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
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。
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:
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
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。
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。
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。
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。
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 |
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—— | 7-[[(2Z)-2-(2-aminothiazol-4-yl)-2-(carboxymethyloxyimino)acetyl]amino]-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 79350-37-1 | C16H15N5O7S2 |
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—— | Pharmakon1600-01505249 | 37321-09-8 | C21H41N5O11 |
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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 | 122841-10-5 | C19H22N8O6S2 |
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—— | 7-[{2-(2-amino-4-thiazolyl)-2-methoxyiminoacetyl}amino]-3-[(1-methyl-tetrazol-5-yl)-thiomethyl]-ceph-3-eme-4-carboxylic acid | 65085-01-0 | C16H17N9O5S3 |
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—— | Cefditoren sodium | 104146-53-4 | C19H18N6NaO5S3+ |
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—— | Tylosin, 4A-O-de(2,6-dideoxy-3-C-methyl-alpha-L-ribo-hexopyranosyl)-20-deoxo-20-[(3R,5S)-3,5-dimethyl-1-piperidinyl]- | 108050-54-0 | C46H80N2O13 |
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—— | (6S,7S)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | 91832-40-5 | C14H13N5O5S2 |
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—— | (6R,7R)-7-[[(2E)-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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—— | Pharmakon1600-01503869 | 70797-11-4 | C25H24N8O7S2 |
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—— | 2,2-dimethylpropanoyloxymethyl (6S,7S)-7-[[(2E)-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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—— | Disodium 7-{2-[(2-amino-2-carboxylatoethyl)sulfanyl]acetamido}-7-methoxy-3-{[(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 92636-39-0 | C16H19N7Na2O7S3 |
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—— | HR 111V sulfate;HR-111V sulfate;HR111V sulfate | 84957-30-2 | C23H26N6O9S3 |
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—— | Cefodizime (sodium) | 86329-79-5 | C20H18N6Na2O7S4 |
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—— | sodium 7-[[2-(2-azanyl-1,3-thiazol-4-yl)-2-methoxyimino-ethanoyl]amino]-3-[[2-methyl-5,6-bis(oxidanylidene)-1H-1,2,4-triazin-3-yl]sulfanylmethyl]-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 74578-69-1 | C18H17N8NaO7S3 |
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—— | Sodium;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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—— | Pharmakon1600-01502420 | 123171-59-5 | C19H25ClN6O5S2 |
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—— | Pharmakon1600-01502041 | 42540-40-9 | C19H18N6NaO6S2+ |
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—— | (6S,7S)-7-[[(2E)-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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—— | 64953-12-4 | C20H20N6NaO9S |
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—— | sodium;7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | 104376-79-6 | C18H17N8NaO7S3 |
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—— | (7R)-7-[[(2E)-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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—— | ceftazidime pentahydrate | 78439-06-2 | C22H22N6O7S2*5H2O |
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—— | Cefminox sodium salt | 92636-39-0 | C16H19N7Na2O7S3 |
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—— | Pharmakon1600-01505782 | 72558-82-8 | C22H22N6O7S2 |
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—— | (6S,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-carboxylate;sulfuric acid | 98753-19-6 | C22H24N6O9S3 |
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—— | sodium;(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-carboxylate | 68401-82-1 | C13H12N5NaO5S2 |
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—— | (4R,5S,6S,7R,9R,11Z,13Z,15R,16R)-6-[(2R,3R,4S,5S,6R)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-7-[2-[(3R,5S)-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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—— | Ceftriaxone Sodium | 74578-69-1 | C36H46N16Na4O21S6 |
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—— | 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[2-(2-amino-4-thiazolyl)-4-carboxy-1-oxo-2-butenyl]amino]-8-oxo-,hydrate, [6R-[6a,7b(Z)]]- | 118081-34-8 | C15H16N4O7S2 |
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—— | 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 |
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—— | 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 |
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—— | (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 |
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—— | 7-aminoceph-3-em-4-carboxylic acid ester | 36923-17-8 | C7H8N2O3S |
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—— | (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 |
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—— | (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 |
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—— | (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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