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Chloramphenicol

Alias: Chloramphenicol; Chlornitromycin; Chloromycetin; Levomycetin; Chlorocid; Globenicol; Detreomycin; Kloramfenikol; Levomycetin; Ophthochlor; Syntomycin;
Cat No.:V18163 Purity: ≥98%
Chloramphenicol (Globenicol;Chlorocid; Detreomycin;Levomycetin) is a bacteriostatic antibiotic agent with abroad-spectrum activity against a wide range of gram-positive and gram-negative organisms.
Chloramphenicol
Chloramphenicol Chemical Structure CAS No.: 56-75-7
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10g
25g
50g
100g
Other Sizes

Other Forms of Chloramphenicol:

  • Chloramphenicol-d5 (chloramphenicol d5 deuterated compound)
  • Chloramphenicol palmitate
  • Levomecol
  • DL-threo-Chloramphenicol-d5 (chloramphenicol d5)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Chloramphenicol is an orally active, potent and broad-spectrum antibiotic. Chloramphenicol possesses antimicrobial properties. In hypoxic A549 and H1299 cells, chloramphenicol represses the oxygen-labile transcription factor and hypoxia inducible factor-1 alpha (HIF-1α). Vascular endothelial growth factor (VEGF) and glucose transporter 1 mRNA levels are suppressed by chloramphenicol, which eventually reduces VEGF release. Research on anaerobic infections and lung cancer can benefit from the use of chloramphenicol.
Biological Activity I Assay Protocols (From Reference)
Targets
JNK;MMP13
ln Vitro
The HIF-1α pathway in NSCLC cells is inhibited by chloramphenicol (1-100 μg/mL, 18-24 h) in a concentration-dependent manner.NSCLC cells are exposed to 100 μg/mL of chloramphenicol for 0–24 hours, which causes autophagy induction and significantly raises the levels of autophagic biomarkers (beclin-1, Atg12–Atg5 conjugates, and LC3–II)[1].
In activated T cells, chloramphenicol inhibits apoptosis and causes aberrant differentiation[2].
Chloramphenicol can cause reduced ATP biosynthesis and mitochondrial stress by blocking the synthesis of proteins in both bacteria and mitochondria[3].
Chloramphenicol (1-100 μg/mL) has the ability to upregulate MMP-13 protein and stimulate the expression of matrix metalloproteinase (MMP)-13[3].
Chloramphenicol (1-100 μg/mL) has the ability to stimulate PI-3K/Akt signaling, c-Jun protein phosphorylation, and c-Jun N-terminal kinases (JNK)[3].
By inhibiting peptidyl transferase activity, chloramphenicol mainly affects the 50S subunit of bacterial 70S rihosomes, which prevents the formation of peptide bonds[5].
ln Vivo
Day 1 post-dosing sees a decrease in marrow erythroid cells and erythrocyte precursors, and by day 14, after 14 days of treatment, erythrocytes and erythrocyte precursors have returned to normal[4].
Animal Protocol
Animal Model: Female B6C3F1 mice (12-14 weeks old)
Dosage: 0, 2500 and 3500 mg/kg
Administration: Gavage, daily, for 5 days
Result: On the first day after dosage, erythropoiesis was clearly stopped. At the 2500 mg/kg dose level on day 7 and between 7 and 14 days at the 3500 mg/kg dose level, respectively, a recovery was observed after the dosage. At every dosage level, the erythroid series showed the greatest myelotoxicity. Day 1 post-dosage: decreased femoral marrow BFU-E and CFU-E. Within 14 days of the dosage, every blood and marrow parameter in the current study was back to normal.
References

[1]. Chloramphenicol Induces Autophagy and Inhibits the Hypoxia Inducible Factor-1 Alpha Pathway in Non-Small Cell Lung Cancer Cells. Int J Mol Sci. 2019 Jan 3;20(1):157.

