四環素類(Tetracyclines)是由鏈霉菌產生或經半合成精制的一類堿性廣譜抗生素。它們廣泛應用于革蘭氏陽性及陰性細菌,如化膿性和草綠色鏈球菌、肺炎球菌、腸球菌、金黃色葡萄球菌、梭狀芽孢桿菌、炭疽桿菌、大腸桿菌、痢疾桿菌、沙門菌、鼠疫桿菌、布魯氏菌、腦膜炎球菌、淋病奈瑟菌、支原體、衣原體、螺旋體、立克次體等的治療。然而,由于長期廣泛使用,20世紀60年代后細菌對抗生素產生了嚴重的耐藥性,從而限制了這類藥物的應用。
當前四環素類主要用于治療立克次體、衣原體和支原體感染,如回歸熱螺旋體感染以及布魯氏菌病等引起的呼吸道、膽道、尿道、皮膚軟組織等部位的感染。值得注意的是,四環素類之間存在密切的交叉耐藥性。
這類藥物常見的不良反應包括:
肝腎損害:在正常劑量下通常無不良反應;然而大劑量長期使用可能導致肝臟黃疸和轉氨酶升高,甚至肝昏迷致死;同時可導致血尿素氮和肌酐值升高等腎臟問題。
胃腸道不適:可能出現惡心、嘔吐、腹痛及腹瀉。患者應多飲水,并采取坐姿服藥以減少食管刺激和潰瘍的風險。
牙齒與骨骼發育受影響:藥物可能沉積于牙齒和骨骼中,導致牙齒變色并影響兒童的骨骼發育;此外,孕婦、哺乳期婦女及8歲以下兒童禁用此藥物,因為它們容易透過胎盤和進入乳汁。
菌群失調:可能導致維生素缺乏或引起由白色念珠菌和耐藥菌引起的二重感染。
皮膚過敏反應:可能出現皮疹、蕁麻疹等皮膚過敏癥狀及光感性皮炎、哮喘等;靜脈滴注時需稀釋并緩慢給藥,避免局部刺激。這類藥物不能肌肉注射。
吸收與相互作用:四環素類不宜與抗酸藥、鈣鹽、鐵鹽、鎂鹽以及含鋁或鉍的藥物同服,以免影響其吸收(包括牛奶);同時它們可能干擾腸道菌群平衡,影響避孕藥的效果。
| 中文名稱 | 英文名稱 | CAS號 | 化學式 |
|---|---|---|---|
| 金霉素 | (4S,4aS,6S,8aR)-6-[(1S)-7-chloro-4-hydroxy-1-methyl-3-oxo-2-benzofuran-1-yl]-4-(dimethylamino)-1,8a-dihydroxy-3,8-dioxo-4a,5,6,7-tetrahydro-4H-naphthalene-2-carboxamide | 514-53-4 | C22H23ClN2O8 |
| 金霉素 | chlortetracycline | 57-62-5 | C22H23ClN2O8 |
| 載脂蛋白-土霉素 | β-apo-oxytetracycline | 18751-99-0 | C22H22N2O8 |
| 賴甲環素 | lymecycline | 992-21-2 | C29H38N4O10 |
| 米諾環素 | Minocycline | 10118-90-8 | C23H27N3O7 |
| 鹽酸金霉素 | chlortetracycline hydrochloride | 64-72-2 | C22H23ClN2O8*ClH |
| 鹽酸米諾環素 | minocycline Hydrochloride | 13614-98-7 | C23H27N3O7*ClH |
| 鹽酸甲烯土霉素 | Metacycline hydrochloride | 3963-95-9 | C22H22N2O8*ClH |
| 鹽酸土霉素 | oxytetracycline hydrochloride | 2058-46-0 | C22H24N2O9*ClH |
| 鹽酸四環素 | tetracycline hydrochloride | 64-75-5 | C22H24N2O8*ClH |
| 甲烯土霉素 | methacycline | 914-00-1 | C22H22N2O8 |
| 氯甲烯土霉素 | meclocycline | 2013-58-3 | C22H21ClN2O8 |
| 替加環素 | Tigecycline | 220620-09-7 | C29H39N5O8 |
| 強力霉素 | doxycycline | 564-25-0 | C22H24N2O8 |
| 差向四環素鹽酸鹽 | 4-epi-tetracycline hydrochloride | 23313-80-6 | C22H24N2O8*ClH |
| 多西環素鈣 | dicalcium;(4S,4aR,5S,5aR,6R,12aR)-2-carbamoyl-4-(dimethylamino)-10-hydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-1,5,11,12a-tetrolate | 94088-85-4 | C22H20Ca2N2O8 |
| 地美環素鹽酸鹽 | demeclocycline hydrochloride | 64-73-3 | C21H21ClN2O8*ClH |
| 土霉素 | Oxytetracycline | 79-57-2 | C22H24N2O9 |
| 四環素 | tetracycline | 60-54-8 | C22H24N2O8 |
| 4-環氧氯丙烷強力霉素 | doxycyline | 6543-77-7 | C22H24N2O8 |
| 4-差向土霉素 | (4R,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide | 14206-58-7 | C22H24N2O9 |
