Cephathiamidine
Cephathiamidine
CAS: 33075-00-2
Molecular Formula: C19H28N4O6S2
Cephathiamidine - Names and Identifiers
| Name | Cephathiamidine |
| Synonyms | CEFATHIAMIDINE Cefathiamidine Cephathiamidine 7-[α-[(N,N'-Diisopropylamidino)thio]acetylamino]cephalosporanic acid 7-(alpha-((n,n'-diisopropylamidino)thio)acetylamino)cephalosporanic acid 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(2-((n,n'-diisopropyla 7-(2-((n,n'-diisopropylamidino)thio)acetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic aci acetate (6R)-3-[(Acetyloxy)methyl]-7α-[2-[(N,N'-diisopropylamidino)thio]acetylamino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 3-(Acetoxymethyl)-7-({[(N,N'-diisopropylcarbamimidoyl)sulfanyl]acetyl}amino)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (6R,7R)-3-(acetoxymethyl)-7-(2-(((E)-N,N'-diisopropylcarbamimidoyl)thio)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid 3-[(acetyloxy)methyl]-7-[({[N,N'-di(propan-2-yl)carbamimidoyl]sulfanyl}acetyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (6R,7R)-3-(acetyloxymethyl)-7-[[2-[N,N'-di(propan-2-yl)carbamimidoyl]sulfanylacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[2-[[(Z)-[(1-methylethyl)amino][(1-methylethyl)imino]methyl]thio]acetyl]amino]-8-oxo- |
| CAS | 33075-00-2 |
| EINECS | 278-355-8 |
| InChI | InChI=1/C19H28N4O6S2/c1-9(2)20-19(21-10(3)4)31-8-13(25)22-14-16(26)23-15(18(27)28)12(6-29-11(5)24)7-30-17(14)23/h9-10,14,17H,6-8H2,1-5H3,(H,20,21)(H,22,25)(H,27,28) |
Cephathiamidine - Physico-chemical Properties
| Molecular Formula | C19H28N4O6S2 |
| Molar Mass | 472.58 |
| Density | 1.45±0.1 g/cm3(Predicted) |
| Melting Point | >140°C (dec.) |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 2.67±0.50(Predicted) |
| Storage Condition | -20°C Freezer, Under Inert Atmosphere |
| Stability | Unstable in Solution |
| Refractive Index | 1.652 |
| Use | Mainly used for the treatment of hepatobiliary infections caused by sensitive bacteria, urinary tract infections, respiratory infections, sepsis, endocarditis and meningitis and other diseases |
Cephathiamidine - Standard
Authoritative Data Verified Data
This product is (6R,7R-3-[ (Acetoxy) methyl]-7-[a-(N,N-diisopropylamidinothio)) acetamido] oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-carboxylic acid internal ammonium salt. The content of C19H28N406S2 shall not be less than 97.0% calculated as anhydrous.
Last Update：2024-01-02 23:10:35
Cephathiamidine - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Almost odorless, with hygroscopicity.
- This product is very soluble in water, slightly soluble in ethanol, insoluble in acetone or ether.
specific rotation
take this product, precision weighing, adding water to dissolve and quantitative dilution to make a solution containing about 10 mg per 1 ml, according to the law (General 0621), the specific rotation is 135 ° to 145°C.
Last Update：2022-01-01 11:41:44
Cephathiamidine - Differential diagnosis
Authoritative Data Verified Data
- take this product and cefathiamidine reference material, add water to dissolve and make a solution containing about 20mg per 1 ml, as the test solution and the reference solution, the reference solution and the test solution were mixed in equal amounts as a mixed solution. According to the thin layer chromatography (General 0502) test, absorb the above three kinds of solution of each lul, respectively, in the same silica gel G thin layer plate [take silica gel G2.5g, plus 1% sodium carboxymethyl cellulose phosphate buffer (pH 5.8)) the appropriate amount of slurry plate, activated at 105°C for 1 hour, put into the desiccator for use], with freshly prepared methanol-isopropanol-phosphate buffer (pH5.8)(7:2:1) after filtration, it was a developer, was developed, dried, and heated at 100 ° C. For 30 minutes to display color in iodine vapor. The position and color of the main spot of the test solution should be the same as that of the reference solution, and the mixed solution should show a single spot.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 924).
