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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20N2.2C16H18N2O5S.4H2O
Molecular Weight 1013.184
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENICILLIN V BENZATHINE TETRAHYDRATE

SMILES

O.O.O.O.C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2.[H][C@]34SC(C)(C)[C@@H](N3C(=O)[C@H]4NC(=O)COC5=CC=CC=C5)C(O)=O.[H][C@]67SC(C)(C)[C@@H](N6C(=O)[C@H]7NC(=O)COC8=CC=CC=C8)C(O)=O

InChI

InChIKey=WGLORUYLLMHSJU-CJHXQPGBSA-N
InChI=1S/2C16H18N2O5S.C16H20N2.4H2O/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;4*1H2/t2*11-,12+,14-;;;;;/m11...../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 4 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H20N2
Molecular Weight 240.3434
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H18N2O5S
Molecular Weight 350.39
Charge 0
Count
MOL RATIO 2 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Penicillin V
Curative
Penicillin V
Curative
Penicillin V

Cmax

ValueDoseCo-administeredAnalytePopulation
15 mg/L
1 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens
26.3 mg/L
2 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens
35.5 mg/L
3 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens
6.1 mg/L
0.4 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
19.01 mg × h/L
1 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens
33.36 mg × h/L
2 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens
43.94 mg × h/L
3 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens
6.89 mg × h/L
0.4 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.78 h
1 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens
0.91 h
2 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens
1.05 h
3 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens
0.52 h
0.4 g single, oral
PENICILLIN V POTASSIUM serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
20%
unknown, oral
PENICILLIN V POTASSIUM serum
Homo sapiens

Doses

AEs

PubMed

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
Substance Class Chemical
Record UNII
44MHH77OIC
Record Status Validated (UNII)
Record Version