Home
Browse
Submission
Downloads
FAQ
Team
Contact Us
Chloramphenicol
Chloramphenicol :
Antibiotic ID :
UD0018
Full Name :
Chloramphenicol
Synonyms :
Chloromycetin, Chlornitromycin, Levomycetin, Detreomycin, Globenicol, Halomycetin, Aquamycetin, Chloramficin, Chloramfilin
Class :
Beta Lactum
Chemical Description :
Molecular Formula :
C
11
H
12
C
12
N
2
O
5
Molecular Weight :
323.12938
InChIKey :
WIIZWVCIJKGZOK-RKDXNWHRSA-N
IUPAC Name :
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Structural Description :
Canonical SMILES :
C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
Isomeric SMILES :
C1=CC(=CC=C1[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
2D Structure :
2D
3D Structure :
3D
SDF :
SDF file
Fuctional Description :
Chloramphenicol Target :
An antibiotic first isolated from cultures of Streptomyces venequelae in 1947 but now produced synthetically. It has a relatively simple structure and was the first broad-spectrum antibiotic to be discovered. It acts by interfering with bacterial protein synthesis and is mainly bacteriostatic
(MeSH)
.
KEGG :
D00104
DRUG BANK :
DB00446
Pub Chem CID :
5959
Antibiotics Resistance Reports :
Upregulators :
Genes :
cat1
,
cmlA
,
catII
,
catIII
,
cml
,
mfdA
mfdA
Downregulators :
Genetic element :
Loss of plasmid correlated to loss of antibiotic resistance
Note :
NA* - Not Available
Bibliography :
Shiga toxin-producing Escherichia coli isolated from bovine mastitic milk: serogroups, virulence factors, and antibiotic resistance properties
, Momtaz H, Safarpoor Dehkordi F, Taktaz T, Rezvani A, Yarali S.,
The Scientific World Journal
, 2012,
2012
:618709.
PMID:
22512857.
High prevalence of antibiotic resistance in commensal Escherichia coli among children in rural Vietnam
, Dyar O.J., Hoa N Q., Trung N. V., Phuc H. D, Larsson M., Chuc N. T. K. and Lundborg C. S.,
BMC Infectious Diseases
, 2012,
12
:92.
PMID:
22512857.
Multidrug Resistance and Plasmid Patterns of Escherichia coli O157 and Other E. coli Isolated from Diarrhoeal Stools and Surface Waters from Some Selected Sources in Zaria, Nigeria
, Chigor V. N., Umoh V. J., Smith S. I., Igbinosa E. O., and Okoh A. I.,
International Journal of Environmental Research and Public Health
, 2009,
7
:3831-3841.
PMID:
21139863
Antimicrobial resistance in equine faecal Escherichia coli isolates from North West England
, Ahmed M. O., Clegg P.D., Williams N. J., Baptiste K. E. and Bennett M.
, Annals of Clinical Microbiology and Antimicrobials
, 2010,
9
:12.
PMID:
20374640.
Distribution and characterization of ampicillin- and tetracycline-resistant Escherichia coli from feedlot cattle fed subtherapeutic antimicrobials
, Mirzaagha P, Louie M, Sharma R, Yanke LJ, Topp E, McAllister TA.,
BMC Microbiology
, 2011,
11
:78.
PMID:
21504594.
NDM-4 Metallo-β-Lactamase with Increased Carbapenemase Activity from Escherichia coli
, Nordmann P, Boulanger AE, Poirel L.,
Antimicrobial Agents and Chemotherapy
, 2012,
56
(4): 2184-2186.
PMID:
22252797.
MdfA, an Escherichia coli multidrug resistance protein with an extraordinarily broad spectrum of drug recognition
, Edgar R, Bibi E.
, Journal of Bactriology
, 1997,
179
(7): 2274-80.
PMID:
9079913.
Antimicrobial Resistance Genes in Enterotoxigenic Escherichia coli O149:K91 Isolates Obtained over a 23-Year Period from Pigs
, Maynard C., Fairbrother J. M., Bekal S., Sanschagrin F., Levesque R. C., Brousseau R., Masson L., Larivière S., and Harel J.
, Antimicrobial Agents and Chemotherapy
, 2003,
47
(10):3214–3221.
PMID:
14506033.