| Size | Price | Stock | Qty |
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| 10mg |
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| 50mg |
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| 100mg |
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| Targets |
Pivmecillinam Hydrochloride targets penicillin-binding protein 2 (PBP2). As a prodrug of mecillinam, it is converted by hydrolysis to the active antibiotic after oral administration. Mecillinam binds specifically to penicillin-binding protein 2 (PBP2), which is essential for bacterial cell wall synthesis. This binding inhibits the transpeptidase activity of PBP2, disrupting cell wall biosynthesis and leading to bacterial cell lysis and death. Its unique mechanism of action makes it effective against many gram-negative pathogens.
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| ln Vitro |
Pivmecillinam Hydrochloride demonstrates potent antibacterial activity in vitro against a wide range of gram-negative bacteria, including Escherichia coli, Salmonella, Shigella, and other Enterobacteriaceae. Its minimum inhibitory concentrations (MICs) against susceptible strains are typically in the range of 0.5-8 μg/mL. The compound shows activity against multidrug-resistant E. coli. Its activity is assessed by standard broth microdilution or agar dilution methods according to CLSI guidelines.
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| ln Vivo |
Pivmecillinam Hydrochloride demonstrates in vivo efficacy in animal models of urinary tract infection and other bacterial infections. In mice, subcutaneous injection at 0.5 and 1 mg per mouse showed efficacy against multidrug-resistant E. coli infections. As an orally active prodrug, it is absorbed from the gastrointestinal tract and converted to the active antibiotic mecillinam. It is the first-line drug for empirical treatment of acute cystitis and has been used for paratyphoid fever and shigellosis.
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| Enzyme Assay |
Antibacterial susceptibility testing is performed using broth microdilution or agar dilution methods according to CLSI (Clinical and Laboratory Standards Institute) guidelines. Bacterial strains (e.g., E. coli ATCC 25922, clinical isolates) are cultured in Mueller-Hinton broth or agar. Pivmecillinam Hydrochloride is serially diluted in 96-well plates or agar plates. Bacterial inoculum is added and plates are incubated at 35°C for 16-20 hours. MIC (minimum inhibitory concentration) values are determined as the lowest concentration causing complete inhibition of visible growth. Quality control strains are included to ensure assay validity.
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| Cell Assay |
Cellular antibacterial activity is evaluated in bacterial cell cultures using standard microbiological methods. Broth microdilution assays are performed in 96-well plates with Mueller-Hinton broth. Bacteria are cultured to logarithmic phase and diluted to a standard inoculum (approximately 5 × 10^5 CFU/mL). Pivmecillinam Hydrochloride is serially diluted and added to wells. Plates are incubated at 35°C for 16-20 hours. MIC values are determined visually or using a microplate reader. Time-kill curve assays are performed to assess bactericidal activity. Each experiment includes appropriate quality control strains and antibiotic standards.
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| Animal Protocol |
In vivo efficacy is evaluated in animal models of urinary tract infection or systemic infection. Mice are infected with pathogenic bacteria (e.g., E. coli) via intravesical or intravenous inoculation. Pivmecillinam Hydrochloride is administered orally or subcutaneously at various doses. Treatment begins 1-4 hours post-infection and continues for 3-10 days. Survival is monitored daily. At study endpoint, bacterial burden is quantified in kidneys, bladder, spleen, or blood by CFU plating. Pharmacokinetic parameters are assessed in parallel. Sample sizes typically range from 8-10 animals per group.
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| ADME/Pharmacokinetics |
Pivmecillinam Hydrochloride has a molecular weight of 476.03 g/mol and a molecular formula of C21H33N3O5S·ClH. Melting point: 172-173°C. Specific rotation: D20 +219° (c = 1 in 0.1N HCl). Solubility: freely soluble in water, anhydrous ethanol, and methanol; slightly soluble in acetone. Storage: under inert gas (nitrogen or argon) at 2-8°C. As an orally active prodrug, it is absorbed and hydrolyzed to mecillinam. Bioavailability is approximately 50-60%.
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| Toxicity/Toxicokinetics |
Effects During Pregnancy and Lactation
◉ Overview of Use During Lactation Ampicillin (pimidocilin; pitavali ester of mecillin) is not marketed in the United States but is sold internationally. Limited information suggests that concentrations of ampicillin in breast milk are low and are not expected to have adverse effects on breastfed infants. Breastfed infants should be monitored for diarrhea and thrush. ◉ Effects on Breastfed Infants No published information found as of the revision date. ◉ Effects on Lactation and Breast Milk No published information found as of the revision date. Pivmecillinam Hydrochloride is generally well-tolerated at therapeutic doses. Common adverse effects may include gastrointestinal disturbances (nausea, diarrhea), skin rash, and allergic reactions. As a penicillin antibiotic, it is contraindicated in patients with a history of penicillin hypersensitivity. Standard toxicology studies have demonstrated an acceptable safety profile. It is approved for clinical use in many countries for the treatment of uncomplicated urinary tract infections, paratyphoid fever, and shigellosis. |
| References |
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| Additional Infomation |
Ampicillin valerate methyl ester is well absorbed orally but breaks down into ampicillin in the intestinal mucosa. It is effective against Gram-negative bacteria and has the same uses as ampicillin.
See also: Ampicillin ester (note moved to). Pivmecillinam Hydrochloride is also known as Melysin. Its chemical name is 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, 2,2-dimethylpropionate, monohydrochloride. It is an orally active prodrug of mecillinam, a first-in-class amidinopenicillin antibiotic. It is the first-line drug for acute cystitis and has been used for paratyphoid fever and shigellosis. It is approved for clinical use in many countries. |
| Molecular Formula |
C21H34CLN3O5S
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|---|---|
| Molecular Weight |
476.03
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| Exact Mass |
475.19
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| CAS # |
32887-03-9
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| Related CAS # |
Pivmecillinam;32886-97-8
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| PubChem CID |
115162
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| Appearance |
White to off-white solid powder
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| Density |
1.3g/cm3
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| Boiling Point |
581ºC at 760mmHg
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| Melting Point |
172-173°
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| Flash Point |
305.2ºC
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| LogP |
3.089
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
31
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| Complexity |
710
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| Defined Atom Stereocenter Count |
3
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| SMILES |
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C.Cl
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| InChi Key |
UHPXMYLONAGUPC-WKLLBTDKSA-N
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| InChi Code |
InChI=1S/C21H33N3O5S.ClH/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23;/h12,14-15,17H,6-11,13H2,1-5H3;1H/t14-,15+,17-;/m1./s1
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| Chemical Name |
2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrochloride
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| Synonyms |
Pivmecillinam (hydrochloride); Melysin; Pivmecillinam Hydrochloride
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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) |
H2O : ~100 mg/mL (~210.07 mM)
DMSO : ≥ 34 mg/mL (~71.42 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: 12.5 mg/mL (26.26 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1007 mL | 10.5035 mL | 21.0071 mL | |
| 5 mM | 0.4201 mL | 2.1007 mL | 4.2014 mL | |
| 10 mM | 0.2101 mL | 1.0504 mL | 2.1007 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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