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Details

Stereochemistry EPIMERIC
Molecular Formula C17H20N2O5S
Molecular Weight 364.416
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENETICILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C(C)OC3=CC=CC=C3)C(O)=O

InChI

InChIKey=NONJJLVGHLVQQM-JHXYUMNGSA-N
InChI=1S/C17H20N2O5S/c1-9(24-10-7-5-4-6-8-10)13(20)18-11-14(21)19-12(16(22)23)17(2,3)25-15(11)19/h4-9,11-12,15H,1-3H3,(H,18,20)(H,22,23)/t9?,11-,12+,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H20N2O5S
Molecular Weight 364.416
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Pheneticillin (phenoxyethylpenicillin) is an oral penicillin used for the treatment of upper respiratory tract infections; lower respiratory tract infections; skin and soft tissue infections. Pheneticillin inhibits the synthesis of the cell wall by inhibiting the penicillin binding proteins (PBPs) function. It is well absorbed from the gastrointestinal tract. It reaches the pleural and peritoneal cavities but doesn’t cross the blood-brain barrier. Diarrhea has sometimes occurred with therapeutic doses in man.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Broxil
Curative
Broxil
Curative
Broxil

Cmax

ValueDoseCo-administeredAnalytePopulation
23 μg/mL
500 mg 1 times / day steady-state, oral
PHENETICILLIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
29.3 μg × h/mL
500 mg 1 times / day steady-state, oral
PHENETICILLIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
63 min
500 mg 1 times / day steady-state, oral
PHENETICILLIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
500 mg 1 times / day steady-state, oral
PHENETICILLIN plasma
Homo sapiens

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
250 mg every 8 hours
Route of Administration: Oral
In Vitro Use Guide
The MIC against S. aureus of Pheneticillin in broth was 0.031 mg/l.
Substance Class Chemical
Record UNII
EFA30X554H
Record Status Validated (UNII)
Record Version