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Faropenem
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administration		Oral
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FormulaC12H15NO5S
Molar mass285.31 g·mol−1
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  • O=C2N1/C(=C(\S[C@@H]1[C@H]2[C@H](O)C)[C@@H]3OCCC3)C(=O)O
  • InChI=1S/C12H15NO5S/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6/h5-7,11,14H,2-4H2,1H3,(H,16,17)/t5-,6-,7+,11-/m1/s1 checkY
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Faropenem is an orally active beta-lactam antibiotic belonging to the penem group.[1] It is resistant to some forms of extended-spectrum beta-lactamase.[2] It is available for oral use.[3]

Forms

[edit]

Faropenem was developed by Daiichi Asubio Pharma, which markets it in two forms.

  • The sodium salt faropenem sodium, available under the trade name Farom, has been marketed in Japan since 1997. (CID 636379 from PubChem)
  • The sodium salt faropenem sodium, available under the trade name Orfanem, has been marketed in Bangladesh by Incepta Pharmaceuticals Ltd.
  • The prodrug form faropenem medoxomil[4] (also known as faropenem daloxate) has been licensed from Daiichi Asubio Pharma by Replidyne, which plans to market it in conjunction with Forest Pharmaceuticals. The trade name proposed for the product was Orapem, but company officials recently announced this name was rejected by the FDA.[5]


Clinical use

[edit]

As of 8 September 2015, Faropenem has yet to receive marketing approval in the United States, and was submitted for consideration by the United States Food and Drug Administration (FDA) on 20 December 2005. The new drug application dossier submitted included these proposed indications:[citation needed]

  • acute bacterial sinusitis
  • community-acquired pneumonia
  • acute exacerbations of chronic bronchitis
  • uncomplicated skin and skin structure infections
  • urinary tract infections

History

[edit]

The FDA refused to approve faropenem, an antibiotic manufactured by Louisville-based Replidyne. The FDA said the drug was “nonapprovable”, but did not refer to specific safety concerns about the product. The company will have to conduct new studies and clinical trials, lasting an estimated two more years, to prove the drug treats community-acquired pneumonia, bacterial sinusitis, chronic bronchitis, and skin infections.[citation needed]

In India it is available under the name Farokaa, and in Bangladesh as Orfanem.

References

[edit]
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Faropenem

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from Grokipedia
Faropenem is a broad-spectrum oral that inhibits bacterial synthesis by binding to , demonstrating activity against many Gram-positive and Gram-negative aerobes, anaerobes, and some beta-lactamase-producing strains. As the of the faropenem medoxomil (molecular formula C17H19NO8S), it achieves high oral of 70-80%, enabling effective treatment of community-acquired infections without intravenous administration. Approved in since 1997 and in since 2010, faropenem is indicated for upper and lower respiratory tract infections (including and ), urinary tract infections, skin and soft tissue infections, and gynecological infections, with dosing typically at 200-300 mg three times daily for adults. It is not approved by the U.S. FDA and is reserved in for specific cases like extended-spectrum beta-lactamase (ESBL)-producing infections due to concerns over resistance development. Pharmacokinetically, faropenem exhibits good tissue penetration into sites such as the and , with a half-life of about 1 hour and primarily renal . Safety data from clinical studies indicate it is generally well-tolerated, with the most common being mild to moderate (incidence 5-12%), and it shows a favorable profile particularly in pediatric populations. Limited randomized controlled trials support its efficacy, particularly for uncomplicated urinary tract infections and respiratory infections, though further research is needed on resistance patterns and cross-resistance to .

Medical Use

Indications

Faropenem exhibits broad-spectrum antibacterial activity against such as and , including and , and anaerobic bacteria like . In and , faropenem is approved for the treatment of , acute bacterial , acute exacerbations of chronic bronchitis, uncomplicated skin and skin structure infections, urinary tract infections, and gynecological infections. Emerging and off-label applications include the management of odontogenic infections and multi-drug resistant infections, particularly where oral beta-lactam alternatives are preferred to intravenous administration; it is approved for pediatric respiratory tract infections in regions where available. Clinical trials conducted in and since 2000 have demonstrated efficacy rates of 80-95% for respiratory infections, with pediatric studies reporting clinical response rates of 91% for infections overall, including 85.7% for . Faropenem's superior oral of 72-84% enables outpatient treatment of infections that often require intravenous , facilitating broader use compared to parenteral options.

