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Aspoxicillin

Aspoxicillin Structure
Aspoxicillin
  • CAS No.63358-49-6
  • Chemical Name:Aspoxicillin
  • CBNumber:CB1452855
  • Molecular Formula:C21H27N5O7S
  • Formula Weight:493.53
  • MOL File:63358-49-6.mol
Aspoxicillin Property
  • Melting point 195-198° (dec)
  • Boiling point 985.1±65.0 °C(Predicted)
  • Density 1.51±0.1 g/cm3(Predicted)
  • storage temp. 2-8°C
  • solubility DMSO (Slightly, Sonicated), Methanol (Slightly)
  • pka 2.44±0.50(Predicted)
  • form Solid
  • color White to Off-White
  • Water Solubility Water : 25 mg/mL (50.66 mM; Need ultrasonic)
  • Stability Hygroscopic
  • CAS DataBase Reference 63358-49-6
  • FDA UNII 0745KNO26J
  • ATC code J01CA19
Safety
  • Hazard Codes  :Xi
  • Risk Statements  :36/37/38
  • Safety Statements  :26
  • WGK Germany  :3
  • RTECS  :MB7548000
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H315-H319-H335
  • Precautionary statements P261-P305+P351+P338

Aspoxicillin Chemical Properties,Usage,Production

  • Description Aspoxicillin is an injectable, amino acid-type penicillin highly active against Gram-positive and Gram-negative bacteria, including the β-lactamase producing Bacillus frugilis. It is reportedly effective in the treatment of peritonitis, pneumonia and bronchitis.
  • Originator Tanabe (Japan)
  • Uses Aspoxicillin is a broad-spectrum antibiotic.
  • Definition ChEBI: Aspoxicillin is a peptide.
  • Manufacturing Process 1). 3 g (23.6 millimoles) of D-2-amino-3-N-methylcarbamoyl-propionic acid hydrochloride (D-N'-methylasparagine HCl), 4.5 g of benzyloxycarbonyl chloride, 30 g of water, 30 ml of tetrahydrofuran and 12 g of potassium carbonate are mixed at 5° to 10°C. Then, the mixture is stirred at the same temperature for 2 hours. During the reaction, the mixture is kept at a slightly alkaline pH (pH 8) with potassium carbonate. 10 ml of water are added to the reaction mixture, and insoluble materials are filtered off. The filtrate is washed twice with ethyl acetate, acidified with citric acid and then extracted three times with 50 ml of ethyl acetate. The ethyl acetate extracts are washed with water, dried and evaporated to remove solvent. 5.1 g of D-2- benzyloxycarbonylamino-3-N-methylcarbamoyl-propionic acid are obtained. MP: 142°-143°C.
    2). 2.8 g (10 millimoles) of D-2-benzyloxycarbonylamino-3-Nmethylcarbamoyl- propionic acid, 2.27 g of dicyclohexylcarbodiimide, 1.27 g of N-hydroxysuccinimide and 120 ml of tetrahydrofuran are mixed at 0° to 5°C, and the mixture is stirred at the same temperature for 16 hours. Insoluble materials are filtered off. Then, the filtrate is evaporated at 20°C under reduced pressure to remove the solvent, and the crystalline precipitates thus obtained are washed with a mixture of benzene-ether. 2.6 g of N-(D-2- benzyloxycarbonylamino-3-N-methylcarbamoyl-propionyloxy)succinimide are obtained. MP: 132°-134°C.
    3). 3.75 g of N-(D-2-benzyloxycarbonylamino-3-Nmethylcarbamoylpropionyloxy) succinimide are dissolved in 50 ml of tetrahydrofuran. 12.5 ml of an aqueous 1 N-sodium hydroxide solution containing 2.3 g of p-hydroxy-D-phenylglycine are added to the solution. The mixture is stirred at room temperature for 24 hours. 20 ml of ethyl acetate and 20 ml of water are added to the reaction mixture, and said mixture is shaken. Then, the aqueous layer is separated, adjusted to pH 3 with citric acid and extracted with a mixture of 20 ml of tetrahydrofuran and 10 ml of ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue thus obtained is washed with ether. 3.0 g of D-2-(D-2- benzyloxycarbonylamino-3-N-methylcarbamoylpropionamido)- 2-phydroxyphenylacetic acid are obtained as colorless crystalline powder. MP: 154°-156°C(decomp.).
    4). 429 mg of D-2-(D-2-benzyloxycarbonylamino-3-Nmethylcarbamoylpropionamido)- 2-p-hydroxyphenylacetic acid and 382 mg of 6-aminopenicillanic acid triethylamine salt are dissolved in 10 ml of dimethylformamide. 303 mg of diphenylphosphoric azide [N3PO(OC6H5)2] and 110 mg of triethylamine are added to the solution at -5°C, and the mixture is stirred at -5°C for 15 hours. After the reaction, the mixture is adjusted to pH 3 with an aqueous 5% citric acid solution and extracted with a mixture of 15 ml of tetrahydrofuran and 10 ml of ethyl acetate. The extract is washed with water, dried and then evaporated at below 40°C to remove the solvent. Ether is added to the residue obtained, and precipitates are collected by filtration. 509 mg of 6-[D-2-(D-2-benzyloxycarbonylamino-3-Nmethylcarbamoylpropionamido)- 2-p-hydroxyphenylacetamido]penicillanic acid are obtained as a colorless powder.
