Synonym
Ranitidine-S-oxide, Ranitidine S-oxide, Ranitidine-S oxide, Ranitidine S oxide, zantac
IUPAC/Chemical Name
1,1-Ethenediamine, N-(2-(((5-((dimethylamino)methyl)-2-furanyl)methyl)sulfinyl)ethyl)-N'-methyl-2-nitro-
InChi Key
SKHXRNHSZTXSLP-UKTHLTGXSA-N
InChi Code
InChI=1S/C13H22N4O4S/c1-14-13(9-17(18)19)15-6-7-22(20)10-12-5-4-11(21-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3/b13-9+
SMILES Code
O=[N+](/C=C(NC)/NCCS(CC1=CC=C(CN(C)C)O1)=O)[O-]
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Ranitidine is a potent, selective and orally active histamine H2-receptor antagonist with an IC50 of 3.3 μM that inhibits gastric secretion.
In vitro activity:
Ranitidine inhibited [3H]-tiotidine binding and histamine-stimulated cAMP production. These findings demonstrate that ranitidine inhibits the human histamine H2 receptor very rapidly.
Reference: Digestion. 2003;68(2-3):145-52. https://pubmed.ncbi.nlm.nih.gov/14671421/
In vivo activity:
Ranitidine reduces tumor-associated immune suppression allowing for the development of more effective antitumor responses mediated by B cells which may include the participation of NK cells.
Reference: Front Immunol. 2018 Aug 15;9:1894. https://pubmed.ncbi.nlm.nih.gov/30158936/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
330.40
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Fukushima Y, Ishikawa T, Saitoh T, Tateishi K, Ogihara T, Fujishiro M, Shojima N, Honda M, Kushiyama A, Anai M, Sakoda H, Ono H, Onishi Y, Otsuka H, Katagiri H, Nagai R, Omata M, Asano T. Extremely early onset of ranitidine action on human histamine H2 receptors expressed in HEK293 cells. Digestion. 2003;68(2-3):145-52. doi: 10.1159/000075349. Epub 2003 Dec 10. PMID: 14671421.
2. Collett A, Higgs NB, Sims E, Rowland M, Warhurst G. Modulation of the permeability of H2 receptor antagonists cimetidine and ranitidine by P-glycoprotein in rat intestine and the human colonic cell line Caco-2. J Pharmacol Exp Ther. 1999 Jan;288(1):171-8. PMID: 9862768.
3. Rogers D, Vila-Leahey A, Pessôa AC, Oldford S, Marignani PA, Marshall JS. Ranitidine Inhibition of Breast Tumor Growth Is B Cell Dependent and Associated With an Enhanced Antitumor Antibody Response. Front Immunol. 2018 Aug 15;9:1894. doi: 10.3389/fimmu.2018.01894. PMID: 30158936; PMCID: PMC6104125.
4. Chung WG, Park CS, Roh HK, Lee WK, Cha YN. Oxidation of ranitidine by isozymes of flavin-containing monooxygenase and cytochrome P450. Jpn J Pharmacol. 2000 Oct;84(2):213-20. doi: 10.1254/jjp.84.213. PMID: 11128045.
In vitro protocol:
1. Fukushima Y, Ishikawa T, Saitoh T, Tateishi K, Ogihara T, Fujishiro M, Shojima N, Honda M, Kushiyama A, Anai M, Sakoda H, Ono H, Onishi Y, Otsuka H, Katagiri H, Nagai R, Omata M, Asano T. Extremely early onset of ranitidine action on human histamine H2 receptors expressed in HEK293 cells. Digestion. 2003;68(2-3):145-52. doi: 10.1159/000075349. Epub 2003 Dec 10. PMID: 14671421.
2. Collett A, Higgs NB, Sims E, Rowland M, Warhurst G. Modulation of the permeability of H2 receptor antagonists cimetidine and ranitidine by P-glycoprotein in rat intestine and the human colonic cell line Caco-2. J Pharmacol Exp Ther. 1999 Jan;288(1):171-8. PMID: 9862768.
