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> Chloramphenicol [56-75-7]

Chloramphenicol [56-75-7]

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Chloramphenicol is an orally active, potent and broad-spectrum antibiotic. Chloramphenicol shows antibacterial activity. Chloramphenicol represses the oxygen-labile transcription factor and hypoxia inducible factor-1 alpha (HIF-1α) in hypoxic A549 and H1299 cells. Chloramphenicol suppresses the mRNA levels of vascular endothelial growth factor (VEGF) and glucose transporter 1, eventually decreasing VEGF release. Chloramphenicol can be used for anaerobic infections and lung cancer research.

For research use only. We do not sell to patients.

Chloramphenicol Chemical Structure

Chloramphenicol Chemical Structure

CAS No. : 56-75-7

This product is a controlled substance and not for sale in your territory.

Based on 8 publication(s) in Google Scholar

Other Forms of Chloramphenicol:

  • Levomecol Get quote
  • Chloramphenicol-d5 Get quote
  • DL-threo-Chloramphenicol-d5 Get quote
  • Threo-Chloramphenicol-d6 Get quote
  • Chloramphenicol-d4 Get quote
  • Chloramphenicol palmitate Get quote
  • Chloramphenicol (Standard) Get quote

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Aminoglycoside Glycopeptide Lipopeptide Macrolide Oxazolidinone Quinolone Tetracycline β-lactam

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HIF-1α HIF

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VEGFR1/Flt-1 VEGFR2/KDR/Flk-1 VEGFR3/Flt-4

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JNK1 JNK2 JNK3 JNK

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Akt Akt1 Akt2 Akt3

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MMP-1 MMP-2 MMP-3 MMP-8 MMP-9 MMP-13 MMP-14 MMP-17 ADAM10 ADAM17 MMP-7 MMP-12 MMP-10 MMP ADAM8
Description

Chloramphenicol is an orally active, potent and broad-spectrum antibiotic. Chloramphenicol shows antibacterial activity. Chloramphenicol represses the oxygen-labile transcription factor and hypoxia inducible factor-1 alpha (HIF-1α) in hypoxic A549 and H1299 cells. Chloramphenicol suppresses the mRNA levels of vascular endothelial growth factor (VEGF) and glucose transporter 1, eventually decreasing VEGF release. Chloramphenicol can be used for anaerobic infections and lung cancer research[1][2][3].

IC50 & Target

JNK

 

MMP13

 

In Vitro

Chloramphenicol (1-100 μg/mL, 18-24 h) inhibits the HIF-1α pathway in NSCLC cells in a concentration-dependent manner[1].
Chloramphenicol (100 μg/mL, 0-24 h) induces autophagy in NSCLC cells, substantially increases the levels of autophagic biomarkers (beclin-1, Atg12-Atg5 conjugates, and LC3-II)[1].
Chloramphenicol induces abnormal differentiation and inhibits apoptosis in activated T cells[2].
Chloramphenicol can inhibit both bacterial and mitochondrial protein synthesis, causing mitochondrial stress and decreased ATP biosynthesis[3].
chloramphenicol (1-100 μg/mL) can induce matrix metalloproteinase (MMP)-13 expression and increase MMP-13 protein[3].
chloramphenicol (1-100 μg/mL) can activate c-Jun N-terminal kinases (JNK) and phosphatidylinositol 3-kinase (PI-3K)/Akt signaling, leading to c-Jun protein phosphorylation[3].
Chloramphenicol acts primarily on the 50S subunit of bacterial 70S rihosomes and inhibits peptide bond formation by suppressing peptidyl transferase activity[5].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Chloramphenicol Related Antibodies

Cell Viability Assay[1]

Cell Line: A549 and H1299 cells
Concentration: 0, 1, 10, 100 μg/mL
Incubation Time: 3 h and 24 h
Result: In the 3-h-treated group, the viability of A549 and H1299 cells at 100 μg/mL concentration was 97.0 ± 3.9% and 98.1 ± 5.0%, respectively. The viability of A549 cells was 102.9 ± 1.3% and 99.2 ± 0.9%, whereas the viability of H1299 cells was 103.3 ± 1.9% and 93.8 ± 4.5%, under hypoxia and treatment with CoCl2, respectively.

Western Blot Analysis[1]

Cell Line: A549 and H1299 cells
Concentration: 0, 1, 10, 50, 100 μg/mL
Incubation Time: 18-24 h
Result: Inhibited HIF-1α protein accumulation in NSCLC cells in a concentration-dependent manner, while the expression levels of ARNT remained unaltered. Had no effect on CoCl2 (250 μM, 3 h treatment)-mediated HIF-1α protein accumulation and SENP-1 protein reduction.

Western Blot Analysis[1]

Cell Line: A549 and H1299 cells
Concentration: 100 μg/mL
Incubation Time: 0, 6, 12, 24 h
Result: Induced autophagy in NSCLC cells in a time-dependent manner. Upregulats the expression of beclin-1 and increased the levels of Atg12-Atg5 conjugates in both NSCLC cell lines, both in a time dependent and concentration-dependent manner. Augmented LC3-II and downregulated p62/STSQM1 in A549 cells. Induced an augmentation of p62/STSQM1, and a decrease in LC3-II levels in H1299 cells.
In Vivo

Chloramphenicol (0-3500 mg/kg, Gavage, daily, for 5 days) decreases erythrocytes and erythrocyte precursors and reduces marrow erythroid cells were at day 1 post-dosing, and returns to normal by 14 days post-dosing[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: Female B6C3F1 mice (12-14 weeks old)[4]
Dosage: 0, 2500 and 3500 mg/kg
Administration: Gavage, daily, for 5 days
Result: Cessation of erythropoiesis was evident at day 1 post-dosing. A recovery was seen at day 7 post-dosing at the 2500 mg/kg dose level and at between 7 and 14 days at the 3500 mg/kg dose level. Myelotoxicity was most pronounced in the erythroid series at each dose level. Depressed femoral marrow BFU-E and CFU-E at day 1 post-dosing. All the blood and marrow parameters in the present study returned to normal by 14 days post-dosing.
Molecular Weight

323.13

Formula

C11H12Cl2N2O5
CAS No.

