Ketotifen

Modify Date: 2024-01-03 11:56:41

Ketotifen structure	Common Name	Ketotifen
	CAS Number	34580-13-7	Molecular Weight	309.42500
	Density	1.236g/cm3	Boiling Point	488.9ºC at 760mmHg
	Molecular Formula	C₁₉H₁₉NOS	Melting Point	152-153ºC
	MSDS	N/A	Flash Point	249.5ºC

Use of Ketotifen

Ketotifen (HC 20-511) is an orally active second-generation noncompetitive histamine 1 (H1) receptor blocker and mast cell stabilizer. Ketotifen can block 6-phosphogluconate dehydrogenase (PGD) in vitro. Ketotifen also has antiviral activity against SARS-CoV-2 and Influenza virus. Ketotifen can be used to the research of autoimmune encephalomyelitis (EAE) and asthma attack prevention[1][2][3][4].

Name	10-(1-methylpiperidin-4-ylidene)-5H-benzo[1,2]cyclohepta[3,4-b]thiophen-4-one
Synonym	More Synonyms

Description	Ketotifen (HC 20-511) is an orally active second-generation noncompetitive histamine 1 (H1) receptor blocker and mast cell stabilizer. Ketotifen can block 6-phosphogluconate dehydrogenase (PGD) in vitro. Ketotifen also has antiviral activity against SARS-CoV-2 and Influenza virus. Ketotifen can be used to the research of autoimmune encephalomyelitis (EAE) and asthma attack prevention[1][2][3][4].
Related Catalog	Signaling Pathways >> Anti-infection >> Influenza Virus Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor Research Areas >> Endocrinology Research Areas >> Infection Signaling Pathways >> Anti-infection >> SARS-CoV Research Areas >> Inflammation/Immunology Signaling Pathways >> GPCR/G Protein >> Histamine Receptor
Target	Histamine 1, SARS-CoV-2, Influenza virus[1][3][4]
In Vitro	Ketotifen (0-100 μM; 2 or 4 days) inhibits SARS-CoV-2 with an EC50 of 48.9 μM; and increases the percentage inhibition of SARS-CoV-2 to 79%, 83% and 93% when co-administers with 25, 50 and 100 μM Indomethacin, respectively[3]. Ketotifen (0-50 μM; 24 h) has inhibitory activity against PR8, pH1N1 and H3N2 with EC50s of 5.9 μM, 33.7 μM and 48.5 μM, respectively; and exhibits relatively low cytotoxicity in MDCK cells (EC50=291 μM)[4].
In Vivo	Ketotifen (80 mg/kg; i.g.; daily for 3 days) reduces end organ damage and mortality in mice infected with influenza virus[4]. Ketotifen (0.4 mg/kg; i.p.; daily for 10 days) reduces encephalomyelitis (EAE) prevalence and severity[5]. Animal Model: Female C57BL/6 mice (4-6 weeks; intranasal infection with 1×103 TCID50 of PR8 in 30 μL of DMEM)[4] Dosage: 80 mg/kg Administration: i.g.; daily for 3 days Result: Reduced end organ damage and mortality in infected mice. Animal Model: Female C57BL/6 mice (5-6 weeks old; subcutaneously immunized with 150 μg of MOG35-55 peptide containing 4 mg/mL of Mycobacterium tuberculosis)[5] Dosage: 0.4 mg/kg Administration: i.p.; daily for 10 days (from the 7th day of infection) Result: Reduced EAE prevalence and severity; reduced oxidative stress status and inflammasome activation at the CNS; reduced the amount of T cells, especially Th1, in the CNS; downregulated local mRNA expression for mast cell enzymes and preserves blood-CNS barrier permeability; triggered lymphocyte accumulation in draining lymph nodes.
References	[1]. Klooker TK, et al. The mast cell stabiliser ketotifen decreases visceral hypersensitivity and improves intestinal symptoms in patients with irritable bowel syndrome. Gut. 2010 Sep;59(9):1213-21. [2]. Zhang H, et al. Advances in the discovery of exosome inhibitors in cancer. J Enzyme Inhib Med Chem. 2020;35(1):1322-1330. [3]. Kiani P, et al. In Vitro Assessment of the Antiviral Activity of Ketotifen, Indomethacin and Naproxen, Alone and in Combination, against SARS-CoV-2. Viruses. 2021 Mar 26;13(4):558. [4]. Enkirch T, et al. Identification and in vivo Efficacy Assessment of Approved Orally Bioavailable Human Host Protein-Targeting Drugs With Broad Anti-influenza A Activity. Front Immunol. 2019 Jun 5;10:1097. [5]. Pinke KH, et al. Calming Down Mast Cells with Ketotifen: A Potential Strategy for Multiple Sclerosis Therapy? Neurotherapeutics. 2020 Jan;17(1):218-234.

Density	1.236g/cm3
Boiling Point	488.9ºC at 760mmHg
Melting Point	152-153ºC
Molecular Formula	C₁₉H₁₉NOS
Molecular Weight	309.42500
Flash Point	249.5ºC
Exact Mass	309.11900
PSA	48.55000
LogP	3.95230

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DE8255000

CHEMICAL NAME :: 10H-Benzo(4,5)cyclohepta(1,2-b)thiophen-10-one, 4,9-dihydro-4-(1-methyl-4-piperidinylidene)-

CAS REGISTRY NUMBER :: 34580-13-7

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C19-H19-N-O-S

MOLECULAR WEIGHT :: 309.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 179 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 30,13,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 108 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 30,13,1987

Hazard Codes	Xn

Precursor 9
CAS#:59743-88-3 4H-Benzo[4,5]cy... CAS#:126939-27-3 10-hydroxy-10-(... CAS#:59743-84-9 10-Methoxy-4H-b... CAS#:5570-77-4 4-Chloro-1-meth...
CAS#:34580-12-6 4-(10-bromo-ben... CAS#:1622-55-5 4H-Benzo[4,5]cy... CAS#:34580-10-4 9,10-DIBROMO-9,... CAS#:63463-36-5 magnesium,1-met...
CAS#:34580-11-5 10-bromo-4H-ben...
DownStream 3
CAS#:88456-70-6 10-(1-methyl-1-... CAS#:43076-12-6 10-(1-methylpip... CAS#:43076-16-0 Ketotifen Impurity G