Hetacillin Potassium

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Cat Number

API0232093

CAS Number

5321-32-4

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Product Detail Description Customer Q&A

CAS Number

5321-32-4

EINECS

226-182-3

Storage

Store at 2-8°C

Synonyms

Natacillin; Potassium hetacillin; Versapen-k; Versatrex; Hetacin-K; UNII-95PFX5932Y; 95PFX5932Y; Hetacillin potassium salt

Molecular Formula

C19H22KN3O4S

Molecular Weight

427.6

Smiles

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N3C(=O)[C@H](NC3(C)C)C4=CC=CC=C4)C(=O)[O-])C.[K+]

Appearance

White solid

General Description

Hetacillin potassium is a semisynthetic, beta-lactam antibiotic prodrug belonging to the aminopenicillin family. It has no inherent antibacterial activity itself, requiring conversion in the body to exert its effect.

Mechanism of Action

Hetacillin acts as a molecular prodrug that rapidly hydrolyzes in the human body, splitting off an acetone molecule to liberate ampicillin. The released ampicillin then binds to penicillin-binding proteins (PBPs) in susceptible bacteria, inhibiting the final transpeptidation step of peptidoglycan synthesis and leading to bacterial cell death.

Application

Hetacillin is used for the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. As a prodrug of ampicillin, it shares the same spectrum of activity as other aminopenicillins and has been used for respiratory, urinary, and skin infections. The prodrug approach was intended to improve absorption and stability.

Does Hetacillin Potassium require refrigerated storage as a penicillin derivative?

Yes, it must be stored at 2-8°C. The beta-lactam ring and the hetacillin structure are highly susceptible to hydrolysis at room temperature.

Is Hetacillin Potassium sensitive to moisture, and how is this prevented?

Yes, it is hygroscopic and rapidly hydrolyzes to ampicillin. Our packaging includes moisture-barrier foil bags with desiccant; open only in low-humidity environments.

What is the stability of Hetacillin Potassium after reconstitution for injection?

Reconstituted solutions degrade rapidly (within 24 hours under refrigeration).

How is the impurity ampicillin (the primary hydrolysis product) monitored?

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