| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
Penicillin G benzathine targets the bacterial cell wall. Penicillin G, the active moiety, inhibits the synthesis of peptidoglycan, a critical component of the bacterial cell wall. It does this by binding to and inactivating penicillin-binding proteins (PBPs), which are enzymes responsible for the final stages of peptidoglycan cross-linking. This disruption weakens the cell wall, leading to bacterial lysis and death, primarily against susceptible gram-positive bacteria.
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| ln Vitro |
In vitro, Penicillin G benzathine is an antibiotic effective against numerous bacterial infections. As a prodrug, its in vitro activity is attributed to the release of penicillin G, which is the active antibacterial agent. Susceptibility testing, such as determining the minimum inhibitory concentration (MIC), is performed to assess its efficacy against specific bacterial isolates.
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| ln Vivo |
In CD-I mice infected with Staphylococcus aureus Smith, penicillin G benzathine tetrahydrate shows action and antibacterial properties [2].
In vivo, Penicillin G benzathine displays antibacterial activity and effect in CD-1 mice infected with Staphylococcus aureus Smith. It is the drug of choice for the treatment of pharyngitis and tonsillitis caused by Streptococcus pyogenes (group A β-hemolytic streptococci) and for the prevention of initial attacks of rheumatic fever. It is also used to treat syphilis, yaws, bejel, and pinta. |
| Enzyme Assay |
In vitro assays for Penicillin G benzathine involve standard microbiological susceptibility testing. Broth microdilution or agar dilution methods are employed to determine the minimum inhibitory concentration (MIC) against bacterial strains. The compound's activity is compared to that of penicillin G. Quality control strains with known MIC ranges are used to validate the assay.
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| Cell Assay |
Penicillin G benzathine is not typically used in standard cell-based assays, as its target is bacterial. Its mechanism of action is assessed in bacterial cultures. However, cytotoxicity assays in mammalian cell lines may be performed to assess its safety profile. The compound is intended for intramuscular injection, not for direct addition to cell cultures.
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| Animal Protocol |
In vivo animal experiments with Penicillin G benzathine are conducted to evaluate its efficacy and pharmacokinetics. A common model is the CD-1 mouse infected with Staphylococcus aureus Smith. The compound is administered via intramuscular injection, and its antibacterial effect is assessed by measuring bacterial load in tissues, survival rates, and clinical signs of infection.
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| ADME/Pharmacokinetics |
Following intramuscular injection, Penicillin G benzathine forms a depot from which penicillin G is slowly released, resulting in prolonged, low-level antibiotic concentrations in the blood. This allows for infrequent dosing. Penicillin G is primarily excreted unchanged by the kidneys. The tetrahydrate form is a crystalline salt that is poorly soluble, contributing to its sustained-release properties.
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| Toxicity/Toxicokinetics |
Penicillin G benzathine is generally well-tolerated, but common adverse effects include pain at the injection site, allergic reactions (ranging from rash to anaphylaxis), and gastrointestinal disturbances. Serious but rare side effects include neurotoxicity and nephrotoxicity. It is contraindicated in patients with a history of penicillin hypersensitivity.
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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 |
Benzathine penicillin G is a prescription antimicrobial drug approved by the U.S. Food and Drug Administration (FDA) for the treatment of certain bacterial infections, such as upper respiratory tract infections, syphilis, and yaws, Bejell's disease, and pinta disease (skin infections). Benzathine penicillin G is also FDA-approved for the prevention of certain bacterial diseases, such as rheumatic fever and other illnesses. Syphilis may be an opportunistic infection associated with HIV. Benzathine penicillin G is a long-acting benzathine salt form of the broad-spectrum penicillin antibiotic penicillin G. Benzathine penicillin G binds to penicillin-binding protein (PBP), an enzyme that catalyzes the synthesis of peptidoglycan, an important component of the bacterial cell wall. This leads to the interruption of cell wall synthesis, thereby inhibiting bacterial cell growth and causing cell lysis. It is a semi-synthetic antibiotic prepared by conjugating penicillin G sodium salt with N,N'-dibenzylethylenediamine. See also: Penicillin G (with active moiety); Benzathine penicillin G; Procaine penicillin G (component).
Penicillin G benzathine tetrahydrate (Benzathine Benzylpenicillin Tetrahydrate) is a long-acting antibiotic used to treat a variety of bacterial infections. It is the drug of choice for streptococcal pharyngitis and for preventing rheumatic fever. It is also used for syphilis and other treponemal infections. Brand names include Permapen and Pfizerpen. It is administered via deep intramuscular injection. |
| Molecular Formula |
2[C16H18N2O4S].C16H20N2.4[H2O]
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|---|---|
| Molecular Weight |
981.18476
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| Exact Mass |
980.402
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| CAS # |
41372-02-5
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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;1538-09-6;Penicillin G;61-33-6
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| PubChem CID |
656811
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| Appearance |
Off-white to light yellow solid powder
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| Boiling Point |
1299.8ºC at 760 mmHg
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| Melting Point |
123-124°C
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| Flash Point |
739.9ºC
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| LogP |
5.469
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| Hydrogen Bond Donor Count |
10
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| Hydrogen Bond Acceptor Count |
16
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| Rotatable Bond Count |
15
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| Heavy Atom Count |
68
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| Complexity |
701
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| Defined Atom Stereocenter Count |
6
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| SMILES |
O.O.O.O.C(NCC1C=CC=CC=1)CNCC1C=CC=CC=1.C1C=CC(CC(N[C@@H]2C(=O)N3[C@H](C(S[C@H]23)(C)C)C(=O)O)=O)=CC=1.C1C=CC(CC(N[C@@H]2C(=O)N3[C@H](C(S[C@H]23)(C)C)C(=O)O)=O)=CC=1
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| InChi Key |
WIDKTXGNSOORHA-CJHXQPGBSA-N
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| InChi Code |
InChI=1S/2C16H18N2O4S.C16H20N2.4H2O/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;4*1H2/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;tetrahydrate
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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) |
DMSO : ≥ 250 mg/mL (~254.80 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.12 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (2.12 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (2.12 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0192 mL | 5.0959 mL | 10.1918 mL | |
| 5 mM | 0.2038 mL | 1.0192 mL | 2.0384 mL | |
| 10 mM | 0.1019 mL | 0.5096 mL | 1.0192 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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