Aspoxicillin

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Aspoxicillin
Category Antibiotics
Catalog number BBF-00569
CAS 63358-49-6
Molecular Weight 493.53
Molecular Formula C21H27N5O7S
Purity >98%

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BBF-00569 100 mg $439 In stock

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Description

Aspoxicillin is a semi-synthetic penicillin prepared from 6-aminopenicillanic acid (6-APA) or Amoxicillin. It has a broad antibacterial spectrum and has an effect on Pseudomonas aeruginosa.

Specification

Synonyms Aspoxicilina; Aspoxicilline; Aspoxicillinum
Storage Store at -20°C
IUPAC Name (2S,5R,6R)-6-[[(2R)-2-[[(2R)-2-amino-4-(methylamino)-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Canonical SMILES CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)NC(=O)C(CC(=O)NC)N)C(=O)O)C
InChI InChI=1S/C21H27N5O7S/c1-21(2)15(20(32)33)26-18(31)14(19(26)34-21)25-17(30)13(9-4-6-10(27)7-5-9)24-16(29)11(22)8-12(28)23-3/h4-7,11,13-15,19,27H,8,22H2,1-3H3,(H,23,28)(H,24,29)(H,25,30)(H,32,33)/t11-,13-,14-,15+,19-/m1/s1
InChI Key BHELIUBJHYAEDK-OAIUPTLZSA-N

Properties

Appearance Colorless Crystal Powder
Antibiotic Activity Spectrum bacteria
Boiling Point 985.1°C at 760 mmHg
Melting Point 195-198°C (dec.)
Density 1.51 g/cm3
Solubility Soluble in DMSO

Reference Reading

1.[Positive seroconversion syphilis in a patient with acute lymphocytic leukemia after allogeneic bone marrow transplantation].
Naohara T1, Suzuki G, Masauzi N, Ohizumi H, Kobayashi N, Ogasawara M, Kiyama Y, Saitoh M, Higa Y, Kasai M. Rinsho Ketsueki. 1997 Mar;38(3):228-30.
An acute lymphocytic leukemia patient underwent allogeneic bone marrow transplantation (BMT) from a sibling who was serologically positive for syphilis. After the donor was administered antibiotic therapy, the titration of treponema pallidum hemagglutination (TPHA) decreased from x1260 to x320. Thereafter, the graft consisting of mononuclear cells was transplanted. TPHA of the recipient turned positive on day +63, but became negative 1.5 years after BMT. Although the cause of the seroconversion of TPHA seemed to be the contamination of treponema to the graft, the adoptive transfer could not be ruled out as an another possible cause.
2.[Revaluation of current antimicrobials. Series 23: aspoxicillin].
Iwai S, Shishido H. Jpn J Antibiot. 1994 Dec;47(12):1621-8.
3.Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae.
Yoshimura H1, Takagi M, Ishimura M, Endoh YS. Vet Res Commun. 2002 Jan;26(1):11-9.
Sixteen antimicrobial agents were tested for their activity against 68 isolates of Actinobacillus pleuropneumoniae by determining the minimum inhibitory concentrations (MICs). Ceftiofur and the fluoroquinolones danofloxacin and enrofloxacin were the most active compounds, with a MIC for 90% of the isolates (MIC90) of (0.05 microg/ml. The MIC90 values of benzylpenicillin, amoxicillin and aspoxicillin were 0.78 units/ml, 0.39 microg/ml and < or = 0.05 microg/ml, respectively. Three isolates (4.4%) were resistant to penicillins, but aspoxicillin was as active as ceftiofur against the susceptible isolates, with MICs of < or = 0.05 microg/ml for all isolates. Resistance to oxytetracycline, chloramphenicol and thiamphenicol occurred in 22 (32.4%), 14 (20.6%) and 15 (22.1%) of the isolates, respectively. Doxycycline was more active than oxytetracycline, with a MIC90 of 1.56 microg/ml as against 25 microg/ml. Florfenicol was not only as active as thiamphenicol, with a MIC for 50% of the isolates (MIC50) of 0.
4.Incidence of diarrhea with antibiotics and the increase of clostridia in rabbits.
Hara-Kudo Y1, Morishita Y, Nagaoka Y, Kasuga F, Kumagai S. J Vet Med Sci. 1996 Dec;58(12):1181-5.
Rabbits were treated with a single intravenous injection of various antibiotics. More than 40 per cent of the animals showed diarrhea after being treated with sulbactam/cefoperazone, cefmetazole, clindamycin, piperacillin or aspoxicillin. Clostridium difficile was isolated from sulbactam/cefoperazone-treated diarrheic rabbits, with their cecal contents showing positive reaction in a latex agglutination test for C. difficile enterotoxin. However, 27 cefmetazole-induced diarrheic cases were not associated with C. difficile. Other enteropathogenic bacteria, such as Campylobacter spp., Bacillus cereus, enteropathogenic Escherichia coli, coagulase positive Staphylococcus aureus, Salmonella spp., Vibrio spp., Clostridium perfringens and Clostridium spiroforme, were not isolated from either of diarrheic rabbit. However, the counts of clostridia remarkably increased in the intestine of cefmetazole-associated diarrheic rabbits. This was ascribed to the overgrowth of Clostridium innocuum and Clostridium sporogenes.

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