57-62-5

• 常用中文名：金霉素
• 常用英文名：Chlortetracycline
• CAS号：57-62-5
• 分子式：C₂₂H₂₃ClN₂O₈
• 分子量：478.880
• 相关类别： 原料药 抗生素类药物 四环素类药
• 发布时间：2018-08-25 00:19:23
• 更新时间：2024-01-02 16:39:37
• Chlortetracycline (7-Chlorotetracycline) 是一种特异性的有效钙离子载体抗生素, 抑制氨酰 tRNA 结合到核糖体。

名称

• 中文名: 氯四环素
• 英文名: chlortetracycline
• 中文别名: 金霉素
• 英文别名: Aurofac; auromycin; Aurofac 10; Duomycin; Orospray; Centraureo; EINECS 200-341-7; Chrysomykine; 2-Naphthacenecarboximidic acid, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, (4S,4aS,5aS,6S,12aS)-; Uromycin; Acronize; Biomycin; (4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboximidic acid; Flamycin; Chlorotetracycline; 7-Chlorotetracycline; Biovetin; (4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide; Chlortetracycline; MFCD00864876; Biomitsin; (4S,4aS,5aS,6S,12aS)-7-Chloro-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-2-tetracenecarboxamide; AUREOCINA; 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-, (4S,4aS,5aS,6S,12aS)-; Aureomycin

物化性质

• 密度: 1.7±0.1 g/cm3
• 沸点: 821.1±65.0 °C at 760 mmHg
• 熔点: 168.5ºC
• 分子式: C₂₂H₂₃ClN₂O₈
• 分子量: 478.880
• 闪点: 450.4±34.3 °C
• 精确质量: 478.114288
• PSA: 181.62000
• LogP: -0.53
• 外观性状: 金色黄色晶体粉末
• 蒸汽压: 0.0±3.1 mmHg at 25°C
• 折射率: 1.745
• 储存条件: 2-8°C
• 稳定性:

  金霉素又称氯四环素，其盐酸盐溶于水，游离碱基特别是钙盐难溶于水。为四环素类抗生素，是在放线菌的培养液中发现的抗菌物质。可以杀 灭立克次体、支原体、衣原体、非典型分枝杆菌以及螺旋体等，适用于敏感金黄色葡萄球菌、化脓性链球菌、肺炎链球菌等革兰阳性菌及流感 嗜血杆菌等敏感革兰阴性菌所致浅表眼部感染的治疗，但同时也可用于其他部位敏感菌感染的治疗。

  金霉素眼膏适应症及用法:结膜炎：俗称红眼病，可先用温水清除分泌物后，涂少许本品，闭眼休息片刻，让药物充分发挥作用，1天3次，晚上临睡前再涂1次。; 麦粒肿：俗称偷针眼，发病后切勿用手挤压，以避免引起其他并发症。尚未形成脓肿前，热敷疗效很好。用热毛巾热敷20分钟，接着涂金霉素 眼膏，闭眼休息片刻。一天3次。; 口角糜烂：口角出现糜烂时，可服用维生素B2，同时用棉签蘸温开水清洗伤口，揩干，再抹上本品，就可加快愈合。一般三天即可好转。; 疖肿：当鼻黏膜有小疖胀痛时，可用药棉蘸取金霉素眼膏涂于鼻腔处，并轻压鼻子，促使疖肿吸收，加速痊愈，其他部位的疖肿也可同样使用 。; 口角及手足干裂：先用热水洗净擦干，再涂少许本品，手足部分需用胶布固定，可加快伤口愈合。

  金黄色结晶性粉末，无臭，味苦。熔点168-169℃（分解）。极微溶于水，溶于盐溶液。盐酸盐微溶于甲醇、水、乙醇，不溶于丙酮、乙醚、氯仿。在空气中稳定，遇光颜色渐暗。

• 分子结构:

  1、 摩尔折射率：113.91

  2、 摩尔体积（cm³/mol）：281.5

  3、 等张比容（90.2K）：893.2

  4、 表面张力（dyne/cm）：101.9

  5、 极化率（10^-24cm³）：45.15

• 更多:

  一、物性数据

  1. 性状：结晶性粉末，无臭，味苦。

  2. 密度（g/mL,25/4℃）：168～169

  3. 相对蒸汽密度（g/mL,空气=1）：不确定

  4. 熔点（ºC）：不确定

  5. 沸点（ºC,0.67kpa或5 mmHg）：不确定

  6. 折射率：不确定

  7. 闪点（ºC）：不确定

  8. 比旋光度（ºC）：不确定

  9. 自燃点或引燃温度（ºC）不确定

  10. 蒸气压（kPa,25ºC）：不确定

  11. 饱和蒸气压（kPa,60ºC）：不确定

  12. 燃烧热（KJ/mol）：不确定

  13. 临界温度（ºC）：不确定

  14. 临界压力（KPa）：不确定

  15. 油水（辛醇/水）分配系数的对数值：不确定

  16. 爆炸上限（%,V/V）：不确定

  17. 爆炸下限（%,V/V）：不确定

  18. 溶解性：极微溶于水，溶于盐溶液。其盐酸盐微溶于甲醇、水、乙醇，不溶于丙酮、乙醚、氯仿。在空气中稳定，遇光颜色渐暗。

生物活性

• 描述: Chlortetracycline (7-Chlorotetracycline) 是一种特异性的有效钙离子载体抗生素, 抑制氨酰 tRNA 结合到核糖体。
• 相关类别:
  研究领域 >> 感染
  信号通路 >> 抗感染 >> 细菌
• 参考文献:

  [1]. Elmund GK, et al. Role of excreted chlortetracycline in modifying the decomposition process in feedlot waste. Bull Environ Contam Toxicol. 1971 Mar-Apr;6(2):129-32.