Dosage and Administration

Faropenem is administered orally, available as film-coated tablets or dry syrup for reconstitution into an oral suspension. The standard adult dosage is 200 mg three times daily for most infections, with treatment duration typically ranging from 5 to 14 days depending on the infection site, such as 7 days for urinary tract infections and 10 to 14 days for . For pediatric patients over 3 months of age, the recommended dosage is 15 mg/kg/day divided into three doses, not exceeding 600 mg/day. Faropenem can be taken with or without food. In patients with renal impairment, dosage reduction or interval prolongation is advised due to prolonged and increased plasma concentrations; no adjustment is required for mild hepatic impairment. Clinical response should be monitored within 48 to 72 hours, and the full course must be completed to minimize resistance development. Dosing follows regulatory guidelines in and , where it is approved, but it is not authorized in regions like the .

Adverse Effects

Faropenem is generally well-tolerated, with a favorable safety profile similar to other β-lactam antibiotics. The most common adverse effects are gastrointestinal () in nature, primarily mild to moderate resulting from disruption of gut flora. In post-marketing surveillance conducted in from 1997 to 2000 involving over 17,000 patients, the overall incidence of adverse events was 2.96%, with GI disorders accounting for 2.38% (primarily diarrhea at 2.1%). Clinical trials report higher rates in specific populations; for example, diarrhea occurred in 5.8% of pediatric patients across multiple studies and up to 12.4% in adults with uncomplicated urinary tract infections. Other common GI effects include , , and , though these are less frequent, with incidences typically under 5% in reviewed trials. Less common adverse effects (1-10% incidence) include dermatologic reactions such as (0.24% in post-marketing data) and elevated liver enzymes (e.g., ALT/AST), observed in up to 19% of patients in a randomized trial for pulmonary . and taste disturbances have been reported anecdotally in clinical use but lack robust incidence data from large-scale studies. These effects are usually self-limiting and resolve upon discontinuation. Serious adverse effects are rare (<1%) and include anaphylaxis in patients with known β-lactam hypersensitivity, Clostridium difficile-associated diarrhea as a potential complication of broad-spectrum antibiotic use, seizures (particularly in high doses or renal impairment, though less common than with carbapenems), and hematologic changes such as thrombocytopenia or leukopenia (4.55% in the tuberculosis trial). Post-marketing data indicate no severe events leading to death, with most cases resolving after drug withdrawal. Management of adverse effects focuses on symptomatic relief; for GI issues, probiotics or antidiarrheal agents may be used alongside hydration, while severe allergic reactions necessitate immediate discontinuation and supportive care such as antihistamines or epinephrine. Liver function tests should be monitored during prolonged therapy, especially in patients with hepatic risk factors. Long-term use or overuse of faropenem contributes to the broader risk of antibiotic resistance development, particularly among , as evidenced by increasing resistance patterns in surveillance studies.

Pharmacology

Mechanism of Action

Faropenem is a beta-lactam antibiotic belonging to the penem subclass, which exerts its antibacterial effects by binding irreversibly to penicillin-binding proteins (PBPs) 1 through 3 located on the bacterial cell membrane. This binding mimics the D-alanine-D-alanine terminus of peptidoglycan precursors, covalently attaching to the active-site serine residue of these PBPs and inactivating their transpeptidase activity. As a result, faropenem prevents the cross-linking of peptidoglycan chains essential for bacterial cell wall integrity during synthesis, leading to weakened cell walls, osmotic instability, bacterial lysis, and ultimately bactericidal cell death. This time-dependent killing is observed in vitro against a range of pathogens, with rapid cytolysis demonstrated in models such as Mycobacterium tuberculosis. Faropenem demonstrates high affinity for key PBPs in clinically relevant bacteria, including PBP1A, PBP1B, PBP2B, and PBP3 in , though it shows lower affinity for PBP2X. In , it effectively targets PBP3, contributing to activity against beta-lactamase-producing strains, while in anaerobes like Bacteroides fragilis, it inhibits multiple PBPs to disrupt cell wall formation. These interactions underpin its broad-spectrum efficacy, with MIC90 values typically ≤1 μg/mL for many susceptible pathogens, including species, , and various anaerobes. Regarding resistance, faropenem's penem structure confers activity against many beta-lactamase-producing strains, but it is susceptible to by certain extended-spectrum beta-lactamases (ESBLs) such as those of the CTX-M type, as well as carbapenemases, including the class A KPC-2 (with measurable kinetics) and metallo-beta-lactamases such as VIM-2, NDM-1, and L1, which can significantly reduce its effectiveness against producing strains. Faropenem exhibits a significant post-antibiotic effect against certain pathogens, such as , , and .