- two items (1) and (2) above can be selected as one item.
Last Update：2022-01-01 11:41:45
Cephathiamidine - Exam
Authoritative Data Verified Data
crystallinity
take a small amount of this product, according to the law inspection (General 0981), should comply with the provisions.
acidity
take this product, add water to make a solution containing 0.lg per lml, according to the law (General 0631),pH value should be 4.0~6.0.
clarity and color of solution
take 5 parts of this product and add water respectively to make each lml containing 0.lg solution, the solution should be clear and colorless; If it is turbid, it should not be more concentrated than the 1# turbidity standard solution (General 0902 first method); If it is colored, no deeper color shall be compared with the yellow or yellow-green standard colorimetric solution No. 6 (General rule 0901, Method 1).
Related substances
take an appropriate amount of this product, add the mobile phase to dissolve and dilute to make a solution containing about 0.5mg per lml as a test solution; Take an appropriate amount for precision measurement, quantitative dilution with mobile phase to prepare a solution containing about 5ug per lml, as a control solution; Precise amount of appropriate amount of control solution, quantitative dilution with mobile phase to prepare a solution containing about 0.5ug per lml, as a sensitivity solution. An appropriate amount of the impurity C control was taken, dissolved and diluted with the mobile phase to prepare a solution containing about 0.25ug per 1 ml as the impurity C control solution. According to the test of high performance liquid chromatography (General rule 0512), silica gel bonded with eighteen alkyl silane is used as the filler (the column of 4.6mm x mm,5um or equivalent performance); phosphate buffer (anhydrous disodium hydrogen phosphate 2.76g, citric acid 1.29g, dissolved in water and diluted to 1000ml)-acetonitrile (86:14) as mobile phase; The detection wavelength was 254nm. Take the system applicable solution 10 u1 under the content determination item, inject it into human liquid chromatograph, record the chromatogram, and the separation degree between impurity D Peak (relative retention time is about 0.9) and cefathiamidine peak should meet the requirements. Take the sensitivity of the solution 10ul injection of human liquid chromatography, the signal to noise ratio of the peak height of the main component should be greater than 10. The sample solution, the control solution and the impurity C reference solution are respectively injected with human liquid chromatography, and the chromatogram is recorded to 2.5 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the peak area of impurity C shall not be greater than 0.1 times (0.1%) of the main peak area of the control solution, other single impurity peak area shall not be greater than 0.5 times (0.5%) of the main peak area of the control solution, and the sum of each impurity peak area shall not be greater than 1.5 times (1.5%) of the main peak area of the control solution. The peaks in the chromatogram of the test solution which are 0.5 times smaller than the main peak area of the sensitivity solution are ignored.
residual solvent
take 0.2g of this product, precision weighing, top empty bottle, precision add water 2ml to dissolve, seal, as a test solution; Precision weighing methanol, ethanol, acetone, each appropriate amount of dichloromethane is diluted quantitatively by adding water to prepare a mixed solution containing 0.3mg of methanol, 0.5mg of ethanol, 0.5mg of acetone and 0.06mg of dichloromethane per 1 ml. 2ml of the mixed solution is accurately measured and placed in the top empty bottle and sealed, as a reference solution, the capillary column with 6% cyanopropylphenyl -0861 dimethyl polysiloxane (or similar polarity) as the stationary liquid is used as the chromatographic column according to the determination of residual solvent (General 94% second method), the initial temperature is 40°C, and after eluting with dichloromethane, the temperature is raised to 150°C at a rate of 30°C per minute for 5 minutes; The temperature of the sample inlet is 200°C; And the temperature of the detector is 250°C; the equilibrium temperature of the headspace bottle is 80 ° C., and the equilibrium time is 30 minutes; The headspace injection of the reference solution is taken, and the separation degree between peaks shall meet the requirements. The test solution and the reference solution are injected in Headspace respectively, and the chromatogram is recorded. The residual amount of methanol, ethanol, acetone and dichloromethane shall be calculated by peak area according to external standard method.
moisture
take this product, according to the moisture determination method (General 0832 first method 1), the water content shall not exceed 1.5%.
