| Identification | Back Directory | [Name]
(pivaloyloxy)methyl [2S-[2alpha,5alpha,6beta(S*)]]-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate monohydrochloride | [CAS]
26309-95-5 | [Synonyms]
Alphacilina
Alphacillin
PIVAMPICILLINHYDROCHLORIDE
AMpicillin PivaloxyoxyMethyl Ester Hydrochloride
(pivaloyloxy)methyl [2S-[2alpha,5alpha,6beta(S*)]]-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate monohydrochloride
(2S,5R,6R)-6-[[(2R)-2-AMino-2-phenylacetyl]aMino]-3,3-diMethyl-7-oxo-4-thia-
1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (2,2-DiMethyl-1-oxopropoxy)Methyl Ester Hydrochloride | [EINECS(EC#)]
247-604-2 | [Molecular Formula]
C22H30ClN3O6S | [MOL File]
26309-95-5.mol | [Molecular Weight]
500.008 |
| Questions And Answer | Back Directory | [Description]
Pivampicillin Hydrochloride is a pivaloyloxymethyl ester of ampicillin. It is a prodrug, which is thought to enhance the oral bioavailability of ampicillin because of its greater lipophilicity compared to that of ampicillin. | [Mechanism of action]
Pivampicillin hydrochloride is not due to the drug itself but to pivalate, which is mostly removed from the body by forming a conjugate with carnitine. Although short-term use of these drugs can cause a marked decrease in blood levels of carnitine,it is unlikely to be of clinical significance;long-term use, however, is not recommended. | [Acute toxicity]
Oral-rat LD50: 5000 mg/kg; Oral-mouse LD50: 3340 mg/kg. |
| Chemical Properties | Back Directory | [Melting point ]
155-156° (decomp) | [alpha ]
D20 +196° (c = 1 in water) | [pka]
pKa ~7.0(at 25℃) | [Contact allergens]
Pivampicillin is a prodrug of ampicillin. It caused sensitization
in 56 workers at a penicillin factory. Pivampicillin
and pivmecillinam were responsible for contact dermatitis
in pharmaceutical production workers. Ampicillin,
mecillinam or amdinocillin, penicillin V and penicillin
G were also implicated in cross-reactions. |
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Energy Chemical
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