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Amoxicillin

CAS# 26787-78-0

Amoxicillin

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Chemical structure

Amoxicillin

3D structure

Chemical Properties of Amoxicillin

Cas No. 26787-78-0 SDF Download SDF
PubChem ID 33613 Appearance Powder
Formula C16H19N3O5S M.Wt 365.4
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Amoxicillin anhydrous
Solubility DMSO : 100 mg/mL (273.67 mM; Need ultrasonic)
H2O : 2 mg/mL (5.47 mM; Need ultrasonic)
Chemical Name (2S,5R,6R)-6-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C
Standard InChIKey LSQZJLSUYDQPKJ-NJBDSQKTSA-N
Standard InChI InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Amoxicillin

DescriptionAmoxicillin is a moderate- spectrum, bacteriolytic, β-lactam antibiotic. Target: Antibacterial Amoxicillin is a moderate-spectrum, bacteriolytic, β-lactam antibiotic in the aminopenicillin family used to treat bacterial infections caused by susceptible Gram-positive and Gram-negative microorganisms. It is usually the drug of choice within the class because it is better-absorbed, following oral administration, than other β-lactam antibiotics. Amoxicillin is susceptible to degradation by β-lactamase-producing bacteria, which are resistant to a narrow spectrum of β-lactam antibiotics, such as penicillin. For this reason, it is often combined with clavulanic acid, a β-lactamase inhibitor. This increases effectiveness by reducing its susceptibility to β-lactamase resistance. From Wikipedia.

References:
[1]. http://en.wikipedia.org/wiki/Amoxicillin

Amoxicillin Dilution Calculator

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Preparing Stock Solutions of Amoxicillin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7367 mL 13.6836 mL 27.3673 mL 54.7345 mL 68.4182 mL
5 mM 0.5473 mL 2.7367 mL 5.4735 mL 10.9469 mL 13.6836 mL
10 mM 0.2737 mL 1.3684 mL 2.7367 mL 5.4735 mL 6.8418 mL
50 mM 0.0547 mL 0.2737 mL 0.5473 mL 1.0947 mL 1.3684 mL
100 mM 0.0274 mL 0.1368 mL 0.2737 mL 0.5473 mL 0.6842 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Amoxicillin

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References on Amoxicillin

A combination of mecillinam and amoxicillin/clavulanate can restore susceptibility of high-level TEM-1-producing Escherichia coli to mecillinam.[Pubmed:28369441]

J Antimicrob Chemother. 2017 Jul 1;72(7):1911-1914.

Objectives: Mecillinam is recommended in France as a first-line treatment for lower urinary tract infections, due to the large increase in resistance of Escherichia coli to other oral treatments, such as co-trimoxazole or fluoroquinolones, its limited impact on faecal microbiota and its stability in the presence of numerous beta-lactamases. However, we recently identified several mecillinam-resistant E. coli isolates with a high-level expression penicillinase (HEP) phenotype that merit further study. Patients and methods: We studied two isogenic clinical isolates from one patient (one susceptible to mecillinam and one resistant to mecillinam) by WGS to determine the mechanism of mecillinam resistance and compared it with other mecillinam-resistant E. coli . We evaluated the synergistic combination of Amoxicillin/clavulanate and mecillinam using a simple test, suitable for daily laboratory practice, to determine the MIC of this combination. Results: We showed that the presence of an SNP in the promoter of the plasmidic TEM-1 beta-lactamase gene is sufficient to confer resistance to mecillinam. This mechanism was present in 67% of HEP-phenotype E. coli tested. Combining mecillinam with Amoxicillin/clavulanate abolished resistance, with an MIC compatible with clinical use. This association was not sensitive to the inoculum effect, in contrast to mecillinam alone. Conclusions: An HEP phenotype can confer mecillinam resistance in vitro . This resistance is abolished, regardless of the inoculum, by combining mecillinam with Amoxicillin/clavulanate, and can be easily tested in the laboratory. This combination may be used as an oral relay treatment of non-complicated pyelonephritis due to multiresistant E. coli strains.

