Capreomycin sulfate
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| Category | Antibiotics |
| Catalog number | BBF-04221 |
| CAS | 1405-37-4 |
| Molecular Weight | 752.76 |
| Molecular Formula | C24H42N14O8.H2SO4 |
| Purity | ≥95% |
Ordering Information
| Catalog Number | Size | Price | Stock | Quantity |
|---|---|---|---|---|
| BBF-04221 | 1 g | $199 | In stock | |
| BBF-04221 | 5 g | $733 | In stock |
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Add to cartDescription
Capreomycin sulfate is a salt of a complex of cyclic pentopeptides isolated from streptomyces capreolus. It is an antibiotic with potent anti-tuberculosis activity.
Specification
| Related CAS | 11003-38-6 (free base) |
| Synonyms | Kapreomycin; Capostatin; HSDB 3211; HSDB-3211; HSDB3211; Capastat sulfate; Caprocin sulfate; (2S)-2,5-diamino-N-(((2S,5R,11S,15R,Z)-15-amino-11-(2-amino-3,4,5,6-tetrahydropyrimidin-4-yl)-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-8-(ureidomethylene)-1,4,7,10,13-pentaazacyclohexadecan-5-yl)methyl)pentanamide, monosulfate |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2,5-diamino-N-[[(2S,5S,8Z,11S,15S)-15-amino-11-(2-amino-1,4,5,6-tetrahydropyrimidin-6-yl)-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]pentanamide;sulfuric acid |
| Canonical SMILES | C1CN=C(NC1C2C(=O)NCC(C(=O)NC(C(=O)NC(C(=O)NC(=CNC(=O)N)C(=O)N2)CNC(=O)C(CCCN)N)CO)N)N.OS(=O)(=O)O |
| InChI | InChI=1S/C24H42N14O8.H2O4S/c25-4-1-2-10(26)17(40)32-7-13-19(42)34-14(8-33-24(29)46)20(43)38-16(12-3-5-30-23(28)37-12)22(45)31-6-11(27)18(41)36-15(9-39)21(44)35-13;1-5(2,3)4/h8,10-13,15-16,39H,1-7,9,25-27H2,(H,31,45)(H,32,40)(H,34,42)(H,35,44)(H,36,41)(H,38,43)(H3,28,30,37)(H3,29,33,46);(H2,1,2,3,4)/b14-8-;/t10-,11-,12?,13-,15-,16-;/m0./s1 |
| InChI Key | LFFNIXQXRKNZCE-XYHGUWSSSA-N |
Properties
| Appearance | White Solid |
| Boiling Point | 1376.7°C at 760 mmHg |
| Melting Point | >220°C (dec.) |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO, Water |
Reference Reading
1. Capreomycin supergenerics for pulmonary tuberculosis treatment: preparation, in vitro, and in vivo characterization
Maurizio Ricci, Maria Luisa Marenzoni, Stefano Giovagnoli, Carlo Cirotto, Paolo Blasi, Lanfranco Barberini, Aurélie Schoubben Eur J Pharm Biopharm . 2013 Apr;83(3):388-95. doi: 10.1016/j.ejpb.2012.11.005.
The pulmonary route is one of the main strategies investigated to improve tuberculosis therapy. The aim of this study was to develop a simple and scalable method to produce capreomycin inhalable powders to use as supergeneric. In vitro antimycobacterial activity and in vivo acute toxicity were assessed using agar proportion susceptibility test on Mycobacterium tuberculosis and chicken chorioallantoic membrane assay, respectively. Capreomycin and three different hydrophobic counterions, namely oleate, linoleate, and linolenate, were combined in solution to obtain hydrophobic ion-pairs that were successively spray-dried. Ion-pairing efficiency was influenced by the spray-dryer employed to produce the powder. In the case of capreomycin oleate, both instruments, mini and nano spray-dryer, were suitable to maintain a high ion-paired content, while for capreomycin linoleate and linolenate, mini spray-dryer was the most appropriate instrument. The three formulations showed morphology and particle sizes potentially suitable for inhalation. Capreomycin oleate and linoleate showed the same efficacy of capreomycin sulfate against M. tuberculosis, while capreomycin linolenate showed a reduced efficacy, even though strain growth was inhibited at 10(-4) mycobacterial inoculum. In vivo acute toxicity studies evidenced the lowest toxic potential for capreomycin oleate when compared to the single components or the other two salts. Overall, capreomycin oleate seems to possess the most promising characteristics to be used as supergenerics in pulmonary tuberculosis treatment.
2. Ototoxicity of Non-aminoglycoside Antibiotics
Vickram Ramkumar, Leonard P Rybak, Debashree Mukherjea Front Neurol . 2021 Mar 9;12:652674. doi: 10.3389/fneur.2021.652674.
It is well-known that aminoglycoside antibiotics can cause significant hearing loss and vestibular deficits that have been described in animal studies and in clinical reports. The purpose of this review is to summarize relevant preclinical and clinical publications that discuss the ototoxicity of non-aminoglycoside antibiotics. The major classes of antibiotics other than aminoglycosides that have been associated with hearing loss in animal studies and in patients are discussed in this report. These antibiotics include: capreomycin, a polypeptide antibiotic that has been used to treat patients with drug-resistant tuberculosis, particularly in developing nations; the macrolides, including erythromycin, azithromycin and clarithromycin; and vancomycin. These antibiotics have been associated with ototoxicity, particularly in neonates. It is critical to be aware of the ototoxic potential of these antibiotics since so much attention has been given to the ototoxicity of aminoglycoside antibiotics in the literature.
3. Capreomycin
Capreomycin is an injectable broad spectrum antibiotic used in the therapy of drug resistant tuberculosis as a second line agent, always in combination with other antituberculosis drugs. Capreomycin has not been linked to cases of clinically apparent liver disease.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
