Azacitidin

Azacitidin
Klinički podaci
Prodajno ime	Ladakamycin, Mylosar, Vidaza
Drugs.com	Monografija
Način primene	Subkutano
Identifikatori
CAS broj	320-67-2
ATC kod	None
PubChem	CID 9444
DrugBank	DB00928
ChemSpider	9072
KEGG	C11262
ChEBI	CHEBI:2038
ChEMBL	CHEMBL1489

Azacitidin je organsko jedinjenje, koje sadrži 8 atoma ugljenika i ima molekulsku masu od 244,205 Da.^[1]^[2]^[3]^[4]^[5]^[6]^[7]^[8]^[9]^[10]^[11]^[12]^[13]^[14]^[15]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	8
Broj donora vodonika	4
Broj rotacionih veza	2
Particioni koeficijent^[16] (ALogP)	-1,9
Rastvorljivost^[17] (logS, log(mol/L))	-0,3
Polarna površina^[18] (PSA, Å²)	141,0

Reference

^ Cihák, A. (1974). „Biological effects of 5-azacytidine in eukaryotes”. Oncology. 30 (5): 405—22. PMID 4142650. doi:10.1159/000224981. }-
^ Kaminskas, E.; Farrell, A. T.; Wang, Y. C.; Sridhara, R.; Pazdur, R. (2005 Mar). „FDA drug approval summary: Azacitidine (5-azacytidine, Vidaza) for injectable suspension”. The Oncologist. 10 (3): 176—82. PMID 15793220. doi:10.1634/theoncologist.10-3-176. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-
^ Leone, G.; Voso, M. T.; Teofili, L.; Lübbert, M. (2003 Oct). „Inhibitors of DNA methylation in the treatment of hematological malignancies and MDS”. Clinical Immunology (Orlando, Fla.). 109 (1): 89—102. PMID 14585280. doi:10.1016/s1521-6616(03)00207-9. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-
^ Ghoshal, K.; Bai, S. (2007 Jun). „DNA methyltransferases as targets for cancer therapy”. Drugs of Today (Barcelona, Spain : 1998). 43 (6): 395—422. PMID 17612710. doi:10.1358/dot.2007.43.6.1062666. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-
^ Silverman, L. R.; Demakos, E. P.; Peterson, B. L.; Kornblith, A. B.; Holland, J. C.; Odchimar-Reissig, R.; Stone, R. M.; Nelson, D.; Powell, B. L.; Decastro, C. M.; Ellerton, J.; Larson, R. A.; Schiffer, C. A.; Holland, J. F. (2002 May 15). „Randomized controlled trial of azacitidine in patients with the myelodysplastic syndrome: A study of the cancer and leukemia group B”. Journal of Clinical Oncology : Official Journal of the American Society of Clinical Oncology. 20 (10): 2429—40. PMID 12011120. doi:10.1200/JCO.2002.04.117. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-
^ Silverman, L. R. (2001). „Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS)”. The Oncologist. 6 Suppl 5: 8—14. PMID 11700387. doi:10.1634/theoncologist.6-suppl_5-8. }-
^ Issa, J. P.; Kantarjian, H.; Kirkpatrick, Peter (2005). „Azacitidine”. Nature Reviews. Drug Discovery. Suppl (5): S6—7. PMID 15962522. doi:10.1038/nrd1726. }-
^ O'Dwyer, K.; Maslak, P. (2008 Aug). „Azacitidine and the beginnings of therapeutic epigenetic modulation”. Expert Opinion on Pharmacotherapy. 9 (11): 1981—6. PMID 18627335. doi:10.1517/14656566.9.11.1981. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-
^ Siddiqui MA, Scott LJ: Azacitidine: in myelodysplastic syndromes. Drugs. 65 (13): 1781—9. 2005. Недостаје или је празан параметар |title= (помоћ); discussion 1790-1. PMID 16114977
^ Abdulhaq, H.; Rossetti, J. M. (2007 Dec). „The role of azacitidine in the treatment of myelodysplastic syndromes”. Expert Opinion on Investigational Drugs. 16 (12): 1967—75. PMID 18042004. doi:10.1517/13543784.16.12.1967. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-
^ Keating, Gillian M. (2009). „Azacitidine”. Drugs. 69 (17): 2501—18. PMID 19911860. doi:10.2165/11202840-000000000-00000. . . PMID 19911860}-
^ Sullivan, M.; Hahn, K.; Kolesar, J. M. (2005 Aug 1). „Azacitidine: A novel agent for myelodysplastic syndromes”. American Journal of Health-System Pharmacy : Ajhp : Official Journal of the American Society of Health-System Pharmacists. 62 (15): 1567—73. PMID 16030365. doi:10.2146/ajhp040385. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-
^ Dapp MJ, Clouser CL, Patterson S, Mansky LM: 5-Azacytidine can induce lethal mutagenesis in human immunodeficiency virus type 1. J Virol. 2009 Nov;. 83 (22): 11950—8. PMID 19726509. Недостаје или је празан параметар |title= (помоћ). Epub 2009 Sep 2.
^ Knox, C.; Law, V.; Jewison, T.; Liu, P.; Ly, S.; Frolkis, A.; Pon, A.; Banco, K.; Mak, C.; Neveu, V.; Djoumbou, Y.; Eisner, R.; Guo, A. C.; Wishart, D. S. (2011). „DrugBank 3.0: A comprehensive resource for 'Omics' research on drugs”. Nucleic Acids Research. 39 (Database issue): D1035—D1041. PMC 3013709 . PMID 21059682. doi:10.1093/nar/gkq1126.
^ Wishart, David S.; Knox, Craig; Guo, An Chi; Cheng, Dean; Shrivastava, Savita; Tzur, Dan; Gautam, Bijaya; Hassanali, Murtaza (2008). „DrugBank: A knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Research. 36 (Database issue): D901—D906. PMC 2238889 . PMID 18048412. doi:10.1093/nar/gkm958.
^ Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o.
^ Tetko, Igor V.; Tanchuk, Vsevolod Yu.; Kasheva, Tamara N.; Villa, Alessandro E. P. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t.
^ Ertl, Peter; Rohde, Bernhard; Selzer, Paul (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”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

