Identification
- Generic Name
- Roxatidine acetate
- DrugBank Accession Number
- DB08806
- Background
Roxatidine acetate is a specific and competitive H2 receptor antagonist. It is currently approved in South Africa under the tradename Roxit.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Roxatidine acetate (DB08806)
- Weight
- Average: 348.4366
Monoisotopic: 348.204907394 - Chemical Formula
- C19H28N2O4
- Synonyms
- Pifatidine
Pharmacology
- Indication
For the treatment of disorders of the upper gastro-intestinal region that are due to an excess of hydrochloric acid in the gastric juice, i.e. duodenal ulcers, benign gastric ulcers. Also for prophylaxis of recurrent gastric and duodenal ulcers
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Roxatidine acetate suppresses the effect of histamine on the parietal cells of the stomach (H2-receptor antagonist). This suppressive action is dose-dependent. As a result, the production and secretion, particularly of gastric acid, are reduced. Roxatidine acetate has no antiandrogenic effects and does not influence drug-metabolizing enzymes in the liver.
- Mechanism of action
The H2 antagonists are competitive inhibitors of histamine at the parietal cell H2 receptor. They suppress the normal secretion of acid by parietal cells and the meal-stimulated secretion of acid. They accomplish this by two mechanisms: histamine released by ECL cells in the stomach is blocked from binding on parietal cell H2 receptors which stimulate acid secretion, and other substances that promote acid secretion (such as gastrin and acetylcholine) have a reduced effect on parietal cells when the H2 receptors are blocked.
Target Actions Organism AHistamine H2 receptor antagonistHumans - Absorption
Well absorbed orally (80–90% bioavailability).
- Volume of distribution
Not Available
- Protein binding
5-7%
- Metabolism
Roxatidine acetate is rapidly metabolised to the primary, active desacetyl metabolite.
- Route of elimination
Not Available
- Half-life
5-6 hours
- Clearance
Not Available
- Adverse Effects
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Oral, mouse LD50: 1000 mg/kg
- Pathways
Pathway Category Roxatidine Acetate Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAmphetamine Amphetamine may decrease the sedative activities of Roxatidine acetate. Amprenavir Roxatidine acetate can cause a decrease in the absorption of Amprenavir resulting in a reduced serum concentration and potentially a decrease in efficacy. Asunaprevir Roxatidine acetate can cause a decrease in the absorption of Asunaprevir resulting in a reduced serum concentration and potentially a decrease in efficacy. Atazanavir Roxatidine acetate can cause a decrease in the absorption of Atazanavir resulting in a reduced serum concentration and potentially a decrease in efficacy. Benzphetamine Benzphetamine may decrease the sedative activities of Roxatidine acetate. Benzylpenicilloyl polylysine Roxatidine acetate may decrease effectiveness of Benzylpenicilloyl polylysine as a diagnostic agent. Betahistine The therapeutic efficacy of Betahistine can be decreased when used in combination with Roxatidine acetate. Bifonazole Roxatidine acetate can cause a decrease in the absorption of Bifonazole resulting in a reduced serum concentration and potentially a decrease in efficacy. Bisacodyl The therapeutic efficacy of Bisacodyl can be decreased when used in combination with Roxatidine acetate. Bosutinib Roxatidine acetate can cause a decrease in the absorption of Bosutinib resulting in a reduced serum concentration and potentially a decrease in efficacy. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Roxatidine acetate hydrochloride 60426GOR1E 93793-83-0 FEWCTJHCXOHWNL-UHFFFAOYSA-N - International/Other Brands
- Roxit
Categories
- ATC Codes
- A02BA06 — Roxatidine
- Drug Categories
- Acid Reducers
- Alimentary Tract and Metabolism
- Anti-Ulcer Agents
