Pharmakon1600-01500168

Base Information

• Chemical Name: Pharmakon1600-01500168
• CAS No.: 38821-53-3
• Molecular Formula: C₁₆H₁₉N₃O₄S
• Molecular Weight: 349.411
• Hs Code.: 29419054
• NSC Number: 756672
• ChEMBL ID: CHEMBL3039443
• Mol file: 38821-53-3.mol

Synonyms:Spectrum_001279;Spectrum2_001234;Spectrum3_000334;Spectrum4_000271;Spectrum5_000673;BSPBio_001967;KBioGR_000762;KBioSS_001759;SPECTRUM1500168;SPBio_001108;CHEMBL3039443;SCHEMBL16072830;KBio2_001759;KBio2_004327;KBio2_006895;KBio3_001187;HMS1920M11;HMS2091A18;Pharmakon1600-01500168;CCG-39136;NSC756672;NCGC00178890-01;AB01562926_01;SR-05000002032;SR-05000002032-1

Chemical Property of Pharmakon1600-01500168

Chemical Property:

• Appearance/Colour: Solid
• Melting Point: 140-142 °C
• Refractive Index: 1.684
• Boiling Point: 693.1 °C at 760 mmHg
• PKA: 2.63, 7.27(at 25℃)
• Flash Point: 373 °C
• PSA: 138.03000
• Density: 1.47 g/cm³
• LogP: 1.37770
• Storage Temp.: Store at 0-5°C
• Solubility.: 1 M NH4OH: soluble50mg/mL
• Water Solubility.: Soluble in water
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 349.10962727
• Heavy Atom Count: 24
• Complexity: 697

Purity/Quality:

99% ^*data from raw suppliers

Cephradine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-42/43-20/21/22
• Safety Statements: 26-36-45-36/37-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(N2C(C(C2=O)NC(=O)C(C3=CCC=CC3)N)SC1)C(=O)O
• Isomeric SMILES: CC1=C(N2C([C@@H](C2=O)NC(=O)[C@@H](C3=CCC=CC3)N)SC1)C(=O)O
• Description: Cefradine is an orally bioavailable β-lactam cephalosporin antibiotic. It is active against S. pyogenes, E. coli, K. pneumoniae, and E. cloacae (MICs = 0.04, 9.4, 9.4, and 6.3 μg/ml, respectively). Cefradine is also active against clinical isolates of S. aureus (MICs = 0.8-6 μg/ml) and S. pyogenes (MICs = 0.1-0.4 μg/ml), as well as H. influenzae, E. coli, and K. pneumoniae (MICs = 6.2-12.5 μg/ml). It increases survival in mouse models of systemic lethal infection by S. pyogenes, E. coli, K. pneumoniae, or E. cloacae (ED50s = 5, 37, 122, and 50 mg/kg, respectively), as well as by penicillin-susceptible or -resistant strains of S. aureus (ED50s = 18 and 91 mg/kg, respectively). Formulations containing cefradine have previously been used in the treatment of respiratory and urinary tract infections, skin infections, and otitis media. This drug is very similar to cephalexin in its antimicrobial activity and in most other respects (Moellering and Swartz, 1976). Unlike cephalexin, for which a parenteral preparation is not generally available, cephradine is marketed in some countries (for example, Portugal) for both oral and parenteral use. In cephradine, an interesting drug design device has been used. The aromatic ring in the ampicillin side chain has been partially hydrogenated by a Birch reduction such that the resulting molecule is still planar and π-electron excessive but has no conjugated olefinic linkages. It is comparatively acid stable and, therefore, is rapidly and nearly completely absorbed from the GI tract. Cephradine has the useful characteristic that it can be used both orally and IM so that parenteral therapy can be started in an institutional setting and then the patient can be sent home with the oral form, thus avoiding the risk of having to establish a different antibiotic. This is consistent with the present economics requiring sending patients home earlier than some physicians prefer. Unfortunately, however, for other reasons the IM and intravenous (IV) versions of cephradine are no longer available in the United States.
• Uses: Cephalosporin antibacterial. Cephradine is a first generation cephalosporin antibiotic. Cephradine has broad spectrum of bactericidal activity against infections caused by Streptococcus, Staphylococcus, Diplococcus pneumoniae, Es cherichia, Klebsiella, Salmonella, and indole-negative Proteus. A semi-synthetic cephalosporin antibiotic that is used to study the effect of expression, binding, and inhibition of PBP3 and other penicillin-binding proteins (PBPs) on bacterial cell wall mucopeptide synthesis
• Therapeutic Function: Antibiotic
• Clinical Use: Cephradine (Anspor, Velosef) is the only cephalosporinderivative available in both oral and parenteral dosageforms. It closely resembles cephalexin chemically (it maybe regarded as a partially hydrogenated derivative ofcephalexin) and has very similar antibacterial and pharmacokineticproperties.It occurs as a crystalline hydrate that is readily soluble inwater. Cephradine is stable to acid and absorbed almostcompletely after oral administration. It is minimally proteinbound and excreted almost exclusively through the kidneys.It is recommended for the treatment of uncomplicated urinarytract and upper respiratory tract infections caused bysusceptible organisms. Cephradine is available in both oraland parenteral dosage forms.
• Drug interactions: Potentially hazardous interactions with other drugsAnticoagulants: effects of coumarins may be enhanced.

Technology Process of Pharmakon1600-01500168

There total 9 articles about Pharmakon1600-01500168 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: 95.0%

cephradine/α-naphthol complex → Cefradine (30959-67-2,38821-53-3,52842-45-2)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; at 5 ℃; for 0.5h; pH=4;

DOI:10.1002/1099-0690(200105)2001:10<1817::AID-EJOC1817>3.0.CO;2-C

Reference yield: 17.4%

3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) + methyl (R)-2-amino-2-(cyclohexa-1,4-dien-1-yl)acetate hemisulfuric acid salt → Cefradine (30959-67-2,38821-53-3,52842-45-2)

Guidance literature:

With ammonium hydroxide; sulfuric acid; In water; at 5 ℃; pH=6-6.9; Enzymatic reaction;

Reference yield:

3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) + dihydrophenylglycine acid chloride hydrochloride → Cefradine (30959-67-2,38821-53-3,52842-45-2)

Guidance literature:

3-deacetyloxy-7-aminocephalosporanic acid; With N-methyl-acetamide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 45 ℃; for 2h; Inert atmosphere; Reflux;

dihydrophenylglycine acid chloride hydrochloride; In dichloromethane; at -5 - 0 ℃; for 2h;

With hydrogenchloride; In dichloromethane; water; at 2 - 10 ℃; for 0.25h;

upstream raw materials:

(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

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

N-tert-butyloxycarbonylcefradine

3-deacetyloxy-7-aminocephalosporanic acid

Refernces

• 1、 -. "SALT OF DIHYDROPHENYLGLYCINE METHYL ESTER". Page/Page column 11. . Retrieved 2017/02/28.
• 2、 -. "MANUFACTURING METHOD AND APPARATUS OF ULTRAFINE PARTICLES HAVING UNIFORM PARTICLE SIZE DISTRIBUTION". . . Retrieved 2011/09/14.