In vivo protocol:
1. Rogers D, Vila-Leahey A, Pessôa AC, Oldford S, Marignani PA, Marshall JS. Ranitidine Inhibition of Breast Tumor Growth Is B Cell Dependent and Associated With an Enhanced Antitumor Antibody Response. Front Immunol. 2018 Aug 15;9:1894. doi: 10.3389/fimmu.2018.01894. PMID: 30158936; PMCID: PMC6104125.
2. Chung WG, Park CS, Roh HK, Lee WK, Cha YN. Oxidation of ranitidine by isozymes of flavin-containing monooxygenase and cytochrome P450. Jpn J Pharmacol. 2000 Oct;84(2):213-20. doi: 10.1254/jjp.84.213. PMID: 11128045.
1: Kang JH, Chung WG, Lee KH, Park CS, Kang JS, Shin IC, Roh HK, Dong MS, Baek HM, Cha YN. Phenotypes of flavin-containing monooxygenase activity determined by ranitidine N-oxidation are positively correlated with genotypes of linked FM03 gene mutations in a Korean population. Pharmacogenetics. 2000 Feb;10(1):67-78. doi: 10.1097/00008571-200002000-00009. PMID: 10739174.
2: Viñas P, Campillo N, López-Erroz C, Hernández-Córdoba M. Use of post-column fluorescence derivatization to develop a liquid chromatographic assay for ranitidine and its metabolites in biological fluids. J Chromatogr B Biomed Sci Appl. 1997 Jun 6;693(2):443-9. doi: 10.1016/s0378-4347(97)00075-3. PMID: 9210451.
3: Davies MH, Ngong JM, Pean A, Vickers CR, Waring RH, Elias E. Sulphoxidation and sulphation capacity in patients with primary biliary cirrhosis. J Hepatol. 1995 May;22(5):551-60. doi: 10.1016/0168-8278(95)80450-1. PMID: 7650336.
4: Cross DM, Bell JA, Wilson K. Kinetics of ranitidine metabolism in dog and rat isolated hepatocytes. Xenobiotica. 1995 Apr;25(4):367-75. doi: 10.3109/00498259509061858. PMID: 7645303.
5: Prueksaritanont T, Sittichai N, Prueksaritanont S, Vongsaroj R. Simultaneous determination of ranitidine and its metabolites in human plasma and urine by high-performance liquid chromatography. J Chromatogr. 1989 May 5;490(1):175-85. doi: 10.1016/s0378-4347(00)82772-3. PMID: 2760148.
6: Rahman A, Hoffman NE, Rustum AM. Determination of ranitidine in plasma by high-performance liquid chromatography. J Pharm Biomed Anal. 1989;7(6):747-53. doi: 10.1016/0731-7085(89)80119-0. PMID: 2490777.
7: Lant MS, Martin LE, Oxford J. Qualitative and quantitative analysis of ranitidine and its metabolites by high-performance liquid chromatography-mass spectrometry. J Chromatogr. 1985 Apr 17;323(1):143-52. doi: 10.1016/s0021-9673(01)90379-6. PMID: 4008551.
8: Rendić S, Kajfez F, Ruf HH. Characterization of cimetidine, ranitidine, and related structures' interaction with cytochrome P-450. Drug Metab Dispos. 1983 Mar-Apr;11(2):137-42. PMID: 6133718.
9: Martin LE, Oxford J, Tanner RJ. Use of high-performance liquid chromatography-mass spectrometry for the study of the metabolism of ranitidine in man. J Chromatogr. 1982 Apr 9;251(2):215-24. doi: 10.1016/s0021-9673(00)98519-4. PMID: 6284777.
10: Martin LE, Oxford J, Tanner RJ. The use of on-line high-performance liquid chromatography-mass spectrometry for the identification of ranitidine and its metabolites in urine. Xenobiotica. 1981 Dec;11(12):831-40. doi: 10.3109/00498258109045320. PMID: 6281996.
11: Carey PF, Martin LE, Owen PE. Determination of ranitidine and its metabolites in human urine by reversed-phase ion-pair high-performance liquid chromatography. J Chromatogr. 1981 Sep 11;225(1):161-8. doi: 10.1016/s0378-4347(00)80255-8. PMID: 6271798.
