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Arazasetron

Catalog No: 20535
CAS Number: 2025360-90-9
Purity: 98% Min.

Arazasetron is an antiemetic which acts as a 5-HT3 receptor antagonist, pKi = 9.27.

For research use only. We do not sell to patients.

Chemical Information

NameArazasetron
Iupac Chemical NameN-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-6-chloro-4-methyl-3-oxo-1,4-benzoxazine-8-carboxamide
SynonymsR-Azasetron; Azasetron, R; 61JC7L0Q4O; 2025360-90-9; UNII-61JC7L0Q4O
Molecular FormulaC17H20ClN3O3
Molecular Weight349.81
SmileO=C(C1=C(OCC(N2C)=O)C2=CC(Cl)=C1)N[C@H]3CN4CCC3CC4
InChiKeyWUKZPHOXUVCQOR-ZDUSSCGKSA-N
InChiInChI=1S/C17H20ClN3O3/c1-20-14-7-11(18)6-12(16(14)24-9-15(20)22)17(23)19-13-8-21-4-2-10(13)3-5-21/h6-7,10,13H,2-5,8-9H2,1H3,(H,19,23)/t13-/m0/s1
CAS Number2025360-90-9
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Ordering Information

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FormulationSolid powder
Purity98% Min.
StorageDry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
SolubilitySoluble in DMSO
Handling
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
HS Code
Coming soon.
Targets
Mechanism
Cell study
Animal study
Clinical study

