) gives PC12898565 (5). W.K. deprotection with hydrazine yielded (3-(1-piperidinylmethyl)phenoxy)propylamine [73278-98-5] (6). Heating with glycolic acid [79-14-1] (7) gave the amide (8). Acetylation with acetic anhydride completed the synthesis of (9).
References
- ^ a b 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.
- ^ a b BioSpectrum Bureau 1 November 2012 Sinhuan's generic heart drug gets production approval
- ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 444. ISBN 9783527607495.
- ^ Castaer, J.; Serradell, MN; TZU-0460. Drugs Fut 1985, 10, 12, 995.
- ^ Kenyu Shibata, 7 More », EP0024510 (1983 to Teikoku Hormone Mfg. Co., Ltd.).
- ^ Zhang Yang, et al. WO2019075976 (to Beijing Xuansheng Pharmaceutical Co Ltd).
- ^ Guo Rongyao & Wang Xiaofeng, CN107698538 (2018 to Inner Mongolia Jingdong Pharmaceutical Co Ltd).
- ^ 刘占滨, et al. CN102993121 (2013 to HARBIN PHARMACEUTICAL GROUP SANJING PHARMACEUTICAL CO Ltd).
- ^ He Minrong, CN101717363 (2012 to Jiangsu Baosheng Longcheng Pharmaceutical Co Ltd).
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- See also
- Receptor/signaling modulators
- Monoamine metabolism modulators
- Monoamine reuptake inhibitors
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