Trifluoperazin

Trifluoperazin
(IUPAC) ime
	10-[3-(4-metilpiperazin-1-il)propil]-; 2-(trifluorometil)-10H-fenotiazin
Klinički podaci
AHFS/Drugs.com	Monografija
MedlinePlus	a682121
Identifikatori
CAS broj	117-89-5
ATC kod	N05AB06
PubChem	5566
DrugBank	DB00831
ChemSpider	5365
UNII	214IZI85K3
ChEBI	CHEBI:45951
ChEMBL	CHEMBL422
Hemijski podaci
Formula	C21H24F3N3S
Mol. masa	407,497
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C21H24F3N3S/c1-25-11-13-26(14-12-25)9-4-10-27-17-5-2-3-6-19(17)28-20-8-7-16(15-18(20)27)21(22,23)24/h2-3,5-8,15H,4,9-14H2,1H3 ; Key: ZEWQUBUPAILYHI-UHFFFAOYSA-N
Farmakokinetički podaci
Metabolizam	Hepatički
Poluvreme eliminacije	10–20 sata
Farmakoinformacioni podaci
Trudnoća	C(AU) C(US)
Pravni status	POM (UK) ℞-only (SAD)
Način primene	oralno, IM

Trifluoperazin (Eskazinil, Eskazin, Jatroneural, Modalina, Stelazin, Terfluzin, Trifluoperaz, Triftazin) je tipični antipsihotik iz fenotiazinske hemijske klase.

Farmakologija

Trifluoperazin je centralni simpatolitik,^[5] antagonist dopaminskog receptora,^[6]^[7] sa minimalnim antiholinergičnim dejstvom.^[8]

Hemija

Trifluoperazin (2-trifluorometil-10-[3-(4-metil-1-piperazinil)propil]fenotazin) se sintetiše na sličan način kao i prohlorperazin. Alkilacija se izvodi koristeći 2-trifluorometilfenotazin-4-metil-1-piperazinilpropilhlorid kao supstrat.^[9]^[10]^[11]^[12]^[13]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Huerta-Bahena J, Villalobos-Molina R, García-Sáinz JA (January 1983). „Trifluoperazine and chlorpromazine antagonize alpha 1- but not alpha2- adrenergic effects”. Molecular Pharmacology 23 (1): 67–70. PMID 6135146. Arhivirano iz originala na datum 2021-08-29. Pristupljeno 2009-06-21.
↑ Seeman P, Lee T, Chau-Wong M, Wong K (June 1976). „Antipsychotic drug doses and neuroleptic/dopamine receptors”. Nature 261 (5562): 717–9. Bibcode 1976Natur.261..717S. DOI:10.1038/261717a0. PMID 945467.
↑ Creese I, Burt DR, Snyder SH (1996). „Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs”. The Journal of Neuropsychiatry and Clinical Neurosciences 8 (2): 223–6. PMID 9081563. Arhivirano iz originala na datum 2011-07-27. Pristupljeno 2009-06-21.
↑ Ebadi, Manuchair S (1998). „Trifluoperazine Hydrochloride”. CRC desk reference of clinical pharmacology (illustrated izd.). CRC Press. ISBN 978-0-8493-9683-0. Pristupljeno 2009-06-21.
↑ Craig, P.; Nodiff, E.; Lafferty, J.; Ullyot, G. (1957). „Notes - New Trifluoromethylphenothiazine Derivatives”. Journal of Organic Chemistry 22 (6): 709. DOI:10.1021/jo01357a618.
↑ G.E. Ullyot, U.S. Patent 2.921.069 (1960).
↑ Sharma, H.; Banerjee, S.; Sharma, V.; Mital, R. (1968). „Phenothiazines Exhibiting Lesser Extraparamidal Manifestations”. Journal of Medicinal Chemistry 11 (6): 1244. DOI:10.1021/jm00312a600. PMID 5680054.
↑ P.N. Craig, G.E. Ullyot, DE 1165034 (1956).
↑ B.H. Chung, F. Zimalkowski, Arch. Pharm., 317, 323 (1984).

Vanjske veze

Trifluoperazine bound to proteins

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[5] Huerta-Bahena J, Villalobos-Molina R, García-Sáinz JA (January 1983). „Trifluoperazine and chlorpromazine antagonize alpha 1- but not alpha2- adrenergic effects”. Molecular Pharmacology 23 (1): 67–70. PMID 6135146. Arhivirano iz originala na datum 2021-08-29. Pristupljeno 2009-06-21.

[6] Seeman P, Lee T, Chau-Wong M, Wong K (June 1976). „Antipsychotic drug doses and neuroleptic/dopamine receptors”. Nature 261 (5562): 717–9. Bibcode 1976Natur.261..717S. DOI:10.1038/261717a0. PMID 945467.

[7] Creese I, Burt DR, Snyder SH (1996). „Dopamine receptor binding predicts clinical and pharmacological potencies of antischizophrenic drugs”. The Journal of Neuropsychiatry and Clinical Neurosciences 8 (2): 223–6. PMID 9081563. Arhivirano iz originala na datum 2011-07-27. Pristupljeno 2009-06-21.

[8] Ebadi, Manuchair S (1998). „Trifluoperazine Hydrochloride”. CRC desk reference of clinical pharmacology (illustrated izd.). CRC Press. ISBN 978-0-8493-9683-0. Pristupljeno 2009-06-21.

[9] Craig, P.; Nodiff, E.; Lafferty, J.; Ullyot, G. (1957). „Notes - New Trifluoromethylphenothiazine Derivatives”. Journal of Organic Chemistry 22 (6): 709. DOI:10.1021/jo01357a618.

[10] G.E. Ullyot, U.S. Patent 2.921.069 (1960).

[11] Sharma, H.; Banerjee, S.; Sharma, V.; Mital, R. (1968). „Phenothiazines Exhibiting Lesser Extraparamidal Manifestations”. Journal of Medicinal Chemistry 11 (6): 1244. DOI:10.1021/jm00312a600. PMID 5680054.

[12] P.N. Craig, G.E. Ullyot, DE 1165034 (1956).

[13] B.H. Chung, F. Zimalkowski, Arch. Pharm., 317, 323 (1984).

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