Faropenem daloxate

Oral penem,beta-lactam antibiotic CAS# 141702-36-5

Faropenem daloxate

Catalog No. BCC1571----Order now to get a substantial discount!

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Quality Control of Faropenem daloxate

Number of papers citing our products

Chemical structure

Faropenem daloxate

3D structure

Chemical Properties of Faropenem daloxate

Cas No. 141702-36-5 SDF Download SDF
PubChem ID 6918218 Appearance Powder
Formula C17H19NO8S M.Wt 397.41
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Faropenem medoxil
Solubility DMSO : ≥ 100 mg/mL (251.64 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
SMILES CC1=C(OC(=O)O1)COC(=O)C2=C(SC3N2C(=O)C3C(C)O)C4CCCO4
Standard InChIKey JQBKWZPHJOEQAO-DVPVEWDBSA-N
Standard InChI 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Faropenem daloxate

DescriptionFaropenem daloxate is the first oral penem in a new class of beta-lactam antibiotics. IC50 Value: Target: Antibacterial Faropenem daloxate is useful for penem and antibiotics. Faropenem medoxomil has excellent in vitro activity against Streptococcus pneumoniae, Haemophilus influenzae and other key pathogens implicated in acute bacterial rhinosinusitis. Clinical studies have demonstrated that, in the treatment of acute bacterial rhinosinusitis in adults, 7 days of treatment with faropenem medoxomil is as clinically and bacteriologically effective as 10 days of treatment with cefuroxime axetil. One study showed faropenem medoxomil to be superior to cefuroxime axetil. Overall, the safety profile of faropenem medoxomil is similar to that of most comparators.

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.

Faropenem daloxate Dilution Calculator

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Faropenem daloxate Molarity Calculator

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Preparing Stock Solutions of Faropenem daloxate

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5163 mL 12.5815 mL 25.1629 mL 50.3259 mL 62.9073 mL
5 mM 0.5033 mL 2.5163 mL 5.0326 mL 10.0652 mL 12.5815 mL
10 mM 0.2516 mL 1.2581 mL 2.5163 mL 5.0326 mL 6.2907 mL
50 mM 0.0503 mL 0.2516 mL 0.5033 mL 1.0065 mL 1.2581 mL
100 mM 0.0252 mL 0.1258 mL 0.2516 mL 0.5033 mL 0.6291 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Faropenem daloxate

Faropenem daloxate is useful for penem and antibiotics.

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References on Faropenem daloxate

Comparison of the efficacy and safety of faropenem daloxate and cefuroxime axetil for the treatment of acute bacterial maxillary sinusitis in adults.[Pubmed:12709801]

Eur Arch Otorhinolaryngol. 2003 Apr;260(4):186-94.

In this multicentre, multinational, comparative, double-blind clinical trial, outpatients with both clinical signs and symptoms and radiographic evidence of acute sinusitis were randomly assigned to receive for 7 days either a twice-daily oral regimen of Faropenem daloxate (300 mg) or a twice daily oral regimen of cefuroxime axetil (250 mg). Among 452 patients considered valid for clinical efficacy, Faropenem daloxate treatment was found to be statistically equivalent to cefuroxime axetil (89.0% vs. 88.4%-95% CI=-5.2%; +6.4%) at the 7-16 days post-therapy assessment. At 28-35 days post-therapy, the continued clinical cure rate in the Faropenem daloxate group was 92.6% and that for the cefuroxime axetil group was 94.9% (95% CI: -6.8%; +1.2%). A total of 148 organisms was obtained in 136 microbiologically valid patients (30.1%). The predominant causative organisms were Streptococcus pneumoniae (47.1%), Haemophilus influenzae (30.1%), Staphylococcus aureus (14.7%) and Moraxella catarrhalis (8.8%). The bacteriological success rate at the 7-16 days post-therapy evaluation was similar in both treatment groups: 91.5% and 90.8% in the Faropenem daloxate and cefuroxime axetil groups, respectively (95% CI=-9.2%; +9.5%). Eradication or presumed eradication was detected for 97.3% and 96.3% of S. pneumoniae, 85.0% and 90.5% of H. influenzae, 88.9% and 90.9% of S. aureus and 100.0% and 83.3% of M. catarrhalis in Faropenem daloxate and cefuroxime axetil recipients, respectively. At least one drug-related event was reported by 9.5% of the Faropenem daloxate-treated patients and by 10.3% of those who received cefuroxime axetil. The most frequently reported drug-related events were diarrhoea (2.2% versus 2.9%), nausea/vomiting (1.5% vs. 0.7%), abdominal pain (0.7% vs 1.5%) and skin reactions (1.5% vs. 1.1%). Overall, Faropenem daloxate was at least as effective clinically and bacteriologically as cefuroxime axetil and was well tolerated.

