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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18N2O5S
Molecular Weight 350.39
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENICILLIN V

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)COC3=CC=CC=C3)C(=O)N2[C@H]1C(O)=O

InChI

InChIKey=BPLBGHOLXOTWMN-MBNYWOFBSA-N
InChI=1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

HIDE SMILES / InChI

Description

Penicillin V is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Penicillin V has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Penicillin V results from the inhibition of cell wall synthesis and is mediated through Penicillin V binding to penicillin binding proteins (PBPs). Penicillin V is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Penicillin V inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Penicillin V interferes with an autolysin inhibitor. Used for the treatment of mild to moderately severe infections (e.g. dental infection, infections in the heart, middle ear infections, rheumatic fever, scarlet fever, skin infections, upper and lower respiratory tract infections) due to microorganisms.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[The antiviral activity of the antibiotics beromycin and carminomycin].
1974 Feb
[Immune hemolytic anemia and thrombocytopenia after peroral therapy with a penicillin derivative (phenoxymethylpenicillin)].
1977
Assessment of the "E' book as a tool for drug monitoring.
1981 Mar
[Leukocytoclastic vasculitis due to drug allergy presenting as generalized pustular exanthema].
1981 Sep
Effect of drugs influencing synthesis of prostaglandins on haloperidol-induced catalepsy in rats.
1984 Jul-Sep
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Tigecycline: an evidence-based review of its antibacterial activity and effectiveness in complicated skin and soft tissue and intraabdominal infections.
2006
Drug use in children: cohort study in three European countries.
2008 Nov 24
Prevalence of Group A b-Hemolytic Streptococcus Among Children with Tonsillopharyngitis in Kyrgyzstan: The Difficulty of Diagnostics and Therapy.
2010 Oct 13
Evaluation of the sensitizing potential of antibiotics in vitro using the human cell lines THP-1 and MUTZ-LC and primary monocyte-derived dendritic cells.
2012 Aug 1
Identification of urinary microRNA profiles in rats that may diagnose hepatotoxicity.
2012 Feb
Synthesis of novel hapten and production of generic monoclonal antibody for immunoassay of penicillins residues in milk.
2013
Patents

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Bacterial Infection Mild to moderate infections: 125 to 500 mg orally every 6 to 8 hours
Route of Administration: Oral
In Vitro Use Guide
Penicillin V inhibited Staphylococcus aureus in human THP-1 macrophages (intracellular) with MIC90 of 0.015 mg/L
Name Type Language
PENICILLIN V
HSDB   MI   ORANGE BOOK   USAN   USP   USP-RS  
USAN  
Official Name English
PENICILLIN V [HSDB]
Common Name English
VEBECILLIN
Common Name English
PHENOXYMETHYLPENICILLIN [INN]
Common Name English
PHENOXYMETHYLPENICILLIN [WHO-IP]
Common Name English
PENICILLIN PHENOXYMETHYL
Common Name English
PENICILLIN V [USP]
Common Name English
PENICILLIN V [USP-RS]
Common Name English
PENICILLIN V [ORANGE BOOK]
Common Name English
PHENOXYMETHYLPENICILLIN
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
DISTAQUAINE V
Common Name English
PHENOXYMETHYLPENICILLIN [WHO-DD]
Common Name English
PHENOXYMETHYLPENICILLIN [MART.]
Common Name English
PHENOXYMETHYLPENICILLIN [EP]
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-((PHENOXYACETYL)AMINO)-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-
Common Name English
PENICILLIN V [MI]
Common Name English
PHENOXYMETHYLPENICILLINUM [WHO-IP LATIN]
Common Name English
(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(2-PHENOXYACETAMIDO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
V-CILLIN
Brand Name English
PENICILLIN V [USAN]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01CE02
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
WHO-ATC J01CE02
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
WHO-ATC J01CE10
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
CFR 21 CFR 520.1696C
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
CFR 21 CFR 520.1696D
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
LIVERTOX 753
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
Code System Code Type Description
EPA CompTox
87-08-1
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
RXCUI
7984
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY RxNorm
ChEMBL
CHEMBL615
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
LactMed
87-08-1
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
ECHA (EC/EINECS)
201-722-0
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
EVMPD
SUB09779MIG
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
PUBCHEM
6869
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY SWITZERF
MESH
D010404
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
HSDB
87-08-1
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
DRUG BANK
DB00417
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
WIKIPEDIA
PHENOXYMETHYLPENICILLIN
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
CAS
87-08-1
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
NCI_THESAURUS
C62064
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY
MERCK INDEX
M8479
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
PENICILLIN V
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY Description: A white, fine crystalline powder. Solubility: Soluble in 1700 parts of water and in 7 parts of ethanol (~750 g/l) TS. Category: Antibiotic. Storage: Phenoxymethylpenicillin should be kept in a tightly closed container, protected from light. Additional information: Even in the absence of light, Phenoxymethylpenicillin is gradually degraded on exposure to a humidatmosphere, the decomposition being faster at higher temperatures. Definition: Phenoxymethylpenicillin contains not less than 95.0% and not more than 102.0% of C16H18N2O5S, calculated withreference to the anydrous substance.
INN
518
Created by admin on Tue Mar 06 11:22:19 UTC 2018 , Edited by admin on Tue Mar 06 11:22:19 UTC 2018
PRIMARY