Ketotifen fumarate
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MedKoo CAT#: 318082

CAS#: 34580-14-8 (fumarate);

Description: Ketotifen is a second-generation noncompetitive H1 antihistamine and mast cell stabilizer. It is most commonly sold as a salt with fumaric acid, ketotifen fumarate, and is available in two forms. In its ophthalmic form, it is used to treat allergic conjunctivitis, or the itchy red eyes caused by allergies. In its oral form, it is used to prevent asthma attacks.


Chemical Structure

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Ketotifen fumarate
CAS# 34580-14-8 (fumarate);

Theoretical Analysis

MedKoo Cat#: 318082
Name: Ketotifen fumarate
CAS#: 34580-14-8 (fumarate);
Chemical Formula: C23H23NO5S
Exact Mass: 0.00
Molecular Weight: 425.499
Elemental Analysis: C, 64.92; H, 5.45; N, 3.29; O, 18.80; S, 7.53

Price and Availability

Size Price Availability Quantity
100mg USD 250 2 Weeks
250mg USD 450 2 Weeks
1g USD 850 2 Weeks
Bulk inquiry

Related CAS #: 34580-14-8 (fumarate); 34580-13-7 (free base)  

Synonym: Ketotifen, Ketotifene, Zaditor, Zaditen, Ketotiphen

IUPAC/Chemical Name: 4-(1-methylpiperidin-4-ylidene)-4,9-dihydro-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one fumarate

InChi Key: YNQQEYBLVYAWNX-WLHGVMLRSA-N

InChi Code: InChI=1S/C19H19NOS.C4H4O4/c1-20-9-6-13(7-10-20)18-15-5-3-2-4-14(15)12-17(21)19-16(18)8-11-22-19;5-3(6)1-2-4(7)8/h2-5,8,11H,6-7,9-10,12H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1+

SMILES Code: O=C(C1=C/2C=CS1)CC3=CC=CC=C3C2=C4CCN(C)CC/4.O=C(O)/C=C/C(O)=O

Appearance: White to off-white solid powder.

Purity: >95% (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:

Product Data:
Biological target: Ketotifen (HC 20-511) fumarate is an orally active second-generation noncompetitive histamine 1 (H1) receptor blocker and mast cell stabilizer. Ketotifen fumarate can block 6-phosphogluconate dehydrogenase (PGD) in vitro.
In vitro activity: Ket also triggered an evident lymphadenomegaly due to accumulation of T cells that produced higher levels of encephalitogenic cytokines in response to in vitro stimulation with MOG. Altogether these findings reinforce the concept that mast cells are particularly relevant in MS immunopathogenesis and that Ket, a known stabilizer of their activity, has the potential to be used in MS control. Reference: Neurotherapeutics. 2020 Jan;17(1):218-234. https://pubmed.ncbi.nlm.nih.gov/31463682/
In vivo activity: In the guinea-pig colon ketotifen evoked non-cholinergic contractions with a pD2 of 4.5, but still it inhibited responses to bradykinin (IC50 = 75 microM). Ketotifen relaxed the unstimulated mouse colon with a pD2 of 4.2. Reference: Eur J Pharmacol. 1996 Aug 8;309(2):189-93. https://pubmed.ncbi.nlm.nih.gov/8874138/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 58.75
DMSO 43.9 103.14
DMSO:PBS (pH 7.2) (1:2) 0.3 0.71
Ethanol 0.5 1.18
Water 16.7 39.18