visible foreign body
take 5 parts of this product, each 2g, plus particle inspection water dissolution, inspection according to law (General 0904), should comply with the provisions. (For aseptic dispensing)
insoluble particles
Take 3 parts of this product, and add the particle inspection water to make a solution containing 80mg per 1 ml, and check according to law (General rule 0903), no more than 6000 particles of 10um and more than 10um in each lg sample, and no more than 600 particles of 25um and more than 25um. (For aseptic dispensing)
bacterial endotoxin
take this product, check according to law (General rule 1143), each 1 mg cefathiamidine containing endotoxin amount should be less than 0.075EU. (For injection)
sterile
take this product, dissolve and dilute with appropriate solvent, after membrane filtration treatment, inspection according to law (General rule 1101), should comply with the provisions. (For aseptic dispensing)
Last Update：2022-01-01 11:41:46
Cephathiamidine - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
silica gel bonded with OCTA alkyl silane as filler; Phosphate buffer solution (2.76g of anhydrous disodium hydrogen phosphate, 1.29g of citric acid, dissolved in water and diluted to 1000ml)-acetonitrile (80:20) mobile phase; The detection wavelength was 254mn. Take an appropriate amount of cefathiamidine reference, add water to dissolve and quantitatively dilute to make a solution containing about 0.5mg per 1 ml, heat in a water bath at 90°C for 30 minutes, and cool, as a system applicable solution, 10u1 was injected into the liquid chromatograph, and the chromatogram was recorded. The separation degree between cefathiamidine peak and impurity D Peak (relative retention time is about 1.3) should be greater than 2.0.
assay
take an appropriate amount of this product, weigh it accurately, add water to dissolve and quantitatively dilute it to make it contain about 0 in each lml. lmg solution, as a test solution, take the precision of 10u1 injection liquid chromatography, record the chromatogram; Another appropriate amount of cefathiamidine reference, the same method for determination. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 11:41:47
Cephathiamidine - Category
Authoritative Data Verified Data
B-lactam antibiotics, cephalosporins.
Last Update：2022-01-01 11:41:47
Cephathiamidine - Category
Authoritative Data Verified Data
sealed and stored in a cold dark dry place.
Last Update：2022-01-01 11:41:47
Cephathiamidine - Cefathiamidine for injection
Authoritative Data Verified Data
This product is a sterile powder of cefathiamidine. Calculated as anhydrous, containing cefathiamidine (C19H28N406S2) shall not be less than 97.0%; Calculated as the average loading, containing cefathiamidine (C19H28N406S2) shall be 90.0% ~ 110.0% of the label amount.
trait
This product is white to yellowish crystalline powder.
identification
The same results should be shown in the identification test under cefathiamidine.
examination
- the clarity and color of the solution take 5 bottles of this product, and add water according to the labeled amount to make each lml containing 0.lg solution, the solution should be clear and colorless; If it is turbid, compared with No. 1 turbidity standard solution (General 0902 first method); Shall not be more concentrated; If it is colored, no deeper color shall be compared with the yellow or yellow-green Standard No. 7 color solution (General rule 0901 method 1).
- the contents under the item of difference in loading amount of related substances are mixed evenly, and the appropriate amount is accurately weighed and determined according to the method under the item of cefathiamidine. If there are impurity peaks in the chromatogram of the test solution, the Peak area of impurity C shall not be greater than 0.1 times (0.1%) of the main peak area of the control solution, and the peak area of other individual impurities shall not be greater than the main peak area of the control solution (1.0% ), the sum of each impurity peak area shall not be greater than 2 times (2.0%) of the main peak area of the control solution.
- the moisture content of this product shall not exceed 0832 as determined by the method for determination of moisture (General rule 2.0%, first method 1).
- insoluble particles this product is taken, and a solution containing 80mg per 1 ml is made with particle inspection water according to the labeled amount, and inspected according to law (General rule 0903), and the labeled amount is 1. The conversion below Og is that 6000 particles with lOum and more than 10um and 600 particles with 25um and more than 25um should not be exceeded per lg; The labeled amount is l. No more than 6000 particles with lOum and l0um or more and no more than 600 particles with 25um and 25um or more in each container of test article above Og (including 1.og).
