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C4142

Sigma-Aldrich

Capreomycin sulfate from Streptomyces capreolus

antibacterial peptide

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About This Item

Numéro CAS:
1405-37-4
Numéro CE :
215-776-8
Numéro MDL:
MFCD00079032
Code UNSPSC :
51281628
ID de substance PubChem :
24892668
Nomenclature NACRES :
NA.85

Forme

powder

Spectre d'activité de l'antibiotique

Gram-negative bacteria
Gram-positive bacteria
mycobacteria

Mode d’action

DNA synthesis | interferes

Température de stockage

−20°C

Chaîne SMILES 

OS(O)(=O)=O.NCCC[C@H](N)C(=O)NC[C@H]1NC(=O)[C@H](CO)NC(=O)[C@H](N)CNC(=O)[C@@H](NC(=O)\C(NC1=O)=C\NC(N)=O)[C@H]2CCNC(=N)N2

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

Clé InChI

LFFNIXQXRKNZCE-UBBQZPMLSA-N

Application

Capreomycin is used to study bacterial ribosomal subunit interactions and translocation processes during protein synthesis. It is a second line antibiotic and is used to study multidrug-resistant tuberculosis.

Actions biochimiques/physiologiques

Capreomycin is a cyclic peptide antibiotic that is often grouped with aminoglycosides. It binds across the ribosomal interface involving 23S rRNA helix 69 (H69) and 16S rRNA helix 44 (h44).

Notes préparatoires

Sparingly soluble in water.

Autres remarques

Keep container tightly closed in a dry and well-ventilated place.

Pictogrammes

Health hazardExclamation mark
GHS08,GHS07

Mention d'avertissement

Danger

Mentions de danger

H302 + H312 + H332,H360

Classification des risques

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Repr. 1B

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Consulter la Bibliothèque de documents

B Reisfeld et al.
Antimicrobial agents and chemotherapy, 56(2), 926-934 (2011-12-07)
The emergence of multidrug-resistant tuberculosis (MDR-TB) has led to a renewed interest in the use of second-line antibiotic agents. Unfortunately, there are currently dearths of information, data, and computational models that can be used to help design rational regimens for
Rashid Akbergenov et al.
Antimicrobial agents and chemotherapy, 55(10), 4712-4717 (2011-07-20)
Capreomycin and the structurally similar compound viomycin are cyclic peptide antibiotics which are particularly active against Mycobacterium tuberculosis, including multidrug resistant strains. Both antibiotics bind across the ribosomal interface involving 23S rRNA helix 69 (H69) and 16S rRNA helix 44
Chaiyos Roongruangpitayakul et al.
Journal of the Medical Association of Thailand = Chotmaihet thangphaet, 96(10), 1273-1282 (2013-12-20)
Multi-drug-resistant/extensively drug-resistant tuberculosis (MDR/XDR-TB) becomes an increasing problem in management. Linezolid has been off-label used in treatment of MDR/XDR-TB with major adverse effects. To study outcomes of MDR/XDR-TB patients treated with linezolid in Central Chest Institute of Thailand. MDR/XDR-TB patients
DeDe Kwun-Wai Man et al.
mSphere, 3(4) (2018-07-20)
The mycobacterial cell wall affords natural resistance to antibiotics. Antimicrobial peptides (AMPs) modify the surface properties of mycobacteria and can act synergistically with antibiotics from differing classes. Here, we investigate the response of Mycobacterium smegmatis to the presence of rifampin
Courtney E Maus et al.
Antimicrobial agents and chemotherapy, 49(2), 571-577 (2005-01-28)
Capreomycin, an important drug for the treatment of multidrug-resistant tuberculosis, is a macrocyclic peptide antibiotic produced by Saccharothrix mutabolis subspecies capreolus. The basis of resistance to this drug was investigated by isolating and characterizing capreomycin-resistant strains of Mycobacterium smegmatis and
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