56-75-7
Appearance

Solid

Color

White to off-white

SMILES

O=C(N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1)C(Cl)Cl
Structure Classification
  • Antibiotics
  • Disease Research
  • Antibacterial
  • Antibiotics
  • Disease Research
  • Anticancer
  • Antibiotics
  • Other Antibiotics
  • Antibiotics
  • Animal Husbandry
  • Antibiotics
  • Plant Cell Culture
  • Antibiotics
  • Resistance Selection
Initial Source
  • Endogenous metabolite
  • Human Gut Microbiota Metabolites
  • Microorganisms

Streptomyces venezuelae
Shipping

Room temperature in continental US; may vary elsewhere.
Storage
Powder -20°C 3 years
4°C 2 years

*The compound is unstable in solutions, freshly prepared is recommended.

Solvent & Solubility
In Vitro: 

DMSO : ≥ 150 mg/mL (464.21 mM; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Ethanol : 100 mg/mL (309.47 mM; Need ultrasonic)

H2O : 3.06 mg/mL (9.47 mM; Need ultrasonic)

*"≥" means soluble, but saturation unknown.

Preparing
Stock Solutions
Concentration Solvent Mass 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
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. The compound is unstable in solutions, freshly prepared is recommended.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

  • Molarity Calculator

  • Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass
=
Concentration
×
Volume
×
Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

×
Volume (start)

V1

=
Concentration (final)

C2

×
Volume (final)

V2

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.5 mg/mL (7.74 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.5 mg/mL (7.74 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.

For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  PBS

    Solubility: 2.5 mg/mL (7.74 mM); Clear solution; Need ultrasonic

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
%
DMSO +
% 
+
%
Tween-80 +
%
Saline
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Calculation results:
Working solution concentration: mg/mL
Method for preparing stock solution: mg drug dissolved in μL  DMSO (Stock solution concentration: mg/mL).

*The compound is unstable in solutions, freshly prepared is recommended.

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).
Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.
 If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation

Purity: 99.82%

COA (247 KB) HNMR (165 KB) LCMS (449 KB)

Handling Instructions (2659 KB)
References

  • [1]. Hsu HL, et al. 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.  [Content Brief]

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

    [3]. Li CH, et al. 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.  [Content Brief]

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

    [5]. Bartlett JG. Chloramphenicol. Med Clin North Am. 1982;66(1):91-102.  [Content Brief]

  • [1]. Hsu HL, et al. 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]. Yuan ZR, et al. Chloramphenicol induces abnormal differentiation and inhibits apoptosis in activated T cells. Cancer Res. 2008 Jun 15;68(12):4875-81.

    [3]. Li CH, et al. 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]. Turton JA, et al. Characterization of the myelotoxicity of chloramphenicol succinate in the B6C3F1 mouse. Int J Exp Pathol. 2006 Apr;87(2):101-12.

    [5]. Bartlett JG. Chloramphenicol. Med Clin North Am. 1982;66(1):91-102.

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. The compound is unstable in solutions, freshly prepared is recommended.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
H2O / Ethanol / DMSO 1 mM 3.0947 mL 15.4736 mL 30.9473 mL 77.3682 mL
5 mM 0.6189 mL 3.0947 mL 6.1895 mL 15.4736 mL
Ethanol / DMSO 10 mM 0.3095 mL 1.5474 mL 3.0947 mL 7.7368 mL
15 mM 0.2063 mL 1.0316 mL 2.0632 mL 5.1579 mL
20 mM 0.1547 mL 0.7737 mL 1.5474 mL 3.8684 mL
25 mM 0.1238 mL 0.6189 mL 1.2379 mL 3.0947 mL
30 mM 0.1032 mL 0.5158 mL 1.0316 mL 2.5789 mL
40 mM 0.0774 mL 0.3868 mL 0.7737 mL 1.9342 mL
50 mM 0.0619 mL 0.3095 mL 0.6189 mL 1.5474 mL
60 mM 0.0516 mL 0.2579 mL 0.5158 mL 1.2895 mL
80 mM 0.0387 mL 0.1934 mL 0.3868 mL 0.9671 mL
100 mM 0.0309 mL 0.1547 mL 0.3095 mL 0.7737 mL

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

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Chloramphenicol Related Classifications

  • Infection Cancer
  • Cancer Targeted Therapy Cancer Immunotherapy Cancer Metabolism and Metastasis
  • Anti-infection Metabolic Enzyme/Protease Protein Tyrosine Kinase/RTK Autophagy Apoptosis MAPK/ERK Pathway PI3K/Akt/mTOR
  • Antibiotic Bacterial HIF/HIF Prolyl-Hydroxylase VEGFR Autophagy Apoptosis Beclin1 JNK Akt MMP
Help & FAQs

Keywords:

Chloramphenicol56-75-7AntibioticBacterialHIF/HIF Prolyl-HydroxylaseVEGFRAutophagyApoptosisBeclin1JNKAktMMPHypoxia-inducible factorsHIFsHIF-PHVascular endothelial growth factor receptorAtg6c-Jun N-terminal kinasePKBProtein kinase BMatrix metalloproteinasesA549H1299antibioticbacterialAplastic anaemiaanaerobic infectionsSENP-1PI-3Kmitochondria stressInhibitorinhibitorinhibit

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