- The crystallinity, acidity, bacterial endotoxin and sterility should be checked according to the method of cefathiamidine.
- others should comply with the relevant provisions under injection (General 0102).
Content determination
The contents under the item of loading amount difference were accurately weighed and the appropriate amount was measured according to the method under the item of cefathiamidine.
category
Same as cefathiamidine.
specification
(1)0.5g (2)1.0g (3)2.0g
storage
sealed and stored in a cold dark dry place.
Last Update：2022-01-01 11:41:48
Cephathiamidine - Reference Information
| overview | cefathiamidine is white or white-like crystalline powder. Cefathiamidine is insoluble in acetone, chloroform or ether, and easily dissolves water. Cefathiamidine has a unique molecular structure of zwitterionic internal salt, which is unstable when exposed to heat, light, and wet, and is easy to decompose and change color. Cefathiamidine (cefathiamidine), chemical name (6R,7R)-3-[(acetoxy) methyl]-7-[α- (N,N'-diisopropylamidine thio) acetamido]-8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-formic acid internal ammonium salt, it is the first self-developed broad-spectrum cephalosporin in China, and its injection preparation is used clinically. Its broad antibacterial spectrum, strong antibacterial effect, and small adverse reactions. It is mainly used to treat respiratory tract infections, trauma and surgical infections, skin and soft tissue infections, and urinary tract infections caused by sensitive gram-positive bacteria and gram-negative bacteria., Ear, nose and throat infection, endocarditis and sepsis, etc. [Pharmacological effects] The antibacterial mechanism of cefathiamidine is similar to that of other cephalosporins, mainly by inhibiting the biosynthesis of bacterial cell walls. In vitro antibacterial activity tests show that this drug is against pneumococcus, Streptococcus pyogenes, Haemophilus influenzae, Enterococcus, Staphylococcus aureus (MSSA strain), Staphylococcus epidermidis (MSSE strain) and Bramham catarrhalis Strong antibacterial activity; it also has good antibacterial activity against Streptococcus viridans, hemolytic streptococcus, non-hemolytic streptococcus, Diphtheria, Perfringens, Tetanus and Bacillus anthracis. However, the in vitro antibacterial activity against Staphylococcus aureus and Staphylococcus epidermidis is not as good as vancomycin. The 90% minimum inhibitory concentration (MIC90) of this drug for Streptococcus pneumoniae is 0.25 μg/ml, the MIC90 for Streptococcus pyogenes is 0.5 μg/ml, the MIC90 for Haemophilus influenzae and Enterococcus is 2 μg/ml, and the MIC90 for Staphylococcus aureus (MSSA strain), Staphylococcus epidermidis (MSSE strain) and Branhamella catarrhalis is less than 8 μg/ml. [Purpose] Clinically, it is mainly suitable for the treatment of the following infections caused by sensitive bacteria:(1) Respiratory system infections (such as angina, tonsillitis, pneumonia, lung abscess, etc.). (2) Intra-abdominal infections (such as liver and biliary tract infections, peritonitis, etc.). (3) Urinary and reproductive system infections. (4) skin and soft tissue infection. (5) Endocarditis, sepsis and other serious infections. |
| Pharmacokinetics | Cefathiamidine is not absorbed orally. After intravenous drip of lg, the peak blood concentration (Cmax) was (68.93±6.86)mg/L, the area under the blood concentration-time curve (AUC) was (94.7±9.8)(mg h)/L, the clearance half-life (t1/2 β) was (1.19±0.12)h, and the cumulative urine excretion rate in 12 hours was (93.1±3.2)%. After intramuscular injection of 1g, Cmax was (35.12±4.34)mg/L, peak time (tmax) was (0.78±0. 