Carpetimycin B
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| Category | Antibiotics |
| Catalog number | BBF-00496 |
| CAS | 76094-36-5 |
| Molecular Weight | 422.43 |
| Molecular Formula | C14H18N2O9S2 |
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Description
It is produced by the strain of treptomyces griseus subsp. cryophilus, Str. sp. KC-6643. Carpetimycin is far more stable than Olivanic acid, and has very strong activity against gram-positive and negative bacteria (including β-lactamase producing bacteria). The activity of A is 8-32 times stronger than that of B. It has a strong inhibitory effect on β-lactamase.
Specification
| Related CAS | 76025-74-6 (disodium) |
| Synonyms | C-19393 S(2); 1-Azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid, 3-((2-(acetylamino)ethenyl)sulfinyl)-6-(1-methyl-1-(sulfooxy)ethyl)-7-oxo-, (5R-(3(R*(E)),5alpha,6beta))- |
| IUPAC Name | (5R,6R)-3-[(R)-[(E)-2-acetamidoethenyl]sulfinyl]-7-oxo-6-(2-sulfooxypropan-2-yl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid |
| Canonical SMILES | CC(=O)NC=CS(=O)C1=C(N2C(C1)C(C2=O)C(C)(C)OS(=O)(=O)O)C(=O)O |
| InChI | InChI=1S/C14H18N2O9S2/c1-7(17)15-4-5-26(21)9-6-8-10(14(2,3)25-27(22,23)24)12(18)16(8)11(9)13(19)20/h4-5,8,10H,6H2,1-3H3,(H,15,17)(H,19,20)(H,22,23,24)/b5-4+/t8-,10+,26-/m1/s1 |
| InChI Key | GOODEIVATWULQD-CWYJLJPQSA-N |
Properties
| Melting Point | 130 °C(dec.) |
| Solubility | Soluble in Water |
Reference Reading
1. Synthesis and biological activities of the Z isomers of carbapenem antibiotics
S Harada, S Tsubotani, M Asai, K Okonogi, M Kondo J Med Chem. 1983 May;26(5):753-7. doi: 10.1021/jm00359a600.
Naturally occurring carbapenem antibiotics having a double bond in the side chain, when refluxed in chloroform containing quarternary alkylammonium halides, were converted into Z isomers in high yields. The mechanism of this new equilibration involves intramolecular proton transfer from the carboxylic acid to the carbon alpha to the sulfur atom in the side chain as shown by deuterium-labeling experiments. Some Z isomers showed stronger protective effects in mice infected by Escherichia coli O-111 and more potent synergistic activities with cefotiam in mice infected by Proteus vulgaris GN4815 than did the naturally occurring E isomers. The decomposition rates of the Z isomers in mouse kidney homogenates were about 3-fold slower than those of the E isomers.
2. C-19393 S2 and H2, new carbapenem antibiotics. IV. Inhibitory activity against beta-lactamases
K Okonogi, Y Nozaki, A Imada, M Kuno J Antibiot (Tokyo). 1981 Feb;34(2):212-7. doi: 10.7164/antibiotics.34.212.
New carbapenem antibiotics, C-19393 S2 and H2, have been found to be potent and broad-spectrum inhibitors of beta-lactamases. Among 11 types of beta-lactamases tested, those from Escherichia coli (plasmid-bearing), Klebsiella pneumoniae, Proteus vulgaris, Serratia marcescens and Bacteroides fragilis were especially sensitive. They also inhibited cephalosporinases insensitive to clavulanic acid. The inhibition by C-19393 S2 and H2 was of progressive type, except for the inhibition of E. coli enzyme (plasmid-mediated type I) by C-19393 H2. The inhibition of E. coli beta-lactamase by C-19393 S2 was irreversible, while that by C-19393 H2 was reversible.
3. Antimicrobial and beta-lactamase inhibitory activities of carpetimycins A and B, new carbapenem antibiotics
F Kobayashi, Y Saino, T Koshi, Y Hattori, M Nakayama, A Iwasaki, T Mori, S Mitsuhashi Antimicrob Agents Chemother. 1982 Apr;21(4):536-44. doi: 10.1128/AAC.21.4.536.
Carpetimycins A and B showed widely broad spectra and potent activity against gram-positive and gram-negative bacteria, including various species of anaerobic bacteria. The antimicrobial activity of carpetimycin A was 8 to 64 times greater than that of carpetimycin B and 4 to 128 times greater than that of cefoxitin. The inhibitory concentration of carpetimycin A required to inhibit more than 90% of clinical isolates was 0.39 micrograms/ml for Escherichia coli and klebsiella and 1.56 microgram/ml for Proteus and Staphylococcus aureus. At a concentration of 3.13 micrograms/ml, carpetimycin A inhibited almost all clinical isolates of Enterobacter and Citrobacter, which showed resistance to many clinically used beta-lactam antibiotics. Carpetimycins A and B furthermore were shown to have potent inhibitory activities against several kinds of beta-lactamases produced by beta-lactam-resistant strains; they inhibited not only penicillinase-type beta-lactamases but also cephalosporinase-type beta-lactamases, which were insensitive to clavulanic acid. In combination with beta-lactam antibiotics such as ampicillin, carbenicillin, and cefazolin, carpetimycins A and B showed synergistic activities against beta-lactam-resistant bacteria.
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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 ╳