  [2]. Saling PM, et al. Mouse gamete interactions during fertilization in vitro. Chlortetracycline as a fluorescent probe for the mouse sperm acrosome reaction. J Cell Biol. 1979 Dec;83(3):544-55.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : QI7750000 CHEMICAL NAME : 2-Naphthacenecarboxamide, 7-chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octah ydro- 3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo- CAS REGISTRY NUMBER : 57-62-5 LAST UPDATED : 199701 DATA ITEMS CITED : 17 MOLECULAR FORMULA : C22-H23-Cl-N2-O8 MOLECULAR WEIGHT : 478.92 WISWESSER LINE NOTATION : L E6 C666 BV FV CU GUTTT&J DQ EQ GVZ HQ IN1&1 MQ M1 OG RQ HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 3 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : JAFCAU Journal of Agricultural and Food Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB 57136, West End Stn., Washington, DC 20037) V.1- 1953- Volume(issue)/page/year: 17,497,1969 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 335 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada) TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 118 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 6,623,1956 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 1500 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : AAGAAW Antimicrobial Agents Annual. (New York, NY) 1960. For publisher information, see AMACCQ. Volume(issue)/page/year: -,595,1960 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 192 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : CLDND* Compilation of LD50 Values of New Drugs. (J.R. MacDougal, Dept. of National Health and Welfare, Food and Drug Divisions, 35 John St., Ottawa, Ont., Canada) TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 3 gm/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 6,623,1956 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 134 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ANTCAO Antibiotics and Chemotherapy (Washington, DC). (Washington, DC) V.1-12, 1951-62. For publisher information, see CLMEA3. Volume(issue)/page/year: 6,623,1956 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intracerebral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 48 mg/kg TOXIC EFFECTS : Behavioral - hallucinations, distorted perceptions Behavioral - excitement Musculoskeletal - changes in teeth and supporting structures REFERENCE : CHTHBK Chemotherapy (Basel). (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.13- 1968- Volume(issue)/page/year: 26,196,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 750 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : AAGAAW Antimicrobial Agents Annual. (New York, NY) 1960. For publisher information, see AMACCQ. Volume(issue)/page/year: -,595,1960 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Mammal - dog DOSE/DURATION : 150 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : HBTXAC "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59 Volume(issue)/page/year: 5,52,1959 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - guinea pig DOSE/DURATION : 1800 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : ANTBAL Antibiotiki. (Moscow, USSR) V.1-29, 1956-84. For publisher information, see AMBIEH. Volume(issue)/page/year: 20,793,1975 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2500 mg/kg/5D-I TOXIC EFFECTS : Liver - change in gall bladder structure or function Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases REFERENCE : ANTBAL Antibiotiki. (Moscow, USSR) V.1-29, 1956-84. For publisher information, see AMBIEH. Volume(issue)/page/year: 28,608,1983 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 6 gm/kg/30D-I TOXIC EFFECTS : Gastrointestinal - other changes Kidney, Ureter, Bladder - other changes in urine composition Immunological Including Allergic - decreased immune response REFERENCE : ANTBAL Antibiotiki. (Moscow, USSR) V.1-29, 1956-84. For publisher information, see AMBIEH. Volume(issue)/page/year: 20,793,1975 ** REPRODUCTIVE DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous DOSE : 372 mg/kg SEX/DURATION : female 1-6 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - abortion REFERENCE : ASPHAK Archives des Sciences Physiologique. (Paris, France) V.1-28, 1947-74. Discontinued. Volume(issue)/page/year: 23,481,1969 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 0.1 mg/m3;Skin JAN 1993 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X5542 No. of Facilities: 921 (estimated) No. of Industries: 3 No. of Occupations: 17 No. of Employees: 12911 (estimated) No. of Female Employees: 125 (estimated)

安全

• 符号: GHS07
• 信号词: Warning
• 危害声明: H302
• 个人防护装备: dust mask type N95 (US);Eyeshields;Gloves
• 危害码 (欧洲): Xn
• 风险声明 (欧洲): R22
• 危险品运输编码: NONH for all modes of transport
• RTECS号: QI7750000

合成路线

67-56-1 14297-93-9 ~% 57-62-5

文献：Journal of the American Chemical Society, , vol. 79, p. 2849,2856

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制备

1.由金色链霉菌（Streptomyces aureofacieus）发酵产生，发酵液经酸化、过滤得沉淀物，溶解于乙醇后经酸析得粗品，经溶解、成盐得盐酸盐结晶。

2.由金色链霉菌发酵产生，发酵经酸化、过滤得沉淀物，溶解于乙醇后经酸析得粗品，再进行溶解、成盐得其盐酸盐结晶。