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.
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) |
Biological Activity
| 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. |
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. 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 |