头孢菌素类药
头孢菌素类抗生素是以冠状头孢菌培养得到的天然头孢菌素C为原料，经半合成改造其侧链而获得的一类广谱半合成强杀菌抗生素，属于β-内酰胺类抗生素。它们也被称为“先锋霉素类”。这类抗生素按发明年代和抗菌能力分为第一代、第二代及第三代。
一、概述
头孢菌素家族包括先锋霉素Ⅰ至Ⅷ、头孢硫咪、头孢羟唑、头孢羟氨苄、头孢去甲噻肟以及头霉素的衍生物和羟羧氧酰胺菌素等。它们广泛用于治疗各种细菌感染。
二、抗菌谱
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第一代头孢菌素主要针对β-溶血链球菌及其他链球菌、葡萄球菌（包括产酶株）、流感嗜血杆菌、大肠杆菌、克雷白杆菌、沙门氏菌和志贺氏菌等。这类抗生素对革兰氏阴性菌的β-内酰胺酶抵抗力较弱，导致这些细菌更容易对其产生耐药性。
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第二代头孢菌素在对抗革兰氏阳性菌方面与第一代相近或略低，但在对抗革兰氏阴性菌时表现更为优异。具体来说：
- 抗酶能力强：一些革兰氏阴性菌如大肠杆菌易对第一代头孢耐药，但第二代常对其有效。
- 广泛的抗菌谱：与第一代相比，第二代的抗菌谱有所扩大，能对抗奈瑟菌、部分吲哚阳性变形杆菌、部分枸橼酸杆菌和某些肠杆菌等。
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第三代头孢菌素在对抗革兰氏阳性菌方面普遍低于第一代，但在对抗革兰氏阴性菌时表现更为优秀。此外，其抗菌谱更广，耐酶能力更强。
三、毒副作用
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过敏反应：可能引起皮疹、哮喘、血管神经性水肿及过敏性休克等，头孢菌素的过敏性休克与青霉素类似，两者间存在不同程度的交叉过敏现象。约有10%至30%对青霉素过敏者也可能对头孢菌素过敏。
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胃肠道反应和菌群失调：可能导致恶心、呕吐及食欲不振等症状。第二代和第三代头孢菌素会强力抑制肠道菌群，引起菌群失调，并可能引发二重感染。
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肝毒性：大多数头孢菌素在大剂量使用时会导致转氨酶、碱性磷酸酶、胆红素等指标升高。
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肾毒性：由于绝大多数头孢菌素通过肾脏排泄，可能会导致血尿素氮升高、少尿及蛋白尿等症状。与速尿或氨基糖苷类抗生素联合使用可能加剧肾损害。
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凝血功能障碍：头孢菌素会抑制肠道菌群产生的维生素K，从而潜在地引发出血症状。
| 中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
|---|---|---|---|---|
| —— | Disodium;7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-6-oxido-5-oxo-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 74578-69-1 | C18H16N8Na2O7S3 |
|
| —— | 7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrogen sulfate | 98753-19-6 | C22H24N6O9S3 |
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| —— | 2-[[1-(2-Amino-1,3-thiazol-4-yl)-2-[[2-carboxy-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl]amino]-2-oxoethylidene]amino]oxy-2-methylpropanoate;pentahydrate | 78439-06-2 | C22H32N6O12S2 |
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| —— | 7-Amino-3-(methoxymethyl)-3-cephem-4-carboxylic acid | 24701-69-7 | C9H12N2O4S |
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| —— | 7β-[2-(2-amino-4-thiazoIyl)-2-(Z-hydroxyimino)acetamido]-3-vinyl-3-cephem-4-carboxylic acid | 91832-40-5 | C14H13N5O5S2 |
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| —— | diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 36923-21-4 | C20H18N2O3S |
|
| —— | (6<i>R</i>)-7<i>t</i>-[2-(2-amino-thiazol-4-yl)-2-(<i>Z</i>)-methoxyimino-acetylamino]-8-oxo-3-(1-methyl-1<i>H</i>-tetrazol-5-ylsulfanylmethyl)-(6<i>r</i><i>H</i>)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 65085-01-0 | C16H17N9O5S3 |
|
| —— | 7-aminoceph-3-em-4-carboxylic acid ester | 36923-17-8 | C7H8N2O3S |
|
| —— | (6S,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 68401-81-0 | C13H13N5O5S2 |
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| —— | 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)- | 63527-52-6 | C16H17N5O7S2 |
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| —— | 7-[[(2E)-2-(2-Amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;sulfuric acid | 98753-19-6 | C22H24N6O9S3 |
|
| —— | (6S,7R)-7-((R)-2-Amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((E)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 92665-29-7 | C18H19N3O5S |
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| —— | (R)-cefuroxime 1-acetoxyethyl ester | 64544-07-6 | C20H22N4O10S |
|
| —— | (Z)-tert-Butyl 2-(((1-(2-aminothiazol-4-yl)-2-(benzo[d]thiazol-2-ylthio)-2-oxoethylidene)amino)oxy)-2-methylpropanoate | 89604-92-2 | C20H22N4O4S3 |
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| —— | 2-(2-(((Benzyloxy)carbonyl)amino)thiazol-4-yl)-5-((3-methylbut-2-en-1-yl)oxy)-5-oxopent-2-enoic acid | 102199-30-4 | C21H22N2O6S |
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| —— | 2-Pentenedioic acid, 2-[2-[[(phenylmethoxy)carbonyl]amino]-4-thiazolyl]-, 5-(3-methyl-2-buten-1-yl) ester | 115065-79-7 | C21H21N2O6S- |
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| —— | 2-benzothiazolyl 2-(2-aminothiazol-4-yl)-2-<<1-(tert-butoxycarbonyl)-1-methylethoxy>imino>thioacetate | 89604-92-2 | C20H22N4O4S3 |
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| —— | (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(furan-2-carbonylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 80370-57-6 | C19H17N5O7S3 |
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| —— | (4R,5S,6S,7R,9R,11E,13Z,15R,16S)-6-[(2R,3R,4S,5S,6R)-4-(Dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-7-[2-[(3S,5R)-3,5-dimethylpiperidin-1-yl]ethyl]-16-ethyl-4-hydroxy-15-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-5,9,13-trimethyl-1-oxacyclohexadeca-11,13-diene-2,10-dione | 108050-54-0 | C46H80N2O13 |
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| —— | Pharmakon1600-01505112 | 108050-54-0 | C46H80N2O13 |