| —— | Oxytetracyclin | 35259-39-3 | C22H24N2O9 |
| —— | 4-epi-Chlortetracycline Hydrochloride (>90% by HPLC) | 101342-45-4 | C22H24Cl2N2O8 |
| —— | oxytetracycline hydrochloride | 2058-46-0 | C22H24N2O9*ClH |
| —— | minocycline hydrochloride | 13614-98-7 | C23H27N3O7*ClH |
| —— | oxytetracycline hydrochloride | 2058-46-0 | C22H24N2O9*ClH |
| —— | (4R,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide,hydrochloride | 64-75-5 | C22H24N2O8*ClH |
| —— | (4aS)-4c-dimethylamino-3,6c,10,12,12a-pentahydroxy-6t-methyl-1,11-dioxo-(4ar,5at,12ac)-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide | 60-54-8 | C22H24N2O8 |
| —— | (4aS)-4c-dimethylamino-3,6c,10,12,12a-pentahydroxy-6t-methyl-1,11-dioxo-(4ar,5at,12ac)-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide | 60-54-8 | C22H24N2O8 |
| —— | (4aS)-4c-dimethylamino-3,6c,10,12,12a-pentahydroxy-6t-methyl-1,11-dioxo-(4ar,5at,12ac)-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide | 60-54-8 | C22H24N2O8 |
| —— | doxycycline hyclate | 24390-14-5 | 0C2H6O*C22H24N2O8*ClH |
| —— | Dicalcium;(4S,4aR,5S,5aR,6R,12aR)-2-carbamoyl-4-(dimethylamino)-12a-hydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-1,5,10,11-tetrolate | 94088-85-4 | C22H20Ca2N2O8 |
| —— | 4-epi-anhydrotetracycline hydrochloride | 4465-65-0 | C22H22N2O7*ClH |
| —— | Isochlortetracycline | 514-53-4 | C22H23ClN2O8 |
| —— | Meclocycline | 2013-58-3 | C22H21ClN2O8 |
| —— | doxycycline | 7164-70-7 | C22H24N2O8 |
| —— | 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, hydrochloride | 64-72-2 | C22H24Cl2N2O8 |
| —— | Chlorotetracycline | 57-62-5 | C22H23ClN2O8 |
| —— | 4-Epidoxycycline | 6543-77-7 | C22H24N2O8 |
| —— | 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4R,4aR,5S,5aR,6S,12aS)- | 14206-58-7 | C22H24N2O9 |
| —— | Calcium oxytetracycline | 7179-50-2 | C22H22CaN2O9 |
| —— | Meclosorb | 2013-58-3 | C22H21ClN2O8 |
| —— | Lymecycline | 992-21-2 | C29H38N4O10 |
| —— | 4-EPIOXYTETRACYCLINE | 79-57-2 | C22H24N2O9 |
| —— | (4S,6S,12aR)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide | 57-62-5 | C22H23ClN2O8 |
| —— | 4-EPICHLORTETRACYCLINE HYDROCHLORIDE | 64-72-2 | C22H23ClN2O8*ClH |
| —— | Tetracyclin*HCl | 64-75-5 | C22H24N2O8*ClH |
| —— | doxycyline | 564-25-0 | C22H24N2O8 |
| —— | tetracycline | 60-54-8 | C22H24N2O8 |
| —— | methacycline | 914-00-1 | C22H22N2O8 |