Ranitidine hydrochloride

Base Information

• Chemical Name: Ranitidine hydrochloride
• CAS No.: 66357-35-5
• Molecular Formula: C13H22N4O3S
• Molecular Weight: 314.409
• Hs Code.: 2932999099
• European Community (EC) Number: 266-332-5,275-207-4
• NSC Number: 757851
• DSSTox Substance ID: DTXSID101112063
• Nikkaji Number: J1.096.093B,J19.096I
• Wikipedia: Ranitidine
• Wikidata: Q21971328
• NCI Thesaurus Code: C29412,C66506
• RXCUI: 9143,203136
• Pharos Ligand ID: 4J58WU3QL6MK
• Metabolomics Workbench ID: 37937
• ChEMBL ID: CHEMBL512
• Mol file: 66357-35-5.mol

Synonyms:AH 19065;AH-19065;AH19065;Biotidin;Hydrochloride, Ranitidine;N (2-(((5-((Dimethylamino)methyl)-2-furanyl)methyl)thio)ethyl)-N'-methyl-2-nitro-1,1-ethenediamine;Ranisen;Ranitidin;Ranitidine;Ranitidine Hydrochloride;Sostril;Zantac;Zantic

Chemical Property of Ranitidine hydrochloride

Chemical Property:

• Appearance/Colour: Powder
• Vapor Pressure: 7.66E-08mmHg at 25°C
• Melting Point: 69-70 °C
• Refractive Index: 1.558
• Boiling Point: 437.1 °C at 760 mmHg
• PKA: pKa 2.19±0.04 (Uncertain)
• Flash Point: 218.2 °C
• PSA: 111.56000
• Density: 1.184 g/cm³
• LogP: 2.76400
• Storage Temp.: Desiccate at +4°C
• Solubility.: H2O: 1.8 mg/mL
• Water Solubility.: 24.7 mg/mL
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 314.14126175
• Heavy Atom Count: 21
• Complexity: 347

Purity/Quality:

99% up, ^*data from raw suppliers

Ranitidine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Pharmaceuticals
• Drug Classes: Antiulcer Agents
• Canonical SMILES: CNC(=C[N+](=O)[O-])NCCSCC1=CC=C(O1)CN(C)C
• Isomeric SMILES: CN/C(=C\[N+](=O)[O-])/NCCSCC1=CC=C(O1)CN(C)C
• Recent ClinicalTrials: Safely Stopping Pre-medications in Patients With Breast Cancer Who Are Receiving Paclitaxel
• Recent EU Clinical Trials: The added value of the H2-antagonist ranitidine in premedication regimens during paclitaxel treatment
• Recent NIPH Clinical Trials: Effects of Daijokito on the pharmacokinetics of H2 blocker ranitidine.
• Description: Ranitidine, a H2-receptor agonist, caused contact dermatitis within the pharmaceutical industry.
• Uses: Antagonist (to histamine H2receptors). It simultaneously reduces pepsin activity and is used for treating stomach and duodenum ulcers as well as other conditions accompanied by elevated acidity of the gastrointestinal tract. Synonyms of this drug are zantac, azantac, raniplex, ranidil, and others. Ranitidine (cas# 66357-35-5) was used as a standard for testing the therapeutic effect of brown propolis extract against aspirin and ethanol- induced gastric ulcers.
• Indications: Ranitidine (Zantac) is another H2 receptor antagonist that does not have the same antiandrogen side effects as cimetidine. Note that both cimetidine and ranitidine inhibit the cytochrome P-450 microsomal enzyme system.
• Clinical Use: H2 antagonist: Conditions associated with hyperacidity
• Drug interactions: Potentially hazardous interactions with other drugs Alpha-blockers: effects of tolazoline antagonised. Antifungals: absorption of itraconazole and ketoconazole reduced; concentration of posaconazole possibly reduced - avoid. Antivirals: concentration of atazanavir reduced; concentration of raltegravir possibly increased - avoid; avoid for 12 hours before and 4 hours after rilpivirine. Ciclosporin: may increase or not change ciclosporin levels; nephrotoxicity, additive hepatotoxicity and thrombocytopenia reported. Cytotoxics: reduced gefitinib concentration; reduces concentration of erlotinib and possibly pazopanib, give at least 2 hours before or 10 hours after ranitidine; absorption of dasatinib reduced - avoid; possibly reduced absorption of lapatinib. Ulipristal: contraceptive effect possibly reduced - avoid with high dose ulipristal.

Technology Process of Ranitidine hydrochloride

There total 31 articles about Ranitidine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(E-)-N-methyl-1-(methylthio)-2-nitroethanamine (61832-41-5) + 5-{[(2-aminoethyl)thio]methyl}-N,N-dimethyl-2-furfurylamine (66356-53-4) → Ranitidine (66357-35-5,70956-04-6)

Guidance literature:

In water; at 55 ℃;

DOI:10.1002/anie.201602883

Reference yield: 90.0%

1,1-dichloro-2-nitro ethylene (6061-04-7) + 2-mercaptoethylamine hydrochloride (156-57-0) + 5-(N,N'-dimethylaminomethyl)-2-chloromethyl-furan + methylamine (74-89-5) → Ranitidine (66357-35-5,70956-04-6)

Guidance literature:

1,1-dichloro-2-nitro ethylene; 2-mercaptoethylamine hydrochloride; With sodium hydroxide; at 50 ℃; for 1h;

methylamine; With calcium oxide; In ethanol; at 20 ℃; for 12h;

5-(N,N'-dimethylaminomethyl)-2-chloromethyl-furan; In ethanol; water; at 45 ℃; for 2h; Temperature;

Reference yield: 17.3%

(Z)-1-β-hydroxyethylamino-1-methylamino-2-nitroethene + 5-(N,N-dimethylaminomethyl)-2-thiomethylfuran hydrobromide → Ranitidine (66357-35-5,70956-04-6)

Guidance literature:

(Z)-1-β-hydroxyethylamino-1-methylamino-2-nitroethene; 5-(N,N-dimethylaminomethyl)-2-thiomethylfuran hydrobromide; With hydrogenchloride; at 0 ℃; for 40h;

With sodium hydroxide; sodium chloride; at 0 ℃; pH=9;

upstream raw materials:

nitromethane

N-methyl-N'-(2-<(5-dimethylaminomethyl)-furan-2-ylmethylthio>-ethyl)-carbodiimide

N,N-dimethylammonium chloride

N-methyl-N'-(2-<(5-dimethylaminomethyl)-furan-2-ylmethylthio>-ethyl)-urea

Downstream raw materials:

ranitidine hydrochloride

carbon dioxide

C₁₃H₂₂N₄O₄S

Ranitidine S-oxide

Refernces

• 1、 -. "New method for synthesizing ranitidine". Paragraph 0034; 0039-0044; 0047; 0052-0057; 0059; 0064-0069. . Retrieved 2018/12/14.
• 2、 -. "Novel synthesis method for high-stability ranitidine bismuth citrate". Paragraph 0016. . Retrieved 2018/01/12.