Clarithromycin

Alias: Abbott56268; A56268; A-56268; A 56268; A56268; Abbott 56268; A 56268; Clarithromycin; Abbott-56268; A-56268; brand name Biaxin.
Cat No.:V0814 Purity: ≥98%
Clarithromycin (A56268; Abbott 56268; A 56268; Abbott-56268; A-56268; trade name Biaxin) is an approved macrolide antibiotic medication acting as a CYP3A4 inhibitor.
Clarithromycin Chemical Structure CAS No.: 81103-11-9
Product category: P450 (e.g. CYP)
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
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1g
2g
5g
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Other Forms of Clarithromycin:

  • Clarithromycin-d3 (clarithromycin-d3)
Official Supplier of:
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Clarithromycin (A56268; Abbott 56268; A 56268; Abbott-56268; A-56268; trade name Biaxin) is an approved macrolide antibiotic medication acting as a CYP3A4 inhibitor. It has been widely used for treatment of a number of bacterial infections such as pharyngitis, tonsillitis, acute maxillary sinusitis, acute bacterial exacerbation of chronic bronchitis, pneumonia (especially atypical pneumonias associated with Chlamydophila pneumoniae), skin and skin structure infections. Clarithromycin prevents bacteria from growing by interfering with their protein synthesis.

Biological Activity I Assay Protocols (From Reference)
ln Vitro
Clarithromycin has a similar concentration-dependent block, with an IC50 of 45.7 μM [3]. Clarithromycin causes the formation of numerous intracytoplasmic vacuoles in all cell lines after 24 hours, particularly in HCT116 cells. Prolonged Clarithromycin (40, 80, and 160 μM) treatment alters cell proliferation and triggers apoptotic cell death in colorectal cancer (CRC). Clarithromycin re-administered to the cells increases the inhibition of cell proliferation. Re-adding 160 μM Clarithromycin after 48 hours of incubation causes cell proliferation to stop at 72 hours. Similar effects were observed in LS174T cells[4]. Clarithromycin (80 and 160 μM; 48 hours) significantly increases the LC3-II/LC3-I ratio in a dose- and time-dependent manner, peaking at 24 hours of treatment. This effect is associated with a decrease in p62/SQSTM1[4].
ln Vivo
At 200 mg/kg, clarithromycin is active against four in vivo tests[5].
Cell Assay
Cell Proliferation Assay[4]
Cell Types: HCT116 cells
Tested Concentrations: 40, 80, and 160 µM
Incubation Duration: 24, 48, 72 hrs (hours)
Experimental Results: decreased HCT116 cell proliferation, although did not completely abolished it.

Western Blot Analysis[4]
Cell Types: HCT116 cells
Tested Concentrations: 80 and 160 µM
Incubation Duration: 4, 24, 48 hrs (hours)
Experimental Results: A decrease of LC3-II and a re-increase of p62/SQSTM1 were observed at 48 hrs (hours) treatment.
Animal Protocol
Animal/Disease Models: Sixweeks old beige (C57BL/6J bgj/bgj) mice which had been infected with viable M. avium ATCC 49601[5]
Doses: 50, 100, 200, or 300 mg/kg
Route of Administration: Administered daily by gavage
Experimental Results: decreased organ cell counts compared with those in mice given no treatment at all doses. Had activity against three additional MAC isolates (MICs for the isolates ranged from 1 to 4 µg/mL by broth dilution) at 200 mg/kg.
References
[1]. D H Peters, et al. Clarithromycin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic potential. Drugs. 1992 Jul;44(1):117-64.
[2]. X J Zhao, et al. An in vitro study on the metabolism and possible drug interactions of rokitamycin, a macrolide antibiotic, using human liver microsomes. Drug Metab Dispos. 1999 Jul;27(7):776-85.
[3]. Scott J C Stanat, et al. Characterization of the inhibitory effects of erythromycin and clarithromycin on the HERG potassium channel. Mol Cell Biochem. 2003 Dec;254(1-2):1-7.
[4]. Giulia Petroni, et al. Clarithromycin inhibits autophagy in colorectal cancer by regulating the hERG1 potassium channel interaction with PI3K. Cell Death Dis. 2020 Mar 2;11(3):161.
[5]. S P Klemens, et al. Activity of clarithromycin against Mycobacterium avium complex infection in beige mice. Antimicrob Agents Chemother. 1992 Nov;36(11):2413-7.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C38H69NO13
Molecular Weight
747.95
CAS #
81103-11-9
SMILES
CC[C@@H]1[C@@](C)(O)[C@H](O)[C@@H](C)C([C@H](C)C[C@@](C)(OC)[C@H](O[C@H]2[C@H](O)[C@@H](N(C)C)C[C@@H](C)O2)[C@@H](C)[C@H](O[C@H]3C[C@@](C)(OC)[C@@H](O)[C@H](C)O3)[C@@H](C)C(O1)=O)=O
InChi Key
AGOYDEPGAOXOCK-KCBOHYOISA-N
InChi Code
InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
Chemical Name
(3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
Synonyms
Abbott56268; A56268; A-56268; A 56268; A56268; Abbott 56268; A 56268; Clarithromycin; Abbott-56268; A-56268; brand name Biaxin.
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

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: 25 mg/mL (33.4 mM)
Water:<1 mg/mL
Ethanol:<1 mg/mL
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.3370 mL 6.6849 mL 13.3699 mL
5 mM 0.2674 mL 1.3370 mL 2.6740 mL
10 mM 0.1337 mL 0.6685 mL 1.3370 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:

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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?
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  • 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:
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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
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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)
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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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
  • Clarithromycin

    Representative flow-cytometric analysis demonstrating that pretreatment with clarithromycin significantly inhibited NF-κB activation induced by TNF-α in U-937 (A) and Jurkat cells (B) in a concentration-related manner.Antimicrob Agents Chemother.2001 Jan;45(1):44-7.



    Clarithromycin


    Representative Western blot demonstrating the effect of clarithromycin on TNF-α-induced IκBα degradation in A549 cells.
  • Clarithromycin

    Representative Western blot of nuclear extracts of PBMC demonstrating that pretreatment with clarithromycin inhibited NF-κB activation induced by TNF-α or SEA in a concentration-dependent fashion.Antimicrob Agents Chemother.2001 Jan;45(1):44-7.
  • Clarithromycin

    Representative Western blot of nuclear extracts of PBMC demonstrating that pretreatment with clarithromycin inhibited NF-κB activation induced by TNF-α or SEA in a concentration-dependent fashion.Antimicrob Agents Chemother.2001 Jan;45(1):44-7.



    Clarithromycin


    Representative Western blot of nuclear extracts of U-937, Jurkat, and A549 cells revealing that pretreatment with clarithromycin inhibited NF-κB activation induced by TNF-α in a concentration-dependent manner.
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