Pivmecillinam is a semisynthetic β-lactam antibacterial active pharmaceutical ingredient (API) belonging to the penicillin family. It is an orally active prodrug that is converted in the body to mecillinam, an antibacterial agent with selective activity against bacterial cell-wall synthesis. Pivmecillinam is particularly associated with the treatment of urinary tract infections caused by susceptible bacteria.
For pharmaceutical use, Pivmecillinam is supplied as Pivmecillinam Hydrochloride, the hydrochloride salt of the active substance. The compound has the molecular formula C₂₁H₃₃N₃O₅S·HCl and molecular weight 476.03 g/mol. Its CAS Number is 32887-03-9.
Pivmecillinam Hydrochloride is described in the Japanese Pharmacopoeia as a white to yellowish-white crystalline powder. It is very soluble in methanol and acetic acid (100), freely soluble in water and ethanol (99.5), and soluble in acetonitrile.
The API contains not less than 630 µg and not more than 710 µg of mecillinam potency per mg, calculated on the anhydrous basis, according to JP XVII. The potency is expressed in terms of mecillinam.
Pivmecillinam is used as an antibacterial pharmaceutical ingredient, particularly in oral formulations for urinary tract infections. Current UK product information identifies pivmecillinam hydrochloride 200 mg as the active substance in film-coated tablets.
Following oral administration, Pivmecillinam is hydrolysed to mecillinam, which exerts antibacterial activity by interfering with bacterial cell-wall synthesis.
Pivmecillinam Hydrochloride is subject to comprehensive pharmaceutical quality testing. The JP monograph includes IR identification, chloride identification, optical rotation, heavy metals, arsenic, related substances, water and liquid-chromatographic assay.
The BP monograph additionally specifies controls for N,N-dimethylaniline, water, sulfated ash and related substances. BP sets limits of NMT 1.5% for any individual impurity, NMT 3.0% for total impurities, NMT 0.1% for the disregard limit, NMT 20 ppm for N,N-dimethylaniline, NMT 0.5% water, and NMT 0.1% sulfated ash.
Pivmecillinam Hydrochloride API intended for pharmaceutical manufacturing should be produced under appropriate pharmaceutical quality systems with controlled raw materials, validated manufacturing processes and suitable analytical controls.
Quality testing can include IR identification, chloride identification, optical rotation, potency/assay, related substances, water, sulfated ash, heavy metals and residual process-related impurities, according to the applicable pharmacopoeial or approved product specification.
For commercial pharmaceutical requirements, customers can request the applicable Certificate of Analysis (CoA), product specification, technical documentation, regulatory documentation and quality information for Pivmecillinam Hydrochloride API.
| Parameter | Specification |
|---|---|
| Appearance | white to off-white crystalline powder |
| Identification | IR & HPLC compliant |
| Assay (HPLC) | 98.0% – 102.0% |
| Residue on Ignition | NMT 0.1% |
| Heavy Metals | NMT 20 ppm |
| Individual Impurity | NMT 1.5% each |
| Total Impurities | NMT 3.0% |
| Specific Rotation | +200° to +220° |