Rifampicin

Rifampicin
Klinički podaci
Prodajno ime	Archidyn, Rifadin, Rifadine, Rifagen
Drugs.com	Monografija
Način primene	Oralno
Farmakokinetički podaci
Poluvreme eliminacije	3,35 (+/- 0,66) h
Izlučivanje	30% renalno
Identifikatori
CAS broj	13292-46-1
ATC kod	J04AB02 (WHO)
PubChem	CID 5360416
IUPHAR/BPS	2765
DrugBank	DB01045
ChemSpider	10468813
KEGG	C06688
ChEBI	CHEBI:28077
ChEMBL	CHEMBL180
Hemijski podaci
Formula	C43H58N4O12
Molarna masa	822,95 g·mol−1
	SMILES CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C2=C(O)C(\C=N\N4CCN(C)CC4)=C(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C(O)=C2C(O)=C3C; ;
	InChI InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1; Key:JQXXHWHPUNPDRT-WLSIYKJHSA-N ;
Fizički podaci
Tačka topljenja	183 °C (361 °F)

Rifampicin, takođe poznat kao rifampin, antibiotik je koji se koristi u tretmanu nekoliko tipova bakterijskih infekcija.^[1] Njegov spektar primene obuhvata tuberkulozu, lepru i Legionarsku bolest. On skoro uvek koristi sa drugim antibioticima, izuzev kad se primenjuje sprečavanju Haemophilus influenzae tipa b i meningokokalne bolesti kod ljudi koji su bili izloženi tim bakterijama. Preporučuje se merenje nivoa jetrenih enzima i broja krvnih zrnaca pre dugotrajnog tretiranja osobe. Rifampicin se može dozirati oralno ili intravenozno.^[1]

Česte nuspojave su mučnina, povraćanje, dijareja, i gubitak apetita. On se često pojavljuje u urinu, znoju, i suzama, kojima daje crvenu ili narandžastu boju. Može doći do problema s jetrom ili alergijskih reakcija. On je deo preporučenog tratmana aktivne tuberkuloze tokom trudnoće, iako njegova bezbednost tokom trudnoće nije poznata. Rifampicin pripada rifamicinskog grupi antibiotika. On deluje tako što zaustavlja produkciju RNK bakterija.^[1]

Osobine

Rifampicin je organsko jedinjenje, koje sadrži 43 atoma ugljenika i ima molekulsku masu od 822,940 Da.^[2]^[3]^[4]

Osobina	Vrednost
Broj akceptora vodonika	15
Broj donora vodonika	6
Broj rotacionih veza	5
Particioni koeficijent^[5] (ALogP)	3,3
Rastvorljivost^[6] (logS, log(mol/L))	-6,4
Polarna površina^[7] (PSA, Å²)	220,1

Reference

^ ^а ^б ^в „Rifampin”. The American Society of Health-System Pharmacists. Приступљено 1. 8. 2015.
^ Baysarowich J, Koteva K, Hughes DW, Ejim L, Griffiths E, Zhang K, Junop M, Wright GD: Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr. Proc Natl Acad Sci U S A. 2008 Mar 25;Baysarowich, J.; Koteva, K.; Hughes, D. W.; Ejim, L.; Griffiths, E.; Zhang, K.; Junop, M.; Wright, G. D. (2008). . „Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr”. Proceedings of the National Academy of Sciences of the United States of America. 105 (12): 4886—91. Bibcode:2008PNAS..105.4886B. PMC 2290778 . PMID 18349144. doi:10.1073/pnas.0711939105 . . Epub 2008 Mar 18.
^ 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

Rifampicin

Molimo Vas, obratite pažnju na važno upozorenje
u vezi sa temama iz oblasti medicine (zdravlja).

[AHFS2015-1] а ^б ^в „Rifampin”. The American Society of Health-System Pharmacists. Приступљено 1. 8. 2015.

[2] Baysarowich J, Koteva K, Hughes DW, Ejim L, Griffiths E, Zhang K, Junop M, Wright GD: Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr. Proc Natl Acad Sci U S A. 2008 Mar 25;Baysarowich, J.; Koteva, K.; Hughes, D. W.; Ejim, L.; Griffiths, E.; Zhang, K.; Junop, M.; Wright, G. D. (2008). . „Rifamycin antibiotic resistance by ADP-ribosylation: Structure and diversity of Arr”. Proceedings of the National Academy of Sciences of the United States of America. 105 (12): 4886—91. Bibcode:2008PNAS..105.4886B. PMC 2290778 . PMID 18349144. doi:10.1073/pnas.0711939105 . . Epub 2008 Mar 18.

[3] 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.

[4] 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.

[5] 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.

[6] 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.

[7] 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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