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

[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

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 233 Target ID: CHEMBL2354204 Sources: http://www.microrao.com/micronotes/pg/ESBLs.pdf \| http://db.cbg-meb.nl/IB-teksten/h09101.pdf	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Lower respiratory tract infections 51 Sources: http://db.cbg-meb.nl/Bijsluiters/h04959.pdf	Curative	Approved 8429	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 8429	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 8429	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) n = 120 Health Status: unhealthy Condition: Infection Age Group: 54 (19–71) Sex: M+F Population Size: 120 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) n = 84 Health Status: unhealthy Condition: Infection Age Group: 58.3±15.4(19–90) Sex: M+F Population Size: 84 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 n = 437 Health Status: unhealthy Condition: Infection Age Group: adult Sex: M+F Population Size: 437 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 n = 437 Health Status: unhealthy Condition: Infection Age Group: adult Sex: M+F Population Size: 437 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 n = 437 Health Status: unhealthy Condition: Infection Age Group: adult Sex: M+F Population Size: 437 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 n = 437 Health Status: unhealthy Condition: Infection Age Group: adult Sex: M+F Population Size: 437 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
ChemTik	CTK0H5615
Chemieliva Pharmaceutical Co., Ltd	PBCM0298614
Compound Cloud	23675317
Compound Cloud	272833
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
THE BioTek	bt-459650	https://www.thebiotek.com/product/others/bt-459650
Tetrahedron	TS79729
Tetrahedron	TS81157
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
eMolecules	106291331
eMolecules	110004574
eMolecules	1493271
eMolecules	300532100
eMolecules	72973290

PubMed

Title	Date	PubMed
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.	1990 Nov	1701026
A prospective placebo-controlled double-blind trial of antibiotic prophylaxis in intraoral bone grafting procedures: a pilot study.	2003 Dec	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 Feb	12749189
Deacetoxycephalosporin C synthase isozymes exhibit diverse catalytic activity and substrate specificity.	2003 Jan 28	12586400
The history of penicillin from discovery to the drive to production.	2004 Sep	15382352
A randomized prospective controlled trial of antibiotic prophylaxis in intraoral bone-grafting procedures: preoperative single-dose penicillin versus preoperative single-dose clindamycin.	2006 May	16472987
Levofloxacin vs. ciprofloxacin plus phenethicillin for the prevention of bacterial infections in patients with haematological malignancies.	2007 May	17263835
Risk of major bleeding during concomitant use of antibiotic drugs and coumarin anticoagulants.	2008 Feb	18031295
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 Feb 15	17729280
[Summary of the practice guideline 'Sore throat' (second revision) from the Dutch College of General Practitioners].	2008 Feb 23	18361191
Complete genome sequence and comparative metabolic profiling of the prototypical enteroaggregative Escherichia coli strain 042.	2010 Jan 20	20098708

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.

Name

Type

Language

PHENETICILLIN

Official Name

English

.ALPHA.-PHENOXYETHYLPENICILLIN

Common Name

English

pheneticillin [INN]

Common Name

English

NSC-117548

Code

English

Pheneticillin [WHO-DD]

Common Name

English

ALFACILIN

Brand 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