Pharmacokinetics

Faropenem is typically administered orally as the medoxomil to enhance absorption, achieving a of 70-90% in humans. Peak plasma concentrations (Cmax) of 5-10 μg/mL are reached 1-2 hours (Tmax) after dosing, with absorption unaffected by . The volume of distribution (Vd) for faropenem is approximately 20-30 L in healthy adults, indicating moderate distribution into body tissues. It demonstrates good penetration into key sites of , including respiratory secretions, , and structures, where concentrations can reach 2-5 times those in plasma, supporting its use in at these locations. Faropenem medoxomil is rapidly hydrolyzed by plasma and tissue esterases to the active faropenem form, with no significant hepatic observed. Protein binding is concentration-dependent, approximately 90% at therapeutic concentrations (e.g., 5 μg/mL), with saturable binding to . of faropenem occurs primarily via the renal route, with 80-90% recovered unchanged in urine through a combination of glomerular and active tubular . The elimination is 1-2 hours in healthy adults, necessitating multiple daily dosing to maintain therapeutic levels. In patients with renal impairment, the is prolonged due to reduced clearance, and dose adjustment may be needed; specific data on removal by dialysis are not available. Coadministration with probenecid inhibits tubular secretion, extending drug exposure.

Chemistry

Structure and Properties

Faropenem belongs to the penem class of beta-lactam antibiotics, representing a structural hybrid between penicillins and cephalosporins, characterized by a beta-lactam ring fused to a five-membered thiazoline ring, with a chiral substituent at the C-2 position. This core architecture distinguishes penems from other beta-lactams and contributes to their broad-spectrum activity. The molecular formula of faropenem sodium, the primary pharmaceutical form, is C12H14NNaO5S, with a molecular weight of 307.30 g/mol. It appears as a white to light brown crystalline powder. Faropenem sodium exhibits good in , at least 20 mg/mL, though its stability is pH-dependent, with optimal conditions in neutral to slightly alkaline environments. Faropenem demonstrates against certain beta-lactamases, including the class A enzymes TEM-1 and SHV-1, owing to the of the group at the C-2 position, which hinders enzymatic . However, it remains sensitive to hydrolysis by other beta-lactamases. Its pKa value for the strongest acidic group is approximately 3.97, influencing its and profile. The synthesis of faropenem involves ring expansion of the penicillin nucleus to form the penem core, a method developed by in the 1980s through key patents on penem derivatives. This oral penem's unique stems from its ester form, such as faropenem medoxomil, which features an ester linkage stable in the but hydrolyzable .

Available Forms

Faropenem is primarily administered orally in its form, faropenem medoxomil, which is an derivative designed to enhance gastrointestinal absorption, while faropenem sodium serves as the active moiety but is also formulated for oral use rather than injection. The medoxomil is rapidly cleaved by plasma esterases following absorption to release the active faropenem, thereby improving oral from less than 50% for the parent compound to over 80%. Common formulations include 200 mg film-coated tablets for adult use and an oral suspension at a concentration of 50 mg/5 mL, particularly suited for pediatric patients as a dry syrup that is reconstituted prior to administration. No intravenous formulation of faropenem is commercially available. Trade names vary by region, including Farom in , generic faropenem in (such as Farobact and Faronem), and Orfanem in ; the proposed name Orapem for the U.S. market was rejected by the FDA. These formulations should be stored at (15–30°C), protected from and direct , with a typical of 2–3 years under proper conditions. Faropenem is available by prescription only worldwide and is not sold over-the-counter.

