7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: 7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 79350-37-1
• Molecular Formula: C16H15N5O7S2
• Molecular Weight: 453.456
• Hs Code.: 38210000
• European Community (EC) Number: 616-684-4
• DSSTox Substance ID: DTXSID20861014
• Wikipedia: Cefixime
• NCI Thesaurus Code: C1100
• RXCUI: 25033
• Mol file: 79350-37-1.mol

Synonyms:Cefixime;Cefixime Anhydrous;Cefixime Trihydrate;FK 027;FK-027;FK027;FR 17027;FR-17027;FR17027;Suprax

Chemical Property of 7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

• Appearance/Colour: white to off white powder or off white crystal powder
• Melting Point: 218-225 °C
• PKA: pKa 2.10 (Uncertain)
• PSA: 238.05000
• Density: 1.85 g/cm³
• LogP: 0.36520
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: Slightly soluble in water, soluble in methanol, sparingly soluble in anhydrous ethanol, practically insoluble in ethyl acetate.
• Water Solubility.: 55.11 mg/L
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 453.04129018
• Heavy Atom Count: 30
• Complexity: 861

Purity/Quality:

99% ^*data from raw suppliers

Cefixime ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)C3=CSC(=N3)N)SC1)C(=O)O
• Recent ClinicalTrials: Efficacy of Immunization With 4C-MenB in Preventing Experimental Urethral Infection With Neisseria Gonorrhoeae
• Recent EU Clinical Trials: 3-day intravenous antibiotic treatment versus 3-day intravenous followed by 7-day oral antibiotic treatment for acute pyelonephritis in children 1 month to 3 years old: a non-inferiority open randomized multicentric clinical trial
• Drug Interactions: 1. in combination with aminoglycoside antibiotics have synergistic antibacterial effect on certain sensitive strains. 2. there are reports that aspirin may increase the blood concentration of Cefixime. 3. in combination with aminoglycosides or other cephalosporins will increase the renal toxicity. 4. in combination with strong diuretics such as furosemide can enhance nephrotoxicity. 5. in combination with chloramphenicol may have mutual antagonism. 6. probenecid can prolong the excretion of Cefixime and elevated blood concentrations. The above information is edited by the lookchem of Liu Yujie.
• Uses: The third-generation oral cephalosporin class of broad-spectrum antibiotics, has strong antibacterial effect on Gram-positive bacteria such as Streptococcus, and Gram-negative bacteria such as Neisseria gonorrhoeae, Haemophilus influenzae, , as well as E. coli , Klebsiella pneumoniae, Proteus mirabilis, which are resistance to cefaclor, cephalexin, cefadroxil resistant, and is stable for β-lactamase produced by various bacteria. Long-acting, efficient and can be administered once a day. Clinically used for respiratory tract infections,urinary tract infections and biliary tract infections caused by susceptible strains. Orally active, third generation cephalosporin antibiotic Orally active, third generation cephalosporin antibiotic.
• Description: Cefixime is the first orally active third-generation cephalosponn with a true broad spectrum of activity. It is reportedly more effective against Gram-negative bacteria than conventional oral cephems such as cephalexin and cefaclor.
• Therapeutic Function: Antibiotic
• Clinical Use: Cefixime (Suprax) is the first orally active, third-generationcephalosporin that is not an ester prodrug to be approved fortherapy in the United States. Oral bioavailability is surprisinglyhigh, ranging from 40% to 50%. Facilitated transportof cefixime across intestinal brush border membranes involvingthe carrier system for dipeptides may explain itssurprisingly good oral absorption. This result was not expectedbecause cefixime lacks the ionizable α-amino grouppresent in dipeptides and β-lactams previously known to betransported by the carrier system.Cefixime is a broad-spectrum cephalosporin that is resistantto many β-lactamases. It is particularly effective againstGram-negative bacilli, including E. coli, Klebsiella spp., P.mirabilis, indole-positive Proteus, Providencia, and someCitrobacter spp. Most Pseudomonas, Enterobacter, andBacteroides spp. are resistant. It also has useful activityagainst streptococci, gonococci, H. influenzae, and M. catarrhalis.It is much less active against S. aureus. Cefixime isused for the treatment of various respiratory tract infections(e.g., acute bronchitis, pharyngitis, and tonsillitis) and otitismedia. It is also used to treat uncomplicated urinary tract infectionsand gonorrhea caused by β-lactamase–producingbacterial strains.The comparatively long half-life of cefixime (t1/2 is3–4 hours) allows it to be administered on a twice-a-dayschedule. Renal tubular reabsorption and a relatively high fraction of plasma protein binding (～65%) contribute to thelong half-life. It is provided in two-oral dosage forms: 200-or 400-mg tablets and a powder for the preparation of anaqueous suspension. Cefixime has been used successfully in uncomplicated cystitis, upper and lower respiratory tract infections and various other infections. Its failure to provide adequate cover for staphylococci should be noted.

Technology Process of 7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 14 articles about 7-[[2-(2-Amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.2%

diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-tert-butoxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate (79350-36-0,108908-53-8) → 7β-<(E)-2-(2-amino-4-thiazolyl)-2-carboxymethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylic acid (79350-37-1,97164-56-2,97590-26-6,108691-83-4,116173-42-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.5h;

DOI:10.1248/cpb.34.3458

Reference yield: 62.1%

7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylic acid (95759-14-1,108908-52-7) → 7β-<(E)-2-(2-amino-4-thiazolyl)-2-carboxymethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylic acid (79350-37-1,97164-56-2,97590-26-6,108691-83-4,116173-42-3)

Guidance literature:

With sodium hydroxide; In water; for 0.0833333h;

DOI:10.1248/cpb.34.3458

Reference yield:

7-{2-[(2-aminothiazol)-4-yl]-2-[(Z)(methoxycarbonyl)methoxyimino]acetamido}-3-vinyl-ceph-3-em-4-carboxylic acid (88621-01-6) → cefixime (79350-37-1)

Guidance literature:

7-{2-[(2-aminothiazol)-4-yl]-2-[(Z)(methoxycarbonyl)methoxyimino]acetamido}-3-vinyl-ceph-3-em-4-carboxylic acid; With sodium hydroxide; water; at 0 - 5 ℃; for 0.0833333h;

With hydrogenchloride; In water; at 34 - 36 ℃; pH=2.3; Product distribution / selectivity;

upstream raw materials:

7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylic acid

diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-tert-butoxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate

2-(tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acid

(Z)-2-p-nitrobenzyloxycarbonylmethoxyimino-3-oxobutyric acid

Downstream raw materials:

8-(2-carboxymethoxyimino-2-{2-[(2-hydroxybenzylidene)amino]thiazol-4-yl}acetylamino)-7-oxo-4-vinyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid

Refernces

• 1、 -. "Method of synthesizing cefixime". Paragraph 0077; 0080. . Retrieved 2017/04/03.
• 2、 -. "NOVEL INTERMEDIATES FOR SYNTHESIS OF CEPHALOSPORINS AND PROCESS FOR PREPARATION OF SUCH INTERMEDIATES". Page 32. . Retrieved 2008/06/13.