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MedKoo Cat#: 317528 | Name: Cimetidine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cimetidine is a histamine H2-receptor antagonist that inhibits stomach acid production. It is largely used in the treatment of heartburn and peptic ulcers. Enhancing anti-tumor cell-mediated responses, cimetidine blocks histamine's ability to stimulate suppressor T lymphocyte activity and to inhibit natural killer cell activity and interleukin-2 production. Cimetidine also may inhibit tumor growth by suppressing histamine's growth-factor activity and blocking histamine-induced stimulation of vascular endothelial growth factor, a pro-angiogenic growth factor.

Chemical Structure

Cimetidine
Cimetidine
CAS#51481-61-9 (free)

Theoretical Analysis

MedKoo Cat#: 317528

Name: Cimetidine

CAS#: 51481-61-9 (free)

Chemical Formula: C10H16N6S

Exact Mass: 252.1157

Molecular Weight: 252.34

Elemental Analysis: C, 47.60; H, 6.39; N, 33.30; S, 12.71

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
10g USD 400.00 2 Weeks
25g USD 750.00 2 Weeks
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Related CAS #
51481-61-9 (free) 70059-30-2 (HCl)
Synonym
Cimetidine ; Tagamet; Cimetag; Eureceptor; Ulcedine; SK and F 92334; SK and F-92334; SK and F92334; SKF 92334; SKF-92334; SKF92334; NSC 335308; NSC335308; NSC-335308
IUPAC/Chemical Name
1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine
InChi Key
AQIXAKUUQRKLND-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)
SMILES Code
CC1=C(N=CN1)CSCCNC(=NC)NC#N
Appearance
White crystalline solid.
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
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 252.34 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.

