| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg |
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| 250mg | |||
| 500mg | |||
| Other Sizes |
| Targets |
Penicillin G benzathine targets bacterial cell wall synthesis. It binds to one or more of the penicillin-binding proteins (PBPs) on the bacterial cell membrane. This binding inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls, disrupting the cross-linking of peptidoglycan chains. This disruption weakens the bacterial cell wall, leading to cell lysis and death. It has bacteriostatic and bactericidal actions against most Gram-positive bacteria and Gram-negative cocci. It is a natural penicillin antibiotic.
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| ln Vitro |
In vitro, penicillin G benzathine demonstrates antibacterial activity against susceptible organisms. Its activity is characterized by minimum inhibitory concentration (MIC) values against various bacterial strains. It is effective against most Gram-positive bacteria and Gram-negative cocci. It is less active against Gram-negative bacilli due to poor penetration through the outer membrane. Its in vitro activity is time-dependent, with efficacy related to the duration of time that drug concentrations exceed the MIC. It is used in susceptibility testing to determine bacterial sensitivity.
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| ln Vivo |
Staphylococcus aureus Smith-infected CD-I mice demonstrate activity and antibacterial effects of penicillin G benzathine [2].
In vivo, penicillin G benzathine demonstrates activity and antibacterial effect in CD-1 mice infected with Staphylococcus aureus Smith. Its prolonged-release formulation provides sustained therapeutic concentrations for several days after a single intramuscular injection. It is used for the treatment of early syphilis and other infections requiring prolonged antibiotic coverage. Its long-acting nature makes it suitable for conditions where daily dosing is impractical. Its efficacy is well-established in clinical practice. |
| Enzyme Assay |
In vitro enzyme/receptor binding studies for penicillin G benzathine are not typically performed, as its target is penicillin-binding proteins (PBPs) rather than soluble enzymes or receptors. PBP binding assays involve incubating bacterial membrane preparations with radiolabeled penicillin (e.g., [3H]-penicillin G) in the presence of increasing concentrations of unlabeled penicillin G benzathine, followed by SDS-PAGE and autoradiography to assess binding to specific PBPs. Competition assays determine the affinity of the compound for different PBP subtypes.
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| Cell Assay |
In vitro cellular assays for penicillin G benzathine involve standard antibacterial susceptibility testing using broth microdilution or agar dilution methods according to CLSI or EUCAST guidelines. Bacterial cultures are incubated with serial dilutions of the compound, and the MIC is determined as the lowest concentration that inhibits visible growth. Time-kill curves may be performed to assess bactericidal activity. Synergy studies with other antibiotics may also be conducted. Cytotoxicity in mammalian cells is evaluated using standard viability assays.
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| Animal Protocol |
In vivo animal studies for penicillin G benzathine include murine models of bacterial infection, such as CD-1 mice infected with Staphylococcus aureus Smith. Animals are treated with a single intramuscular or subcutaneous injection of penicillin G benzathine, and survival, bacterial burden in tissues, and pharmacokinetic parameters are assessed. Standard protocols include dose-response studies, comparison to vehicle or reference antibiotics, and evaluation of the duration of therapeutic effect. These studies confirm the prolonged activity of the repository formulation.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of penicillin G benzathine are characterized by slow absorption from the intramuscular injection site, resulting in prolonged, low-level penicillinemia. Peak plasma concentrations are lower than those achieved with aqueous penicillin G, but therapeutic levels are maintained for several days to weeks. It is highly protein-bound and distributed in extracellular fluids. It is excreted renally, with a prolonged elimination half-life due to its slow release from the injection site. Poor oral absorption necessitates intramuscular administration.
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| Toxicity/Toxicokinetics |
Penicillin G benzathine is generally well-tolerated, with the most common adverse effects being pain at the injection site and hypersensitivity reactions (rash, urticaria, anaphylaxis). It is contraindicated in patients with penicillin allergy. Other rare side effects include neurotoxicity (at high doses) and hematological effects. As with all penicillins, the risk of allergic reactions is significant, and skin testing or desensitization may be required in penicillin-allergic patients. It is considered safe for use in pregnancy. Overdose may cause seizures and electrolyte disturbances.
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| References |
[1]. Bowen AC, et al. Short-course oral co-trimoxazole versus intramuscular benzathine benzylpenicillin for impetigo in a highly endemic region: an open-label, randomised, controlled, non-inferiority trial. Lancet. 2014 Dec 13;384(9960):2132-40.
[2]. J A Yurchenco, et al. Substituted Penicillin Amides. Duration of Antibacterial Activity (Depot Effect) in Experimental Infections in Mice. Chemotherapy . 1972;17(6):405-15. |
| Additional Infomation |
semi-synthetic antibiotic prepared by combining penicillin G sodium salt with N,N'-dibenzylethylenediamine.
See also: Penicillin G benzathine (note moved to). Penicillin G benzathine is a long-acting repository penicillin used for the treatment of syphilis and other infections requiring prolonged antibiotic coverage. It is available as an intramuscular injection and is typically administered as a single dose for early syphilis or multiple doses for late syphilis. It is also used for prophylaxis against rheumatic fever in patients with a history of rheumatic heart disease. Its prolonged action makes it a valuable agent for conditions where adherence to daily dosing is challenging. It is on the WHO Model List of Essential Medicines. Its use requires careful attention to dosing and administration to ensure therapeutic efficacy. |
| Molecular Formula |
C48H56N6O8S2
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|---|---|
| Molecular Weight |
909.13
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| Exact Mass |
908.36
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| CAS # |
1538-09-6
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| Related CAS # |
Penicillin G potassium;113-98-4;Penicillin G sodium salt;69-57-8;Penicillin G procaine hydrate;6130-64-9;Penicillin G benzathine tetrahydrate;41372-02-5;Penicillin G;61-33-6
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| PubChem CID |
15232
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| Appearance |
White to light yellow solid powder
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| Boiling Point |
663.3ºCat 760 mmHg
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| Melting Point |
123-124ºC
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| Flash Point |
355ºC
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| Vapour Pressure |
1.69E-18mmHg at 25°C
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| LogP |
5.727
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
12
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| Rotatable Bond Count |
15
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| Heavy Atom Count |
64
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| Complexity |
701
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| Defined Atom Stereocenter Count |
6
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| SMILES |
C(NCC1C=CC=CC=1)CNCC1C=CC=CC=1.C1C=CC(CC(N[C@H]2C(=O)N3[C@@H](C(S[C@@]23[H])(C)C)C(=O)O)=O)=CC=1.C1C=CC(CC(N[C@H]2C(=O)N3[C@@H](C(S[C@@]23[H])(C)C)C(=O)O)=O)=CC=1
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| InChi Key |
BVGLIYRKPOITBQ-ANPZCEIESA-N
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| InChi Code |
InChI=1S/2C16H18N2O4S.C16H20N2/c2*1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;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
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| Chemical Name |
N,N'-dibenzylethane-1,2-diamine;(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
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| Synonyms |
NCI-C56100; Extenicilline; Bicillin I
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1000 mL | 5.4998 mL | 10.9995 mL | |
| 5 mM | 0.2200 mL | 1.1000 mL | 2.1999 mL | |
| 10 mM | 0.1100 mL | 0.5500 mL | 1.1000 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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