CID 6560168

Base Information

• Chemical Name: CID 6560168
• CAS No.: 15686-71-2
• Molecular Formula: C₁₆H₁₇N₃O₄S
• Molecular Weight: 347.395
• Hs Code.: 29419000
• Mol file: 15686-71-2.mol

Synonyms:

Chemical Property of CID 6560168

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 3.27E-22mmHg at 25°C
• Melting Point: 196-198 °C
• Refractive Index: 1.6320 (estimate)
• Boiling Point: 727.4°C at760mmHg
• PKA: 5.2, 7.3(at 25℃)
• Flash Point: 393.7°C
• PSA: 138.03000
• Density: 1.5 g/cm³
• LogP: 1.47400
• Storage Temp.: 2-8°C
• Solubility.: NH4OH 1 M: 50 mg/mL, clear, yellow
• Water Solubility.: 微溶于水，不溶于乙醇、氯仿、乙醚。
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 347.09397721
• Heavy Atom Count: 24
• Complexity: 595

Purity/Quality:

99% ^*data from raw suppliers

Cefalexin VETRANAL ^*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: CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)[NH3+])SC1)C(=O)[O-]
• Isomeric SMILES: CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)[NH3+])SC1)C(=O)[O-]
• Description: Cephalexin is a cephalosporin antibiotic that is used to examine the impact of binding, expression, and inhibition of PBP3 as well as additional penicillin-binding proteins (PBPs) on the cell wall during bacterial mucopeptide synthesis. Cephalexin is used for the treatment of infection-causing bacteria that may induce ear, respiratory, urinary tract, and skin infections. Bacteria that are defenseless against Cephalexin may include Streptococcus pneumonia, Staphylococcus aureus, E. coli, and Haemophilus influenza. Cephalexin is also referred to as Keflex (brand name), and it does not relieve viral infections such as flu or colds. Use of the ampicillin-type side chain conveys oral activity to cephalexin. Whereas it no longer has an activating side chain at C-3 and, as a consequence, is somewhat less potent, it does not undergo metabolic deactivation and, thus, maintains potency. It is rapidly and completely absorbed from the GI tract and has become quite popular. Somewhat puzzling is the fact that the use of the ampicillin side chain in the cephalosporins does not result in a comparable shift in antimicrobial spectrum. Cephalexin, like the other first-generation cephalosporins is active against many Gram-positive aerobic cocci but is limited against Gram-negative bacteria. It is a widely used drug, particularly against Gram-negative bacteria causing urinary tract infections, Gram-positive infections (Staphyl ococcus aureus, Streptococcus pneumoni ae and Streptococcus pyogenes) of soft tissues, pharyngitis, and minor wounds.
• Indications: Cephalexin is prescribed for the treatment of otitis media, genitourinary, bone, respiratory, and skin structure infections.
• Uses: Cephalexin is administered to minimize the development of bacteria that are resistant to drugs. To maintain the overall effectiveness of Cephalexin, the drug should be prescribed as a treatment for infections that can be attributed to bacteria. The availability of susceptibility and culture information should be put into consideration while making modifications to antibacterial therapy. The absence of such information may be backed by susceptibility and epidemiology patterns to influence verifiable adoption of treatment. In some cases, Cephalexin is used for the treatment of patients who are allergic to penicillin and may have a heart condition at the time when they are undergoing a procedure on their respiratory tract, to inhibit the development of infection on their heart valves. Antibacterial.
• Therapeutic Function: Antibiotic
• Clinical Use: Cephalexin, 7α-(D-amino-α-phenylacetamido)-3-methylcephemcarboxylicacid (Keflex, Keforal), was designed purposelyas an orally active, semisynthetic cephalosporin. Theoral inactivation of cephalosporins has been attributed to twocauses: instability of the β-lactam ring to acid hydrolysis(cephalothin and cephaloridine) and solvolysis or microbialtransformation of the 3-methylacetoxy group (cephalothin,cephaloglycin). The α-amino group of cephalexin renders itacid stable, and reduction of the 3-acetoxymethyl to a methylgroup circumvents reaction at that site.Cephalexin occurs as a white crystalline monohydrate. Itis freely soluble in water, resistant to acid, and absorbed wellorally. Food does not interfere with its absorption. Becauseof minimal protein binding and nearly exclusive renal excretion,cephalexin is recommended particularly for the treatmentof urinary tract infections. It is also sometimes used forupper respiratory tract infections. Its spectrum of activity isvery similar to those of cephalothin and cephaloridine.Cephalexin is somewhat less potent than these two agentsafter parenteral administration and, therefore, is inferior tothem for the treatment of serious systemic infections. As for group 2 cephalosporins . It should not be used in infections in which H. influenzae is, or is likely to be, implicated. It should not be used as an alternative to penicillin in syphilis.
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: effects of coumarins may be enhanced.

Technology Process of CID 6560168

There total 34 articles about CID 6560168 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: 97.7%

7-ADCA + (R)-phenylglycine hydrochloride (25705-52-6) → cefalexin (15686-71-2,27726-35-8,34632-04-7,79814-91-8,108260-04-4)

Guidance literature:

7-ADCA; With chloro-trimethyl-silane; triethylamine; In dichloromethane; at 20 ℃; for 1h;

(R)-phenylglycine hydrochloride; With N-trifluoroacetoxy succinimide; triethylamine; In dichloromethane; at -5 - 15 ℃; for 3h;

In dichloromethane; water; at 20 ℃; for 1h; pH=2; Reagent/catalyst; pH-value;

Reference yield: 88.2%

cephalexin p-nitrobenzyl ester tosylate salt (39754-01-3) + MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2) → cephalexin bis-DMF solvate + cefalexin (15686-71-2,27726-35-8,34632-04-7,79814-91-8,108260-04-4)

Guidance literature:

In N-methyl-acetamide; water;

Reference yield: 75.0%

N,N'-dimethylbenzylamine (103-83-3) + p-nitrobenzyl 7-aminodesacetoxycephalosporanate + sodium N-(2-methoxycarbonyl-1-methylvinyl)-D-α-phenylglycine + acetoacetic acid methyl ester (105-45-3) + methyl chloroformate (79-22-1) + (S)-sodium 2-phenylglycinate → cefalexin (15686-71-2,27726-35-8,34632-04-7,79814-91-8,108260-04-4)

Guidance literature:

With hydrogenchloride; triethylamine; In N-methyl-acetamide; water;

upstream raw materials:

(6R)-7t-((R)-2-amino-2-phenyl-acetylamino)-3-methylene-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid

(6R)-3-methyl-8-oxo-7t-(trimethylsilanyl-amino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid trimethylsilanyl ester

Boc-D-Phg-OH

(R)-2-(tert-butoxycarbonylamino)-2-(cyclohexa-1,4-dienyl)acetic acid

Downstream raw materials:

(6R,7R)-3-methyl-7-[(R)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid

3-deacetyloxy-7-aminocephalosporanic acid

(R)-phenylglycine

(6R,7R)-7-[(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Refernces

• 1、 -. "PROCESS FOR THE PRODUCTION OF CEPHALOSPORINS". Page/Page column 12. . Retrieved 2012/03/27.
• 2、 Blum, Janna K.,Bommarius, Andreas S.. "Amino ester hydrolase from Xanthomonas campestris pv. campestris, ATCC 33913 for enzymatic synthesis of ampicillin". experimental part. p. 21 - 28. Retrieved 2010/12/19.