- Drugs for Acid Related Disorders
- Drugs for Peptic Ulcer and Gastro-Oesophageal Reflux Disease (Gord)
- Gastric Acid Lowering Agents
- Gastrointestinal Agents
- Histamine Agents
- Histamine Antagonists
- Histamine H2 Antagonists
- Neurotransmitter Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-benzylpiperidines. These are heterocyclic Compounds containing a piperidine ring conjugated to a benzyl group through one nitrogen ring atom.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Piperidines
- Sub Class
- Benzylpiperidines
- Direct Parent
- N-benzylpiperidines
- Alternative Parents
- Benzylamines / Phenol ethers / Phenoxy compounds / Phenylmethylamines / Alkyl aryl ethers / Aralkylamines / Amino acids and derivatives / Carboxylic acid esters / Secondary carboxylic acid amides / Trialkylamines show 6 more
- Substituents
- Alkyl aryl ether / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Benzylamine / Carbonyl group / Carboxamide group show 19 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- ZUP3LSD0DO
- CAS number
- 78628-28-1
- InChI Key
- SMTZFNFIKUPEJC-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- [(3-{3-[(piperidin-1-yl)methyl]phenoxy}propyl)carbamoyl]methyl acetate
- SMILES
- CC(=O)OCC(=O)NCCCOC1=CC=CC(CN2CCCCC2)=C1
References
- General References
- External Links
- Human Metabolome Database
- HMDB0015695
- KEGG Drug
- D08495
- PubChem Compound
- 5105
- PubChem Substance
- 99445276
- ChemSpider
- 4926
- BindingDB
- 50404032
- 114817
- ChEBI
- 94758
- ChEMBL
- CHEMBL46102
- ZINC
- ZINC000003812908
- PharmGKB
- PA165958424
- Wikipedia
- Roxatidine_acetate
- MSDS
- Download (1.19 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count Not Available Completed Not Available Community Acquired Pneumonia (CAP) / Gastro-esophageal Reflux Disease (GERD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet, coated Tablet, extended release - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 145-146 for HCl salt MSDS - Predicted Properties
Property Value Source Water Solubility 0.0612 mg/mL ALOGPS logP 2.27 ALOGPS logP 1.31 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 14.88 Chemaxon pKa (Strongest Basic) 8.74 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 67.87 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 96.32 m3·mol-1 Chemaxon Polarizability 39.26 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9475 Blood Brain Barrier + 0.8366 Caco-2 permeable - 0.6032 P-glycoprotein substrate Substrate 0.7781 P-glycoprotein inhibitor I Inhibitor 0.7868 P-glycoprotein inhibitor II Non-inhibitor 0.675 Renal organic cation transporter Non-inhibitor 0.645 CYP450 2C9 substrate Non-substrate 0.7803 CYP450 2D6 substrate Non-substrate 0.8415 CYP450 3A4 substrate Substrate 0.5264 CYP450 1A2 substrate Non-inhibitor 0.9143 CYP450 2C9 inhibitor Non-inhibitor 0.8237 CYP450 2D6 inhibitor Non-inhibitor 0.6876 CYP450 2C19 inhibitor Non-inhibitor 0.7797 CYP450 3A4 inhibitor Non-inhibitor 0.9203 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6467 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9324 Biodegradation Not ready biodegradable 0.5199 Rat acute toxicity 2.0100 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8833 hERG inhibition (predictor II) Inhibitor 0.5448
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- The H2 subclass of histamine receptors mediates gastric acid secretion. Also appears to regulate gastrointestinal motility and intestinal secretion. Possible role in regulating cell growth and diff...
- Gene Name
- HRH2
- Uniprot ID
- P25021
- Uniprot Name
- Histamine H2 receptor
- Molecular Weight
- 40097.65 Da
References
- Agrawal SS, Alvin Jose M: Roxatidine, an H(2) receptor blocker, is an estrogenic compound--experimental evidence. Syst Biol Reprod Med. 2010 Aug;56(4):286-91. doi: 10.3109/19396368.2010.496894. [Article]
Drug created at October 18, 2010 22:57 / Updated at March 03, 2023 17:45