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Faropenem medoxomil

Alias: A0026; A-0026; A 0026; Faropenem medoxomil; Faropenem daloxate; Faropenem medoxil.
Cat No.:V20923 Purity: ≥98%
Faropenem medoxomil (Faropenem daloxate; Faropenem medoxil) is an orally bioactive beta-lactam antibiotic of the penem class.
Faropenem medoxomil
Faropenem medoxomil Chemical Structure CAS No.: 141702-36-5
Product category: Bacterial
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
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25mg
50mg
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Product Description

Faropenem medoxomil (Faropenem daloxate; Faropenem medoxil) is an orally bioactive beta-lactam antibiotic of the penem class. It is a prodrug of Faropenem. Faropenem medoxomil is the first oral penem in a new class of beta-lactam antibiotics. Faropenem medoxomil has excellent in vitro activity against Streptococcus pneumoniae, Haemophilus influenzae and other key pathogens implicated in acute bacterial rhinosinusitis.

Biological Activity I Assay Protocols (From Reference)
References

[1].Faqi AS, Lanphear C, Gill S, Colagiovanni DB.Juvenile toxicity study of faropenem medoxomil in beagle puppies.Reprod Toxicol. 2010 Dec;30(4):619-24. Epub 2010 Aug 11.

[2].Hadley JA, Tillotson GS, Tosiello R, Echols RM.Faropenem medoxomil: a treatment option in acute bacterial rhinosinusitis.Expert Rev Anti Infect Ther. 2006 Dec;4(6):923-37.

[3].Siegert R, Berg O, Gehanno P, Leiberman A, Martinkenas JL, Nikolaidis P, Arvis P, Alefelder M, Reimnitz P.Comparison of the efficacy and safety of faropenem daloxate and cefuroxime axetil for the treatment of acute bacterial maxillary sinusitis in adults.

[4].Upchurch J, Rosemore M, Tosiello R, Kowalsky S, Echols R.Randomized double-blind study comparing 7- and 10-day regimens of faropenem medoxomil with a 10-day cefuroxime axetil regimen for treatment of acute bacterial sinusitis.Otolaryngol Head Neck Surg. 2

[5].Gettig, Jacob P.; Crank, Christopher W.; Philbrik, Alexander H. Faropenem medoxomil. Annals of Pharmacotherapy (2008), 42(1), 80-90.

Additional Infomation
Faropenem medoxil is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid.
Faropenem medoxomil is an ester prodrug derivative of the beta-lactam antibiotic [faropenem]. The prodrug form of faropenem offers dramatically improved oral bioavailability and leads to higher systemic concentrations of the drug. Faropenem medoxomil is a broad-spectrum antibiotic that is highly resistant to beta-lactamase degradation. It is being developed jointly by Replidyne, Inc. and Forest Laboratories, Inc.
Faropenem Medoxomil is a daloxate ester prodrug form of faropenem, a penem with a tetrahydrofuran substituent at position C2, with broad-spectrum antibacterial activity against many gram-positive and gram-negative aerobes and anaerobes. Faropenem medoxomil is hydrolyzed in vivo to release the active free acid. Compared with imipenem, faropenem has improved chemical stability and reduced central nervous system effects. In addition, faropenem is resistant to hydrolysis by many beta-lactamases.
Drug Indication
Investigated for use/treatment in bacterial infection, bronchitis, otitis media, and pediatric indications.
Mechanism of Action
Like other beta-lactam antibiotics, faropenem acts by inhibiting the synthesis of bacterial cell walls. It inhibits cross-linkage between the linear peptidoglycan polymer chains that make up a major component of the cell wall of Gram-positive bacteria. It does this by binding to and competitively inhibiting the transpeptidase enzyme used by bacteria to cross-link the peptide (D-alanyl-alanine) used in peptidogylcan synthesis.
Pharmacodynamics
Faropenem has demonstrated excellent in vitro activity against common respiratory pathogens, many aerobic gram-positive organisms, and anaerobes. Activity against gram-negative organisms is more reserved. In vivo data suggest that faropenem is efficacious in treating community-acquired infections including uncomplicated skin and skin structure infections; however, more data may help to characterize faropenem's place in antimicrobial therapy.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H19NO8S
Molecular Weight
397.398
Exact Mass
397.083
Elemental Analysis
C, 51.38; H, 4.82; N, 3.52; O, 32.21; S, 8.07
CAS #
141702-36-5
Related CAS #
141702-36-5;16559-89-1;
PubChem CID
6918218
Appearance
Solid powder
Density
1.55 g/cm3
Boiling Point
622.3ºC at 760 mmHg
Vapour Pressure
4.3E-18mmHg at 25°C
Index of Refraction
1.642
LogP
0.825
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
6
Heavy Atom Count
27
Complexity
775
Defined Atom Stereocenter Count
4
SMILES
O=C(N1[C@@]2(SC([C@@H]3OCCC3)=C1C(OCC4=C(OC(O4)=O)C)=O)[H])[C@@H]2[C@H](O)C
InChi Key
JQBKWZPHJOEQAO-DVPVEWDBSA-N
InChi Code
InChI=1S/C17H19NO8S/c1-7(19)11-14(20)18-12(13(27-15(11)18)9-4-3-5-23-9)16(21)24-6-10-8(2)25-17(22)26-10/h7,9,11,15,19H,3-6H2,1-2H3/t7-,9-,11+,15-/m1/s1
Chemical Name
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5R,6S)-6-((R)-1-hydroxyethyl)-7-oxo-3-((R)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
Synonyms
A0026; A-0026; A 0026; Faropenem medoxomil; Faropenem daloxate; Faropenem medoxil.
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

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 : ≥ 100 mg/mL (~251.64 mM )
H2O : < 0.1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.29 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 (6.29 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 (6.29 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: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (6.29 mM)

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.5164 mL 12.5818 mL 25.1636 mL
5 mM 0.5033 mL 2.5164 mL 5.0327 mL
10 mM 0.2516 mL 1.2582 mL 2.5164 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.

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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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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.

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