08)h,AUC was (85.3±8)(mg h)/L, half-life was (1.38±0.21)h, and the cumulative urinary drug excretion rate was (84.2±5.9)% at 12 hours. Compared with intravenous drip, its absolute bioavailability is (90.3±6.4)%. After the drug is absorbed, the concentration in bile is the highest, followed by liver, kidney, spleen, lung, stomach, intestine, etc.; the concentration in brain tissue is low (it is not easy to penetrate the blood-cerebrospinal fluid barrier). The drug is hardly metabolized in the body, and the plasma protein binding rate is 23%. At 12 hours after injection, about 90% of the dose is excreted with urine in its original form. In patients with renal dysfunction, the plasma half-life is prolonged to 13.2 hours (about 10 times the normal half-life) after intramuscular injection, and only 3.2% of the dose is excreted in the urine at 24 hours. Hemodialysis can remove 20% ~ 30% of the dosage. Fig. 1 is the structural formula of cefathiamidine |
| drug interaction | 1. cefathiamidine is combined with probenecid, which can delay the renal excretion of cefathiamidine and increase the blood concentration of this product. 2. The combination of cefathiamidine and aminoglycoside antibiotics can increase nephrotoxicity. 3. Cefathiamidine combined with strong diuretics such as furosemide can increase nephrotoxicity. |
| usage and dosage | add sterilization water for injection or normal saline to dissolve before use. Intramuscular injection: adults 500mg ~ 1g each time, 4 times a day; Children 50~100mg/kg daily, divided into 3~4 times of administration. Intravenous drip: adults daily 4~8g, divided into 2~4 times of drip; Children 50~100mg/kg daily, divided into 2~4 times of administration. |
| adverse reactions | 1. occasionally urticaria, asthma, skin pruritus, drug fever, angioneurotic edema, etc. A small number of patients may appear alanine aminotransferase, alkaline phosphatase and blood urea nitrogen measurement values increased. 3. A small number of patients may occasionally have reversible blood routine abnormalities (neutropenia) after medication. 4. A small number of patients may occasionally have double infections such as Candida and Staphylococcus after medication. (2016-03-03) |
| attention and taboos | 1. patients with a history of allergy to penicillin or cephalosporin drugs must undergo a skin test when using cefathiamidine, and those with positive skin test reactions cannot use this drug. 2. Cefathiamidine and aminoglycosides are contraindicated, and the two cannot be mixed in the same container when combined. 3. Cefathiamidine should be used now, not for a long time after preparation. 4. Patients with renal insufficiency should be reduced. 5.FDA classified the pregnancy safety of this drug as Class B. 6. Early pregnancy should be used with caution. Although the application of cephalosporins in lactating women has not been reported, its application must still be weighed. 7. Patients with renal function decline, should be appropriately reduced when applied. |
Last Update：2024-04-09 20:49:11
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View History
Cephathiamidine
3-(2-AMINOETHYL)-5-((4-ETHOXYPHENYL)METHYLENE)-2,4-THIAZOLIDINEDIONE HYDROCHLORIDE
Benzamide, N-[4-(2-ethoxyethoxy)phenyl]-2-methoxy-
苯并[D]噁唑-7-甲酸甲酯
(3-溴-5-氟苯基)甲酰胺盐酸盐
CBZ-L-ALA-L-LEU NH2
4-(METHYLSULFANYL)-6-[(METHYLSULFANYL)METHYL]-2-(3-PYRIDINYL)PYRIMIDINE
POTASSIUM PHOSPHITE
6,14-Dioxa-9,11-dithia-10-stannanonadecanedioic acid, 10-butyl-10-[[2-[(5-methoxy-1,5-dioxopentyl)oxy]ethyl]thio]-5,15-dioxo-, 1,19-dimethyl ester
GERMANIUM PHENYL TRICHLORIDE
3-(2-AMINOETHYL)-5-((4-ETHOXYPHENYL)METHYLENE)-2,4-THIAZOLIDINEDIONE HYDROCHLORIDE
Benzamide, N-[4-(2-ethoxyethoxy)phenyl]-2-methoxy-
苯并[D]噁唑-7-甲酸甲酯
(3-溴-5-氟苯基)甲酰胺盐酸盐
CBZ-L-ALA-L-LEU NH2
4-(METHYLSULFANYL)-6-[(METHYLSULFANYL)METHYL]-2-(3-PYRIDINYL)PYRIMIDINE
POTASSIUM PHOSPHITE
6,14-Dioxa-9,11-dithia-10-stannanonadecanedioic acid, 10-butyl-10-[[2-[(5-methoxy-1,5-dioxopentyl)oxy]ethyl]thio]-5,15-dioxo-, 1,19-dimethyl ester
GERMANIUM PHENYL TRICHLORIDE