Azasetron

Azasetron
Clinical data
Trade names	Serotone
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral, intravenous
ATC code	none;
Pharmacokinetic data
Bioavailability	90%
Excretion	60-70%
Identifiers
	IUPAC name N-(1-azabicyclo[2.2.2]octan-8-yl)-6-chloro-4-methyl-3-oxo-1,4-benzoxazine-8-carboxamide;
CAS Number	123040-69-7;
PubChem CID	2264;
IUPHAR/BPS	2285;
ChemSpider	2177 ;
UNII	77HC7URR9Z;
KEGG	D07481 ;
ChEMBL	ChEMBL1598608;
CompTox Dashboard (EPA)	DTXSID7045651 ;
Chemical and physical data
Formula	C17H20ClN3O3
Molar mass	349.82 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1C(=O)COc2c1cc(Cl)cc2C(=O)NC3CN4CCC3CC4;
	InChI InChI=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) ; Key:WUKZPHOXUVCQOR-UHFFFAOYSA-N ;
	(verify)

Azasetron is an antiemetic which acts as a 5-HT₃ receptor antagonist, pK_i = 9.27 ^[1] It is used in the management of nausea and vomiting induced by cancer chemotherapy (such as cisplatin chemotherapy). Azasetron hydrochloride is given in a usual dose of 10 mg once daily by mouth or intravenously. It is approved for marketing in Japan, and marketed exclusively by Torii Pharmaceutical Co., Ltd. under the trade names "Serotone I.V. Injection 10 mg" and "Serotone Tablets 10 mg".^[2] Pharmacokinetics data from S. Tsukagoshi.^[3]

Arazasetron besylate (SENS-401) is an investigational drug formulation containing exclusively the R-enantiomer of azasetron. The compound has been studied to prevent hearing loss related to sudden sensorineural hearing loss (SSNHL),^[4] acoustic trauma,^[5] and cisplatin-induced ototoxicity.^[4]^[6]

References

^ "Azasetron". drugcentral.org/. UNM School of Medicine. 2016-07-31. Retrieved 2016-11-11.
^ "Torii Pharmaceutical to Solely Market Antiemetic Drugs". Torii Pharmaceutical Co Ltd. 2009-01-13. Archived from the original on 2014-06-13. Retrieved 2016-11-11.
^ Tsukagoshi S (June 1999). "[Pharmacokinetics of azasetron (Serotone), a selective 5-HT3 receptor antagonist]". Gan to Kagaku Ryoho. Cancer & Chemotherapy. 26 (7): 1001–1008. PMID 10396331.
^ ^a ^b "Drug and Device News". P & T. 42 (10): 608–651. October 2017. PMC 5614410. PMID 29018295. SENS-401 for Platinum-Induced Ototoxicity Sensorion has received the FDAs orphan drug designation for SENS-401 for the prevention of platinum-induced ototoxicity in pediatric patients. As many as 60% of patients develop severe hearing loss due to platinum-based chemo therapies. There is no approved pharmaceutical treatment. SENS-401 (R-azasetron besylate) is designed to protect and preserve inner ear tissue when lesions may cause progressive hearing impairments. The drug (both oral and injectable) is also in development for the treatment of sudden sensorineural hearing loss. Sensorion expects to initiate a phase 2 clinical trial in this indication in the first half of 2018.
^ Petremann M, Romanet C, Broussy A, Van Ba CT, Poli S, Dyhrfjeld-Johnsen J (February 2019). "SENS-401 Effectively Reduces Severe Acoustic Trauma-Induced Hearing Loss in Male Rats With Twice Daily Administration Delayed up to 96hours". Otology & Neurotology. 40 (2). Ovid Technologies (Wolters Kluwer Health): 254–263. doi:10.1097/mao.0000000000002088. PMID 30570608. S2CID 58575416.
^ Petremann M, Tran Van Ba C, Broussy A, Romanet C, Dyhrfjeld-Johnsen J (October 2017). "Oral Administration of Clinical Stage Drug Candidate SENS-401 Effectively Reduces Cisplatin-induced Hearing Loss in Rats". Otology & Neurotology. 38 (9). Ovid Technologies (Wolters Kluwer Health): 1355–1361. doi:10.1097/mao.0000000000001546. PMID 28796092. S2CID 20081426.

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[1] "Azasetron". drugcentral.org/. UNM School of Medicine. 2016-07-31. Retrieved 2016-11-11.

[2] "Torii Pharmaceutical to Solely Market Antiemetic Drugs". Torii Pharmaceutical Co Ltd. 2009-01-13. Archived from the original on 2014-06-13. Retrieved 2016-11-11.

[3] Tsukagoshi S (June 1999). "[Pharmacokinetics of azasetron (Serotone), a selective 5-HT3 receptor antagonist]". Gan to Kagaku Ryoho. Cancer & Chemotherapy. 26 (7): 1001–1008. PMID 10396331.

[Pharmacy_and_Therapeutics_2022-4] "Drug and Device News". P & T. 42 (10): 608–651. October 2017. PMC 5614410. PMID 29018295. SENS-401 for Platinum-Induced Ototoxicity Sensorion has received the FDAs orphan drug designation for SENS-401 for the prevention of platinum-induced ototoxicity in pediatric patients. As many as 60% of patients develop severe hearing loss due to platinum-based chemo therapies. There is no approved pharmaceutical treatment. SENS-401 (R-azasetron besylate) is designed to protect and preserve inner ear tissue when lesions may cause progressive hearing impairments. The drug (both oral and injectable) is also in development for the treatment of sudden sensorineural hearing loss. Sensorion expects to initiate a phase 2 clinical trial in this indication in the first half of 2018.

[Petremann_2019-5] Petremann M, Romanet C, Broussy A, Van Ba CT, Poli S, Dyhrfjeld-Johnsen J (February 2019). "SENS-401 Effectively Reduces Severe Acoustic Trauma-Induced Hearing Loss in Male Rats With Twice Daily Administration Delayed up to 96hours". Otology & Neurotology. 40 (2). Ovid Technologies (Wolters Kluwer Health): 254–263. doi:10.1097/mao.0000000000002088. PMID 30570608. S2CID 58575416.

[Petremann_2017-6] Petremann M, Tran Van Ba C, Broussy A, Romanet C, Dyhrfjeld-Johnsen J (October 2017). "Oral Administration of Clinical Stage Drug Candidate SENS-401 Effectively Reduces Cisplatin-induced Hearing Loss in Rats". Otology & Neurotology. 38 (9). Ovid Technologies (Wolters Kluwer Health): 1355–1361. doi:10.1097/mao.0000000000001546. PMID 28796092. S2CID 20081426.

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