Azasetron

Azasetron is an antiemetic which acts as a 5-HT3 receptor antagonist, pKi = 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]

Azasetron
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
  • none
Pharmacokinetic data
Bioavailability90%
Excretion60-70%
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
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H20ClN3O3
Molar mass349.82 g·mol−1
3D model (JSmol)
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) Y
  • Key:WUKZPHOXUVCQOR-UHFFFAOYSA-N Y
  (verify)

R-azasetron besylate (SENS-401) 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
  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): 10011008. PMID 10396331.
  4. "Drug and Device News". P & T. 42 (10): 608651. 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.
  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. Ovid Technologies (Wolters Kluwer Health). 40 (2): 254263. doi:10.1097/mao.0000000000002088. PMID 30570608.
  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. Ovid Technologies (Wolters Kluwer Health). 38 (9): 13551361. doi:10.1097/mao.0000000000001546. PMID 28796092.
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