Pivmecillinam Hydrochloride

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Cat Number

API0232252

CAS Number

32887-03-9

For research use only. We do not supply to patients.

For pharmaceutical-grade products or other inquiries, please contact our experts.

Product Detail Description Scientific Support Customer Q&A

CAS Number

32887-03-9

EINECS

251-278-7

Storage

Store at 2-8°C

Synonyms

Melysin; amdinocillin pivoxil hydrochloride; pivmecilinamo clorhidrato; DTXSID1045453; 48FX7N21H2; PIVYA

Molecular Formula

C21H34ClN3O5S

Molecular Weight

476

Smiles

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C.Cl

Appearance

White or almost white crystalline powder

Melting Point

156°C

Boiling Point

551°C

Relative Density

1.44±0.1 (Predicted)

General Description

Pivmecillinam hydrochloride is a prodrug of mecillinam, a penicillin-like antibiotic with a amidino group, belonging to the class of amidinopenicillins. Its chemical structure is (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid pivaloyloxymethyl ester hydrochloride.

Mechanism of Action

Pivmecillinam is a prodrug that is hydrolyzed to mecillinam, which acts by binding to penicillin-binding protein 2 (PBP2) in gram-negative bacteria, inhibiting bacterial cell wall synthesis. This leads to the formation of round cells and cell death. The drug is primarily active against gram-negative organisms, including Escherichia coli, Salmonella, and Shigella.

Application

Pivmecillinam is indicated for the treatment of acute uncomplicated urinary tract infections (UTIs) caused by susceptible organisms, particularly E. coli. It is also used for the treatment of enteric infections (such as salmonellosis and shigellosis). The drug is effective in reducing the symptoms of dysuria and frequency, and is considered a first-line agent for UTIs in many European countries.

In a single‑arm trial, 53 patients with E. coli bacteremic urinary tract infection received 3 days of parenteral antibiotics followed by oral pivmecillinam 400 mg QID for 1 week. The primary composite endpoint (afebrile, no retreatment, improved self‑reported health) was achieved in 88% (44/50) at test‑of‑cure. CRP level strongly predicted outcome. Pivmecillinam appears suitable as step‑down therapy, warranting randomized controlled trials against standard care.

Fig. 1 Patient course from admission to study completion. (Hansen BÅ, et al., 2022)

References

Hansen BÅ, et al. The efficacy of pivmecillinam in oral step-down treatment in hospitalised patients with E. coli bacteremic urinary tract infection; a single-arm, uncontrolled treatment study. BMC Infect Dis. 2022;22(1):478.

Does Pivmecillinam Hydrochloride require refrigerated storage as a penicillin prodrug?

Yes, it must be stored at 2-8°C. At room temperature, rapid hydrolysis of the pivoxil ester and beta-lactam ring occurs, reducing antibacterial activity.

Is Pivmecillinam Hydrochloride extremely sensitive to moisture, and how is this prevented?

Yes, it is highly hygroscopic. Our packaging includes moisture-barrier foil bags with desiccant. Open only in low-humidity environments.

What is the stability of Pivmecillinam Hydrochloride in tablet formulations?

Tablets are stable when formulated with moisture-protective packaging (e.g., blisters).

How is the impurity mecillinam (the active moiety and hydrolysis product) monitored?

This primary degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within pharmacopoeial limits.