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| —— | 2,2-dimethylpropanoyloxymethyl 7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 117467-28-4 | C25H28N6O7S3 |
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| —— | 1-acetyloxyethyl (6S,7R)-3-(carbamoyloxymethyl)-7-[[(2E)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 64544-07-6 | C20H22N4O10S |
|
| —— | (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 118443-89-3 | C23H25N6O5S2+ |
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| —— | (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 84957-29-9 | C22H23N6O5S2+ |
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| —— | Cefatiolene | 77360-52-2 | C20H18N8O8S3 |
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| —— | sodium (6R,7R)-3-[(carbamoyloxy)methyl]-7-[(2E)-2-(furan-2-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 56238-63-2 | C16H15N4NaO8S |
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| —— | 3-Desethenyl-3-methyl Cefixime (Cefixime EP Impurity E) | 72701-01-0 | C15H15N5O7S2 |
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| —— | (6R,7R)-7-({(2Z)-2-(2-Amino-1,3-thiazol-4-yl)-2-[(2-ethoxy-2-oxoethoxy)imino]acetyl}amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 79368-95-9 | C18H19N5O7S2 |
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| —— | (6R,7R)-3-[[3-amino-2-(2-hydroxyethyl)pyrazol-1-ium-1-yl]methyl]-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;sulfuric acid | 122841-12-7 | C19H24N8O10S3 |
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| —— | 2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 82547-81-7 | C22H27N9O7S2 |
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| —— | sodium;3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 56238-63-2 | C16H15N4NaO8S |
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| —— | desfuroylceftiofur | 120882-22-6 | C14H15N5O5S3 |
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| —— | 7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 69739-16-8 | C20H20N6O7S4 |
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| —— | 7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 88040-23-7 | C19H24N6O5S2 |
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| —— | 7-[[(Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 97519-39-6 | C15H14N4O6S2 |
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| —— | (6R,7R)-7-[(2-amino-2-cyclohexa-1,4-dien-1-ylacetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;dihydrate | 31828-50-9 | C16H23N3O6S |
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| —— | 7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-carboxymethoxyimino]-acetylamino}-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 72701-01-0 | C15H15N5O7S2 |
|
| —— | (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrochloride | 75738-58-8 | C32H35ClN18O10S6 |
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| —— | (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(6,7-dihydro-5H-cyclopenta[b]pyridin-1-ium-1-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrogen sulfate | 98753-19-6 | C22H24N6O9S3 |
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| —— | sodium;(6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 68401-82-1 | C13H12N5NaO5S2 |
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| —— | (6S,7S)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 72558-82-8 | C22H22N6O7S2 |
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| —— | sodium;(6S,7S)-3-(carbamoyloxymethyl)-7-[[(2Z)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 56238-63-2 | C16H15N4NaO8S |
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| —— | Cefaloject | 24356-60-3 | C17H17N3NaO6S2+ |
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| —— | benzhydryl (6S)-7-amino-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride | 79349-67-0 | C22H21ClN2O3S |
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| —— | Ceftobiprole medocaril | 376653-43-9 | C26H26N8O11S2 |
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| —— | cefaclor | 53994-73-3 | C15H14ClN3O4S |
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| —— | Ceftobiprole medocaril sodium;BAL5788;Ro 65-5788 | 376653-43-9 | C26H26N8O11S2 |
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| —— | cefradine | 31828-50-9 | C16H19N3O4S*0H2O |
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| —— | latamoxef | 64952-97-2 | C20H20N6O9S |
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| —— | (6<i>R</i>)-7<i>t</i>-[(Ξ)-2-carboxy-2-(4-hydroxy-phenyl)-acetylamino]-7<i>c</i>-methoxy-3-(1-methyl-1<i>H</i>-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6<i>r</i><i>H</i>)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 64952-97-2 | C20H20N6O9S |
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