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From Wikipedia, the free encyclopedia
Cloperastine
Clinical data
Other namesHT-11
AHFS/ Drugs.com International Drug Names
Routes of
administration		 Oral
ATC code
Identifiers
  • 1-[2-[(4-Chlorophenyl)-phenyl-methoxy]ethyl]piperidine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard ( EPA)
ECHA InfoCard 100.020.948 Edit this at Wikidata
Chemical and physical data
FormulaC20H24ClNO
Molar mass329.87 g·mol−1
3D model ( JSmol)
  • Clc1ccc(cc1)C(OCCN2CCCCC2)c3ccccc3
  • InChI=1S/C20H24ClNO/c21-19-11-9-18(10-12-19)20(17-7-3-1-4-8-17)23-16-15-22-13-5-2-6-14-22/h1,3-4,7-12,20H,2,5-6,13-16H2 checkY
  • Key:FLNXBVJLPJNOSI-UHFFFAOYSA-N checkY
 ☒NcheckY  (what is this?)   (verify)

Cloperastine ( INN) or cloperastin, in the forms of cloperastine hydrochloride ( JAN) (brand names Hustazol, Nitossil, Seki) and cloperastine fendizoate, is an antitussive and antihistamine that is marketed as a cough suppressant in Japan, Hong Kong, and in some European countries. [1] [2] [3] It was first introduced in 1972 in Japan, and then in Italy in 1981. [4]

Side effects

Adverse effects may include sedation, drowsiness, heartburn, and thickening of bronchial secretions. [5]

Pharmacology

The precise mechanism of action of cloperastine is not fully clear, but several different biological activities have been identified for the drug, of which include: ligand of the σ1 receptor (Ki = 20 nM) (likely an agonist), [6] GIRK channel blocker (described as "potent"), [7] [8] [9] [10] antihistamine (Ki = 3.8 nM for the H1 receptor), [3] [6] and anticholinergic. [3] [11] It is thought that the latter two properties contribute to side effects, such as sedation and somnolence, while the former two may be involved in or responsible for the antitussive efficacy of cloperastine. [6] [7]

Synthesis

Synthesis: [12] Patents: [13] [14] Isomers: [15] China: [16]

The halogenation of 4-Chlorobenzhydrol [119-56-2] (1) with phosphorus tribromide in tetrachloromethane gives 1-(Bromophenylmethyl)-4-chlorobenzene [948-54-9] (2). Treatment with ethylenechlorohydrin ( 2-Chloroethanol) [107-07-3] (3) gives 1-(4-Chlorobenzhydryl)oxy-2-chloroethane [5321-46-0] (4). Reaction with piperidine (5) completes the synthesis of Cloperastine (6).

