Capreomycin

Capreomycin


Systematic (IUPAC) name
(3S)-3,6-diamino-N-[[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide; (3S)-3,6-diamino-N-[[(2S,5S,8E,11S,15S)-15-amino-11-[(4R)-2-amino-3,4,5,6-tetrahydropyrimidin-4-yl]-8-[(carbamoylamino)methylidene]-2-methyl-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682860
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	11003-38-6^Y
ATC code	J04AB30
PubChem	CID 3032400
DrugBank	APRD00844
ChemSpider	21106276^Y
UNII	232HYX66HC^Y
KEGG	D00135^N
ChEMBL	CHEMBL1201252^N
Chemical data
Formula	C₂₅H₄₄N₁₄O₈
Mol. mass	668.706 g/mol
InChI InChI=1S/C25H44N14O8.C25H44N14O7/c26-4-1-2-11(27)6-17(41)32-8-14-20(43)35-15(9-34-25(30)47)21(44)39-18(13-3-5-31-24(29)38-13)23(46)33-7-12(28)19(42)37-16(10-40)22(45)36-14;1-11-19(41)36-15(9-32-17(40)7-12(27)3-2-5-26)21(43)37-16(10-34-25(30)46)22(44)39-18(14-4-6-31-24(29)38-14)23(45)33-8-13(28)20(42)35-11/h9,11-14,16,18,40H,1-8,10,26-28H2,(H,32,41)(H,33,46)(H,35,43)(H,36,45)(H,37,42)(H,39,44)(H3,29,31,38)(H3,30,34,47);10-15,18H,2-9,26-28H2,1H3,(H,32,40)(H,33,45)(H,35,42)(H,36,41)(H,37,43)(H,39,44)(H3,29,31,38)(H3,30,34,46)/b15-9-;16-10-/t11-,12?,13?,14+,16+,18?;11-,12+,13?,14?,15-,18?/m10/s1^Y Key:VCOPTHOUUNAYKQ-TWKMCICTSA-N^Y
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Capreomycin is a peptide antibiotic, commonly grouped with the aminoglycosides, which is given in combination with other antibiotics for tuberculosis. Adverse effects include nephrotoxicity and 8th cranial nerve toxicity.

The drug should not be given with streptomycin or other drugs that may damage the 8th nerve.

It is a cyclic peptide. Capreomycin is administered intramuscularly and shows bacteriostatic activity. ^[1]

References

^ "Capreomycin binds across the ribosomal subunit interface using tlyA-encoded 2'-O-methylations in 16S and 23S rRNAs". Mol. Cell 23 (2): 173–82. July 2006. doi:10.1016/j.molcel.2006.05.044. PMID 16857584.

Rifamycins/ RNA polymerase inhibitor	Rifampicin^# • Rifabutin • Rifapentine

Antifolates/DSI	Dapsone^# • Acedapsone • Aldesulfone sodium

ASA	4-Aminosalicylic acid^# (Calcium aminosalicylate, Sodium aminosalicylate)

Aminoglycosides	Amikacin^# • Capreomycin^# • Kanamycin^# • Streptomycin^#

Oxazolidone	Linezolid

Peptidoglycan layer	Alanine analogue: Cycloserine^#

Arabinogalactan layer	Ethylenediamine/arabinosyltransferase inhibitor: Ethambutol^# SQ109^†

Mycolic acid layer	Hydrazides/mycolic acid synth. inhibition: Isoniazid^# Thiocarbamides: Ethionamide^# • Prothionamide • Thiocarlide

Other/unknown

phenazine (Clofazimine)^# • pyrazine (Pyrazinamide^#, Morinamide) • isoxazole (Terizidone) • R207910/TMC207^†

Combinations

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)