PHENETICILLIN

First approved in 1959

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 Search

SMILES

CC(OC1=CC=CC=C1)C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)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

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	3 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://db.cbg-meb.nl/IB-teksten/h09101.pdf
Curator's Comment: description was created based on several sources, including: doi: 10.1136/bmj.2.5197.534

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 Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: http://www.microrao.com/micronotes/pg/ESBLs.pdf \| http://db.cbg-meb.nl/IB-teksten/h09101.pdf	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Lower respiratory tract infections 52 Sources: http://db.cbg-meb.nl/Bijsluiters/h04959.pdf	Curative	Approved 8583	Broxil Approved Use It is indicated for the treatment of infections, caused by susceptible microorganisms. In particular streptococcal infections, such as: upper respiratory tract infections (for example, pharyngitis); lower respiratory tract infections (for example, pneumonia); skin and soft tissue infections (for example, abscesses or impetigo). Launch Date 1965
Upper respiratory tract infections 12 Sources: http://db.cbg-meb.nl/IB-teksten/h09101.pdf	Curative	Approved 8583	Broxil Approved Use It is indicated for the treatment of infections, caused by susceptible microorganisms. In particular streptococcal infections, such as: upper respiratory tract infections (for example, pharyngitis); lower respiratory tract infections (for example, pneumonia); skin and soft tissue infections (for example, abscesses or impetigo). Launch Date 1965
Skin and soft tissue infections 33 Sources: http://db.cbg-meb.nl/IB-teksten/h09101.pdf	Curative	Approved 8583	Broxil Approved Use It is indicated for the treatment of infections, caused by susceptible microorganisms. In particular streptococcal infections, such as: upper respiratory tract infections (for example, pharyngitis); lower respiratory tract infections (for example, pneumonia); skin and soft tissue infections (for example, abscesses or impetigo). Launch Date 1965

C_max

Value	Dose	Co-administered	Analyte	Population
23 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3924086/	500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		PHENETICILLIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
29.3 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3924086/	500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		PHENETICILLIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
63 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3924086/	500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		PHENETICILLIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
20% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3924086/	500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		PHENETICILLIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: FASTED

Doses

Dose	Population	Adverse events
250 mg 4 times / day multiple, oral Highest studied dose Dose: 250 mg, 4 times / day Route: oral Route: multiple Dose: 250 mg, 4 times / day Sources: https://www.sciencedirect.com/science/article/pii/S1198743X14614919	unhealthy, 54 (19–71) Health Status: unhealthy Age Group: 54 (19–71) Sex: M+F Sources: https://www.sciencedirect.com/science/article/pii/S1198743X14614919	Sources: https://www.sciencedirect.com/science/article/pii/S1198743X14614919
1 g 1 times / day single, oral Highest studied dose Dose: 1 g, 1 times / day Route: oral Route: single Dose: 1 g, 1 times / day Sources: https://www.mdpi.com/2079-6382/8/3/119/htm	unhealthy, 58.3±15.4(19–90) Health Status: unhealthy Age Group: 58.3±15.4(19–90) Sex: M+F Sources: https://www.mdpi.com/2079-6382/8/3/119/htm	Sources: https://www.mdpi.com/2079-6382/8/3/119/htm
250 mg 3 times / day multiple, oral Recommended Dose: 250 mg, 3 times / day Route: oral Route: multiple Dose: 250 mg, 3 times / day Sources: https://www.nejm.org/doi/full/10.1056/NEJM196011032631805	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.nejm.org/doi/full/10.1056/NEJM196011032631805	Disc. AE: Dermatitis, Throbbing headache... AEs leading to discontinuation/dose reduction: Dermatitis Throbbing headache Hypersensitivity reaction Sources: https://www.nejm.org/doi/full/10.1056/NEJM196011032631805

AEs

AE	Significance	Dose	Population
Dermatitis	Disc. AE	250 mg 3 times / day multiple, oral Recommended Dose: 250 mg, 3 times / day Route: oral Route: multiple Dose: 250 mg, 3 times / day Sources: https://www.nejm.org/doi/full/10.1056/NEJM196011032631805	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.nejm.org/doi/full/10.1056/NEJM196011032631805
Hypersensitivity reaction	Disc. AE	250 mg 3 times / day multiple, oral Recommended Dose: 250 mg, 3 times / day Route: oral Route: multiple Dose: 250 mg, 3 times / day Sources: https://www.nejm.org/doi/full/10.1056/NEJM196011032631805	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.nejm.org/doi/full/10.1056/NEJM196011032631805
Throbbing headache	Disc. AE	250 mg 3 times / day multiple, oral Recommended Dose: 250 mg, 3 times / day Route: oral Route: multiple Dose: 250 mg, 3 times / day Sources: https://www.nejm.org/doi/full/10.1056/NEJM196011032631805	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M+F Sources: https://www.nejm.org/doi/full/10.1056/NEJM196011032631805