Controlled release of antibiotic amoxicillin drug using carboxymethyl cellulose-cl-poly(lactic acid-co-itaconic acid) hydrogel.[Pubmed:28344094]

Int J Biol Macromol. 2017 Aug;101:612-620.

In this paper, microwave assisted preparation of carboxymethyl cellulose-cl-poly(lactic acid-co-itaconic acid) (CMC-cl-P(LA-co-IA)) hydrogel was reported via facile graft copolymerization using N,N(1)-methylene-bis-acrylamide (MBA) and potassium persulphate as cross linker and initiator. Different reaction parameters were optimized to achieve good yield. The formation of hydrogel was confirmed by characterization techniques such as Fourier transform infrared spectroscopy, field emission scanning electron microscopy, X-ray diffraction, thermo gravimetric analysis, transmission electron microscopy etc. The antimicrobial activities of the hydrogel were studied against Staphylococcus aureus and Escherichia coli. About 95% killing of bacteria was recorded after 24h. The controlled release of Amoxicillin drug from hydrogel was evaluated as a function of pH and time. Maximum drug release of 98% was recorded at 2.2 pH after 7h. The kinetic studies showed non-Fickian diffusion of the drug.

A Case of Amoxicillin-Induced Acute Generalized Exanthematous Pustulosis Presenting as Septic Shock.[Pubmed:28358593]

J Cutan Med Surg. 2017 Jul/Aug;21(4):351-355.

This case report demonstrates the challenges of diagnosing and managing acute generalized exanthematous pustulosis (AGEP) presenting as septic shock. The disseminated, erythematous, pustular rash is a common feature. However, extensive organ involvement and life-threatening hypotension are unusual. The constellation of signs has not previously been documented following Amoxicillin therapy. Toxic epidermal necrolysis (TEN) and toxic shock syndrome (TSS) were considered in addition to AGEP because of the systemic presentation. AGEP was diagnosed following histopathology (TEN was ruled out based on limited necrotic keratinocytes and lack of epidermal necrosis) and a negative antistreptolysin O titer (eliminated TSS). Antibiotic therapy for septic shock was provided before the diagnosis was confirmed as AGEP. Upon confirmation of the AGEP diagnosis, antibiotics were discontinued and a 5-day course of oral prednisone (40 mg/d) was initiated in addition to topical half-strength (0.05%) betamethasone valerate. The patient rapidly improved and was discharged. Outpatient patch testing confirmed Amoxicillin as the culprit drug. In conclusion, it is critical to realize that AGEP cannot be ruled out with a septic shock presentation. Recent drug history is critical in recognizing an adverse drug reaction, and patch testing is useful for determining the culpable drug when the diagnosis is AGEP.

Determinants of initiation, implementation, and discontinuation of amoxicillin by adults with acute cough in primary care.[Pubmed:28352162]

Patient Prefer Adherence. 2017 Mar 15;11:561-569.

AIM: To investigate the determinants of adherence to Amoxicillin in patients with acute lower respiratory tract infection. MATERIALS AND METHODS: Three European data sets were used. Adherence data were collected using self-reported diaries. Candidate determinants included factors relating to patient, condition, therapy, health care system/provider, and the study in which the patient participated. Logistic and Cox regression models were used to investigate the determinants of initiation, implementation, and discontinuation of Amoxicillin. RESULTS: Although initiation differed across samples, implementation and discontinuation were similar. Determinants of initiation were days waited before consulting, duration of prescription, and being in a country where a doctor-issued sick certificate is required for being off work for <7 days. Implementation was higher for older participants or those with abnormal auscultation. Implementation was lower for those prescribed longer courses of Amoxicillin (>/=8 days). Time from initiation to discontinuation was longer for longer prescriptions and shorter for those from countries where single-handed practices were widespread. CONCLUSION: Nonadherence to Amoxicillin was largely driven by noninitiation. Differing sets of determinants were found for initiation, implementation, and discontinuation. There is a need to further understand the reasons for these determinants, the impact of poor adherence to antibiotics on outcomes, and to develop interventions to improve antibiotic use when prescribed.

Description

Amoxicillin is an antibiotic with good oral absorption and broad spectrum antimicrobial activity.

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