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Faropenem

Faropenem structure

CAS No:
106560-14-9
Formula:
C12H15NO5S
Chemical Name:
Faropenem
Synonyms:
4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-,(5R,6S)-;4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,6-(1-hydroxyethyl)-7-oxo-3-(tetrahydro-2-furanyl)-,[5R-[3(R*),5α,6α(R*)]]-;(5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydro-2-furanyl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid;(+)-(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 acid;Faropenem;(5R,6S,8R,2′R)-2-(2′-tetrahydrofuryl)-6-(1-hydroxyethyl)-2-penem-3-carboxylic acid
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Farom 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 enterobacteria

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.|Faropenem has been used in trials studying the treatment of Tuberculosis, Pulmonary Tuberculosis, and Community Acquired Pneumonia.|Faropenem is a penem with a tetrahydrofuran substituent at position C2, with broad-spectrum antibacterial activity against many gram-positive and gram-negative aerobes and anaerobes. 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.

Faropenem Basic Attributes

Molecular Weight：

285.32

Exact Mass：

285.32

EC Number：

1312995-182-4

UNII：

F52Y83BGH3

DSSTox ID：

DTXSID0046430

NCI Thesaurus Code：

C72776

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

112

XLogP3：

-0.45

Appearance：

Light yellow powder

Density：

1.56±0.1 g/cm3(Predicted)

Boiling Point：

570.2±50.0 °C(Predicted)

Flash Point：

298.7±30.1 °C

Refractive Index：

1.668

Vapor Pressure：

2.23E-15mmHg at 25°C

Safety Information

hazard class code：

R20/21/22

Drug Information

MeSH Entry Terms：

(5R,6S)-6-(R)-1-hydroxyethyl-7-oxo-3-(R)-2-tetrahydrofuryl-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylate

Faropenem Use and Manufacturing

Methods of Manufacturing

The compound (I) and trityl mercaptan (TrSH) are reacted under basic conditions, and the acetyl group is substituted to obtain the compound (II). Then, acylation with allyloxy oxalyl chloride in the presence of diisopropylethylamine affords compound (III). It was directly dissolved in methanol, and silver nitrate was added in the presence of pyridine, and the compound (IV) was obtained at a low temperature and protected from light. It was dissolved in dichloromethane, and ?-tetrahydrofuran-2-formyl chloride was added at a low temperature for reaction to obtain compound (V). Dissolve in benzene, add triethoxyphosphorus and react to obtain compound (Ⅵ). Next, in the presence of tetrabutylammonium fluoride, the protective group on the hydroxyl group is removed, and the carboxyl group is freed, and the sodium salt of faropenem is neutralized to obtain a melting point of 160-162°C. The total yield reached 29.8%.

Uses

Treatmentof bacterial infections.

Computed Properties

Molecular Weight:285.32
XLogP3:0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:285.06709375
Monoisotopic Mass:285.06709375
Topological Polar Surface Area:112
Heavy Atom Count:19
Complexity:477
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Oxalyl chloride

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