Capreomycin

Title: Capreomycin
CAS Registry Number: 11003-38-6
Trademarks: Capastat (Lilly)
Literature References: Cyclic peptide antibiotic similar to viomycin; produced by Streptomyces capreolus NRRL 2773; Herr et al., 140th Am. Chem. Soc. Meet. (Chicago, Sept. 1961), Abstracts of Papers, p 49C; Chem. Eng. News 39, 57 (Sept. 18, 1961); GB 920563; US 3143468 (1963, 1964 both to Lilly). Mixture of capreomycins IA, IB, IIA, and IIB in the approx percentages, 25%, 67%, 3%, 6%, resp.: Herr, Redstone, Ann. N.Y. Acad. Sci. 135, 940 (1966). Activity studies: Sutton et al., ibid. 947; Lucchesi, Antibiot. Chemother. 16, 27 (1970). Proposed structure: Bycroft et al., Nature 231, 301 (1971). Revised structure and total synthesis: T. Shiba et al., Tetrahedron Lett. 1976, 3907; S. Nomoto et al., Tetrahedron 34, 921 (1978). Structure of IA and IB: eidem, J. Antibiot. 30, 955 (1977). Toxicity study: Welles et al., Ann. N.Y. Acad. Sci. 135, 960 (1966).
Properties: The mixture is a white solid. Sol in water. Practically insol in most organic solvents. pKa in 66% aq DMF: 6.2, 8.2, 10.1, 13.3. Stable in aq soln at pH 4-8; unstable in strongly acidic or strongly basic solns.
pKa: pKa in 66% aq DMF: 6.2, 8.2, 10.1, 13.3
Derivative Type: Disulfate
CAS Registry Number: 1405-36-3
Trademarks: Caprocin (Lilly); Ogostal (Lilly)
Properties: Solubility data: March, Weiss, J. Assoc. Off. Anal. Chem. 50, 457 (1967). LD50 in mice, rats (mg/kg): 250, 325 i.v.; 514, 1191 s.c. (Welles).
Toxicity data: LD50 in mice, rats (mg/kg): 250, 325 i.v.; 514, 1191 s.c. (Welles)
Derivative Type: Capreomycin IA
CAS Registry Number: 37280-35-6
Molecular Formula: C25H44N14O8
Molecular Weight: 668.71
Percent Composition: C 44.90%, H 6.63%, N 29.32%, O 19.14%
Properties: mp 246-248° (dec). [a]D22 -21.9° (c = 0.5 in water). uv max (0.1N HCl): 269 nm (e 24000); (H2O): 268 nm (e 23900); (0.1N NaOH): 287 nm (e 15900) (all for hydrochloride ethanolate).
Melting point: mp 246-248° (dec)
Optical Rotation: [a]D22 -21.9° (c = 0.5 in water)
Absorption maximum: uv max (0.1N HCl): 269 nm (e 24000)
Derivative Type: Capreomycin IB
CAS Registry Number: 33490-33-4
Molecular Formula: C25H44N14O7
Molecular Weight: 652.71
Percent Composition: C 46.00%, H 6.79%, N 30.04%, O 17.16%
Properties: mp 253-255° (dec). [a]D22 -44.6° (c = 0.5 in water). uv max (0.1N HCl): 268 nm (e 22700); (H2O): 268 nm (e 22300); (0.1N NaOH): 290 nm (e 14400) (all for hydrochloride ethanolate).
Melting point: mp 253-255° (dec)
Optical Rotation: [a]D22 -44.6° (c = 0.5 in water)
Absorption maximum: uv max (0.1N HCl): 268 nm (e 22700)
NOTE: Capreomycin IIA, capreomycin IIB. Structures corresp to capreomycins IA and IB but lack b-lysine residues.
Therap-Cat: Antibacterial (tuberculostatic).
Keywords: Antibacterial (Antibiotics); Polypeptides; Antibacterial (Tuberculostatic).
Caproic Aldehyde Caprolactam Capromab Caproyl Chloride Caprylene

Capreomycin
Capreomycin IA.svg
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
Legal status  ?
Identifiers
CAS number 11003-38-6 YesY
ATC code J04AB30
PubChem CID 3032400
DrugBank DB00314
ChemSpider 21106276 YesY
UNII 232HYX66HC YesY
KEGG D00135 N
ChEMBL CHEMBL1201252 N
NIAID ChemDB 007653
Chemical data
Formula C25H44N14O8 
Mol. mass 668.706 g/mol
 N (what is this?)  (verify)

Capreomycin is a peptide antibiotic, commonly grouped with the aminoglycosides, which is given in combination with other antibiotics for MDR-tuberculosis. 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. Patients on this drug will often require audiology tests.

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