History and Society

Development

Faropenem was discovered by scientists at the Institute for Biomedical Research in , which later became part of Asubio Pharma under , as part of efforts to develop orally active penem antibiotics offering broad-spectrum activity similar to but suitable for oral administration. The compound emerged from research aimed at creating beta-lactam agents resistant to hydrolysis by beta-lactamases, addressing limitations of earlier parenteral-only options in the class. Key milestones in its development included the initial synthesis and preclinical evaluation during the late 1980s and 1990s, where studies demonstrated faropenem's potent and activity against a wide range of Gram-positive, Gram-negative, and anaerobic , including producers. Phase I safety trials in healthy volunteers were conducted in in the mid-1990s, followed by Phase II and III efficacy studies focused on infections, culminating in the approval of faropenem sodium for marketing in in 1997 as the first oral penem antibiotic. Clinical development faced challenges, including early concerns over potential resistance emergence due to its structural similarity to , prompting careful monitoring of susceptibility patterns in preclinical models. A major focus was optimizing the faropenem medoxomil, an that enhances oral from 20-30% for the parent compound to approximately 70-80%, enabling effective gastrointestinal absorption while maintaining stability against . This innovation was critical for positioning faropenem as a viable oral alternative to intravenous beta-lactams. In the early , Daiichi Asubio Pharma partnered with Replidyne for further development outside , with Replidyne sublicensing U.S. rights to in 2006 to advance Phase III trials for indications like acute bacterial and . Core included Japanese Patent No. H07-165700 (1995) covering the medoxomil ester , which provided exclusivity until around 2015 in . These efforts underscored faropenem's role in expanding oral beta-lactam options amid rising pressures.

Regulatory Status and Availability

Faropenem was first approved in in 1997 by the (PMDA) under the brand name Farom for the treatment of various bacterial infections, including respiratory tract, urinary tract, skin, and gynecological infections. In , the (CDSCO) authorized faropenem sodium tablets in 2005, followed by approval for oral suspension in 2010, enabling widespread generic production and use for similar indications. Bangladesh's of Drug Administration (DGDA) approved faropenem in 2005 as Orfanem tablets, primarily for community-acquired infections. Limited approvals exist in other Asian countries, such as where prescribing information supports its use for respiratory and urinary tract infections, and the where it is supplied for similar purposes through regional distribution networks. In the United States, the (FDA) received a (NDA) for faropenem medoxomil in December 2005 from Replidyne, targeting acute exacerbations of chronic bronchitis, , sinusitis, and uncomplicated skin infections. The FDA issued a non-approvable letter in October 2006 citing insufficient efficacy data, followed by another rejection in 2007 requiring additional superiority trials. Efforts halted after Replidyne discontinued late-stage trials in 2008 to conserve resources and filed for in 2009, leaving faropenem investigational only with no marketing approval as of 2025. The (EMA) has not approved faropenem for marketing in the , though it may be accessible via special import mechanisms in select member states for compassionate use in resistant infections. The (WHO) classifies faropenem in the AWaRe RESERVE group for monitoring but does not include it on the Model List of , recommending its use primarily for multidrug-resistant infections under stewardship guidelines. Generics dominate the faropenem market in , accounting for the majority of global supply and sales, with annual consumption reaching approximately 18.9 million standard units by 2014 and continuing to grow; the overall faropenem sodium market was valued at around USD 241 million globally in 2024, driven largely by Asian demand. In , the branded Farom maintains a stable market position for niche applications. Access remains affordable in , with treatment costs estimated at USD 1-2 per day based on standard dosing of 200-300 mg three times daily, though resistance monitoring is emphasized per WHO guidelines to prevent overuse. As of 2025, no new regulatory approvals have been granted globally, though ongoing clinical trials in , including a randomized controlled study (ChiCTR2000033085) evaluating faropenem for pulmonary and prospective observational research on its safety in pediatric respiratory and urinary tract infections, suggest potential expansion for pediatric indications.

References

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