Basic information
- CAS
106560-14-9- Standard SMILES
C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O)=C([C@H]3CCCO3)S[C@H]12- InChIKey
HGGAKXAHAYOLDJ-FHZUQPTBSA-N- Molecular formula
- C12H15NO5S
- Average molar mass
- 285.32 g/mol
- Monoisotopic mass
- 285.06709375
Overview
6alpha-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid is a faropenem. It is a conjugate acid of a 6alpha-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylate.
Names & identifiers
- Preferred name
- Faropenem
- IUPAC
- (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
- English name
- Faropenem
- Molecular formula
- C12H15NO5S
- Molecular weight
- 285.32
Names & synonyms
faropenemFropenem106560-14-9(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidDTXSID0046430F52Y83BGH3(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidCHEBI:51257(+)-(5R,6S)-6-((1R)-1-Hydroxyethyl)-7-oxo-3-((2R)-tetrahydro-2-furyl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acidDTXCID8026430(5R,6S)-6-((1R)-1-HYDROXYETHYL)-7-OXO-3-((2R)-TETRAHYDROFURAN-2-YL)-4-THIA-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACIDCHEBI:51788
Show more names
Faropenem sodium hemipentahydrateFaropenem Sodium Impurity GFaropenem sodium hemi 5-hydrateFaropenem sodium hemipentahydrate USP/EP/BP6α-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid(5R,6S,8R,2'R)-2-(2'-tetrahydrofuryl)-6-(1-hydroxyethyl)-2-penem-3-carboxylic acid6alpha-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acid
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 477
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 570.2 · 570.2±50.0 °C(Predicted)
- Density
- 1.56 · 1.56±0.1 g/cm3(Predicted)
- pka
- 4 · 4.00±0.40(Predicted)
- CAS DataBase Reference
- 106560 · 106560-14-9
- FDA UNII
- 52 Y83BGH3 · F52Y83BGH3
- ATC code
- 1 DI03 · J01DI03
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Applications
DescriptionFarom was launched in Japan for use as an antibiotic against common respiratory tract pathogens. It can be prepared by several related routes of about seven steps starting with tetrahydrofuran-2-thiocarboxylic acid and a silylated azetidinone. It is a broad spectrum oral penem antibiotic that is β-lactamase stable. Farom is the most active β-lactam against anaerobes (more than cefaclor, cefixime and amoxicillin) but also has activity against Gram-positive, Gram-negative and enterobacteriaceae. It is equally active against strains carrying plasmid and chromosome mediated β-lactamases. The short plasma elimination half-life is the result of hydrolysis by renal dehydropeptidase. It is more stable to hydrolysis by extended spectrum β-lactamases than some second and third generation cephalosporins.
UsesFaropenem (cas# 106560-14-9) is a compound useful in organic synthesis.
UsesTreatmentof bacterial infections.
Upstream & downstream products
Upstream raw materials
Suppliers
Related reactions
1 records
Compound notes
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