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Benzathine phenoxymethylpenicillin

Phenoxymethylpenicillin is narrow spectrum antibiotic used to treat mild to moderate infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered orally. Phenoxymethylpenicillin may also be used in some cases as prophylaxis against susceptible organisms. Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.

Therapeutic use

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.

Dosage and Administration

 

Toxicology

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 intramuscular 1363mg/kg (1363mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
guinea pig LD50 intraperitoneal 629mg/kg (629mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
mouse LD50 intramuscular > 2gm/kg (2000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
mouse LD50 intraperitoneal 994mg/kg (994mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
mouse LD50 oral > 2gm/kg (2000mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
rat LD50 intramuscular > 2gm/kg (2000mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
rat LD50 intraperitoneal 477mg/kg (477mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956.
rat LD50 oral > 3200mg/kg (3200mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Antibiotics Annual. Vol. 3, Pg. 534, 1955/1956

 

Pharmacokinetic

Bioavailability  
Protein binding  
Metabolism  
Half-life  
Cmax (mg/ml)  
tmax (hrs)  
Distribution volume Vd (l/kg)  
Clearance  
Excretion  

Absorption

Distribution


Excretion

Metabolism

 

Mechanism of Action

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.

Other pharmacological effects

 


Medicinal Chemistry

CAS number:  5928-84-7 EINECS: 227-667-2

Molecular Formula: C48H56N6O10S2

Average mass: 941.122375 Da

Monoisotopic mass:  940.349915 Da

Systematic name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid - N,N'-dibenzyl-1,2-ethanediamine (2:1)

SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C.CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C.C1=CC=C(C=C1)CNCCNCC2=CC=CC=C2

Std. InChI: 1S/2C16H18N2O5S.C16H20N2/c2*1-16(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;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h2*3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,17-18H,11-14H2/t2*11-,12+,14-;/m11./s1

ACD/LogP:   # of Rule of 5 Violations:  
ACD/LogD (pH 5.5):   ACD/LogD (pH 7.4):  
ACD/BCF (pH 5.5):   ACD/BCF (pH 7.4):  
ACD/KOC (pH 5.5):   ACD/KOC (pH 7.4):  
#H bond acceptors:   #H bond donors:  
#Freely Rotating Bonds:   Polar Surface Area: 2
Index of Refraction:   Molar Refractivity: cm3
Molar Volume: cm3 Polarizability: 10-24cm3
Surface Tension: dyne/cm Density: g/cm3
Flash Point: C Enthalpy of Vaporization: kJ/mol
Boiling Point: C at 760 mmHg Vapour Pressure: mmHg at 25C

 

Major Impurities:

Appearance:

Melting point:

Optical rotation:

Solubility:

logP:

pKa:
 

Stability:

 


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