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Merck

C4142

Capreomycin sulfate from Streptomyces capreolus

antibacterial peptide

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About This Item

CAS Number:
1405-37-4
NACRES:
NA.85
PubChem Substance ID:
24892668
UNSPSC Code:
51281628
EC Number:
215-776-8
MDL number:
MFCD00079032

Key Documents

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Product Name

Capreomycin sulfate from Streptomyces capreolus, antibacterial peptide

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-UBBQZPMLSA-N

SMILES string

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

form

powder

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria

mode of action

DNA synthesis | interferes

storage temp.

−20°C

Quality Level

200

Related Categories

Preparation Note

Sparingly soluble in water.

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.

Biochem/physiol Actions

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).

Other Notes

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

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000506790
0000506790
0000506791
0000506791
0000414754

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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
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
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
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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