Sourcing

Vendor/Aggregator	ID	URL
AAA Chemistry	AR-1A3548
ABI Chem	AC1L6SCV
ABI Chem	AC1Q5QWQ
AbovChem LLC	HY-B1003
Alfa Chemistry	ACM132934
AmicBase - Antimicrobial Activities	5993
Angene	AGN-PC-0O40XQ
Asinex	BAS07100915
BOC Sciences	132-93-4
BOC Sciences	147-55-7
Chem Scene	CS-4500	http://www.chemscene.com/Phenethicillin.html
ChemDiv	6465-0732
Chemieliva Pharmaceutical Co., Ltd	PBCM0298614
ChemTik	CTK0H5615
Compound Cloud	23675317
Compound Cloud	272833
eMolecules	106291331
eMolecules	110004574
eMolecules	1493271
eMolecules	300532100
eMolecules	72973290
Kingston Chemistry	KST-1A1519
MedChem Express	HY-B1003	http://www.medchemexpress.com/Phenethicillin.html
MolPort	MolPort-046-843-053
MuseChem	M068974	https://www.musechem.com/product/M068974.html
NCI Plated 2007	117548
NovoSeek	272833
Princeton BioMolecular Research	OSSK_573137
Smolecule	S570601	https://www.smolecule.com/products/s570601
Tetrahedron	TS79729
Tetrahedron	TS81157
THE BioTek	bt-459650	https://www.thebiotek.com/product/others/bt-459650
TimTec	ST50282471
Toronto Research Chemicals	P296320
Vitas-M Laboratory	STK177352
ZINC	ZINC000001707475	http://zinc15.docking.org/substances/ZINC000001707475
ZINC	ZINC000001707476	http://zinc15.docking.org/substances/ZINC000001707476
ZINC	ZINC000003831306	http://zinc15.docking.org/substances/ZINC000003831306
ZINC	ZINC000003875872	http://zinc15.docking.org/substances/ZINC000003875872
ZINC	ZINC000009231497	http://zinc15.docking.org/substances/ZINC000009231497

PubMed

Title	Date	PubMed
Complete genome sequence and comparative metabolic profiling of the prototypical enteroaggregative Escherichia coli strain 042.	2010-01-20	20098708
[Summary of the practice guideline 'Sore throat' (second revision) from the Dutch College of General Practitioners].	2008-02-23	18361191
A complete library of amino acid alterations at R306 in Streptomyces clavuligerus deacetoxycephalosporin C synthase demonstrates its structural role in the ring-expansion activity.	2008-02-15	17729280
Risk of major bleeding during concomitant use of antibiotic drugs and coumarin anticoagulants.	2008-02	18031295
Levofloxacin vs. ciprofloxacin plus phenethicillin for the prevention of bacterial infections in patients with haematological malignancies.	2007-05	17263835
A randomized prospective controlled trial of antibiotic prophylaxis in intraoral bone-grafting procedures: preoperative single-dose penicillin versus preoperative single-dose clindamycin.	2006-05	16472987
The history of penicillin from discovery to the drive to production.	2004-09	15382352
A prospective placebo-controlled double-blind trial of antibiotic prophylaxis in intraoral bone grafting procedures: a pilot study.	2003-12	14676756
[Simultaneous determination of five penicillins in muscle, liver and kidney from slaughtered animals using liquid chromatography coupled with electrospray ionization tandem mass spectrometry].	2003-02	12749189
Deacetoxycephalosporin C synthase isozymes exhibit diverse catalytic activity and substrate specificity.	2003-01-28	12586400
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.	1990-11	1701026

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 Created by `admin` on `Mon Mar 31 19:10:30 GMT 2025` Edited by `admin` on `Mon Mar 31 19:10:30 GMT 2025`
Record UNII	EFA30X554H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENETICILLIN

Official Name

English

ALFACILIN

Preferred Name

English

.ALPHA.-PHENOXYETHYLPENICILLIN

Common Name

English

pheneticillin [INN]

Common Name

English

NSC-117548

Code

English

Pheneticillin [WHO-DD]

Common Name

English

FENETICILLIN

Common Name

English

SYNTHEPEN

Brand Name

English

4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-((1-OXO-2-PHENOXYPROPYL)AMINO)-, (2S,5R,6R)-

Common Name

English

(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(2-PHENOXYPROPIONAMIDO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE

Systematic Name

English

PHENETHICILLIN

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01CE05