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Sulbactam pivoxil, the pivoxil prodrug form of sulbactam, is a semi-synthetic beta-lactamase inhibitor used to improve the efficacy of beta lactam antibiotics (e.g. cefoperazone/sulperazon).
Sulbactam pivoxil is a penicillanic acid ester that results from the formal condensation of the carboxy group of sulbactam with the hydroxy group of hydroxymethyl 2,2-dimethylpropanoate. It is a prodrug of the beta-lactamase inhibitor sulbactam. It has a role as a prodrug. It is a pivaloyloxymethyl ester and a penicillanic acid ester. Sulbactam Pivoxil is the pivoxil prodrug form of sulbactam, a semi-synthetic beta-lactamase inhibitor, with beta-lactam antibiotic adjuvant activity. After oral administration of sulbactam pivoxil, the ester bond is cleaved, releasing active sulbactam. The beta-lactam ring of sulbactam irreversibly binds to beta-lactamase at or near its active site, thereby blocking enzyme activity and preventing metabolism of other beta-lactam antibiotics by the enzyme.| Targets |
- Sulbactam pivoxil is a prodrug that is hydrolyzed in vivo to release sulbactam, which targets bacterial β-lactamases (no specific Ki/IC50 values available). [2]
- The active metabolite sulbactam irreversibly binds to β-lactamases (Types II to IV) to inhibit their activity, protecting β-lactam antibiotics from hydrolysis. [6] |
|---|---|
| ln Vitro |
- Sulbactam pivoxil undergoes hydrolysis in vitro to release sulbactam, which exhibits inhibitory activity against β-lactamases from various bacteria, including penicillin-resistant strains. This restoration of β-lactam antibiotic activity was observed in bacterial cultures (no specific MIC values provided). [6]
- The prodrug itself shows no direct antibacterial activity in vitro; its activity is dependent on conversion to sulbactam via esterase-mediated hydrolysis. [2] |
| ln Vivo |
- Oral administration of Sulbactam pivoxil in rats resulted in higher serum concentrations of sulbactam compared to oral administration of sulbactam alone, indicating improved oral bioavailability (specific concentration data not available). [2]
- In combination with β-lactam antibiotics, Sulbactam pivoxil enhanced bacterial clearance in animal models of infections caused by β-lactamase-producing strains (detailed efficacy parameters not provided). [6] |
| Enzyme Assay |
- No specific enzyme assay protocols for Sulbactam pivoxil were identified in the available literature summaries. The inhibitory activity of its metabolite sulbactam against β-lactamases was inferred to involve incubation with bacterial β-lactamase extracts and measurement of substrate hydrolysis inhibition (details not specified). [2]
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| Cell Assay |
- No detailed cell assay protocols for Sulbactam pivoxil were identified in the available literature summaries. In vitro susceptibility tests likely involved bacterial cultures incubated with hydrolyzed Sulbactam pivoxil to evaluate restored antibiotic sensitivity (methodology not specified). [6]
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| Animal Protocol |
- In oral bioavailability studies, Sulbactam pivoxil was administered to rats via oral gavage (specific dose and frequency not provided). Serum samples were collected at intervals to measure sulbactam concentrations. [2]
- Animal models of bacterial infection received oral Sulbactam pivoxil in combination with β-lactam antibiotics. Efficacy was evaluated by monitoring bacterial load reduction and survival rates (specific infection models and treatment durations not specified). [6] |
| ADME/Pharmacokinetics |
Compared with sulbactam, sulbactam pivoxil has a higher oral absorption rate and can achieve higher serum sulbactam concentrations after oral administration. [1][2] After oral administration, sulbactam pivoxil is hydrolyzed in the body to sulbactam, which has an elimination half-life of approximately 0.75-1 hour. [7] The metabolite sulbactam is mainly excreted unchanged in the urine, and 50-75% of the dose can be eliminated within 24 hours. [7]
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| Toxicity/Toxicokinetics |
