头孢呋肟
头孢呋肟用途
Cefuroxime 是一种具有口服活性的第二代头孢菌素抗生素 (antibiotic),增加了对乳酸酶 (β-lactamase) 的稳定性。Cefuroxime 具有广谱的抑制活性,对革兰氏阳性菌和革兰氏阴性菌都有效。
头孢呋肟名称
[ CAS 号 ]:
55268-75-2
[ 中文名 ]:
头孢呋辛
[ 英文名 ]:
Cefuroxime
[中文别名 ]:
[英文别名 ]:
- EINECS 259-560-1
- cefuroxim
- U1troxim
- Ketocef
- Cefuroxime
- Biocidin
- cefaloxime
- Cephuroxime
- MFCD00864991
- CXM
头孢呋肟生物活性
[ 描述 ]:
Cefuroxime 是一种具有口服活性的第二代头孢菌素抗生素 (antibiotic),增加了对乳酸酶 (β-lactamase) 的稳定性。Cefuroxime 具有广谱的抑制活性,对革兰氏阳性菌和革兰氏阴性菌都有效。
[ 相关类别 ]:
[体外研究]
头孢呋辛对金黄色葡萄球菌(MIC=0.25μg/ml)具有很高的活性,无论菌株是否产生青霉素酶。对甲氧西林敏感的金黄色葡萄球菌、耐甲氧西林的金黄色葡萄球菌、化脓性链球菌、肺炎链球菌、绿色链球菌、粪链球菌和梭状芽孢杆菌的MIC值分别为0.25μg/ml、5.9μg/ml、0.125μg/ml、0.125μg/ml、0.125μg/ml、>125.0μg/ml和1.2μg/ml[1]。头孢呋辛(10-100μg/ml；2-6小时)杀菌迅速,对金黄色葡萄球菌的作用相对较慢,但即使如此,6小时内99%以上的初始接种物被杀死,革兰氏阴性菌被迅速杀死,大多数情况下99%以上的超大接种物在2小时内被杀死；产β-内酰胺酶菌株与非产酶菌株一样被杀死[1]。
[体内研究]
家兔(体重2.0～2.5kg)静脉注射金黄色葡萄球菌630株(青霉素酶产生菌),经保护试验,头孢呋辛的中位有效剂量为3mg/kg。
[参考文献]
头孢呋肟物理化学性质
[ 密度 ]:
1.8±0.1 g/cm3
[ 熔点 ]:
171.5-173°C
[ 分子式 ]:
C16H16N4O8S
[ 分子量 ]:
424.385
[ 精确质量 ]:
424.068878
[ PSA ]:
199.06000
[ LogP ]:
0.47
[ 外观性状 ]:
白色结晶，[α]召+63.7°(C=1.0，0.2mol/L磷酸盐缓冲液pH=7)。UV最大吸收(pH=6磷酸缓冲液)：274nm(ε17600)。头孢呋辛钠(Cefuroxime Sodium)：C16H15N4aO8SNa。[56238-63-2]。白色固体，易溶于水或缓冲溶液，溶于甲醇，极微溶于乙醇乙酯、乙醚、辛醇、苯或氯仿，水中溶解度为500mg/2.5ml。pKa(水)：2.5；pKa(Z.甲基甲酰胺)：5.1。[α]D20 +60°(C=0.91，水)。
[ 折射率 ]:
1.735
[ 储存条件 ]:
2-8°C，干燥
头孢呋肟毒性和生态
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- XI0329000
- CHEMICAL NAME :
- 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(((aminocarbonyl)oxy)methyl)-7-((2- furanyl(methyoxyimino)acetyl)amino)-8-oxo-, (6R-(6-alpha,7-beta(Z)))-
- CAS REGISTRY NUMBER :
- 55268-75-2
- LAST UPDATED :
- 199707
- DATA ITEMS CITED :
- 19
- MOLECULAR FORMULA :
- C16-H16-N4-O8-S
- MOLECULAR WEIGHT :
- 424.42
- WISWESSER LINE NOTATION :
- T46 ANV ES GUTJ G1OVZ HVQ CMVYUNO1&- BT5OJ
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Human - man
- DOSE/DURATION :
- 64 mg/kg/16H-I
- TOXIC EFFECTS :
- Behavioral - toxic psychosis
- REFERENCE :
- LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,965,1984
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 10 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >10 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >10 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >8 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intramuscular
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >2 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >10 gm/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - ptosis Behavioral - ataxia Nutritional and Gross Metabolic - weight loss or decreased weight gain
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >10 gm/kg
- TOXIC EFFECTS :
- Gastrointestinal - hypermotility, diarrhea
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >10 gm/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - ptosis Behavioral - ataxia
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 10400 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- DRUGAY Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. (ADIS Press International Inc., Suite B-30, Oxford Ct. Business Center, 582 Middletown Blvd., Langhorne, PA 19047) V.1- 1971- Volume(issue)/page/year: 17,233,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intramuscular
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- >2 gm/kg
- TOXIC EFFECTS :
- Sense Organs and Special Senses (Eye) - ptosis Behavioral - ataxia
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- >1500 mg/kg
- TOXIC EFFECTS :
- Behavioral - food intake (animal) Lungs, Thorax, or Respiration - respiratory depression Gastrointestinal - hypermotility, diarrhea
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intramuscular
