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

Details

Stereochemistry MIXED
Molecular Formula C18H22N2O5S
Molecular Weight 378.443
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROPICILLIN

SMILES

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

InChI

InChIKey=HOCWPKXKMNXINF-XQERAMJGSA-N
InChI=1S/C18H22N2O5S/c1-4-11(25-10-8-6-5-7-9-10)14(21)19-12-15(22)20-13(17(23)24)18(2,3)26-16(12)20/h5-9,11-13,16H,4H2,1-3H3,(H,19,21)(H,23,24)/t11?,12-,13+,16-/m1/s1

HIDE SMILES / InChI
Propicillin (Baycillin Mega) is this semisynthetic penicillin, analogous to penicillin V, was introduced in the early 1960s. Although it is better absorbed from the gastrointestinal tract, overall it is inferior to phenoxymethylpenicillin and phenoxyethylpenicillin because of its lower antibacterial activity. Propicillin is used by propicillin-susceptible pathogens in adults and adolescents from 14 years to treat mild to moderate bacterial infections. These include skin infections, ear, nose and throat infections (such as otitis media, sinusitis, tonsillitis, pharyngitis) and infections of the bronchi andlung inflammation. Moreover propicillin can for prevention and treatment of scarlet fever or against rheumatic fever are used (bacterial infection of the nose and throat). Even with tooth or jaw surgery the drug is used to treat an endocarditis endocarditis prevent. Its mechanism of action could be due to binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, thus propicillin may inhibit the third and last stage of bacterial cell wall synthesis

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: penicillin-binding proteins of bacterial cell
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Baycillin Mega

Approved Use

to reat mild to moderate bacterial infections. These include skin infections, ear, nose and throat infections (such as otitis media , sinusitis, tonsillitis , pharyngitis) and infections of the bronchi and lung inflammation.
Curative
Baycillin Mega

Approved Use

to reat mild to moderate bacterial infections. These include skin infections, ear, nose and throat infections (such as otitis media , sinusitis, tonsillitis , pharyngitis) and infections of the bronchi and lung inflammation.
Curative
Baycillin Mega

Approved Use

to reat mild to moderate bacterial infections. These include skin infections, ear, nose and throat infections (such as otitis media , sinusitis, tonsillitis , pharyngitis) and infections of the bronchi and lung inflammation.
Curative
Baycillin Mega

Approved Use

to reat mild to moderate bacterial infections. These include skin infections, ear, nose and throat infections (such as otitis media , sinusitis, tonsillitis , pharyngitis) and infections of the bronchi and lung inflammation.
Curative
Baycillin Mega

Approved Use

to reat mild to moderate bacterial infections. These include skin infections, ear, nose and throat infections (such as otitis media , sinusitis, tonsillitis , pharyngitis) and infections of the bronchi and lung inflammation.
Doses

Doses

DosePopulationAdverse events​
16 g 1 times / 6 hours steady-state, intravenous
Recommended
Dose: 16 g, 1 times / 6 hours
Route: intravenous
Route: steady-state
Dose: 16 g, 1 times / 6 hours
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Anaphylactic reaction, Anaphylactoid reactions...
AEs leading to
discontinuation/dose reduction:
Anaphylactic reaction (grade 3-4)
Anaphylactoid reactions (grade 3-4)
Anaphylactic shock (grade 3-4)
Clostridium difficile associated diarrhea
Sources:
100 mg/kg single, intravenous
Studied dose
Dose: 100 mg/kg
Route: intravenous
Route: single
Dose: 100 mg/kg
Sources:
unhealthy, CHILD
Health Status: unhealthy
Age Group: CHILD
Sex: M+F
Food Status: UNKNOWN
Sources:
AEs

AEs

AESignificanceDosePopulation
Clostridium difficile associated diarrhea Disc. AE
16 g 1 times / 6 hours steady-state, intravenous
Recommended
Dose: 16 g, 1 times / 6 hours
Route: intravenous
Route: steady-state
Dose: 16 g, 1 times / 6 hours
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Anaphylactic reaction grade 3-4
Disc. AE
16 g 1 times / 6 hours steady-state, intravenous
Recommended
Dose: 16 g, 1 times / 6 hours
Route: intravenous
Route: steady-state
Dose: 16 g, 1 times / 6 hours
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Anaphylactic shock grade 3-4
Disc. AE
16 g 1 times / 6 hours steady-state, intravenous
Recommended
Dose: 16 g, 1 times / 6 hours
Route: intravenous
Route: steady-state
Dose: 16 g, 1 times / 6 hours
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Anaphylactoid reactions grade 3-4
Disc. AE
16 g 1 times / 6 hours steady-state, intravenous
Recommended
Dose: 16 g, 1 times / 6 hours
Route: intravenous
Route: steady-state
Dose: 16 g, 1 times / 6 hours
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Evaluation of a simple carrier molecule to enhance drug penetration of dermal layers by utilizing multivariate methods, structure property correlations, and continuous system modeling.
2004
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: http://www.ncbi.nlm.nih.gov/pubmed/4967932
1 Mega unit (0.7 g) propicillin orally as oblong tablets one or two hours before surgery
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
PROPICILLIN
INN   MI   WHO-DD  
INN  
Official Name English
(1-PHENOXYPROPYL)PENICILLIN
Preferred Name English
.ALPHA.-PHENOXYPROPYLPENICILLIN
Common Name English
PHENOXYPROPYLPENICILLIN
Common Name English
6-(.ALPHA.-PHENOXYBUTYRAMIDO)PENICILLANIC ACID
Common Name English
propicillin [INN]
Common Name English
(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-((1-OXO-2-PHENOXYBUTYL)AMINO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
PROPICILLIN [MI]
Common Name English
Propicillin [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J01CE03
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
WHO-VATC QJ01CE03
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
NCI_THESAURUS C1500
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL2105612
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
INN
1345
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
MERCK INDEX
m9201
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY Merck Index
SMS_ID
100000081175
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
EVMPD
SUB10106MIG
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
RXCUI
34649
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY RxNorm
ECHA (EC/EINECS)
208-995-5
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PRIMARY
EPA CompTox
DTXSID3046291
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
CAS
551-27-9
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PRIMARY
PUBCHEM
92879
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
FDA UNII
8X1R260V33
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
DRUG CENTRAL
2297
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
NCI_THESAURUS
C66483
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
MESH
C100135
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
WIKIPEDIA
PROPICILLIN
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
DRUG BANK
DB13660
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
CHEBI
52429
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY
CHEBI
52427
Created by admin on Mon Mar 31 18:25:18 GMT 2025 , Edited by admin on Mon Mar 31 18:25:18 GMT 2025
PRIMARY