Nonclinical toxicology studies in rats, mice, and rabbits showed that administration of sulbactam pivoxil did not cause significant toxicity. [10] - Common adverse reactions in humans included mild gastrointestinal reactions (e.g., diarrhea, nausea) and rash (incidence not specified). [10] - The metabolite sulbactam has low plasma protein binding (approximately 29%). [2][7]
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| References | |
| Additional Infomation |
Sulbactam pivoxil is a lipophilic ester prodrug of sulbactam designed to improve its oral bioavailability, as sulbactam has low gastrointestinal absorption. [1][2] Sulbactam pivoxil is synthesized by reacting sulbactam sodium salt with chloromethyl pentanoate in dimethyl sulfoxide (DMSO) at room temperature for 18 hours, followed by filtration. [1] Sulbactam pivoxil is primarily used in combination with β-lactam antibiotics (e.g., amoxicillin) to treat infections caused by β-lactamase-producing bacteria, including respiratory and skin infections. [6][10] Sulbactam pivoxil has greater chemical stability in oral formulations compared to other β-lactamase inhibitors (e.g., clavulanic acid). [8] Sulbactam pivoxil is a penicillin ester formed by the condensation of the carboxyl group of sulbactam with the hydroxyl group of 2,2-dimethylpropionate. It is a prodrug of the β-lactamase inhibitor sulbactam. It is a prodrug belonging to the neopentyloxymethyl ester and penicillin ester classes. Sulbactam pivoxil is the pivoxil prodrug form of sulbactam, a semi-synthetic β-lactamase inhibitor with adjuvant activity against β-lactam antibiotics. After oral administration of sulbactam pivoxil, the ester bond breaks, releasing active sulbactam. The β-lactam ring of sulbactam irreversibly binds to or near the active site of a β-lactamase, thereby blocking enzyme activity and preventing other β-lactam antibiotics from being metabolized by this enzyme.
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| Molecular Formula |
C14H21NO7SMOLECULARWEIGHT
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|---|---|
| Molecular Weight |
347.382
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| Exact Mass |
347.103
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| Elemental Analysis |
C, 48.41; H, 6.09; N, 4.03; O, 32.24; S, 9.23
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| CAS # |
69388-79-0
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| Related CAS # |
69388-84-7 (Na+);69388-79-0 (pivoxil);68373-14-8 (free acid);
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| PubChem CID |
50491
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
537.5±50.0 °C at 760 mmHg
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| Flash Point |
278.9±30.1 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.538
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| LogP |
-0.02
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| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
23
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| Complexity |
654
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(C)(C)C(=O)OCOC(=O)[C@H]1C(C)(C)S(=O)(=O)[C@@H]2CC(=O)N21
|
| InChi Key |
OHPVYKXTRACOSQ-ZJUUUORDSA-N
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| InChi Code |
InChI=1S/C14H21NO7S/c1-13(2,3)12(18)22-7-21-11(17)10-14(4,5)23(19,20)9-6-8(16)15(9)10/h9-10H,6-7H2,1-5H3/t9-,10+/m1/s1
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| Chemical Name |
(pivaloyloxy)methyl (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4,4-dioxide
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| Synonyms |
CP 47,904; CP47,904; SULBACTAM PIVOXIL; 69388-79-0; Sulbactam pivoxyl; Pivsulbactam; CP-47904; 2X0WTA96KX; CP-47,904; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-, 4,4-dioxide, (2,2-dimethyl-1-oxopropoxy)methyl ester, (2S-cis)-; CP-47,904
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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 : ~12.5 mg/mL (~35.98 mM)
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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 | 2.8787 mL | 14.3935 mL | 28.7869 mL | |
| 5 mM | 0.5757 mL | 2.8787 mL | 5.7574 mL | |
| 10 mM | 0.2879 mL | 1.4393 mL | 2.8787 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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