U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H19NO8S
Molecular Weight 397.4
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FAROPENEM MEDOXOMIL

SMILES

[H][C@]12SC([C@H]3CCCO3)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(=O)OCC4=C(C)OC(=O)O4

InChI

InChIKey=JQBKWZPHJOEQAO-DVPVEWDBSA-N
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

HIDE SMILES / InChI
Molecular Formula C17H19NO8S
Molecular Weight 397.4
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 was under development for the treatment of acute bacterial sinusitis, community-acquired pneumonia, acute exacerbation of chronic bronchitis, and uncomplicated skin and skin structure infections.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1064
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Not Provided
504
FAROPENEM MEDOXOMIL

Approved Use

Unknown
Curative
Not Provided
504
FAROPENEM MEDOXOMIL

Approved Use

Unknown
Curative
Not Provided
504
FAROPENEM MEDOXOMIL

Approved Use

Unknown
Curative
Not Provided
504
FAROPENEM MEDOXOMIL

Approved Use

Unknown
Curative
Phase II
1132
FAROPENEM MEDOXOMIL

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
300 mg 2 times / day multiple, oral (unknown)
Studied dose
Dose: 300 mg, 2 times / day
Route: oral
Route: multiple
Dose: 300 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17011409
unhealthy
n = 365
Health Status: unhealthy
Condition: sinusitis
Sex: M+F
Food Status: UNKNOWN
Population Size: 365
Sources:
https://pubmed.ncbi.nlm.nih.gov/17011409
Disc. AE: Nausea, vomiting...
AEs leading to
discontinuation/dose reduction:
Nausea (10 patients)
vomiting (6 patients)
vomiting (9 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/17011409
AEs

AEs

AESignificanceDosePopulation
Nausea 10 patients
Disc. AE
300 mg 2 times / day multiple, oral (unknown)
Studied dose
Dose: 300 mg, 2 times / day
Route: oral
Route: multiple
Dose: 300 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17011409
unhealthy
n = 365
Health Status: unhealthy
Condition: sinusitis
Sex: M+F
Food Status: UNKNOWN
Population Size: 365
Sources:
https://pubmed.ncbi.nlm.nih.gov/17011409
vomiting 6 patients
Disc. AE
300 mg 2 times / day multiple, oral (unknown)
Studied dose
Dose: 300 mg, 2 times / day
Route: oral
Route: multiple
Dose: 300 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17011409
unhealthy
n = 365
Health Status: unhealthy
Condition: sinusitis
Sex: M+F
Food Status: UNKNOWN
Population Size: 365
Sources:
https://pubmed.ncbi.nlm.nih.gov/17011409
vomiting 9 patients
Disc. AE
300 mg 2 times / day multiple, oral (unknown)
Studied dose
Dose: 300 mg, 2 times / day
Route: oral
Route: multiple
Dose: 300 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17011409
unhealthy
n = 365
Health Status: unhealthy
Condition: sinusitis
Sex: M+F
Food Status: UNKNOWN
Population Size: 365
Sources:
https://pubmed.ncbi.nlm.nih.gov/17011409
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P001HE4
https://www.1pchem.com/search?query=1P001HE4
AK Scientific
3667AH
https://aksci.com/item_detail.php?cat=3667AH
BLD Pharm
BD129998
http://www.bldpharm.com/search/Search.html?keyword=BD129998
BOC Sciences
141702-36-5
http://www.bocsci.com/description.asp?cas=141702-36-5
Capot Chemical
18820
https://www.capotchem.com/search.do?q=18820
Chem Scene
CS-0390
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0390
Lab Network
LN01343325
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01343325
MedChem Express
HY-10004
https://www.medchemexpress.com/search.html?q=HY-10004&ft=&fa=&fp=
MolPort
MolPort-006-170-106
https://www.molport.com/shop/molecule-link/MolPort-006-170-106
Toronto Research Chemicals
F103305
https://www.trc-canada.com/product-detail/?CatNum=F103305
Toronto Research Chemicals
M199505
https://www.trc-canada.com/product-detail/?CatNum=M199505
eMolecules
44811725
https://orderbb.emolecules.com/search/#?query=44811725
mcule
MCULE-3412531430
https://mcule.com/MCULE-3412531430/
PubMed

PubMed

TitleDatePubMed
Patents

Patents

20040133016
1

Sample Use Guides

In Vivo Use Guide
Acute bacterial sinusitis: faropenem medoxomil 300 mg twice daily for 7-10 days. Community-acquired pneumonia: faropenem medoxomil 300 mg twice daily for 10 days. Acute exacerbation of chronic bronchitis: faropenem medoxomil 300 mg twice daily for 5 days. Uncomplicated skin and skin structure infections: faropenem medoxomil 300 mg twice daily for 7 days.
Route of Administration: Oral
In Vitro Use Guide
The MIC90 values for faropenem were: ≤0.06-0.25 mg/L (Staphylococcus aureus, 53 isolates), 0.5-100 mg/L (Staphylococcus epidermidis, 219 isolates), >16->64 mg/L (Staphylococcus haemolyticus, 26 isolates).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:22 UTC 2023
Edited
by admin
on Fri Dec 15 15:54:22 UTC 2023
Record UNII
5OK523O4FU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FAROPENEM MEDOXOMIL
USAN  
USAN  
Official Name English
SUN-A0026
Code English
A0026
Code English
FAROPENEM DALOXATE
MI  
Common Name English
(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
Common Name English
FAROPENEM DALOXATE [MI]
Common Name English
BAY-56-6854
Code English
A-0026
Code 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)-, (5-METHYL-2-OXO-1,3-DIOXOL-4-YL)METHYL ESTER, (5R,6S)
Common Name English
FAROPENEM MEDOXOMIL [USAN]
Common Name English
FROPENEM DALOXATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C260
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
Code System Code Type Description
FDA UNII
5OK523O4FU
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
MESH
C528565
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL1257070
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
USAN
RR-63
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
SMS_ID
300000032424
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
MERCK INDEX
m5246
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY Merck Index
CAS
141702-36-5
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
NCI_THESAURUS
C65621
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID30931176
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
PUBCHEM
6918218
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
DRUG BANK
DB05659
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
DRUG CENTRAL
5145
Created by admin on Fri Dec 15 15:54:22 UTC 2023 , Edited by admin on Fri Dec 15 15:54:22 UTC 2023
PRIMARY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966