See also

References

  1. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 301–. ISBN  978-1-4757-2085-3.
  2. ^ Swiss Pharmaceutial Society, ed. (January 2000). Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 261–. ISBN  978-3-88763-075-1.
  3. ^ a b c Catania MA, Cuzzocrea S (2011). "Pharmacological and clinical overview of cloperastine in treatment of cough". Therapeutics and Clinical Risk Management. 7: 83–92. doi: 10.2147/TCRM.S16643. PMC  3061847. PMID  21445282.
  4. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1103–. ISBN  978-0-8155-1856-3.
  5. ^ Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 29. ISBN  0-8103-7177-4.
  6. ^ a b c Gregori-Puigjané E, Setola V, Hert J, Crews BA, Irwin JJ, Lounkine E, et al. (July 2012). "Identifying mechanism-of-action targets for drugs and probes". Proceedings of the National Academy of Sciences of the United States of America. 109 (28): 11178–83. Bibcode: 2012PNAS..10911178G. doi: 10.1073/pnas.1204524109. PMC  3396511. PMID  22711801.
  7. ^ a b Chung KF, Widdicombe J (30 September 2008). Pharmacology and Therapeutics of Cough. Springer Science & Business Media. pp. 230–. ISBN  9783540798422.
  8. ^ Soeda F, Fujieda Y, Kinoshita M, Shirasaki T, Takahama K (May 2016). "Centrally acting non-narcotic antitussives prevent hyperactivity in mice: Involvement of GIRK channels". Pharmacology, Biochemistry, and Behavior. 144: 26–32. doi: 10.1016/j.pbb.2016.02.006. ISBN  978-3-540-79842-2. OCLC  612742272. PMID  26892760. S2CID  30118634.
  9. ^ Yamamoto G, Soeda F, Shirasaki T, Takahama K (April 2011). "[Is the GIRK channel a possible target in the development of a novel therapeutic drug of urinary disturbance?]". Yakugaku Zasshi. 131 (4): 523–32. doi: 10.1248/yakushi.131.523. PMID  21467791.
  10. ^ Kawaura K, Honda S, Soeda F, Shirasaki T, Takahama K (May 2010). "[Novel antidepressant-like action of drugs possessing GIRK channel blocking action in rats]". Yakugaku Zasshi. 130 (5): 699–705. doi: 10.1248/yakushi.130.699. PMID  20460867.
  11. ^ Korolkovas A (16 August 1988). Essentials of Medicinal Chemistry. Wiley. ISBN  978-0-471-88356-2.
  12. ^ Arnold H, Brock N, Kuhas E, Lorenz D (March 1954). "[Effect of antihistaminic substances. I. Chemical constitution and pharmacological effect of the basic benzhydrylethers]". Arzneimittel-Forschung. 4 (3): 189–194. PMID  13159698.
  13. ^ Anon., GB 1179945  (1970 to Yoshitomi Pharmaceutical).
  14. ^ Anon., GB 670622  (1952 to Parke Davis & Co).
  15. ^ Laura Puricelli, EP 0894794  (1999 to AESCULAPIUS FARMACEUTICI S.r.l.).
  16. ^ 陶文潘, 潘文驰, 潘兴长, 罗泳萍, 樊希祥, CN 104327014A  (2015 to 重庆市恒安化工有限公司).


Stub icon

This drug article relating to the respiratory system is a stub. You can help Wikipedia by expanding it.

Retrieved from " https://en.wikipedia.org/?title=Cloperastine&oldid=1202483634"
From Wikipedia, the free encyclopedia
Cloperastine
Clinical data
Other namesHT-11
AHFS/ Drugs.com International Drug Names
Routes of
administration		 Oral
ATC code
Identifiers
  • 1-[2-[(4-Chlorophenyl)-phenyl-methoxy]ethyl]piperidine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard ( EPA)
ECHA InfoCard 100.020.948 Edit this at Wikidata
Chemical and physical data
FormulaC20H24ClNO
Molar mass329.87 g·mol−1
3D model ( JSmol)
  • Clc1ccc(cc1)C(OCCN2CCCCC2)c3ccccc3
  • InChI=1S/C20H24ClNO/c21-19-11-9-18(10-12-19)20(17-7-3-1-4-8-17)23-16-15-22-13-5-2-6-14-22/h1,3-4,7-12,20H,2,5-6,13-16H2 checkY
  • Key:FLNXBVJLPJNOSI-UHFFFAOYSA-N checkY
 ☒NcheckY  (what is this?)   (verify)

Cloperastine ( INN) or cloperastin, in the forms of cloperastine hydrochloride ( JAN) (brand names Hustazol, Nitossil, Seki) and cloperastine fendizoate, is an antitussive and antihistamine that is marketed as a cough suppressant in Japan, Hong Kong, and in some European countries. [1] [2] [3] It was first introduced in 1972 in Japan, and then in Italy in 1981. [4]

Side effects

Adverse effects may include sedation, drowsiness, heartburn, and thickening of bronchial secretions. [5]

Pharmacology

The precise mechanism of action of cloperastine is not fully clear, but several different biological activities have been identified for the drug, of which include: ligand of the σ1 receptor (Ki = 20 nM) (likely an agonist), [6] GIRK channel blocker (described as "potent"), [7] [8] [9] [10] antihistamine (Ki = 3.8 nM for the H1 receptor), [3] [6] and anticholinergic. [3] [11] It is thought that the latter two properties contribute to side effects, such as sedation and somnolence, while the former two may be involved in or responsible for the antitussive efficacy of cloperastine. [6] [7]

Synthesis

Synthesis: [12] Patents: [13] [14] Isomers: [15] China: [16]

The halogenation of 4-Chlorobenzhydrol [119-56-2] (1) with phosphorus tribromide in tetrachloromethane gives 1-(Bromophenylmethyl)-4-chlorobenzene [948-54-9] (2). Treatment with ethylenechlorohydrin ( 2-Chloroethanol) [107-07-3] (3) gives 1-(4-Chlorobenzhydryl)oxy-2-chloroethane [5321-46-0] (4). Reaction with piperidine (5) completes the synthesis of Cloperastine (6).