[2]. Chloramphenicol induces abnormal differentiation and inhibits apoptosis in activated T cells. Cancer Res. 2008 Jun 15;68(12):4875-81.

[3]. Chloramphenicol causes mitochondrial stress, decreases ATP biosynthesis, induces matrix metalloproteinase-13 expression, and solid-tumor cell invasion. Toxicol Sci. 2010 Jul;116(1):140-50.

[4]. Characterization of the myelotoxicity of chloramphenicol succinate in the B6C3F1 mouse. Int J Exp Pathol. 2006 Apr;87(2):101-12.

[5]. Jardetzky, O., Studies on the mechanism of action of chloramphenicol. I. The conformation of chlioramphenicol in solution. J Biol Chem, 1963. 238: p. 2498-508.

[6]. Wolfe, A.D. and F.E. Hahn, Mode of Action of Chloramphenicol. Ix. Effects of Chloramphenicol Upon a Ribosomal Amino Acid Polymerization System and Its Binding to Bacterial Ribosome. Biochim Biophys Acta, 1965. 95: p. 146-55

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H12CL2N2O5
Molecular Weight
323.13
Exact Mass
322.0123
Elemental Analysis
C, 40.89; H, 3.74; Cl, 21.94; N, 8.67; O, 24.76
CAS #
56-75-7
Related CAS #
Chloramphenicol-d5;202480-68-0;Chloramphenicol palmitate;530-43-8;Levomecol;118573-58-3;DL-threo-Chloramphenicol-d5;1420043-66-8;Threo-Chloramphenicol-d6;Chloramphenicol-d4
Appearance
White to off-white crystalline powder.
SMILES
C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
InChi Key
WIIZWVCIJKGZOK-RKDXNWHRSA-N
InChi Code
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-/m1/s1
Chemical Name
2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
Synonyms
Chloramphenicol; Chlornitromycin; Chloromycetin; Levomycetin; Chlorocid; Globenicol; Detreomycin; Kloramfenikol; Levomycetin; Ophthochlor; Syntomycin;
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product is not stable in solution, please use freshly prepared working solution for optimal results.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO :65~150 mg/mL (201.15~464.21 mM )
Ethanol : ~100 mg/mL (~309.47 mM )
H2O : ~3.06 mg/mL (~9.47 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.74 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (7.74 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (7.74 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: ≥ 2.5 mg/mL (7.74 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 5: ≥ 2.5 mg/mL (7.74 mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

Solubility in Formulation 6: ≥ 2.5 mg/mL (7.74 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH stock solution to 900 μL of corn oil and mix evenly.

Solubility in Formulation 7: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (7.74 mM)

Solubility in Formulation 8: 2.5 mg/mL (7.74 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.0947 mL 15.4736 mL 30.9473 mL
5 mM 0.6189 mL 3.0947 mL 6.1895 mL
10 mM 0.3095 mL 1.5474 mL 3.0947 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Biological Data
  • Chloramphenicol inhibited HIF-1α protein accumulation in NSCLC cells in a concentration-dependent manner. [1].Int J Mol Sci. 2019 Jan 3;20(1):157.
  • Chloramphenicol inhibited the HIF-1α pathway in NSCLC cells. [1]Int J Mol Sci. 2019 Jan 3;20(1):157..
  • Chloramphenicol destabilized the HIF-1α protein. [1].Int J Mol Sci. 2019 Jan 3;20(1):157.
  • Chloramphenicol induced autophagy in NSCLC cells in a time-dependent manner. [1].Int J Mol Sci. 2019 Jan 3;20(1):157.
  • Chloramphenicol potentiated HIF-1α protein degradation via the autophagy pathway. [1].Int J Mol Sci. 2019 Jan 3;20(1):157.
  • Chloramphenicol interrupted protein interaction between SENP-1 and HIF-1α and promoted HIF-1α degradation via the autophagy pathway. [1].Int J Mol Sci. 2019 Jan 3;20(1):157.
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