Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Faropenem medoxomil
- DrugBank Accession Number
- DB05659
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Faropenem medoxomil (DB05659)
- Weight
- Average: 397.4
Monoisotopic: 397.083137279 - Chemical Formula
- C17H19NO8S
- Synonyms
- Faropenem daloxate
- Faropenem medoxil
- Faropenem medoxomil
- External IDs
- A 0026
- A-0026
- A0026
- BAY-56-6854
- SUN-A0026
Pharmacology
- Indication
Investigated for use/treatment in bacterial infection, bronchitis, otitis media, and pediatric indications.
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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.
- 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.
Target Actions Organism UPenicillin-binding protein 1A Not Available Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) UPenicillin-binding protein 2B Not Available Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) UPeptidoglycan D,D-transpeptidase FtsI Not Available Escherichia coli O157:H7 - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Orapem
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acids and derivatives
- Alternative Parents
- Penems / Thiazolecarboxylic acids and derivatives / Vinylogous thioesters / Carbonic acid diesters / Enoate esters / Heteroaromatic compounds / Tertiary carboxylic acid amides / Tetrahydrofurans / Thiazolines / Azetidines show 12 more
- Substituents
- Alcohol / Alpha,beta-unsaturated carboxylic ester / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Beta-lactam / Carbonic acid diester / Carbonyl group / Carboxamide group show 26 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Gram-positive Bacteria
Chemical Identifiers
- UNII
- 5OK523O4FU
- CAS number
- 141702-36-5
- InChI Key
- JQBKWZPHJOEQAO-DVPVEWDBSA-N
- 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
- IUPAC Name
- (5-methyl-2-oxo-2H-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
- [H][C@]12SC(=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(=O)OCC1=C(C)OC(=O)O1)[C@@]1([H])CCCO1
References
- General References
- External Links
- PubChem Compound
- 6918218
- PubChem Substance
- 175427025
- ChemSpider
- 5293428
- ChEBI
- 134710
- ChEMBL
- CHEMBL1257070
- ZINC
- ZINC000003806644
- Wikipedia
- Faropenem
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Terminated Treatment Chronic Bronchitis 1 somestatus stop reason just information to hide 2 Completed Treatment Otitis Media (OM) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.18 mg/mL ALOGPS logP 0.64 ALOGPS logP 0.23 Chemaxon logS -2.5 ALOGPS pKa (Strongest Acidic) 14.85 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 111.6 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 95.39 m3·mol-1 Chemaxon Polarizability 38.77 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7489 Blood Brain Barrier - 0.8881 Caco-2 permeable - 0.5799 P-glycoprotein substrate Substrate 0.5766 P-glycoprotein inhibitor I Non-inhibitor 0.7197 P-glycoprotein inhibitor II Non-inhibitor 0.9655 Renal organic cation transporter Non-inhibitor 0.8901 CYP450 2C9 substrate Non-substrate 0.7947 CYP450 2D6 substrate Non-substrate 0.8009 CYP450 3A4 substrate Substrate 0.5586 CYP450 1A2 substrate Non-inhibitor 0.6407 CYP450 2C9 inhibitor Non-inhibitor 0.6173 CYP450 2D6 inhibitor Non-inhibitor 0.8494 CYP450 2C19 inhibitor Non-inhibitor 0.5615 CYP450 3A4 inhibitor Non-inhibitor 0.7569 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.757 Ames test Non AMES toxic 0.724 Carcinogenicity Non-carcinogens 0.8605 Biodegradation Not ready biodegradable 0.6121 Rat acute toxicity 2.3262 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9881 hERG inhibition (predictor II) Non-inhibitor 0.8275
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0029000000-3419a0204502549b9660 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-01r2-3459000000-bf41e1304db5bfe5e3b5 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0fl0-0039000000-ec02b50105693ba28232 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0009000000-b8f1df67336713e59a4c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-008j-0629000000-c0f7df6668a7ad5fa336 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-03e9-2659000000-c0ed93958ea68c228121 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 188.158 predictedDeepCCS 1.0 (2019) [M+H]+ 190.41956 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.33208 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
- Pharmacological action
- Unknown
- General Function
- Cell wall formation.
- Specific Function
- penicillin binding
- Gene Name
- ponA
- Uniprot ID
- Q04707
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 79757.96 Da
References
- Dalhoff A, Nasu T, Okamoto K: Target affinities of faropenem to and its impact on the morphology of gram-positive and gram-negative bacteria. Chemotherapy. 2003 Jul;49(4):172-83. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
- Pharmacological action
- Unknown
- General Function
- A transpeptidase that forms peptide cross-links between adjacent glycan strands in cell wall peptidoglycan (PG). Part of the elongasome machinery that synthesizes peripheral PG.
- Specific Function
- penicillin binding
- Gene Name
- penA
- Uniprot ID
- P0A3M5
- Uniprot Name
- Penicillin-binding protein 2B
- Molecular Weight
- 73872.305 Da
References
- Dalhoff A, Nasu T, Okamoto K: Target affinities of faropenem to and its impact on the morphology of gram-positive and gram-negative bacteria. Chemotherapy. 2003 Jul;49(4):172-83. [Article]
- Kind
- Protein
- Organism
- Escherichia coli O157:H7
- Pharmacological action
- Unknown
- General Function
- Catalyzes cross-linking of the peptidoglycan cell wall at the division septum.
- Specific Function
- penicillin binding
- Gene Name
- ftsI
- Uniprot ID
- P0AD69
- Uniprot Name
- Peptidoglycan D,D-transpeptidase FtsI
- Molecular Weight
- 63876.925 Da
References
- Dalhoff A, Nasu T, Okamoto K: Target affinities of faropenem to and its impact on the morphology of gram-positive and gram-negative bacteria. Chemotherapy. 2003 Jul;49(4):172-83. [Article]
Drug created at November 18, 2007 18:26 / Updated at February 21, 2021 18:51