Faropenem medoxomil: A0026, BAY 56-6854, BAY 566854, faropenem daloxate, SUN 208, SUN A0026.[Pubmed:18298129]

Drugs R D. 2008;9(2):115-24.

Replidyne is developing faropenem medoxomil, the ester-type prodrug of faropenem, for the treatment of bacterial infections and respiratory tract infections, including acute exacerbations of chronic bronchitis (AECB), acute bacterial sinusitis (ABS) and community-acquired pneumonia (CAP). Faropenem medoxomil is also being developed for the treatment of tonsillitis, pharyngitis and otitis media in children. Faronpenem medoxomil was discovered by scientists at Suntory Institute for Biomedical Research (now Asubio Pharma). The compound has significantly improved oral bioavailability and is dehydropeptidase-I stable. Following absorption, faropenem medoxomil is rapidly hydrolysed to the active drug faropenem. An NDA was filed in the US but was deemed not approvable by the US authorities. Following the termination of the license agreement between Replidyne and Forest Laboratories, Replidyne is now exploring other partnering opportunities for faropenem medoxomil. Daiichi Suntory Pharma (now Asubio Pharma) has granted Replidyne the exclusive rights to faropenem medoxomil for the US and Canada and an exclusive option to develop and commercialize the compound in the rest of the world, excluding Japan. Replidyne has rights to the preclinical and clinical data generated up to the time of the agreement (August 2004) and will complete clinical development of the drug. Replidyne is also developing a paediatric formulation for the treatment of common bacterial infections. In February 2006, Replidyne sublicensed development, commercialization and distribution rights of faropenem medoxomil in the US to Forest Laboratories Holdings (Forest Laboratories). However, the agreement was terminated in February 2007, following the US FDA's non-approvable letter for the product. Replidyne re-acquired all US adult and paediatric rights previously granted to Forest. Bayer AG previously licensed exclusive worldwide rights to develop faropenem medoxomil from Suntory (now Asubio Pharma) and conducted a number of phase III clinical trials. This agreement appears to have been superseded by the agreement with Replidyne in 2004. In April 2007, Daiichi Asubio Pharma was renamed as Asubio Pharma Co., Ltd. Daiichi Asubio Pharma was the name used by Daiichi Suntory Pharma after it became a wholly owned subsidiary of Daiichi Pharmaceutical in September 2005. Daiichi Suntory Pharma was the joint venture company owned by Daiichi Pharmaceutical and Suntory. In April 2006, Daiichi Pharmaceutical merged with Sankyo to form Daiichi Sankyo Inc. The FDA issued a non-approvable letter in October 2006 for faropenem medoxomil in the treatment of ABS, CAP, AECB and uncomplicated skin and skin structure infections. Consequently, drug development has reverted back to phase III in the US. The agency has indicated that four phase III trials in three adult respiratory indications, ABS, CAP and AECB, will be required for a US marketing application. According to this advice, Replidyne may be required to conduct one superiority study (versus placebo) each for the ABS and AECB indications and two non-inferiority, active-controlled studies for the treatment of CAP. The required dose of faropenem medoxomil in future trials will be 600 mg, administered twice daily, and trials will involve approximately 1500 patients to ensure an acceptable database of safety information for review. Replidyne is continuing to work with the FDA on further trial details. Replidyne first filed the NDA seeking approval for faropenem medoxomil in December 2005. This submission marked the first marketing approval application for faropenem medoxomil worldwide. The NDA, which was accepted in February 2006, was primarily based on data from 11 phase III trials in patients with respiratory tract and skin infections; the safety data included information from more than 5000 patients treated with the drug. The proposed commercial name for faropenem medoxomil, Orapemtrade mark, was not approved by the FDA due to its similarity to another commercially approved drug. Replidyne and the FDA are working together to identify a suitable alternative. Two phase III trials have been conducted that demonstrated faropenem medoxomil was non-inferio o azithromycin and clarithromycin in the treatment of AECB. Replidyne's phase II trial evaluating an oral liquid formulation of faropenem medoxomil (7.5-40 mg/kg) in paediatric patients with acute otitis media (AOM), met its primary endpoint. The trial was completed in March 2007 and enrolled approximately 310 patients in Costa Rica and Israel. Replidyne intends to meet with the US authorities to discuss the design of the planned phase III trial in paediatric AOM. In addition to 5 years of Hatch-Waxman exclusivity granted upon approval, faropenem medoxomil is protected by an issued US composition of matter patent, which expires in 2015. Extension of exclusivity under Hatch-Waxman legislation is expected.

Description

Faropenem daloxate is the first oral penem in a new class of beta-lactam antibiotics.

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