Literatura

Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803.
Thomas L. Lemke; David A. Williams, ур. (2007). Foye's Principles of Medicinal Chemistry (6. изд.). Baltimore: Lippincott Willams & Wilkins. ISBN 0781768799.

Spoljašnje veze

Azacitidine Архивирано на веб-сајту Wayback Machine (3. април 2014)

[1] Cihák, A. (1974). „Biological effects of 5-azacytidine in eukaryotes”. Oncology. 30 (5): 405—22. PMID 4142650. doi:10.1159/000224981. }-

[2] Kaminskas, E.; Farrell, A. T.; Wang, Y. C.; Sridhara, R.; Pazdur, R. (2005 Mar). „FDA drug approval summary: Azacitidine (5-azacytidine, Vidaza) for injectable suspension”. The Oncologist. 10 (3): 176—82. PMID 15793220. doi:10.1634/theoncologist.10-3-176. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-

[3] Leone, G.; Voso, M. T.; Teofili, L.; Lübbert, M. (2003 Oct). „Inhibitors of DNA methylation in the treatment of hematological malignancies and MDS”. Clinical Immunology (Orlando, Fla.). 109 (1): 89—102. PMID 14585280. doi:10.1016/s1521-6616(03)00207-9. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-

[4] Ghoshal, K.; Bai, S. (2007 Jun). „DNA methyltransferases as targets for cancer therapy”. Drugs of Today (Barcelona, Spain : 1998). 43 (6): 395—422. PMID 17612710. doi:10.1358/dot.2007.43.6.1062666. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-

[5] Silverman, L. R.; Demakos, E. P.; Peterson, B. L.; Kornblith, A. B.; Holland, J. C.; Odchimar-Reissig, R.; Stone, R. M.; Nelson, D.; Powell, B. L.; Decastro, C. M.; Ellerton, J.; Larson, R. A.; Schiffer, C. A.; Holland, J. F. (2002 May 15). „Randomized controlled trial of azacitidine in patients with the myelodysplastic syndrome: A study of the cancer and leukemia group B”. Journal of Clinical Oncology : Official Journal of the American Society of Clinical Oncology. 20 (10): 2429—40. PMID 12011120. doi:10.1200/JCO.2002.04.117. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-

