Okonogi K, Sugiura A, Kuno M, Ono H, Harada S, Higashide E
J Antibiot (Tokyo). 1985 Nov;38(11):1555-63. doi: 10.7164/antibiotics.38.1555.
Cephem and nocardicin-type monocyclic beta-lactam antibiotics with a formylamino substituent were highly resistant to hydrolysis by both penicillinases and cephalosporinases. Among antibiotics with a methoxy substituent, an N-sulfonated monocyclic beta-lactam antibiotic, sulfazecin was resistant to beta-lactamases, but cephem antibiotics were sensitive to the cephalosporinase of Enterobacter cloacae. The resistance of the antibiotics to the beta-lactamases depended primarily on the presence of the substituent, but affinity for the beta-lactamases was affected not only by the substituent but also by the presence of other side chains. Formylamino compounds and sulfazecin were as good inducers of beta-lactamases as semisynthetic 7-methoxycephalosporins, but naturally occurring 7-methoxycephalosporins were poor inducers. The inducer activities of the antibiotics were not necessarily related to their beta-lactamase stabilities. The stabilities of the compounds to the beta-lactamases were well reflected in their antibacterial activities against beta-lactamase producing bacteria.
具有甲酰氨基取代基的头孢烯类和诺卡菌素型单环β-内酰胺抗生素对青霉素酶和头孢菌素酶的水解具有高度抗性。在具有甲氧基取代基的抗生素中，一种N-磺化单环β-内酰胺抗生素，硫霉素对β-内酰胺酶具有抗性，但头孢烯类抗生素对阴沟肠杆菌的头孢菌素酶敏感。抗生素对β-内酰胺酶的抗性主要取决于取代基的存在，但对β-内酰胺酶的亲和力不仅受取代基影响，还受其他侧链存在的影响。甲酰氨基化合物和硫霉素与半合成7-甲氧基头孢菌素一样，都是很好的β-内酰胺酶诱导剂，但天然存在的7-甲氧基头孢菌素是较差的诱导剂。抗生素的诱导活性不一定与其β-内酰胺酶稳定性相关。这些化合物对β-内酰胺酶的稳定性在它们对产β-内酰胺酶细菌的抗菌活性中得到了很好的体现。