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- >300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),124,1979 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 30 gm/kg/5W-I
- TOXIC EFFECTS :
- Lungs, Thorax, or Respiration - changes in lung weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),130,1979
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 45 gm/kg/5W-I
- TOXIC EFFECTS :
- Liver - changes in liver weight Blood - normocytic anemia Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),130,1979 ** REPRODUCTIVE DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 8800 mg/kg
- SEX/DURATION :
- female 7-17 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - other postnatal measures or effects
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),245,1979
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 24 gm/kg
- SEX/DURATION :
- male 60 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Paternal Effects - testes, epididymis, sperm duct
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),245,1979
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 32 gm/kg
- SEX/DURATION :
- male 9 week(s) pre-mating female 2 week(s) pre-mating female 1-7 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),245,1979
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Subcutaneous
- DOSE :
- 4400 mg/kg
- SEX/DURATION :
- female 7-17 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord)
- REFERENCE :
- NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 27(Suppl 6),245,1979
头孢呋肟安全信息
[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
[ 危害码 (欧洲) ]:
Xn
[ 风险声明 (欧洲) ]:
R42/43
[ 安全声明 (欧洲) ]:
22-24-37-45
[ 危险品运输编码 ]:
NONH for all modes of transport
[ RTECS号 ]:
XI0329000
头孢呋肟合成路线
头孢呋肟上下游产品
头孢呋肟上游产品
头孢呋肟下游产品
头孢呋肟制备
方法1：以头孢噻吩钠(Ⅰ)为原料，用酶进行水解脱去3位侧链上的乙酰基，再先后和二苯基偶氮甲烷及三氯乙酰基异氰酸酯反应，对羧基和醇进行保护，得化合物(Ⅱ)。化合物(Ⅱ)用五氯化磷进行处理，使7位侧链断裂，得化合物(Ⅲ)。化合物(Ⅲ)先用弱碱的甲醇溶液，再用强酸水解，脱去保护基，得化合物(Ⅳ)。化合物(Ⅳ)和侧链反应可得头孢呋辛。头孢呋辛和2-乙基己酸钠作用，可得头孢呋辛钠。
其中侧链的制备及和化合物(Ⅳ)的反应可进行如下。在0℃和搅拌下，往14.99g(0.072mol)五氯化磷悬浮于150ml干燥的二氯甲烷溶液中，加入27.5mlN,N-二甲基甲酰胺。冷却至-10℃，再加入12.17g(0.072mol)2-(呋喃-2-基)-2-甲氧亚氨基乙酸(Ⅸ)。在－10℃，继续搅拌反应15min后，加入35g碎冰在0继续搅拌10min后，分出下层的二氯甲烷层，留待后用。
75mlN,N-二甲基甲酰胺、75ml乙腈、42ml三乙胺和(6R,7R)-7-氨基-3-[(氨甲酰氧基)甲基]头孢-3-烯-4-羧酸混合，搅拌下浸入冰浴中，再加入10ml水。在0～2℃下搅拌45mol，直到固体全部溶解，形成黄色的溶液。然后在10min内，－10℃和搅拌下，往该黄色溶液中加入上面制得的二氯甲烷溶液，此时温度会缓慢升至0℃。接着在0～2℃下继续反应1g。移去冷浴，让其在1g内自然升温至20℃。在5℃下，把该反应液慢慢加入100ml的2mol／L盐酸和1.15L的冷水所成的溶液中。用2mol/L盐酸（约10ml）调节，使该二相混合液的PH值在2以下，继续搅拌，并再冷却至5℃。析出沉淀，过滤，用100ml二氯甲烷和250ml水洗，于40℃真空干燥过夜，得22.04g头孢呋辛，收率86.6％。
头孢呋肟文献
Antibiotic exposure in a low-income country: screening urine samples for presence of antibiotics and antibiotic resistance in coagulase negative staphylococcal contaminants.
PLoS ONE 9(12) , e113055, (2014)
Development of antimicrobial resistance has been assigned to excess and misuse of antimicrobial agents. Staphylococci are part of the normal flora but are also potential pathogens that have become ess...
Beta- lactam antibiotics stimulate biofilm formation in non-typeable haemophilus influenzae by up-regulating carbohydrate metabolism.PLoS ONE 9(7) , e99204, (2014)
Non-typeable Haemophilus influenzae (NTHi) is a common acute otitis media pathogen, with an incidence that is increased by previous antibiotic treatment. NTHi is also an emerging causative agent of ot...
Pharmacokinetics of cefuroxime in porcine cortical and cancellous bone determined by microdialysis.Antimicrob. Agents Chemother. 58(6) , 3200-5, (2014)
Traditionally, the pharmacokinetics of antimicrobials in bone have been investigated using bone biopsy specimens, but this approach suffers from considerable methodological limitations. Consequently, ...
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