Recalculate based on batch purity %
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
1: Fazelipour S, Kiaei SB, Tootian Z, Haeri SA, Zehtabvar O, Sadeghinezhad J. Cimetidine administration decreases radiogenic damage on the thyroid gland in mice. Int J Radiat Biol. 2015 Mar;91(3):218-23. doi: 10.3109/09553002.2014.980464. Epub 2014 Nov 20. PubMed PMID: 25347146. 2: Kokhaei P, Barough MS, Hassan ZM. Cimetidine effects on the immunosuppression induced by burn injury. Int Immunopharmacol. 2014 Sep;22(1):273-6. doi: 10.1016/j.intimp.2014.07.003. Epub 2014 Jul 16. PubMed PMID: 25038319. 3: Feng Y, Li X, Xu K, Zou H, Li H, Liang B. Qualitative and simultaneous quantitative analysis of cimetidine polymorphs by ultraviolet-visible and shortwave near-infrared diffuse reflectance spectroscopy and multivariate calibration models. J Pharm Biomed Anal. 2015 Feb;104:112-21. doi: 10.1016/j.jpba.2014.11.023. Epub 2014 Nov 18. PubMed PMID: 25497893. 4: Wang Z, Ma L, Wang X, Cai H, Huang J, Liu J, Hu J, Su D. Cimetidine attenuates vinorelbine-induced phlebitis in mice by militating E-selectin expression. Cancer Chemother Pharmacol. 2014 Aug;74(2):239-47. doi: 10.1007/s00280-014-2487-8. Epub 2014 May 31. PubMed PMID: 24879290. 5: Longhini R, Aparecida de Oliveira P, Sasso-Cerri E, Cerri PS. Cimetidine reduces alveolar bone loss in induced periodontitis in rat molars. J Periodontol. 2014 Aug;85(8):1115-25. doi: 10.1902/jop.2013.130453. Epub 2013 Nov 28. PubMed PMID: 24283656. 6: Ikeda K, Ueda C, Yamada K, Nakamura A, Hatsuda Y, Kawanishi S, Nishii S, Ogawa M. Carrier-mediated placental transport of cimetidine and valproic acid across differentiating JEG-3 cell layers. Pharmazie. 2015 Jul;70(7):471-6. PubMed PMID: 26373208. 7: Calvo NL, Kaufman TS, Maggio RM. A PCA-based chemometrics-assisted ATR-FTIR approach for the classification of polymorphs of cimetidine: application to physical mixtures and tablets. J Pharm Biomed Anal. 2015 Mar 25;107:419-25. doi: 10.1016/j.jpba.2015.01.016. Epub 2015 Jan 15. PubMed PMID: 25659533. 8: Hosseinifard SM, Ahmadpour A, Mojazi Amiri B, Razeghi Mansour M, Ebrahimpour A. Immunomodulatory effect of cimetidine in common carp (Cyprinus carpio L.). Fish Physiol Biochem. 2013 Dec;39(6):1505-11. doi: 10.1007/s10695-013-9804-8. Epub 2013 May 24. PubMed PMID: 23703690. 9: Sprowl JA, van Doorn L, Hu S, van Gerven L, de Bruijn P, Li L, Gibson AA, Mathijssen RH, Sparreboom A. Conjunctive therapy of cisplatin with the OCT2 inhibitor cimetidine: influence on antitumor efficacy and systemic clearance. Clin Pharmacol Ther. 2013 Nov;94(5):585-92. doi: 10.1038/clpt.2013.145. Epub 2013 Jul 17. PubMed PMID: 23863876; PubMed Central PMCID: PMC3832209. 10: Jamrógiewicz M, Ciesielski A. Application of vibrational spectroscopy, thermal analyses and X-ray diffraction in the rapid evaluation of the stability in solid-state of ranitidine, famotidine and cimetidine. J Pharm Biomed Anal. 2015 Mar 25;107:236-43. doi: 10.1016/j.jpba.2015.01.012. Epub 2015 Jan 13. PubMed PMID: 25625474. 11: Dumitras S, Sechaud R, Drollmann A, Pal P, Vaidyanathan S, Camenisch G, Kaiser G. Effect of cimetidine, a model drug for inhibition of the organic cation transport (OCT2/MATE1) in the kidney, on the pharmacokinetics of glycopyrronium. Int J Clin Pharmacol Ther. 2013 Oct;51(10):771-9. doi: 10.5414/CP201946. PubMed PMID: 24040847. 12: Arakawa-Todo M, Ueyama J, Nomura H, Abe F, Tsukiyama I, Matsuura K, Hasegawa T. Drug interaction between sunitinib and cimetidine and contribution of the efflux transporter ATP-binding cassette C2 to biliary excretion of sunitinib in rats. Anticancer Res. 2013 Aug;33(8):3105-11. PubMed PMID: 23898066. 13: Masoud M, Ebrahimi F, Minai-Tehrani D. Effect of cimetidine on catalase activity of Pseudomonas aeruginosa: a suggested mechanism of action. J Mol Microbiol Biotechnol. 2014;24(3):196-201. doi: 10.1159/000364872. Epub 2014 Jul 2. PubMed PMID: 24993120. 14: Calvo NL, Maggio RM, Kaufman TS. A dynamic thermal ATR-FTIR/chemometric approach to the analysis of polymorphic interconversions. Cimetidine as a model drug. J Pharm Biomed Anal. 2014 Apr;92:90-7. doi: 10.1016/j.jpba.2013.12.036. Epub 2014 Jan 7. PubMed PMID: 24509287. 15: Cotton RB, Shah LP, Poole SD, Ehinger NJ, Brown N, Shelton EL, Slaughter JC, Baldwin HS, Paria BC, Reese J. Cimetidine-associated patent ductus arteriosus is mediated via a cytochrome P450 mechanism independent of H2 receptor antagonism. J Mol Cell Cardiol. 2013 Jun;59:86-94. doi: 10.1016/j.yjmcc.2013.02.010. Epub 2013 Feb 27. PubMed PMID: 23454087; PubMed Central PMCID: PMC3646934. 16: Zheng Y, Xu M, Li X, Jia J, Fan K, Lai G. Cimetidine suppresses lung tumor growth in mice through proapoptosis of myeloid-derived suppressor cells. Mol Immunol. 2013 May;54(1):74-83. doi: 10.1016/j.molimm.2012.10.035. Epub 2012 Dec 5. PubMed PMID: 23220070. 17: Beltrame FL, Cerri PS, Sasso-Cerri E. Cimetidine-induced Leydig cell apoptosis and reduced EG-VEGF (PK-1) immunoexpression in rats: Evidence for the testicular vasculature atrophy. Reprod Toxicol. 2015 Nov;57:50-8. doi: 10.1016/j.reprotox.2015.05.009. Epub 2015 May 27. PubMed PMID: 26021711. 18: Koshimizu JY, Beltrame FL, de Pizzol JP Jr, Cerri PS, Caneguim BH, Sasso-Cerri E. NF-kB overexpression and decreased immunoexpression of AR in the muscular layer is related to structural damages and apoptosis in cimetidine-treated rat vas deferens. Reprod Biol Endocrinol. 2013 Apr 9;11:29. doi: 10.1186/1477-7827-11-29. PubMed PMID: 23570504; PubMed Central PMCID: PMC3727959. 19: Jafarzadeh A, Nemati M, Rezayati MT, Ebrahimi M, Hassan ZM. Cimetidine enhances delayed-type hypersensitivity responses and serum interleukin (IL)-2, -10, -12, and IL-17 levels after burn injury in an animal model. J Immunotoxicol. 2013 Apr-Jun;10(2):201-9. doi: 10.3109/1547691X.2012.708365. Epub 2012 Sep 5. PubMed PMID: 22946962. 20: Li B, Cao F, Zhu Q, Li B, Gan M, Wang D. Perioperative cimetidine administration improves systematic immune response and tumor infiltrating lymphocytes in patients with colorectal cancer. Hepatogastroenterology. 2013 Mar-Apr;60(122):244-7. PubMed PMID: 22944376.