Preparing Stock Solutions

The following data is based on the product molecular weight 425.50 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
Formulation protocol: 1. Pinke KH, Zorzella-Pezavento SFG, de Campos Fraga-Silva TF, Mimura LAN, de Oliveira LRC, Ishikawa LLW, Fernandes AAH, Lara VS, Sartori A. Calming Down Mast Cells with Ketotifen: A Potential Strategy for Multiple Sclerosis Therapy? Neurotherapeutics. 2020 Jan;17(1):218-234. doi: 10.1007/s13311-019-00775-8. PMID: 31463682; PMCID: PMC7007452. 2. Rezaei F, Ebrahimzadeh MA, Daryani A, Sharif M, Ahmadpour E, Sarvi S. The inhibitory effect of cromolyn sodium and ketotifen on Toxoplasma gondii entrance into host cells in vitro and in vivo. J Parasit Dis. 2016 Sep;40(3):1001-5. doi: 10.1007/s12639-014-0623-3. Epub 2014 Dec 20. PMID: 27605827; PMCID: PMC4996236. 3. Huang Z, Wang G, Yang B, Li P, Yang T, Wu Y, Yang X, Liu J, Li J. Mechanism of ketotifen fumarate inhibiting renal calcium oxalate stone formation in SD rats. Biomed Pharmacother. 2022 Jul;151:113147. doi: 10.1016/j.biopha.2022.113147. Epub 2022 May 25. PMID: 35643070. 4. Abu-Dalu R, Zhang JM, Hanani M. The actions of ketotifen on intestinal smooth muscles. Eur J Pharmacol. 1996 Aug 8;309(2):189-93. doi: 10.1016/0014-2999(96)00342-1. PMID: 8874138.
In vitro protocol: 1. Pinke KH, Zorzella-Pezavento SFG, de Campos Fraga-Silva TF, Mimura LAN, de Oliveira LRC, Ishikawa LLW, Fernandes AAH, Lara VS, Sartori A. Calming Down Mast Cells with Ketotifen: A Potential Strategy for Multiple Sclerosis Therapy? Neurotherapeutics. 2020 Jan;17(1):218-234. doi: 10.1007/s13311-019-00775-8. PMID: 31463682; PMCID: PMC7007452. 2. Rezaei F, Ebrahimzadeh MA, Daryani A, Sharif M, Ahmadpour E, Sarvi S. The inhibitory effect of cromolyn sodium and ketotifen on Toxoplasma gondii entrance into host cells in vitro and in vivo. J Parasit Dis. 2016 Sep;40(3):1001-5. doi: 10.1007/s12639-014-0623-3. Epub 2014 Dec 20. PMID: 27605827; PMCID: PMC4996236.
In vivo protocol: 1. Huang Z, Wang G, Yang B, Li P, Yang T, Wu Y, Yang X, Liu J, Li J. Mechanism of ketotifen fumarate inhibiting renal calcium oxalate stone formation in SD rats. Biomed Pharmacother. 2022 Jul;151:113147. doi: 10.1016/j.biopha.2022.113147. Epub 2022 May 25. PMID: 35643070. 2. Abu-Dalu R, Zhang JM, Hanani M. The actions of ketotifen on intestinal smooth muscles. Eur J Pharmacol. 1996 Aug 8;309(2):189-93. doi: 10.1016/0014-2999(96)00342-1. PMID: 8874138.

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1: Schwarzer G, Bassler D, Mitra A, Ducharme FM, Forster J. Ketotifen alone or as additional medication for long-term control of asthma and wheeze in children. Cochrane Database Syst Rev. 2004;(1):CD001384. Review. PubMed PMID: 14973969.

2: Pérez-Padilla JR. [Ketotifen (Zaditen and K-Asthmal): a drug with sales disproportionate to its demonstrated effectiveness]. Gac Med Mex. 1999 Mar-Apr;135(2):165-70. Review. Spanish. PubMed PMID: 10327750.

3: Grant SM, Goa KL, Fitton A, Sorkin EM. Ketotifen. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in asthma and allergic disorders. Drugs. 1990 Sep;40(3):412-48. Review. Erratum in: Drugs 1991 Feb;41(2):192. PubMed PMID: 2226222.

4: Oehling A, Castillo JG, Gamboa PM. Membrane IgE and adenyl cyclase activity in the dynamics of bronchospasm. Ketotifen as a blocker of antigen action. Allergol Immunopathol (Madr). 1990 Jul-Aug;18(4):237-40. Review. PubMed PMID: 1702264.

5: Nowak D, Magnussen H. [Ketotifen (Zaditen) and disodium cromoglycinic acid (Intal) in the therapy of bronchial asthma]. Prax Klin Pneumol. 1987 Sep;41(9):319-23. Review. German. PubMed PMID: 3124092.

6: Craps L. Prophylaxis of asthma with ketotifen in children and adolescents: a review. Pharmatherapeutica. 1983;3(5):314-26. Review. PubMed PMID: 6405397.

7: Craps L. [Ketotifen in the prevention of bronchial asthma. International therapeutic evaluation]. Allergol Immunopathol (Madr). 1981;Suppl 9:177-90. Review. French. PubMed PMID: 6131598.

8: Doligalska M. [Effect of ketotifen on the immune response in BALB/c mice infected with Trichinella spiralis]. Wiad Parazytol. 2000;46(2):217-24. Review. Polish. PubMed PMID: 16886340.

9: Paquette D, Rothe MJ. Unapproved dermatologic indications for H2 receptor antagonists, cromolyn sodium, and ketotifen. Clin Dermatol. 2000 Jan-Feb;18(1):103-11. Review. PubMed PMID: 10701091.

10: Mancel E, Drouet M, Sabbah A. [Membrane stabilizers (chromones and ketotifen)]. Allerg Immunol (Paris). 1999 Apr;31(4):103-5. Review. French. PubMed PMID: 10370721.

11: Govil YC, Misra PK. Ketotifen. Indian Pediatr. 1992 Jan;29(1):85-9. Review. PubMed PMID: 1601503.

12: Lieberman D, Lieberman D. [Prophylaxis of bronchial asthma--disodium cromoglycate and ketotifen]. Harefuah. 1987 May 1;112(9):462-6. Review. Hebrew. PubMed PMID: 3117649.

13: Warner JO, Goldsworthy SJ. Ketotifen in childhood allergic disease. Clin Allergy. 1982 Oct;12 Suppl:21-7. Review. PubMed PMID: 6814787.

14: Craps L. Ketotifen in the oral prophylaxis of bronchial asthma: a review. Pharmatherapeutica. 1981;3(1):18-35. Review. PubMed PMID: 6119703.