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 category	C
Routes of administration	intramuscular
Identifiers
CAS Number	11003-38-6^Y
ATC code	J04AB30
PubChem	CID 3000502
DrugBank	DB00314^Y
ChemSpider	2272094
UNII	232HYX66HC^Y
KEGG	D00135^N
ChEMBL	CHEMBL2221250^N
NIAID ChemDB	007653
Chemical data
Formula	C₂₅H₄₄N₁₄O₈
Molar mass	668.706 g/mol
SMILES 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 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
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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

↑ "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.
↑ Tomlinson, Catherine. "TB Online - Capreomycin". Retrieved 14 September 2014.
↑ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
↑ http://www.toku-e.com/Assets/MIC/Capreomycin%20sulfate.pdf

Antimycobacterials, including tuberculosis treatment and leprostatic agents (J04)

Nucleic acid inhibitor

Rifamycins/ RNA polymerase inhibitor	Rifampicin^# Rifabutin Rifapentine Rifalazil^§

Antifolates/DSI	Dapsone^# Acedapsone Aldesulfone sodium

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

Protein synthesis inhibitor

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

Oxazolidone	Linezolid

Cell envelope antibiotic

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

Combinations

Rifampicin/isoniazid/pyrazinamide

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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