    5). 627 mg of 6-[D-2-(D-2-benzyloxycarbonylamino-3-N-methylcarbamoylpropionamido)- 2-p-hydroxyphenylacetamido]penicillanic acid and 400 mg of 30% palladium-BaCO3 are suspended in 10 ml of methanol. The suspension is shaken at room temperature for 30 minutes. Said shaking step is carried out in a hydrogen gas atmosphere under atmospheric pressure. After the reaction is completed, the catalysts are removed by filtration. The filtrate is evaporated at below 40°C to remove the solvent, and ether is added to the residue. Then, a colorless crystalline powder is collected by filtration and washed with tetrahydrofuran. 443 mg of 6-[D-2-(D-2-amino-3-N-methylcarbamoylpropionamido)- 2-p-hydroxyphenylacetamido]penicillanic acid are obtained. MP: 198°-201°C(decomp.).
  • brand name Doyle
  • Therapeutic Function Antibiotic
  • Antimicrobial activity An acylaminopenicillin, synthesized from amoxicillin. It is more active than carbenicillin against Ps. aeruginosa and is less active than piperacillin against Staph. aureus, H. influenzae, the Enterobacteriaceae and Ps. aeruginosa. It is not absorbed when dosed orally; the plasma half-life is 87 min after intravenous infusion.
    Aspoxicillin has been used in the treatment of respiratory, skin and soft tissue and urinary infections in adults and children, and, in combination with aminoglycosides, against gynecological infections and infections in patients with hematological disorders.
Aspoxicillin Preparation Products And Raw materials
Raw materials
Preparation Products
Aspoxicillin Suppliers
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Aspoxicillin Spectrum
63358-49-6, AspoxicillinRelated Search:
  • Pharmacology Standards
  • OthersAnalytical Standards
  • Chromatography
  • Chemical Structure
  • Alphabetic
  • A
  • AR to AZAntibiotics
  • 抑制剂
  • 医药原料
  • 药物
  • 抗生素
  • β-内酰胺类抗生素
  • C21H27N5O7S3H2O
  • C21H27N5O7S
  • 91878-06-9
  • 阿朴西林/天冬西林
  • 天冬西林
  • ASPOXICILLIN 标准品
  • 阿扑西林
  • 天冬羟氨霉素
  • (2S,5R,6R)-6-[(2R)-2-[(2R)-2-氨基-3-(甲氨基甲酰基)丙酰胺基]-2-(4-羟基苯基)乙酰胺基]-3,3-二甲基-7-氧代-4-硫杂-1-氮杂双环[3.2.0]庚烷-2-羧酸
  • 天冬羟氨青霉素
  • 羟戊酰胺青霉素
  • 萘啶青霉素
  • 阿扑西林三水酸
  • 阿帕西林
  • 阿朴西林
  • (2S,5R,6R)-6-[(2R)-2-[(2R)-2-氨基-3-(N-甲基氨基甲酰)-丙酰胺基]-2-(4-羟基苯基)乙酰胺基]-3,3-二甲基-7-氧代-4-硫-1-氮杂双环[3.2.0]庚烷-2-羧酸三水物
  • 63358-49-6
  • C10305500 Aspoxicillin
  • Aspoxicillin,inhibit,pleuropneumoniae,Inhibitor,penicillin,Actinobacillus,antimicrobial,Bacterial
  • Benzenemethanamine,N-2-propen-6-yl-
  • Aspoxicillin (~80%)
  • Aspoxicillin USP/EP/BP
  • N4-Methyl-D-aspariginylamoxicillin
  • N4-Methyl-D-Asn-4-hydroxy-D-phenyl Gly-N-[(2S,5β)-2β-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6α-yl]-NH2
  • 6α-[(R)-2-(4-Hydroxyphenyl)-2-[[(2R)-3-(methylcarbamoyl)-2-aminopropanoyl]amino]acetylamino]penicillanic acid
  • (2S,5R,6R)-6α-[[(R)-[[(2R)-2-Amino-4-(methylamino)-1,4-dioxobutyl]amino](4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid
  • (2S，5R，6R)-6-[(2R)-2-[(2R)-2-Amino-3-(methylearbamoyl)propionamido]-2-(ρ-hydroxyphenyl)acetamido]-3，3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • DOYE
  • ASPC
  • ASPOXICILLIN 3-HYDRATE
  • TA 058
  • Glycinamide, N-methyl-D-asparaginyl-N-[(2S,5R,6R)-2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl]-2-(4-hydroxyphenyl)-, (2R)-
  • Glycinamide, N-methyl-D-asparaginyl-N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-D-2-(4-hydroxyphenyl)-, [2S-(2a,5a,6b)]-
  • Doyle
  • Aspoxicilin
  • zabicyclo(3.2.0)hept-6-yl)-d-2-(4-hydroxyphenyl)-,(2s-(2-alpha,5-alpha,6-beta)
  • n(sup4)-methyl-d-asparagininylamoxicillin
  • glycinamide,n-methyl-d-asparaginyl-n-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-a
  • (2s,5r,6r)-6-[(2r)-2-[(2r)-2-amino-3-(n-methylcarbamoyl)-propionamido]-2-(p-hydroxyphenyl)acetamido]-3,3-dimehtyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate
  • ASPOXICILLIN

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