Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H12Cl2N2O5 |
| Molecular Weight | 323.129 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC[C@H](NC(=O)C(Cl)Cl)[C@@H](O)C1=CC=C(C=C1)[N+]([O-])=O
InChI
InChIKey=WIIZWVCIJKGZOK-IUCAKERBSA-N
InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m0/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21742120Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/120206 | https://www.ncbi.nlm.nih.gov/pubmed/4432410 | https://www.ncbi.nlm.nih.gov/pubmed/403980
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21742120
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/120206 | https://www.ncbi.nlm.nih.gov/pubmed/4432410 | https://www.ncbi.nlm.nih.gov/pubmed/403980
Dextramycin ((S, S)-p-Chloramphenicol) is an optical isomer of Chloramphenicol, a broad-spectrum antibiotic with historical veterinary use in all major food-producing animals. The drug is biosynthesized by the soil organism Streptomyces venezuelae and several other actinomycetes and is chemically synthesized for commercial use. Chloramphenicol occurs in the meta-configuration and in the para-configuration and it contains two chiral centers thus in total eight different isomeric configurations exist. All para-stereoisomers are biologically active and 0.5% solution of Dextramycin shows antimicrobial activity. Currently, Chloramphenicol has banned for use in all food-producing animals.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0015934 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4599619 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Unknown Approved UseUnknown |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator​
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 1.0 |
inconclusive [IC50 10 uM] | |||
Page: 2.0 |
no | |||
Page: 9.0 |
no | |||
Page: 11.0 |
no | |||
Page: 8.0 |
no | |||
Page: 9.0 |
no |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 11.0 |
no | |||
Page: 9.0 |
no |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Antimicrobial resistance of nosocomial strain of Acinetobacter baumannii in Children's Medical Center of Tehran: a 6-year prospective study. | 2010-12-09 |
|
| Differential heat stability of amphenicols characterized by structural degradation, mass spectrometry and antimicrobial activity. | 2010-12-01 |
|
| Three serendipitous pathways in E. coli can bypass a block in pyridoxal-5'-phosphate synthesis. | 2010-11-30 |
|
| Crystal structure of the RNA recognition motif of yeast translation initiation factor eIF3b reveals differences to human eIF3b. | 2010-09-16 |
|
| Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. | 2010-09 |
|
| Comparative genomics reveals a functional thyroid-specific element in the far upstream region of the PAX8 gene. | 2010-05-14 |
|
| Relationships between chemical oxygen demand (COD) components and toxicity in a sequential anaerobic baffled reactor/aerobic completely stirred reactor system treating Kemicetine. | 2010-04-15 |
|
| 3-Methyl-1-butanol production in Escherichia coli: random mutagenesis and two-phase fermentation. | 2010-04 |
|
| Prevention, treatment and rehabilitation. | 2009-12 |
|
| Latherin: a surfactant protein of horse sweat and saliva. | 2009-05-29 |
|
| Rab11A-controlled assembly of the inner membrane complex is required for completion of apicomplexan cytokinesis. | 2009-01 |
|
| Cloning and functional characterization of carotenoid cleavage dioxygenase 4 genes. | 2009 |
|
| Mage-b vaccine delivered by recombinant Listeria monocytogenes is highly effective against breast cancer metastases. | 2008-09-02 |
|
| Characteristics of the Turkish isolates of Francisella tularensis. | 2008-05 |
|
| Isolation of Scopulariopsis spp. fungi from Psoroptes cuniculi body surface and evaluation of their entomopathogenic role. | 2008-04 |
|
| A study on tinea gladiatorum in young wrestlers and dermatophyte contamination of wrestling mats from Sari, Iran. | 2007-05 |
|
| Expression, purification and crystallization of 2-oxo-hept-4-ene-1,7-dioate hydratase (HpcG) from Escherichia coli C. | 2006-10-01 |
|
| Amphenicol and macrolide derived antibiotics inhibit paraoxonase enzyme activity in human serum and human hepatoma cells (HepG2) in vitro. | 2006-01 |
|
| A Role for the SmpB-SsrA system in Yersinia pseudotuberculosis pathogenesis. | 2006-01 |
|
| Conserved and variable functions of the sigmaE stress response in related genomes. | 2006-01 |
|
| Human autoantibodies against the 54 kDa protein of the signal recognition particle block function at multiple stages. | 2006 |
|
| Separation of basic compounds by capillary electrochromatography on an X-Terra RP18 stationary phase. | 2004-09-17 |
|
| [Study of antibiotic influence on adherence capacity of gram positive and gram negative bacteria to the cellular substrate]. | 2004-04-17 |
|
| [Drug resistance of Staphylococcus aureus strains, isolated from children with intestinal dysbacteriosis]. | 2001-03-10 |
|
| [Retrospective clinical analysis of the emergent comprehensive repair of electrical injury]. | 2001-02 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/403980
Rats were treated with Dextramycin 0.05-1.0 mg/g.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23644214
Antibacterial activity was screened against two Gram positive (Staphylococcus aureus MTCC 96, Streptococcus pyogenes MTCC 442) and two Gram negative (Escherichia coli MTCC 443, Pseudomonas aeruginosa MTCC 441) bacteria by using gentamycin, ampicillin, chloramphenicol, ciprofloxacin, norfloxacin as a standard antibacterial agents. Serial dilutions were prepared in primary and secondary screening. The control tube containing no antibiotic was immediately subcultured (before inoculation) by spreading a loopful evenly over a quarter of plate of medium suitable for the growth of the test organism and put for incubation at 37 C overnight. The tubes were then incubated overnight. The MIC of the control organismwas read to check the accuracy of the drug concentrations. The lowest concentration inhibiting growth of the organism was recorded as the MIC. All the tubes not showing visible growth (in the same manner as control tube described above) was subcultured and incubated overnight at 37 C. The amount of growth from the control tube before incubation (which represents the original inoculum) was compared. Subcultures might show: similar number of colonies indicating bacteriostatic; a reduced number of colonies indicating a partial or slow bactericidal activity and no growth if the whole inoculum has been killed. The test must include a second set of the same dilutions inoculated with an organism of known sensitivity. Each synthesized drug was diluted obtaining 2000 mg/mL concentration, as a stock solution. In primary screening 500, 250 and 125 mg/mL concentrations of the synthesized drugs were taken. The active synthesized drugs found in this primary screening were further tested in a second set of dilution against all microorganisms. The drugs found active in primary screening were similarly diluted to obtain 100, 50, 25, 12.5, 6.250, 3.125 and 1.5625 mg/mL concentrations. The highest dilution showing at least 99% inhibition is taken as MIC.
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ACTIVE MOIETY