Vantin

Base Information

• Chemical Name: Vantin
• CAS No.: 87239-81-4
• Molecular Formula: C21H27N5O9S2
• Molecular Weight: 557.605
• Hs Code.: 30042000
• European Community (EC) Number: 918-886-0,688-311-3
• NSC Number: 759161
• UNII: K9VK627SN2
• Nikkaji Number: J227.713A
• Wikidata: Q1052672
• NCI Thesaurus Code: C28916
• RXCUI: 47835
• Mol file: 87239-81-4.mol

Synonyms:1-(isopropoxycarbonyloxy)ethyl-7-(2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetamido)-3-methoxymethyl-8-oxo-5-thia-1-azabicyclo(4,2,0)-oct-2-ene-2-carboxylate;cefpodoxime proxetil;cephalosporin 807;CS 807;CS-807;Doxef;U 76252;U-76,252;Vantin

Chemical Property of Vantin

Chemical Property:

• Appearance/Colour: pale yellow solid
• Melting Point: 111-113 °C
• Refractive Index: 1.67
• PKA: 8.13±0.60(Predicted)
• PSA: 234.51000
• Density: 1.58 g/cm³
• LogP: 1.73700
• Storage Temp.: -20?C Freezer
• Sensitive.: Light Sensitive
• Solubility.: Soluble in DMSO
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 13
• Exact Mass: 557.12501980
• Heavy Atom Count: 37
• Complexity: 976

Purity/Quality:

Cefpodoxime proxetil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)OC(=O)OC(C)OC(=O)C1=C(CSC2N1C(=O)C2NC(=O)C(=NOC)C3=CSC(=N3)N)COC
• Isomeric SMILES: CC(C)OC(=O)OC(C)OC(=O)C1=C(CS[C@H]2N1C(=O)[C@H]2NC(=O)/C(=N/OC)/C3=CSC(=N3)N)COC
• Recent ClinicalTrials: A Study to Evaluate the Safety, Tolerability, and Pharmacokinetics (PK, the Measure of How the Human Body Processes a Substance) of ETX0282 When Administered Orally to Healthy Participants
• Description: Cefpodoxime proxetil is an orally active, broad-spectrum cephalosporin especially useful in the treatment of bacterial infections in children. It is a prodrug converted by esterases in the GI walls to cefpodoxime, which reportedly has a bacteriostatic spectrum comparable to injectable third-generation cephem antibiotics.
• Uses: An antibacterial. A broad spectrum, orally absorbed third generation cephalosporin, ester prodrug of the active free acid metabolite, Cefpodoxime A broad spectrum antibiotic. Cefpodoxime proxetil is commonly used in clinical in vitro microbiological antimicrobial susceptibility tests (panels, discs, and MIC strips) against gram positive and gram negative microbial isolates. Medical microbiologists use AST results to recommend antibiotic treatment options for infected patients. Product is to be used for research and development only.
• Therapeutic Function: Antibiotic
• Clinical Use: Cefpodoxime proxetil (Vantin) is the isopropyloxycarbonylethylester of the third-generation cephalosporincefpodoxime. This orally active prodrug derivative is hydrolyzedby esterases in the intestinal wall and in theplasma to provide cefpodoxime. Tablets and a powder forthe preparation of an aqueous suspension for oral pediatricadministration are available. The oral bioavailability of cefpodoximefrom the proxetil is estimated to be about 50%.Administration of the prodrug with food enhances its absorption.The plasma half-life is 2.2 hours, which permitsadministration on a twice-daily schedule. Cefpodoxime is a broad-spectrum cephalosporin withuseful activity against a relatively wide range of Grampositiveand Gram-negative bacteria. It is also resistant tomany β-lactamases. Its spectrum of activity includes S.pneumoniae, Streptococcus pyogenes, S. aureus, H. influenzae,M. catarrhalis, and Neisseria spp. Cefpodoxime is alsoactive against members of the Enterobacteriaceae family,including E. coli, K. pneumoniae, and P. mirabilis. It thusfinds use in the treatment of upper and lower respiratory infections,such as pharyngitis, bronchitis, otitis media, andcommunity-acquired pneumonia. It is also useful for thetreatment of uncomplicated gonorrhea.

Technology Process of Vantin

There total 16 articles about Vantin 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: 94.5%

1-iodoethyl isopropyl carbonate (84089-73-6,91508-00-8) + cefpodoxime (80210-62-4) → cefpodoxime proxetil (87239-81-4)

Guidance literature:

cefpodoxime; With 1-butyl-3-methylimidazolium hydroxide; potassium carbonate; In N,N-dimethyl-formamide; at -18 - -15 ℃; for 0.333333h; Inert atmosphere;

1-iodoethyl isopropyl carbonate; In N,N-dimethyl-formamide; for 0.5h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;

Reference yield: 80.5%

1-iodoethyl isopropyl carbonate (84089-73-6,91508-00-8) + cefpodoxime (80210-62-4) → cefpodoxime proxetil (87239-81-4) + 1-(isopropoxycabonyloxy) ethyl (6R, 7R) [7-[2-(2-AMINOTHIAZOL-4-YL)-2-METHOXYIMINO-] [ACETAMIDO]-3-(METHOXYMETHYL) 3-CEPHEM-4-CARBOXYLATE] (339528-86-8)

Guidance literature:

With disodium hydrogenphosphate; sodium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ISOPROPYLAMIDE; at -10 - -5 ℃; for 2.16667h;

Reference yield:

1-[(isopropoxycarbonyl)oxy]ethyl-(6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (96661-80-2) + C13H13N3O5S2 → cefpodoxime proxetil (87239-81-4)

Guidance literature:

With triethylamine; In ethyl acetate; at -30 - 0 ℃; for 0.5h;

DOI:10.1002/ejoc.201900277

upstream raw materials:

(6R,7R)-7-{2-[2-(2-Chloro-acetylamino)-thiazol-4-yl]-2-[(Z)-methoxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-isopropoxycarbonyloxy-ethyl ester

cefotaxime

1-(isopropoxycarbonyloxy)ethyl chloride

1-iodoethyl isopropyl carbonate

Downstream raw materials:

1-(isopropoxycabonyloxy) ethyl (6R, 7R) [7-[2-(2-AMINOTHIAZOL-4-YL)-2-METHOXYIMINO-] [ACETAMIDO]-3-(METHOXYMETHYL) 3-CEPHEM-4-CARBOXYLATE]

Refernces

• 1、 Reddy, Peketi Rajesh,Musunuri, Sivanadh,Reddy, D. Ramasekhara,Chittala, V. Subrahmanyam,Murthy,Krishnamohan. "Synthesis and characterization of novel analogues of cefpodoxime proxetil". . p. 1751 - 1755. Retrieved 2020/07/30.
• 2、 Pieper, Matthias,Schleich, Herbert,Gr?ger, Harald. "General Synthesis of Industrial Cephalosporin-Based Antibiotics Through Amidation with Tosyl Chloride as a Coupling Reagent". . p. 3259 - 3263. Retrieved 2019/06/04.