Hloramfenikol

Hloramfenikol
Klinički podaci
Prodajno ime	Ak-chlor, Ak-Chlor Ophthalmic Ointment, Ak-Chlor Ophthalmic Solution, Alficetyn
Drugs.com	Monografija
Način primene	Oftalmički, intramuskularno
Farmakokinetički podaci
Poluvreme eliminacije	1,5 - 3,5 h
Identifikatori
CAS broj	56-75-7
ATC kod	D06AX02 (WHO), S03AA08
PubChem	CID 298
DrugBank	DB00446
ChemSpider	5744
KEGG	C00918
ChEBI	CHEBI:17698
ChEMBL	CHEMBL130
Hemijski podaci
Formula	C11H12Cl2N2O5
Molarna masa	323,129
	SMILES OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)C1=CC=C(C=C1)[N+]([O-])=O; ;
	InChI InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1 ; Key:WIIZWVCIJKGZOK-RKDXNWHRSA-N ;
Fizički podaci
Tačka topljenja	1.505 °C (2.741 °F)

Hloramfenikol je organsko jedinjenje, koje sadrži 11 atoma ugljenika i ima molekulsku masu od 323,129 Da.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	5
Broj donora vodonika	3
Broj rotacionih veza	6
Particioni koeficijent^[8] (ALogP)	1,0
Rastvorljivost^[9] (logS, log(mol/L))	-4,1
Polarna površina^[10] (PSA, Å²)	115,4

Kristali levomicetina pod mikroskopom u polarizovanoj svetlosti

Reference

^ Bhutta, Z. A.; Niazi, S. K.; Suria, A. (1992). „Chloramphenicol clearance in typhoid fever: Implications for therapy”. Indian Journal of Pediatrics. 59 (2): 213—9. PMID 1398851. S2CID 13369284. doi:10.1007/BF02759987.
^ Wali, S. S.; MacFarlane, J. T.; Weir, W. R.; Cleland, P. G.; Ball, P. A.; Hassan-King, M.; Whittle, H. C.; Greenwood, B. M. (1979). „Single injection treatment of meningococcal meningitis. 2. Long-acting chloramphenicol”. Transactions of the Royal Society of Tropical Medicine and Hygiene. 73 (6): 698—702. PMID 538813. doi:10.1016/0035-9203(79)90024-5.
^ Puddicombe, J. B.; Wali, S. S.; Greenwood, B. M. (1984). „A field trial of a single intramuscular injection of long-acting chloramphenicol in the treatment of meningococcal meningitis”. Transactions of the Royal Society of Tropical Medicine and Hygiene. 78 (3): 399—403. PMID 6464136. doi:10.1016/0035-9203(84)90132-9.
^ Pécoul, B.; Varaine, F.; Keita, M.; Soga, G.; Djibo, A.; Soula, G.; Abdou, A.; Etienne, J.; Rey, M. (1991-10-05). „Long-acting chloramphenicol versus intravenous ampicillin for treatment of bacterial meningitis”. Lancet (London, England). 338 (8771): 862—6. PMID 1681224. S2CID 31211632. doi:10.1016/0140-6736(91)91511-r.
^ Nathan, N.; Borel, T.; Djibo, A.; Evans, D.; Djibo, S.; Corty, J. F.; Guillerm, M.; Alberti, K. P.; Pinoges, L.; Guerin, P. J.; Legros, D. (2005). „Ceftriaxone as effective as long-acting chloramphenicol in short-course treatment of meningococcal meningitis during epidemics: A randomised non-inferiority study”. Lancet (London, England). 366 (9482): 308—13. PMID 16039333. S2CID 20885088. doi:10.1016/S0140-6736(05)66792-X.
^ 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 AC, Wishart DS (2011). „DrugBank 3.0: a comprehensive resource for omics research on drugs”. Nucleic Acids Res. 39 (Database issue): D1035—41. PMC 3013709  . PMID 21059682. doi:10.1093/nar/gkq1126.
^ David S. Wishart; Craig Knox; An Chi Guo; Dean Cheng; Savita Shrivastava; Dan Tzur; Bijaya Gautam; Murtaza Hassanali (2008). „DrugBank: a knowledgebase for drugs, drug actions and drug _targets”. Nucleic acids research. 36 (Database issue): D901—6. PMC 2238889  . PMID 18048412. doi:10.1093/nar/gkm958.
^ Ghose, A.K.; Viswanadhan V.N. & 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. PMID 11749573. doi:10.1021/ci000392t.
^ 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. 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

Chloramphenicol

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

[1] Bhutta, Z. A.; Niazi, S. K.; Suria, A. (1992). „Chloramphenicol clearance in typhoid fever: Implications for therapy”. Indian Journal of Pediatrics. 59 (2): 213—9. PMID 1398851. S2CID 13369284. doi:10.1007/BF02759987.

[2] Wali, S. S.; MacFarlane, J. T.; Weir, W. R.; Cleland, P. G.; Ball, P. A.; Hassan-King, M.; Whittle, H. C.; Greenwood, B. M. (1979). „Single injection treatment of meningococcal meningitis. 2. Long-acting chloramphenicol”. Transactions of the Royal Society of Tropical Medicine and Hygiene. 73 (6): 698—702. PMID 538813. doi:10.1016/0035-9203(79)90024-5.

[3] Puddicombe, J. B.; Wali, S. S.; Greenwood, B. M. (1984). „A field trial of a single intramuscular injection of long-acting chloramphenicol in the treatment of meningococcal meningitis”. Transactions of the Royal Society of Tropical Medicine and Hygiene. 78 (3): 399—403. PMID 6464136. doi:10.1016/0035-9203(84)90132-9.

[4] Pécoul, B.; Varaine, F.; Keita, M.; Soga, G.; Djibo, A.; Soula, G.; Abdou, A.; Etienne, J.; Rey, M. (1991-10-05). „Long-acting chloramphenicol versus intravenous ampicillin for treatment of bacterial meningitis”. Lancet (London, England). 338 (8771): 862—6. PMID 1681224. S2CID 31211632. doi:10.1016/0140-6736(91)91511-r.

[5] Nathan, N.; Borel, T.; Djibo, A.; Evans, D.; Djibo, S.; Corty, J. F.; Guillerm, M.; Alberti, K. P.; Pinoges, L.; Guerin, P. J.; Legros, D. (2005). „Ceftriaxone as effective as long-acting chloramphenicol in short-course treatment of meningococcal meningitis during epidemics: A randomised non-inferiority study”. Lancet (London, England). 366 (9482): 308—13. PMID 16039333. S2CID 20885088. doi:10.1016/S0140-6736(05)66792-X.

[6] 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 AC, Wishart DS (2011). „DrugBank 3.0: a comprehensive resource for omics research on drugs”. Nucleic Acids Res. 39 (Database issue): D1035—41. PMC 3013709  . PMID 21059682. doi:10.1093/nar/gkq1126.

[7] David S. Wishart; Craig Knox; An Chi Guo; Dean Cheng; Savita Shrivastava; Dan Tzur; Bijaya Gautam; Murtaza Hassanali (2008). „DrugBank: a knowledgebase for drugs, drug actions and drug _targets”. Nucleic acids research. 36 (Database issue): D901—6. PMC 2238889  . PMID 18048412. doi:10.1093/nar/gkm958.

[8] Ghose, A.K.; Viswanadhan V.N. & 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.

[9] 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. PMID 11749573. doi:10.1021/ci000392t.

[10] 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. PMID 11020286. doi:10.1021/jm000942e.

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