[6] Silverman, L. R. (2001). „Targeting hypomethylation of DNA to achieve cellular differentiation in myelodysplastic syndromes (MDS)”. The Oncologist. 6 Suppl 5: 8—14. PMID 11700387. doi:10.1634/theoncologist.6-suppl_5-8. }-

[7] Issa, J. P.; Kantarjian, H.; Kirkpatrick, Peter (2005). „Azacitidine”. Nature Reviews. Drug Discovery. Suppl (5): S6—7. PMID 15962522. doi:10.1038/nrd1726. }-

[8] O'Dwyer, K.; Maslak, P. (2008 Aug). „Azacitidine and the beginnings of therapeutic epigenetic modulation”. Expert Opinion on Pharmacotherapy. 9 (11): 1981—6. PMID 18627335. doi:10.1517/14656566.9.11.1981. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-

[9] Siddiqui MA, Scott LJ: Azacitidine: in myelodysplastic syndromes. Drugs. 65 (13): 1781—9. 2005. Недостаје или је празан параметар |title= (помоћ); discussion 1790-1. PMID 16114977

[10] Abdulhaq, H.; Rossetti, J. M. (2007 Dec). „The role of azacitidine in the treatment of myelodysplastic syndromes”. Expert Opinion on Investigational Drugs. 16 (12): 1967—75. PMID 18042004. doi:10.1517/13543784.16.12.1967. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-

[11] Keating, Gillian M. (2009). „Azacitidine”. Drugs. 69 (17): 2501—18. PMID 19911860. doi:10.2165/11202840-000000000-00000. . . PMID 19911860}-

[12] Sullivan, M.; Hahn, K.; Kolesar, J. M. (2005 Aug 1). „Azacitidine: A novel agent for myelodysplastic syndromes”. American Journal of Health-System Pharmacy : Ajhp : Official Journal of the American Society of Health-System Pharmacists. 62 (15): 1567—73. PMID 16030365. doi:10.2146/ajhp040385. Проверите вредност парамет(а)ра за датум: |date= (помоћ)}-

[13] Dapp MJ, Clouser CL, Patterson S, Mansky LM: 5-Azacytidine can induce lethal mutagenesis in human immunodeficiency virus type 1. J Virol. 2009 Nov;. 83 (22): 11950—8. PMID 19726509. Недостаје или је празан параметар |title= (помоћ). Epub 2009 Sep 2.

[14] Knox, C.; Law, V.; Jewison, T.; Liu, P.; Ly, S.; Frolkis, A.; Pon, A.; Banco, K.; Mak, C.; Neveu, V.; Djoumbou, Y.; Eisner, R.; Guo, A. C.; Wishart, D. S. (2011). „DrugBank 3.0: A comprehensive resource for 'Omics' research on drugs”. Nucleic Acids Research. 39 (Database issue): D1035—D1041. PMC 3013709 . PMID 21059682. doi:10.1093/nar/gkq1126.

[15] Wishart, David S.; Knox, Craig; Guo, An Chi; Cheng, Dean; Shrivastava, Savita; Tzur, Dan; Gautam, Bijaya; Hassanali, Murtaza (2008). „DrugBank: A knowledgebase for drugs, drug actions and drug targets”. Nucleic Acids Research. 36 (Database issue): D901—D906. PMC 2238889 . PMID 18048412. doi:10.1093/nar/gkm958.

[16] Ghose, Arup K.; Viswanadhan, Vellarkad N.; Wendoloski, John J. (1998). „Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragmental Methods: An Analysis of ALOGP and CLOGP Methods”. The Journal of Physical Chemistry A. 102 (21): 3762—3772. Bibcode:1998JPCA..102.3762G. doi:10.1021/jp980230o.

[17] Tetko, Igor V.; Tanchuk, Vsevolod Yu.; Kasheva, Tamara N.; Villa, Alessandro E. P. (2001). „Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices”. Journal of Chemical Information and Computer Sciences. 41 (6): 1488—1493. PMID 11749573. doi:10.1021/ci000392t.

[18] Ertl, Peter; Rohde, Bernhard; Selzer, Paul (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”. Journal of Medicinal Chemistry. 43 (20): 3714—3717. PMID 11020286. doi:10.1021/jm000942e.

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