Basic information
- CAS
90729-43-4- Standard SMILES
CC(C)(C)c1ccc(C(=O)CCCN2CCC(OC(c3ccccc3)c3ccccc3)CC2)cc1- InChIKey
MJJALKDDGIKVBE-UHFFFAOYSA-N- Molecular formula
- C32H39NO2
- Average molar mass
- 469.7 g/mol
- Monoisotopic mass
- 469.29807949
Overview
Ebastine is an organic molecular entity.
Names & identifiers
- Preferred name
- Ebastine
- IUPAC
- 4-(4-benzhydryloxypiperidin-1-yl)-1-(4-tert-butylphenyl)butan-1-one
- English name
- Ebastine
- Molecular formula
- C32H39NO2
- Molecular weight
- 469.66
Names & synonyms
ebastine90729-43-4KestineEbastinaEbastinumRP 64305DTXSID6046472LAS-W-090TQD7Q784P1RP-64305DTXCID40264724-Diphenylmethoxy-1-(3-(4-tert-butylbenzoyl)propyl)piperidine
Show more names
LAS-90EbasineEVASTEL
RefChem:590526R06AX221-(4-(1,1-Dimethylethyl)phenyl)-4-(4-(diphenylmethoxy)piperidin-1-yl)butan-1-one635-609-6EbastelEbastinEstivan4-(4-(benzhydryloxy)piperidin-1-yl)-1-(4-(tert-butyl)phenyl)butan-1-one
Database identifiers
- CAS
90729-43-4- PubChem CID
- 3191
- DTXSID
DTXSID6046472- ChEMBL
CHEMBL305660- ChEBI
CHEBI:31528- UNII
- TQD7Q784P1
- EC Number
- 635-609-6
- Nikkaji
- J22.761G
Properties
Computed structural properties
- XLogP
- 7.2
- Topological polar surface area
- 29.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 10
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 594
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Antihistamines; Milk, Human; Nonsedating Antihistamines
Physicochemical properties
- Melting point
- 80 · 80-82°C
- Boiling point
- 596.3 · 596.3±50.0 °C(Predicted)
- Density
- 1.09 · 1.09±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- Slightly soluble in chloroform, methanol.
- pka
- 8.19 · 8.19±0.10(Predicted)
- form
- solid
- color
- white
- Merck
- 14 · 14,3484
- InChIKey
- MJJALKDDGIKVBE-UHFFFAOYSA-N
- SMILES
- C(C1=CC=C(C(C)(C)C)C=C1)(=O)CCCN1CCC(OC(C2=CC=CC=C2)C2=CC=CC=C2)CC1
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
H413 (97.6%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]
P273, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAquatic Chronic 4 (97.6%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
EBASTINE
DILI Positive
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- EL8140000
- hs_code
- 2933.39.9200
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H303
- Precautionary statements
- P270-P301+P312-P403-P501c
Chemistry & industry
Pharmacology
ATC Code
R06AX22
R - Respiratory system
QR - Respiratory system
Mechanism of ActionEbastine is a second-generation antihistamine that acts as a selective histamine H1-receptor antagonist to relieve allergic symptoms.
Metabolism/MetabolitesEbastine has known human metabolites that include Deslakylebastine and 4-(4-tert-butylphenyl)-4-oxobutanal.
MeSH Pharmacological Classification
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.
Cellular LocationsMembrane
Metabolite PathwaysEbastine H1-Antihistamine Action
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >100
Applications
DescriptionEbastine belongs to an effective second generation histamine H1 receptor antagonist. One important property of it is that it doesn’t penetrate the blood brain barrier. Therefore, it is capable of blocking the H1 receptor in peripheral tissue without having some specific side effects such as sedation and drowsiness. Ebastine is mainly applied for the treatment of allergic rhinitis, pruritus as well as acting as an alternative drug in Decongestant. Upon entering into the human body, it can subject to the action of hepatic cytochrome P450 3A4 to be converted to an active carboxylic acid metabolite, carebastine. The later one is the major active form in vivo. Under certain range, it can inhibit T cell proliferation and the production of Th2-type pro-inflammatory cytokines through macrophages. Ebastine generally has a high safety property without causing cognitive/psychomotor impairment and sedation, like placebo. However, it can cause side effects such as inflammation of the air-cavities around nose, sore throat, indigestion, nausea, headache, and abdominal pain.
Related reactions
3 records
Compound notes
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