Kandesartan

Kandesartan
(IUPAC) ime
	2-etoksi-1-({4-[2-(2H-1,2,3,4-tetrazol-5-il)fenil]fenil}metil)-1H-1,3-benzodiazol-7-karboksilna kiselina
Klinički podaci
Robne marke	Atacand
AHFS/Drugs.com	Monografija
MedlinePlus	a601033
Identifikatori
CAS broj	139481-59-7
ATC kod	C09CA06
PubChem	2541
DrugBank	DB00796
ChemSpider	2445
UNII	S8Q36MD2XX
KEGG	D00626
ChEBI	CHEBI:3347
ChEMBL	CHEMBL1016
Hemijski podaci
Formula	C24H20N6O3
Mol. masa	440,45
SMILES	eMolekuli & PubHem
InChI
	InChI=1S/C24H20N6O3/c1-2-33-24-25-20-9-5-8-19(23(31)32)21(20)30(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-26-28-29-27-22/h3-13H,2,14H2,1H3,(H,31,32)(H,26,27,28,29) ; Key: HTQMVQVXFRQIKW-UHFFFAOYSA-N
Farmakokinetički podaci
Bioraspoloživost	15% (kandesartan cileksetil)
Metabolizam	Kandesartan cileksetil: intestinalni zid; kandesartan: hepatički (CYP2C9)
Poluvreme eliminacije	9 sati
Izlučivanje	Renalno 33%, fakalno 67%
Farmakoinformacioni podaci
Trudnoća	D(AU)
Pravni status	℞ Prescription only
Način primene	oralno

Kandesartan je antagonist angiotenzin II receptora koji se uglavnom koristi za tretman hipertenzije. Prolek kandesartan cileksetil prodaju preduzeća AstraZeneca i Takeda. Neka od prodajnih imena su: Blopress, Atacand, Amias, i Ratacand.

Osobine

Osobina	Vrednost
Broj akceptora vodonika	7
Broj donora vodonika	2
Broj rotacionih veza	7
Particioni koeficijent^[6] (ALogP)	4,6
Rastvorljivost^[7] (logS, log(mol/L))	-6,5
Polarna površina^[8] (PSA, Å²)	118,8

Sinteza

Kandesartan se sintetiše na sledeći način:^[9]

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
↑ Ghose, A.K., Viswanadhan V.N., and Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A 102: 3762-3772. DOI:10.1021/jp980230o.
↑ Tetko IV, Tanchuk VY, Kasheva TN, Villa AE. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488-1493. DOI:10.1021/ci000392t. PMID 11749573.
↑ Ertl P., Rohde B., Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714-3717. DOI:10.1021/jm000942e. PMID 11020286.
↑ Kubo, K.; Kohara, Y.; Imamiya, E.; Sugiura, Y.; Inada, Y.; Furukawa, Y.; Nishikawa, K.; Naka, T. (1993). „Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of benzimidazolecarboxylic acids”. Journal of Medicinal Chemistry 36 (15): 2182–2195. DOI:10.1021/jm00067a016. PMID 8340921.

[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] Ghose, A.K., Viswanadhan V.N., and Wendoloski, J.J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods”. J. Phys. Chem. A 102: 3762-3772. DOI:10.1021/jp980230o.

[7] Tetko IV, Tanchuk VY, Kasheva TN, Villa AE. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Chem Inf. Comput. Sci. 41: 1488-1493. DOI:10.1021/ci000392t. PMID 11749573.

[8] Ertl P., Rohde B., Selzer P. (2000). „Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties”. J. Med. Chem. 43: 3714-3717. DOI:10.1021/jm000942e. PMID 11020286.

[9] Kubo, K.; Kohara, Y.; Imamiya, E.; Sugiura, Y.; Inada, Y.; Furukawa, Y.; Nishikawa, K.; Naka, T. (1993). „Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of benzimidazolecarboxylic acids”. Journal of Medicinal Chemistry 36 (15): 2182–2195. DOI:10.1021/jm00067a016. PMID 8340921.

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