Basic information
- CAS
34580-14-8- Standard SMILES
CN1CCC(=C2c3ccccc3CC(=O)c3sccc32)CC1.O=C(O)/C=C/C(=O)O- InChIKey
YNQQEYBLVYAWNX-WLHGVMLRSA-N- Molecular formula
- C23H23NO5S
- Average molar mass
- 425.5 g/mol
- Monoisotopic mass
- 425.12969401
Overview
Ketotifen Fumarate is the fumarate salt of ketotifen, a cycloheptathiophene derivative with anti-allergic activity. Ketotifen selectively blocks histamine (H1) receptors and prevents the typical symptoms caused by histamine release. This agent also interferes with the release of inflammatory mediators from mast cells involved in hypersensitivity reactions, thereby decreasing chemotaxis and activation of eosinophils.
Names & identifiers
- Preferred name
- Ketotifen Fumarate
- IUPAC
- (E)-but-2-enedioic acid;2-(1-methylpiperidin-4-ylidene)-6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-8-one
- English name
- Ketotifen fumarate
- Molecular formula
- C23H23NO5S
- Molecular weight
- 425.5
Names & synonyms
KETOTIFEN FUMARATE34580-14-8ZaditenKetotifen hydrogen fumarateZaditorAlawayHC 20,511 fumarateKetotifen (as fumarate)HC-20511 fumarateHBD503WOROItchy EyeEye Itch
Show more names
Ketotifene fumarate4,9-Dihydro-4-(1-methyl-4-piperidylidene)-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one fumarateketotifen fuMaratKETOTIFEN FUMARATE EP10H-Benzo4,5cyclohepta1,2-bthiophen-10-one, 4,9-dihydro-4-(1-methyl-4-piperidinylidene)-, (2E)-2-butenedioate (1:1)4-(1-Methylpiperidin-4-ylidene)-4,9-dihydro-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one hydrogen (E)-butenedioateZastenTotifen
Eye Itch ReleifEye Itch ReliefNSC-757415DTXSID3089297010H-Benzo(4,5)cyclohepta(1,2-b)thiophen-10-one, 4,9-dihydro-4-(1-methyl-4-piperidinylidene)-, (E)-2-butenedioate (1:1)10H-Benzo[4,5]cyclohepta[1,2-b]thiophen-10-one, 4,9-dihydro-4-(1-methyl-4-piperidinylidene)-, (E)-2-butenedioate (1:1)CHEBI:31750Allergy Eye Drops
Database identifiers
Properties
Computed structural properties
- Topological polar surface area
- 123 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 595
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Allergic Agents; Antihistamines; Antipruritics
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section177.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 192 C · 192 C
- storage temp.
- 2 · 2-8°C
- solubility
- Sparingly soluble in water, slightly soluble in methanol, very slightly soluble in acetonitrile.
- form
- Solid
- color
- White to Pale Beige
- PH
- pH (10g/l, 25℃) : 3.0～4.0
- Water Solubility
- Soluble in water (10 mg/ml), DMSO (100 mM), and methanol.
- λmax
- 297 nm · 297nm(MeOH)(lit.)
- Merck
- 14 · 14,5307
- Major Application
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 51% (53 of 104) of all reports.
Warning
H302 (49%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 104 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationKetotifen fumarate: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 10H-Benzo[4,5]cyclohepta[1,2-b]thiophen-10-one, 4,9-dihydro-4-(1-methyl-4-piperidinylidene)-, (E)-2-butenedioate (1:1): Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (49%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- 3
- rtecs
- DE8260000
- hs_code
- 29349990
- Toxicity
- child,TDLo,oral,200ug/kg (0.2mg/kg),Drug Safety. Vol. 7, Pg. 387, 1992.
- risk_code
- 22-36/37/38-23/24/25
- Signal word
- Warning
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
KETOTIFEN FUMARATE
Histamine-1 Receptor Inhibitor [EPC]; Histamine H1 Receptor Antagonists [MoA]
MeSH Pharmacological Classification
Agents, usually topical, that relieve itching (pruritus).
Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.
Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475)
Applications
DescriptionKetotifen is a histamine H1 receptor antagonist (Ki = 1.3 nM) and mast cell stabilizer. It is selective for H1 receptors over H2 and H3 receptors (Kis = 987 and 2,500 nM, respectively). Ketotifen (50 and 100 μM) inhibits degranulation of rat peritoneal mast cells induced by compound 48/80 . It inhibits the passive cutaneous anaphylaxis (PCA) reaction in rats by 54.6% when administered orally at a dose of 20 mg/kg. Ketotifen (30 mg/kg) inhibits the quick phase airway response in a rat ovalbumin-induced immediate airway response model. Formulations containing ketotifen have been used in the treatment of itching associated with allergic conjunctivitis.
Usesvasodilator
UsesKetotifen fumarate salt has been used: for mast cell product antagonism, as a positive control in β-hexosaminidase release assay, as mast cell stabilizer to treat pregnant dams added to ad libitum drinking water
UsesAntiasthmatic; antiallergic.
Related reactions
1 records
Compound notes
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