Trimetoprim

Trimetoprim
Klinički podaci


Prodajno ime	Abaprim, Alprim, Apo-Sulfatrim, Bactin
Drugs.com	Monografija
Način primene	Oralno
Farmakokinetički podaci
Poluvreme eliminacije	8-11 h
Izlučivanje	Renalno

Identifikatori
CAS broj	738-70-5^Y
ATC kod	J01EA01 (WHO)
PubChem	CID 5578
DrugBank	DB00440^Y
ChemSpider	5376^Y
KEGG	C01965^Y
ChEBI	CHEBI:9731^Y
ChEMBL	CHEMBL22^Y
Hemijski podaci
Formula	C₁₄H₁₈N₄O₃
Molarna masa	290,318
SMILES COC1=CC(CC2=CN=C(N)N=C2N)=CC(OC)=C1OC
InChI InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)^Y Key:IEDVJHCEMCRBQM-UHFFFAOYSA-N^Y

Fizički podaci
Tačka topljenja	199—203 °C (390—397 °F)

Trimetoprim je organsko jedinjenje, koje sadrži 14 atoma ugljenika i ima molekulsku masu od 290,318 Da.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

Osobine

Osobina	Vrednost
Broj akceptora vodonika	7
Broj donora vodonika	2
Broj rotacionih veza	5
Particioni koeficijent^[8] (ALogP)	1,5
Rastvorljivost^[9] (logS, log(mol/L))	-3,0
Polarna površina^[10] (PSA, Å²)	105,5

Reference

^ Brumfitt W, Hamilton-Miller JM: Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines. J Chemother. 1993 Dec;5(6):465-9. PMID 8195839
^ Brumfitt W, Hamilton-Miller JM: Limitations of and indications for the use of co-trimoxazole. J Chemother. 1994 Feb;6(1):3-11. PMID 8071675
^ Bean DC, Livermore DM, Papa I, Hall LM: Resistance among Escherichia coli to sulphonamides and other antimicrobials now little used in man. J Antimicrob Chemother. 2005 Nov;56(5):962-4. Epub 2005 Sep 8. PMID 16150859
^ Felmingham D, Reinert RR, Hirakata Y, Rodloff A: Increasing prevalence of antimicrobial resistance among isolates of Streptococcus pneumoniae from the PROTEKT surveillance study, and compatative in vitro activity of the ketolide, telithromycin. J Antimicrob Chemother. 2002 Sep;50 Suppl S1:25-37. PMID 12239226
^ Johnson JR, Manges AR, O'Bryan TT, Riley LW: A disseminated multidrug-resistant clonal group of uropathogenic Escherichia coli in pyelonephritis. Lancet. 2002 Jun 29;359(9325):2249-51. PMID 12103291
^ 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

Trimethoprim

Antibiotici: inhibitori nukleinskih kiselina (J01E, J01M)

Antifolati
(inhibira
purinski metabolizam,
i tim putem inhibira
DNK i RNK sintezu)

DR inhibitor

2,4-Diamino-pirimidin (Trimetoprim^#, Brodimoprim, Tetroksoprim, Iklaprim^†)

Sulfonamidi
(DS inhibitor)

Kratkotrajni	Sulfaizodimidin • Sulfametizol • Sulfadimidin • Sulfapiridin • Sulfafurazol • Sulfanilamid (Prontosil) • Sulfatiazol • Sulfatioureja
Srednje trajni	Sulfametoksazol • Sulfadiazin^# • Sulfamoksol
Dugotrajni	Sulfadimetoksin • Sulfalene • Sulfametomidin • Sulfametoksidiazin • Sulfametoksipiridazin • Sulfaperin • Sulfamerazin • Sulfafenazol • Sulfamazon

Drugi/negrupisani

sulfanilamid (Sulfacetamid, Sulfametrol)

Kombinacije

Sulfametoksazol i trimetoprim^#

Inhibitori
topoizomeraze/
hinoloni/
(inhibiraju
DNK replikaciju)

1. generacija

Cinoksacin^‡ • Flumekin • Nalidiksinska kiselina • Oksolinska kiselina • Pipemidinska kiselina • Piromidinska kiselina • Rosoksacin

Fluorohinoloni

2. generacija	Ciprofloksacin^# • Enoksacin^‡ • Fleroksacin^‡ • Lomefloksacin • Nadifloksacin • Ofloksacin • Norfloksacin • Pefloksacin • Rufloksacin
3. generacija	Balofloksacin • Grepafloksacin^‡ • Levofloksacin • Pazufloksacin • Sparfloksacin^‡ • Temafloksacin^‡ • Tosufloksacin
4. generacija	Besifloksacin • Klinafloksacin^† • Garenoksacin • Gemifloksacin • Moksifloksacin • Gatifloksacin^‡ • Sitafloksacin • Trovafloksacin^‡/Alatrofloksacin^‡ • Prulifloksacin
Veterinarski	Danofloksacin • Difloksacin • Enrofloksacin • Ibafloksacin • Marbofloksacin • Orbifloksacin • Pradofloksacin • Sarafloksacin
Srodni agenti (DG)	Aminokumarini: Novobiocin