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APALCILLIN

APALCILLIN Structure
APALCILLIN
  • CAS No.63469-19-2
  • Chemical Name:APALCILLIN
  • CBNumber:CB7151479
  • Molecular Formula:C25H23N5O6S
  • Formula Weight:521.54
  • MOL File:63469-19-2.mol
APALCILLIN Property
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal word
  • Hazard statements
  • Precautionary statements

APALCILLIN Chemical Properties,Usage,Production

  • Originator Lumota,Thomae,W. Germany,1982
  • Uses Antibacterial.
  • Definition ChEBI: Apalcillin is a penicillin and a 1,5-naphthyridine derivative. It is a conjugate acid of an apalcillin(1-).
  • Manufacturing Process (a) Preparation of 6-D-α-aminobenzylpenicillin phenacyl ester: To a suspension of phenacyl 6-aminopenicillanate hydrochloride (1.85 g) and Dphenylglycyl chloride hydrochloride (1.29 g) in dichloromethane (20 ml), sodium bicarbonate (1.05 g) was added, and the resultant mixture was stirred while cooling with ice for 6 hours. The reaction mixture was filtered to eliminate the by-produced sodium chloride. The filtrate was admixed with isopropanol and concentrated under reduced pressure by the aid of a rotary evaporator. After the evaporation of dichloromethane, the precipitate was collected by filtration to give the objective compound in the form of the hydrochloride (2.19 g) MP 142° to 148°C (decomposition).
    (b) Preparation of D-α-(4-hydroxy-1,5-naphthyridine-3- carbonamido)benzylpenicillin: To a solution of 6-D-α-aminobenzylpenicillin phenacyl ester (hydrochloride) (2.01 g) and triethylamine (0.808 g) in dimethylformamide (20 ml), 4-hydroxy-1,5-naphthyridine-3-carboxylic acid Nsuccinimide ester [MP 310° to 311°C (decomposition)] (1.15 g) was added while cooling with ice, and the resultant mixture was stirred for 1 hour. Stirring was further continued at room temperature for 2 hours. After cooling with ice, 1% sodium bicarbonate solution (100 ml) was added thereto. The precipitated crystals were collected by filtration, washed with water and dried over phosphorus pentoxide to give D-(α-4-hydroxy-1,5-naphthyridine-3- carboxamido)benzylpenicillin phenacyl ester (2.17 g).
    The above product was dissolved in dimethylformamide (65 ml), sodium thiophenoxide (0.89 g) was added thereto, and the resultant mixture was stirred at room temperature for 1 hour. To the resultant mixture, acetone (650 ml) was added, and the separated crystals were collected by filtration and washed with acetone and ether in order to give the objective compound in the form of the sodium salt (1.3 g).
    In the above procedure, the use of 4-hydroxy-1,5-naphthyridine-3-carbonyl chloride in place of 4-hydroxy-1,5-naphthyridine-3-carboxylic acid Nsuccinimide ester can also afford the same objective compound as above. The use of sodium thio-n-propoxide in place of sodium thiophenoxide can also give the objective compound in the form of the sodium salt.
  • Therapeutic Function Antibacterial
  • Antimicrobial activity A semisynthetic acylaminopenicillin supplied as the sodium salt for parenteral administration. The antibacterial spectrum and toxicity profile are similar to those of the acylureidopenicillins. It is relatively labile to many β-lactamases, including the common TEM plasmid-mediated enzyme. It has very limited commercial availability.
APALCILLIN Preparation Products And Raw materials
Raw materials
Preparation Products
APALCILLIN Suppliers
Global(9)Suppliers
  • Supplier：
    Henan Tianfu Chemical Co.,Ltd.
  • Tel：+86-0371-55170693<br/>+86-19937530512
  • Email：info@tianfuchem.com
  • Country：China
  • ProdList：21628
  • Advantage：55
APALCILLIN Spectrum
63469-19-2, APALCILLINRelated Search:
  • C25H23N5O6S
  • 63469-19-2
  • APALCILLIN USP/EP/BP
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-[[(4-hydroxy-1,5-naphthyridin-3-yl)carbonyl]amino]-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
  • Lumota
  • Apalcilline
  • Apalcilina [inn-spanish]
  • Apalcilina
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2R)-(((4-hydroxy-1,5-naphthyridin-3-yl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((((4-hydroxy-1,5-naphthyridin-3-yl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2-alpha,5-alpha,6-beta(S*)))-
  • (6R)-6-((R)-2-(4-Hydroxy-1,5-naphthyridin-3-carboxamido)-2-phenylacetamido)penicillansaeure
  • (2S,5R,6R)-6-((R)-2-(4-Hydroxy-1,5-naphthyridin-3-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-5-thia-1-azabicyclo(3.2.0)heptan-2-carboxylic acid
  • (2S,5R,6R)-6-((R)-2-(4-Hydroxy-1,5-naphthyridin-3-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-5-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure
  • 6α-[(R)-2-[(4-Hydroxy-1,5-naphthyridin-3-yl)carbonylamino]-2-phenylacetylamino]penicillanic acid
  • (2S,5R,6R)-6α-[[(R)-(4-Hydroxypyrido[3,2-b]pyridin-3-ylcarbonylamino)phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid
  • APALCILLIN
  • 5-alpha,6-beta(s*)))-ph
  • 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,6-(((((4-hydroxy-1,5-napht
  • 3-dimethyl-7-oxo-hyridin-3-yl)carbonyl)amino)phenylacetyl)amino)-(2s-(2-al

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