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PubMed PMID: 28373467. 4: Koshiyama M, Matsumura N, Imai S, Yamanoi K, Abiko K, Yoshioka Y, Yamaguchi K, Hamanishi J, Baba T, Konishi I. Combination of Aprepitant, Azasetron, and Dexamethasone as Antiemetic Prophylaxis in Women with Gynecologic Cancers Receiving Paclitaxel/Carboplatin Therapy. Med Sci Monit. 2017 Feb 15;23:826-833. PubMed PMID: 28198358; PubMed Central PMCID: PMC5322867. 5: Chen FC, Wang LH, Guo J, Shi XY, Fang BX. Simultaneous Determination of Dexamethasone, Ondansetron, Granisetron, Tropisetron, and Azasetron in Infusion Samples by HPLC with DAD Detection. J Anal Methods Chem. 2017;2017:6749087. doi: 10.1155/2017/6749087. Epub 2017 Jan 11. PubMed PMID: 28168082; PubMed Central PMCID: PMC5266853. 6: Tanaka T, Ago Y, Umehara C, Imoto E, Hasebe S, Hashimoto H, Takuma K, Matsuda T. Role of Prefrontal Serotonergic and Dopaminergic Systems in Encounter-Induced Hyperactivity in Methamphetamine-Sensitized Mice. Int J Neuropsychopharmacol. 2017 May 1;20(5):410-421. doi: 10.1093/ijnp/pyw115. PubMed PMID: 28034961; PubMed Central PMCID: PMC5417057. 7: Han Z, Sun X, Jiang G, Du X. Thalidomide for Control Delayed Vomiting in Cancer Patients Receiving Chemotherapy. J Coll Physicians Surg Pak. 2016 Nov;26(11):900-903. PubMed PMID: 27981924. 8: Sandor ZI, Bencsik T, Dekany A, Bartho L. Serotonin or the Mucosa Do Not Mediate the Motor Effect of Allyl Isothiocyanate in the Guinea-Pig Small Intestine. Pharmacology. 2016;98(5-6):199-203. Epub 2016 Jun 24. PubMed PMID: 27336729. 9: Hashizume J, Higuchi N, Sato K, Kodama Y, Matsunaga N, Sakamoto T, Yamaguchi K, Nakamura T, Kitahara T, Sasaki H. Evaluation of Antiemetic Therapy for Hepatic Transcatheter Arterial Infusion Chemotherapy with Cisplatin. Biol Pharm Bull. 2016;39(4):611-4. doi: 10.1248/bpb.b15-00603. PubMed PMID: 27040634. 10: Ahmadi-Mahmoodabadi N, Nasehi M, Emam Ghoreishi M, Zarrindast MR. Synergistic effect between prelimbic 5-HT3 and CB1 receptors on memory consolidation deficit in adult male Sprague-Dawley rats: An isobologram analysis. Neuroscience. 2016 Mar 11;317:173-83. doi: 10.1016/j.neuroscience.2015.12.010. Epub 2015 Dec 14. PubMed PMID: 26701293. 11: Hasebe S, Ago Y, Nishiyama S, Oka S, Hashimoto H, Takuma K, Matsuda T. Pharmacological profile of encounter-induced hyperactivity in isolation-reared mice. Behav Pharmacol. 2015 Oct;26(7 Spec No):681-90. doi: 10.1097/FBP.0000000000000140. PubMed PMID: 25932719. 12: Nasehi M, Kafi F, Khakpai F, Zarrindast MR. Involvement of the serotonergic system of the ventral hippocampus (CA3) on amnesia induced by ACPA in mice. Behav Brain Res. 2015 Jun 1;286:356-63. doi: 10.1016/j.bbr.2015.03.011. Epub 2015 Mar 11. PubMed PMID: 25771207. 13: Liu J, Tan L, Zhang H, Li H, Liu X, Yan Z, Chen J, Yang H, Zhang D. QoL evaluation of olanzapine for chemotherapy-induced nausea and vomiting comparing with 5-HT3 receptor antagonist. Eur J Cancer Care (Engl). 2015 May;24(3):436-43. doi: 10.1111/ecc.12260. Epub 2014 Nov 18. PubMed PMID: 25404537. 14: Lee HY, Kim HK, Lee KH, Kim BS, Song HS, Yang SH, Kim JH, Kim YH, Kim JG, Kim SW, Kim DW, Kim SY, Park HS. A Randomized Double-Blind, Double-Dummy, Multicenter Trial of Azasetron versus Ondansetron to Evaluate Efficacy and Safety in the Prevention of Delayed Nausea and Vomiting Induced by Chemotherapy. Cancer Res Treat. 2014 Jan;46(1):19-26. doi: 10.4143/crt.2014.46.1.19. Epub 2014 Jan 15. PubMed PMID: 24520219; PubMed Central PMCID: PMC3918522. 15: Nakamura H, Yokoyama H, Takayanagi R, Yoshimoto K, Nakajima A, Okuyama K, Iwase O, Yamada Y. Theoretical evaluation of antiemetic effects of 5-HT3 receptor antagonists for prevention of vomiting induced by cisplatin. Eur J Drug Metab Pharmacokinet. 2015 Mar;40(1):39-44. doi: 10.1007/s13318-014-0175-z. Epub 2014 Jan 28. PubMed PMID: 24470169. 16: Bell R, Duke AA, Gilmore PE, Page D, Bègue L. Anxiolytic-like effects observed in rats exposed to the elevated zero-maze following treatment with 5-HT2/5-HT3/5-HT4 ligands. Sci Rep. 2014 Jan 24;4:3881. doi: 10.1038/srep03881. PubMed PMID: 24457553; PubMed Central PMCID: PMC5379192. 17: Hiramatsu N, Ago Y, Hasebe S, Nishimura A, Mori K, Takuma K, Matsuda T. Synergistic effect of 5-HT1A and σ1 receptor activation on prefrontal dopaminergic transmission under circulating steroid deficiency. Neuropharmacology. 2013 Dec;75:53-61. doi: 10.1016/j.neuropharm.2013.06.026. Epub 2013 Jul 9. PubMed PMID: 23851260. 18: Endo J, Iihara H, Yamada M, Yanase K, Kamiya F, Ito F, Funaguchi N, Ohno Y, Minatoguchi S, Itoh Y. A randomized controlled non-inferiority study comparing the antiemetic effect between intravenous granisetron and oral azasetron based on estimated 5-HT3 receptor occupancy. Anticancer Res. 2012 Sep;32(9):3939-47. PubMed PMID: 22993341. 19: Sun L, Cun D, Yuan B, Cui H, Xi H, Mu L, Chen Y, Liu C, Wang Z, Fang L. Formulation and in vitro/in vivo correlation of a drug-in-adhesive transdermal patch containing azasetron. J Pharm Sci. 2012 Dec;101(12):4540-8. doi: 10.1002/jps.23317. Epub 2012 Sep 12. PubMed PMID: 22972714. 20: Ortega JE, Mendiguren A, Pineda J, Meana JJ. Regulation of central noradrenergic activity by 5-HT(3) receptors located in the locus coeruleus of the rat. Neuropharmacology. 2012 Jun;62(8):2472-9. doi: 10.1016/j.neuropharm.2012.02.018. Epub 2012 Mar 1. PubMed PMID: 22401957.

Chemical Structure

20535 - Arazasetron | CAS 2025360-90-9

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