Capreomycin

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Capreomycin
File:Capreomycin IA.svg
File:Capreomycin IB.svg
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
category
  • C
Routes of
administration
intramuscular
Identifiers
CAS Number 11003-38-6 YesY
ATC code J04AB30 (WHO)
PubChem CID: 3000502
DrugBank DB00314 YesY
ChemSpider 2272094
UNII 232HYX66HC YesY
KEGG D00135 N
ChEMBL CHEMBL2221250 N
NIAID ChemDB 007653
Chemical data
Formula C25H44N14O8
Molecular mass 668.706 g/mol
  • C[C@H]1C(=O)N[C@H](C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@H](C(=O)NC[C@@H](C(=O)N1)N)[C@H]2CCN=C(N2)N)CNC(=O)C[C@H](CCCN)N.C1CN=C(N[C@H]1[C@H]2C(=O)NC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N/C(=C/NC(=O)N)/C(=O)N2)CNC(=O)C[C@H](CCCN)N)CO)N)N
  • 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-/m00/s1
  • Key:VCOPTHOUUNAYKQ-WBTCAYNUSA-N
 NYesY (what is this?)  (verify)

Capreomycin is a antibiotic which is given in combination with other antibiotics for MDR-tuberculosis. Capreomycin is administered intramuscularly and shows bacteriostatic activity.[1]

Adverse effects include nephrotoxicity and 8th cranial auditory vestibular nerve nerve toxicity. The drug should not be given with streptomycin or other drugs that may damage the auditory vestibular nerve. People on this medication should get hearing tests. It is commonly grouped with the aminoglycosides. It is a cyclic peptide.

Capreomycin was discovered in 1960, isolated from Streptomyces capreolus[2] It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[3]

Spectrum of susceptibility

Capreomycin is frequently used to treat Mycobacterium tuberculosis infections. Mycobacterium tuberculosis growth has been found to be inhibited at a concentration of 2.5 μg/mL.[4]

References

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  4. http://www.toku-e.com/Assets/MIC/Capreomycin%20sulfate.pdf


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