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Chemistry

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Also known as: 141702-36-5, Faropenem medoxomil, Faropenem medoxil, Sun-a0026, Fropenem daloxate, Faropenem medoxomil [usan]
Molecular Formula
C17H19NO8S
Molecular Weight
397.4  g/mol
InChI Key
JQBKWZPHJOEQAO-DVPVEWDBSA-N
FDA UNII
5OK523O4FU

Faropenem Medoxomil
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.
1 2D Structure

Faropenem Medoxomil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC 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
2.1.2 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
2.1.3 InChI Key
JQBKWZPHJOEQAO-DVPVEWDBSA-N
2.1.4 Canonical SMILES
CC1=C(OC(=O)O1)COC(=O)C2=C(SC3N2C(=O)C3C(C)O)C4CCCO4
2.1.5 Isomeric SMILES
CC1=C(OC(=O)O1)COC(=O)C2=C(S[C@H]3N2C(=O)[C@@H]3[C@@H](C)O)[C@H]4CCCO4
2.2 Other Identifiers
2.2.1 UNII
5OK523O4FU
2.3 Synonyms
2.3.1 MeSH Synonyms

1. A0026

2. Bay 56-6854

3. Bay 566854

4. Bay-56-6854

5. Bay-566854

6. Bay56-6854

7. Bay566854

8. Faropenem Medoxomil

9. Sun 208

10. Sun A0026

11. Sun-208

12. Sun-a0026

13. Sun208

2.3.2 Depositor-Supplied Synonyms

1. 141702-36-5

2. Faropenem Medoxomil

3. Faropenem Medoxil

4. Sun-a0026

5. Fropenem Daloxate

6. Faropenem Medoxomil [usan]

7. Bay-56-6854

8. A-0026

9. 5ok523o4fu

10. (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

11. A0026

12. Sun-208

13. Faropenem Medoxomil (usan)

14. Orapem

15. 4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-tetrahydro-2-furanyl]-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r,6s)-

16. Unii-5ok523o4fu

17. Faropenem-medoxomil

18. Bay 566854

19. Bay 56-6854

20. A 0026

21. Schembl2334640

22. Sun208

23. Faropenem Daloxate [mi]

24. Chembl1257070

25. Sun A0026

26. Sun 208

27. Chebi:134710

28. Zinc3806644

29. Bay566854

30. Bay-566854

31. Bay56-6854

32. Cs-0390

33. Db05659

34. Hy-10004

35. D08919

36. 702f365

37. A911194

38. Q27095691

39. (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl (5r,6s)-6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydrofuran-2-yl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

40. (5-methyl-2-oxo-1,3-dioxoren-4-yl)methyl(5r,6s)-6-((r)-1-hydroxyethyl)-7-oxo-3-((r)-2-tetrahydrofuryl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

41. (5r,6s)-6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-oxolane-2-yl]-4-thia-1-azabicyclo[3.2.0]hepta-2-ene-2-carboxylic Acid 5-methyl-2-oxo-1,3-dioxole-4-ylmethyl Ester

42. 4-thia-1-azabicyclo(.32.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydro-2-furanyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r,6s)-

43. 4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-((1r)-1-hydroxyethyl)-7-oxo-3-((2r)-tetrahydro-2-furanyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r,6s)

44. 4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic Acid, 6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester, (5r-(3(r*),5alpha,6alpha(r*)))-

45. 4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic Acid, 6-[(1r)-1-hydroxyethyl]-7-oxo-3-[(2r)-tetrahydro-2-furanyl]-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester

2.4 Create Date
2006-07-28
3 Chemical and Physical Properties
Molecular Weight 397.4 g/mol
Molecular Formula C17H19NO8S
XLogP30.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count6
Exact Mass397.08313774 g/mol
Monoisotopic Mass397.08313774 g/mol
Topological Polar Surface Area137 Ų
Heavy Atom Count27
Formal Charge0
Complexity775
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Investigated for use/treatment in bacterial infection, bronchitis, otitis media, and pediatric indications.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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.


5.2 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.


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ABOUT THIS PAGE

Faropenem Medoxomil Manufacturers

A Faropenem Medoxomil manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Faropenem Medoxomil, including repackagers and relabelers. The FDA regulates Faropenem Medoxomil manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Faropenem Medoxomil API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Faropenem Medoxomil Suppliers

A Faropenem Medoxomil supplier is an individual or a company that provides Faropenem Medoxomil active pharmaceutical ingredient (API) or Faropenem Medoxomil finished formulations upon request. The Faropenem Medoxomil suppliers may include Faropenem Medoxomil API manufacturers, exporters, distributors and traders.

click here to find a list of Faropenem Medoxomil suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Faropenem Medoxomil USDMF

A Faropenem Medoxomil DMF (Drug Master File) is a document detailing the whole manufacturing process of Faropenem Medoxomil active pharmaceutical ingredient (API) in detail. Different forms of Faropenem Medoxomil DMFs exist exist since differing nations have different regulations, such as Faropenem Medoxomil USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Faropenem Medoxomil DMF submitted to regulatory agencies in the US is known as a USDMF. Faropenem Medoxomil USDMF includes data on Faropenem Medoxomil's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Faropenem Medoxomil USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Faropenem Medoxomil suppliers with USDMF on PharmaCompass.

Faropenem Medoxomil GMP

Faropenem Medoxomil Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Faropenem Medoxomil GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Faropenem Medoxomil GMP manufacturer or Faropenem Medoxomil GMP API supplier for your needs.

Faropenem Medoxomil CoA

A Faropenem Medoxomil CoA (Certificate of Analysis) is a formal document that attests to Faropenem Medoxomil's compliance with Faropenem Medoxomil specifications and serves as a tool for batch-level quality control.

Faropenem Medoxomil CoA mostly includes findings from lab analyses of a specific batch. For each Faropenem Medoxomil CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Faropenem Medoxomil may be tested according to a variety of international standards, such as European Pharmacopoeia (Faropenem Medoxomil EP), Faropenem Medoxomil JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Faropenem Medoxomil USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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