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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
Structure of DEXTRAMYCIN

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

HIDE SMILES / InChI

Description
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.

Originator

Sources: Giornale di Malattie Infettive e Parassitarie (1949), 1, 287-92.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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

Patents

Sample Use Guides

In Vivo Use Guide
Rats were treated with Dextramycin 0.05-1.0 mg/g.
Route of Administration: Oral
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.
Name Type Language
DEXTRAMYCIN
Common Name English
CHLORAMPHENICOL, L-THREO-
Preferred Name English
L-THREO-(1S,2S)-1-P-NITROPHENYL-2-DICHLOROACETAMIDO-1,3-PROPANEDIOL
Systematic Name English
L-THREO-CHLORAMPHENICOL
Common Name English
L-CHLOROAMPHENICOL
Common Name English
ACETAMIDE, 2,2-DICHLORO-N-((1S,2S)-2-HYDROXY-1-(HYDROXYMETHYL)-2-(4-NITROPHENYL)ETHYL)-
Systematic Name English
L-(+)-THREO-CHLORAMPHENICOL
Common Name English
L-THREO-CHLOROAMPHENICOL
Common Name English
DEXTROMYCETIN
Common Name English
Code System Code Type Description
PUBCHEM
92099
Created by admin on Mon Mar 31 23:16:54 GMT 2025 , Edited by admin on Mon Mar 31 23:16:54 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-161-2
Created by admin on Mon Mar 31 23:16:54 GMT 2025 , Edited by admin on Mon Mar 31 23:16:54 GMT 2025
PRIMARY
SMS_ID
100000153669
Created by admin on Mon Mar 31 23:16:54 GMT 2025 , Edited by admin on Mon Mar 31 23:16:54 GMT 2025
PRIMARY
FDA UNII
U0PWV2Z3IW
Created by admin on Mon Mar 31 23:16:54 GMT 2025 , Edited by admin on Mon Mar 31 23:16:54 GMT 2025
PRIMARY
EPA CompTox
DTXSID40158453
Created by admin on Mon Mar 31 23:16:54 GMT 2025 , Edited by admin on Mon Mar 31 23:16:54 GMT 2025
PRIMARY
CAS
134-90-7
Created by admin on Mon Mar 31 23:16:54 GMT 2025 , Edited by admin on Mon Mar 31 23:16:54 GMT 2025
PRIMARY