FAROPENEM

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H15NO5S
Molecular Weight	285.316
Optical Activity	( + )
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@]12SC(=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O)[C@@]3([H])CCCO3

InChI

InChIKey=HGGAKXAHAYOLDJ-FHZUQPTBSA-N

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

HIDE SMILES / InChI

Molecular Formula	C12H15NO5S
Molecular Weight	285.316
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Faropenem is a unique antimicrobial penem being developed for oral administration. It markets it in two forms: faropenem sodium and faropenem medoxomil. The high binding affinities of faropenem to penicillin-binding proteins from gram-negative and gram-positive bacteria are mirrored by its pronounced and concentration-dependent bactericidal effect. It is usually used to treat a wide range of infections such as skin, respiratory and otorhinologic infections. The most commonly reported adverse reactions include diarrhea, abdominal pain, loose stool, rash and nausea. The FDA refused to approve faropenem – the applicant have to conduct new studies and clinical trials to prove the drug treats community-acquired pneumonia, bacterial sinusitis, chronic bronchitis, and skin infections.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Chronic bronchitis 51	Curative	Approved 8,429	Farom
Community-acquired pneumonia 47	Curative	Approved 8,429	Farom
Acute bacterial sinusitis 26	Curative	Approved 8,429	Farom
Skin infections 59	Curative	Approved 8,429	Farom

C_max

Value	Dose	Analyte	Population
1.32 μg/mL	5 mg single, oral	FAROPENEM plasma	Homo sapiens
2.08 μg/mL	10 mg single, oral	FAROPENEM plasma	Homo sapiens
2.36 μg/mL	150 mg single, oral	FAROPENEM plasma	Homo sapiens
6.24 μg/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens
7.37 μg/mL	600 mg single, oral	FAROPENEM plasma	Homo sapiens
1.9 μg/mL	200 mg 3 times / day multiple, oral	FAROPENEM plasma	Homo sapiens
2.02 μg/mL	200 mg 3 times / day multiple, oral	FAROPENEM plasma	Homo sapiens
1.89 μg/mL	200 mg 3 times / day multiple, oral	FAROPENEM plasma	Homo sapiens
6.24 μg/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens
4.25 μg/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens
3.49 μg/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens
4.25 μg/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
4.1 μg × h/mL	5 mg single, oral	FAROPENEM plasma	Homo sapiens
5.89 μg × h/mL	10 mg single, oral	FAROPENEM plasma	Homo sapiens
3.95 μg × h/mL	150 mg single, oral	FAROPENEM plasma	Homo sapiens
11.73 μg × h/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens
19.59 μg × h/mL	600 mg single, oral	FAROPENEM plasma	Homo sapiens
4.18 μg × h/mL	200 mg 3 times / day multiple, oral	FAROPENEM plasma	Homo sapiens
4.34 μg × h/mL	200 mg 3 times / day multiple, oral	FAROPENEM plasma	Homo sapiens
4.14 μg × h/mL	200 mg 3 times / day multiple, oral	FAROPENEM plasma	Homo sapiens
11.73 μg × h/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens
9.75 μg × h/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens
16.49 μg × h/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens
9.75 μg × h/mL	300 mg single, oral	FAROPENEM plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.66 h	5 mg single, oral	FAROPENEM plasma	Homo sapiens
1.14 h	10 mg single, oral	FAROPENEM plasma	Homo sapiens
0.76 h	150 mg single, oral	FAROPENEM plasma	Homo sapiens
0.85 h	300 mg single, oral	FAROPENEM plasma	Homo sapiens
1.08 h	600 mg single, oral	FAROPENEM plasma	Homo sapiens
0.96 h	200 mg 3 times / day multiple, oral	FAROPENEM plasma	Homo sapiens
0.89 h	200 mg 3 times / day multiple, oral	FAROPENEM plasma	Homo sapiens
0.93 h	200 mg 3 times / day multiple, oral	FAROPENEM plasma	Homo sapiens
0.85 h	300 mg single, oral	FAROPENEM plasma	Homo sapiens
1.01 h	300 mg single, oral	FAROPENEM plasma	Homo sapiens
1.61 h	300 mg single, oral	FAROPENEM plasma	Homo sapiens
1.01 h	300 mg single, oral	FAROPENEM plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
9.3%			FAROPENEM serum	Homo sapiens

Doses

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Dose	Population	Adverse events
300 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT	Disc. AE: Diarrhea, Vomiting... Other AEs: Nausea...

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AEs

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AE	Significance	Dose	Population
Nausea		300 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT
Diarrhea	Disc. AE	300 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT
Vomiting	Disc. AE	300 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT

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PubMed

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Title	Date	PubMed
[Study on Streptococcus pneumoniae isolated from infants in widely-separated primary care facilities in Japan].	2001 May	12638164
[Epidemiological study on patients with pneumococcal respiratory tract infection in a Japanese health facility during the past year].	2001 May	12638138
[Pyogenic sacroiliitis in pregnancy].	2001 Sep	11729713
In vitro activity of faropenem and 20 other compounds against beta-lactamase-positive and -negative Moraxella catarrhalis and Haemophilus influenzae isolates and the effect of serum on faropenem MICs.	2002 Jan	11751796
In vitro activity of faropenem against respiratory pathogens.	2002 Mar	11864964

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Patents

Sample Use Guides

In Vivo Use Guide

150 - 300 mg three times a day

Route of Administration: Oral

In Vitro Use Guide

Exposure of S. aureus to faropenem at minimum inhibitory concentrations (MICs) of 1/8 or 1/4 resulted in irregular septum formation. At 1x MIC or higher, a larger number of lysed cells were observed. Exposure of E. coli to 1/8x MIC or 1/4x MIC also induced changes in cellular shape; the normal rod-shaped form changed to a spherical form in a time-dependent manner. After exposure of E. coli to 1x MIC for 2 h, bulging-shaped E. coli cells were observed and after 4 h of exposure cell lysis was demonstrated. In the presence of 4x MIC, spheroplast-like forms and cell lysis were observed.

Substance Class	Chemical
Record UNII	F52Y83BGH3
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

FAROPENEM

Official Name

English

faropenem [INN]

Common Name

English

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)

Common Name

English

FROPENEM

Common Name

English

FAROPENEM [MI]

Common Name

English

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Classification Tree

Code System

Code

Other cephalosporins and penems

WHO-ATC

J01DI03

Antibiotic

NCI_THESAURUS

C260

Other cephalosporins and penems

WHO-VATC

QJ01DI03

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Code System

Code

Type

Description

DRUG CENTRAL

1131

PRIMARY

SMS_ID

100000081763

PRIMARY

PUBCHEM

65894

PRIMARY

FDA UNII

F52Y83BGH3

PRIMARY

EVMPD

SUB07512MIG

PRIMARY

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Related Record

Type

Details


					N39L5ALZ3M

FAROPENEM SODIUM HEMIPENTAHYDRATE

SALT/SOLVATE -> PARENT

Amount:

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Related Record

Type

Details


					F52Y83BGH3

FAROPENEM

ACTIVE MOIETY

Amount:

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound