Kamptotecin

Kamptotecin
(IUPAC) ime
	(S)-4-etil-4-hidroksi-1H-pirano[3',4':6,7]indolizino[1,2-b]; hinolin-3,14-(4H,12H)-dion
Klinički podaci
Identifikatori
CAS broj	7689-03-4
ATC kod	nije dodeljen
PubChem	2538
DrugBank	DB04690
ChemSpider	22775
UNII	XT3Z54Z28A
KEGG	C01897
ChEBI	CHEBI:27656
ChEMBL	CHEMBL65
Hemijski podaci
Formula	C20H16N2O4
Mol. masa	348,352 g/mol
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1 ; Key: VSJKWCGYPAHWDS-FQEVSTJZSA-N
Farmakoinformacioni podaci
Trudnoća	?
Pravni status

Kamptotecin (CPT) je citotoksični hinolinski alkaloid koji inhibira DNK enzim topoizomerazu I (topo I). Njega su otkrili M. E. Val i M. C. Vani 1966. putem sistematskog testiranja prirodnih proizvoda za lekove protiv kancera. On je izolovan iz kore i stabla Camptotheca acuminata, drveta koji se u tradicionalnoj kineskoj medicini koristi za lečenje kancera^[6]. CPT je pokazao znatnu aktivnost protiv kancera u preliminarnim kliničkim ispitivanjima, međutim ovaj materijal ima nisku rastvorljivost i visoko izražene nepoželjne reakcije leka. Usled tih nedostataka putem sintetičke i medicinske hemije su razvijeni brojni sintetički analozi^[7]^[8]^[9] sa poboljšanim svojstvima. Dva CPT analoga su odobrena i koriste se u hemoterapiji kancera:^[10] topotekan i irinotekan.^[11]^[12]

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
↑ Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.
↑ 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
↑ Efferth T, Fu YJ, Zu YG, Schwarz G, Konkimalla VS, Wink M. (2007). „Molecular target-guided tumor therapy with natural products derived from traditional Chinese medicine.”. Current medicinal chemistry 14 (19): 2024–32.
↑ „Curran Synthesis of Camptothecin”.
↑ „Comins Synthesis of Camptothecin”.
↑ „Rapaport Synthesis of Camptothecin”.
↑ Takimoto CH, Calvo E. "Principles of Oncologic Pharmacotherapy" Arhivirano 2009-05-15 na Wayback Machine-u in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer Management: A Multidisciplinary Approach Arhivirano 2013-10-04 na Wayback Machine-u. 11 ed. 2008.
↑ M.E. Wall, M.C.Wani, C.E. Cook, K.H.Palmer, A.I.McPhail, G.A.Sim (1966). „Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from camptotheca acuminate”. Journal of the American Chemical Society 88 (16): 3888–3890. DOI:10.1021/ja00968a057.
↑ G. Samuelsson (2004). Drugs of Natural Origin: a Textbook of Pharmacognosy (5 izd.). ISBN 91-974318-4-2.

Literatura

Spoljašnje veze

	Portal Medicina
	Portal Hemija

Šablon:Intracelularni hemoterapijski agensi

[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] Joanne Wixon, Douglas Kell (2000). „Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG”. Yeast 17 (1): 48–55. DOI:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H.

[5] 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

[6] Efferth T, Fu YJ, Zu YG, Schwarz G, Konkimalla VS, Wink M. (2007). „Molecular target-guided tumor therapy with natural products derived from traditional Chinese medicine.”. Current medicinal chemistry 14 (19): 2024–32.

[7] „Curran Synthesis of Camptothecin”.

[8] „Comins Synthesis of Camptothecin”.

[9] „Rapaport Synthesis of Camptothecin”.

[10] Takimoto CH, Calvo E. "Principles of Oncologic Pharmacotherapy" Arhivirano 2009-05-15 na Wayback Machine-u in Pazdur R, Wagman LD, Camphausen KA, Hoskins WJ (Eds) Cancer Management: A Multidisciplinary Approach Arhivirano 2013-10-04 na Wayback Machine-u. 11 ed. 2008.

[M.E._Wall_1966-11] M.E. Wall, M.C.Wani, C.E. Cook, K.H.Palmer, A.I.McPhail, G.A.Sim (1966). „Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from camptotheca acuminate”. Journal of the American Chemical Society 88 (16): 3888–3890. DOI:10.1021/ja00968a057.

[G._Samuelsson_2004-12] G. Samuelsson (2004). Drugs of Natural Origin: a Textbook of Pharmacognosy (5 izd.). ISBN 91-974318-4-2.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]