1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride
Synonym(s):[3S-[1(cis),3α,4β]]-1-[4-cyano-4-(4-fluorophenyl)cyclohexyl]-3-methyl-4-phenyl-4-piperidinecarboxylic acid;Levocabastine hydrochloride;Levophta;Levostin;R50547
- CAS NO.:79547-78-7
- Empirical Formula: C26H30ClFN2O2
- Molecular Weight: 456.99
- MDL number: MFCD07787408
- EINECS: 209-062-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-06-08 09:02:49
What is 1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride?
Description
Levocabastine hydrochloride is a new, highly potent and specific histamine HI-receptor antagonist without anticholinergic or antiserotonergic side effects. It is reported to have both a fast onset and long duration of action. Indications are the treatment of allergic conjunctivitis and allergic rhinitis.
Chemical properties
White or almost white powder.
Originator
Janssen (Johnson & Johnson) (U.S.A.)
The Uses of 1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride
A histamine H1 receptor antagonist
The Uses of 1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride
A histamine H1 receptor antagonist used in allergic conjunctivitis.
What are the applications of Application
Levocabastine Hydrochloride is a histamine H1 receptor antagonist and anti-allergic agent
Definition
ChEBI: Livostin (TN) is a member of piperidines.
Manufacturing Process
4-Cyano-4-(4-fluorophenyl)-heptanedioic acid diethyl ester is obtained by addition of ethyl acrylate to the anion from p-fluorophenylacetonitrile. By base catalyzed cyclization of these diester (sodium methoxide, 60°C, xylene) is synthesized an intermediate that after decarboethoxylation gives 1-(4- fluorophenyl)-4-oxycyclohexanecarbonitrile. By condensation of 3-methyl-5- phenylpiperidine-4-carboxylic acid benzyl ester and 1-(4-fluorophenyl)-4- oxycyclohexanecarbonitrile under reductive hydrogenation conditions (palladium-on-charcoal catalyst, 50°C, in ethanol) is prepared benzyl ester 4- piperidinecarboxylic acid, 1-(4-cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl- 4-phenyl-, (3S-(1(cis),3α,4β))-. The benzyl protecting group is then removed by hydrogenation method and 4-piperidinecarboxylic acid, 1-(4-cyano-4-(4- fluorophenyl)cyclohexyl)-3-methyl-4-phenyl-, (3S-(1(cis),3α,4β))- obtained is transformed into 4-piperidinecarboxylic acid, 1-(4-cyano-4-(4-fluorophenyl) cyclohexyl)-3-methyl-4-phenyl-, hydrochloride, (3S-(1(cis), 3α,4β))- (Levocabastine hydrochloride)
brand name
Livostin (Novartis).
Therapeutic Function
Antihistaminic
Properties of 1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride
storage temp. | 2-8°C |
solubility | DMSO: ~10 mg/mL, soluble |
form | solid |
color | white |
Safety information for 1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 1-(4-Cyano-4-(4-fluorophenyl)cyclohexyl)-3-methyl-4-phenylpiperidine-4-carboxylic acid monohydrochloride
Abamectin manufacturer
Sanvin Group of Companies (Pioneer Agro Industries)
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