66357-35-5 Usage
Description
Ranitidine hydrochloride is a medication that acts as an antagonist to histamine H2 receptors, used for treating conditions related to elevated acidity in the gastrointestinal tract.
Uses
Used in Pharmaceutical Industry:
Ranitidine hydrochloride is used as a therapeutic agent for treating stomach and duodenum ulcers, as well as other conditions accompanied by elevated acidity of the gastrointestinal tract. It works by reducing pepsin activity and blocking histamine H2 receptors, which helps in decreasing the production of stomach acid.
Used in Research:
Ranitidine (CAS# 66357-35-5) is used as a standard for testing the therapeutic effect of various treatments, such as brown propolis extract, against aspirin and ethanol-induced gastric ulcers. This helps in evaluating the efficacy of new treatments in comparison to the established effects of ranitidine.
Synonyms:
Ranitidine hydrochloride is also known by various other names, including zantac, azantac, raniplex, ranidil, and others.
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.
Biological Activity
Potent, selective and competitive histamine H 2 receptor antagonist (pA 2 = 6.95-7.2). In vivo, inhibits gastric acid secretion induced by histamine, pentagastrin, bethanecol and food. Also inhibits aspirin-induced gastric lesions.
Clinical Use
H2
antagonist:
Conditions associated with hyperacidity
Synthesis
Ranitidine, N[2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethyl]-
N′-methyl-2-nitro-1,1-ethendiamine (16.2.8), is synthesized from furfuryl alcohol, which
undergoes aminomethylation reaction using dimethylamine and paraform, which form 5-
(dimethylaminomethyl)furfuryl alcohol (16.2.6). Further reaction with 2-mercaptoethylamine
hydrochloride gives a product of substitution of the hydroxyl group in (16.2.6),
5-dimethylaminomethyl-2-(2′-aminoethyl)thiomethylfurane (16.2.7). Reacting this with Nmethyl-
1-methylthio-2-nitroethenaamine gives ranitidine (16.2.8).
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.
Metabolism
Ranitidine is not extensively metabolised. A small
proportion of ranitidine is metabolised in the liver to
the N-oxide, the S-oxide, and desmethylranitidine; the
N-oxide is the major metabolite but accounts for only
about 4-6% of a dose.
The fraction of the dose recovered as metabolites is
similar after both oral and IV dosing; and includes 6%
of the dose in urine as the N-oxide, 2% as the S-oxide,
2% as desmethylranitidine and 1-2% as the furoic acid
analogue. There is also some excretion in the faeces.
Dosage forms
150 mg b.i.d.
Check Digit Verification of cas no
The CAS Registry Mumber 66357-35-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,3,5 and 7 respectively; the second part has 2 digits, 3 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 66357-35:
(7*6)+(6*6)+(5*3)+(4*5)+(3*7)+(2*3)+(1*5)=145
145 % 10 = 5
So 66357-35-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H22N4O3S/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3/b13-9+
66357-35-5Relevant articles and documents
An improved synthesis of the antiulcer drug ranitidine from N-[2-[[[5- (hydroxymethyl)-2-furanyl]-methyl]-thio]-ethyl]-N'-methyl-2-nitro-1,1- ethenediamine
Aasen, Arne Jorgen,Skramstad, Jan
, p. 228 - 229 (1998)
An improved synthesis of the antiulcer drug ranitidine from N-[2-[[[5- (hydroxymethyl)-2-furanyl]-methyl]-thiol]-ethyl]-N'methyl-2-nitro-1,1- ethenediamine is reported.
New method for synthesizing ranitidine
-
Paragraph 0034; 0039-0044; 0047; 0052-0057; 0059; 0064-0069, (2018/12/14)
The invention discloses a new method for synthesizing ranitidine. The method comprises the steps of synthesizing vinylidene chloride, synthesizing 1, 1-dichloro-2-nitroethylene, carrying out a ring-closing reaction, carrying out a ring-opening reaction in presence of a desiccant, and synthesizing the ranitidine. The method adopts an anhydrous environment in the preparation process of a ring-opening product, thus avoiding the interference with the reaction and the generation of impurities due to the presence of water, reducing the post-treatment work and increasing the utilization rate of the raw materials. The preparation method provided by the invention effectively increases the reaction yield of the ring-opening product, improves the purity of the ring-opening reaction, and reduces the reaction time; therefore, the yield and purity of the product ranitidine are improved, the production cost is lowered, and the method is more beneficial to industrial production.
Critical Influence of 5-Hydroxymethylfurfural Aging and Decomposition on the Utility of Biomass Conversion in Organic Synthesis
Galkin, Konstantin I.,Krivodaeva, Elena A.,Romashov, Leonid V.,Zalesskiy, Sergey S.,Kachala, Vadim V.,Burykina, Julia V.,Ananikov, Valentine P.
, p. 8338 - 8342 (2016/07/19)
Spectral studies revealed the presence of a specific arrangement of 5-hydroxymethylfurfural (5-HMF) molecules in solution as a result of a hydrogen–bonding network, and this arrangement readily facilitates the aging of 5-HMF. Deterioration of the quality of this platform chemical limits its practical applications, especially in synthesis/pharma areas. The model drug Ranitidine (Zantac) was synthesized with only 15 % yield starting from 5-HMF which was isolated and stored as an oil after a biomass conversion process. In contrast, a much higher yield of 65 % was obtained by using 5-HMF isolated in crystalline state from an optimized biomass conversion process. The molecular mechanisms responsible for 5-HMF decomposition in solution were established by NMR and ESI-MS studies. A highly selective synthesis of a 5-HMF derivative from glucose was achieved using a protecting group at O(6) position.