See also

References

  1. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 301–. ISBN  978-1-4757-2085-3.
  2. ^ Swiss Pharmaceutial Society, ed. (January 2000). Index Nominum 2000: International Drug Directory. Taylor & Francis. pp. 261–. ISBN  978-3-88763-075-1.
  3. ^ a b c Catania MA, Cuzzocrea S (2011). "Pharmacological and clinical overview of cloperastine in treatment of cough". Therapeutics and Clinical Risk Management. 7: 83–92. doi: 10.2147/TCRM.S16643. PMC  3061847. PMID  21445282.
  4. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 1103–. ISBN  978-0-8155-1856-3.
  5. ^ Schlesser JL (1991). Drugs Available Abroad, 1st Edition. Derwent Publications Ltd. p. 29. ISBN  0-8103-7177-4.
  6. ^ a b c Gregori-Puigjané E, Setola V, Hert J, Crews BA, Irwin JJ, Lounkine E, et al. (July 2012). "Identifying mechanism-of-action targets for drugs and probes". Proceedings of the National Academy of Sciences of the United States of America. 109 (28): 11178–83. Bibcode: 2012PNAS..10911178G. doi: 10.1073/pnas.1204524109. PMC  3396511. PMID  22711801.
  7. ^ a b Chung KF, Widdicombe J (30 September 2008). Pharmacology and Therapeutics of Cough. Springer Science & Business Media. pp. 230–. ISBN  9783540798422.
  8. ^ Soeda F, Fujieda Y, Kinoshita M, Shirasaki T, Takahama K (May 2016). "Centrally acting non-narcotic antitussives prevent hyperactivity in mice: Involvement of GIRK channels". Pharmacology, Biochemistry, and Behavior. 144: 26–32. doi: 10.1016/j.pbb.2016.02.006. ISBN  978-3-540-79842-2. OCLC  612742272. PMID  26892760. S2CID  30118634.
  9. ^ Yamamoto G, Soeda F, Shirasaki T, Takahama K (April 2011). "[Is the GIRK channel a possible target in the development of a novel therapeutic drug of urinary disturbance?]". Yakugaku Zasshi. 131 (4): 523–32. doi: 10.1248/yakushi.131.523. PMID  21467791.
  10. ^ Kawaura K, Honda S, Soeda F, Shirasaki T, Takahama K (May 2010). "[Novel antidepressant-like action of drugs possessing GIRK channel blocking action in rats]". Yakugaku Zasshi. 130 (5): 699–705. doi: 10.1248/yakushi.130.699. PMID  20460867.
  11. ^ Korolkovas A (16 August 1988). Essentials of Medicinal Chemistry. Wiley. ISBN  978-0-471-88356-2.
  12. ^ Arnold H, Brock N, Kuhas E, Lorenz D (March 1954). "[Effect of antihistaminic substances. I. Chemical constitution and pharmacological effect of the basic benzhydrylethers]". Arzneimittel-Forschung. 4 (3): 189–194. PMID  13159698.
  13. ^ Anon., GB 1179945  (1970 to Yoshitomi Pharmaceutical).
  14. ^ Anon., GB 670622  (1952 to Parke Davis & Co).
  15. ^ Laura Puricelli, EP 0894794  (1999 to AESCULAPIUS FARMACEUTICI S.r.l.).
  16. ^ 陶文潘, 潘文驰, 潘兴长, 罗泳萍, 樊希祥, CN 104327014A  (2015 to 重庆市恒安化工有限公司).


Stub icon

This drug article relating to the respiratory system is a stub. You can help Wikipedia by expanding it.

Retrieved from " https://en.wikipedia.org/?title=Cloperastine&oldid=1202483634"

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