Nafcillin SodiumCAS# 7177-50-6 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 7177-50-6 | SDF | Download SDF |
| PubChem ID | 23704143 | Appearance | Powder |
| Formula | C21H23N2NaO6S | M.Wt | 454.47 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | DMSO : 100 mg/mL (220.04 mM; Need ultrasonic) H2O : 1 mg/mL (2.20 mM; Need ultrasonic) | ||
| Chemical Name | sodium;(2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrate | ||
| SMILES | CCOC1=C(C2=CC=CC=C2C=C1)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)[O-].O.[Na+] | ||
| Standard InChIKey | OCXSDHJRMYFTMA-KMFBOIRUSA-M | ||
| Standard InChI | InChI=1S/C21H22N2O5S.Na.H2O/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23;;/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27);;1H2/q;+1;/p-1/t15-,16+,19-;;/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. |
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| 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. |
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| 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. | ||
| Description | Nafcillin sodium monohydrate is a semi-synthetic antibiotic related to penicillin.
Target: Antibacterial
Nafcillin sodium is a narrow-spectrum, beta-lactam antibiotic of the penicillin class. As a beta-lactamase-resistant penicillin, it is used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins. Nafcillin is considered therapeutically equivalent to oxacillin, although its safety profile is somewhat different. Nafcillin was shown to reversibly inhibit beta-lactamase from Staphylococcus aureus PC1 with characteristics indicative of a type A inhibitor [Citri, Samuni & Zyk (1976) Proc. Natl. Acad. Sci. U.S.A. 73, 1048-1052]. At nafcillin concentrations above 80 mM, complete inactivation occurred within 200 s. Upon removal of the excess nafcillin the inhibited enzyme was re-activated completely, with a rate constant of 2.0 x 10(-3) s-1 (25 degrees C) [1, 2]. References: | |||||
Nafcillin Sodium Dilution Calculator
Nafcillin Sodium Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.2004 mL | 11.0018 mL | 22.0037 mL | 44.0073 mL | 55.0091 mL |
| 5 mM | 0.4401 mL | 2.2004 mL | 4.4007 mL | 8.8015 mL | 11.0018 mL |
| 10 mM | 0.22 mL | 1.1002 mL | 2.2004 mL | 4.4007 mL | 5.5009 mL |
| 50 mM | 0.044 mL | 0.22 mL | 0.4401 mL | 0.8801 mL | 1.1002 mL |
| 100 mM | 0.022 mL | 0.11 mL | 0.22 mL | 0.4401 mL | 0.5501 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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Nafcillin sodium reversibly inhibits β-lactamase with Kd of 33 mM.
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Stability of nafcillin sodium after reconstitution in 0.9% sodium chloride injeciton and storage in polypropylene syringes for pediatric use.[Pubmed:23981740]
Int J Pharm Compd. 2000 Nov-Dec;4(6):480-1.
The stability of Nafcillin Sodium (10 mg/mL) in 0.9% sodium chloride injection has been studied at 25 deg C and 5 deg C in polypropylene syringes by means of a stablilty-indicating high-performance liquid chromatograph assay method. The concentrations of the drug were directly related to peak heights and the percent relative standard deviation based on 5 injections was 1.2. The sodium citrate (added as a buffering agent in the powder) did not interfere with the assay procedure. The product(s) of decomposition separated from the intact drug. At 25 deg C, the loss in potency was less than 2% after 7 days of storage, and at 5 deg C it was also less than 2% when stored for 44 days. The pH values of the injections were between 6.2 to 7.0 throughout this study, except after 14 days of storage at room temperature (potency, 82.3%; pH,5.3). The drug did not adsorb to the syringes, and the physical appearance of the injection did not change. Nafcillin Sodium was considered stable for at least 7 days at 25 deg C and 44 days at 5 deg C.
Stability of Ampicillin Sodium, Nafcillin Sodium, And Oxacillin Sodium in AutoDose Infusion System Bags.[Pubmed:23979189]
Int J Pharm Compd. 2002 May-Jun;6(3):226-9.
The objective of this study was to evaluate the physical and chemical stability of ampicillin sodium 1g/100mL, Nafcillin Sodium 1g/100mL, and oxacillin sodium 1g/100mL, each of which was admixed in 0.9% sodium chloride injection and packaged in an AutoDose Infusion System bag. Triplicate test samples were prepared by reconstituting the penicillin antibiotics and bringing the required amount of each drug to a final volume of 100 mL with 0.9% sodium chloride injection. The test solutions were packaged in AutoDose Bags, which are ethylene vinyl acetate plastic containers designed for use in the AutoDose Infusion System. Samples were stored protected from light and were evaluated at appropriate intervals for up to 7 days at 23 deg C and up to 30 days at 4 deg C. Physical stability was assessed by means of a multistep evaluation procedure that included both turbidimetric and particulate measurement as well as visual inspection. Chemical stability was assesed with stability-indicating high-perofrmance liquid chromatographic (HPLC) analytical techniques based on the determination of drug concentrations initially and at appropriate intervals over the study periods. All the penicillin admixtures were initially clear when viewed in normal fluorescent room light. When the admixtures were viewed with a Tyndall beam, a trace haze was observed with the ampicillin sodium and Nafcillin Sodium mixtures but not with the oxacillin sodium mixture. Measured turbidity and particulate content were low and exhibited little change in the ampicillin sodium and oxacillin sodium samples throughout the study. The Nafcillin Sodium samples stored at room temperature remained clear, but a microprecipitate developed in the refrigerated samples between 14 and 21 days of storage. All samples were essentially colorless throughout the study. HPLC analysis indicated some decomposition in the samples. Ampicillin sodium, which was the least stable, exhibited a 10% loss after 24 hours at 23 deg C. In the samples stored at 4 deg C, ampicillin losses were 6% and 11% after 3 days and 5 days,respecively. Nafcillin Sodium exhiibited a 10% loss after 5 days at 23 deg C. Less than 3% loss occurred after 14 days at 4 deg C, but the microprecipitation that developed resulted in the termination of that portion of the study. Oxacillin sodium was the most stable; it exhibited less than a 10% loss after 7 days at 23 deg C and less than a 5% loss after 30 days at 4 deg C. Ampicillin sodium, Nafcillin Sodium, and oxacillin sodium exhibited physical and chemical stability consistent with previous studies on these drugs. The AutoDose Infusion System bags did not adversely affect the physical and chemical stability of those three penicillin antibiotics.
Identification, Isolation, and Characterization of a New Degradation Impurity in Nafcillin Sodium.[Pubmed:26839804]
Sci Pharm. 2014 Oct 15;83(1):95-106.
A new degradant of Nafcillin Sodium was found at a level of 1.8% w/w during the gradient reversed-phase HPLC analysis in stability storage samples. This impurity was identified by LC-MS and was characterized by (1)H-NMR, (13)C-NMR, LC/MS/MS, elemental analysis, and IR techniques. Based on the structural elucidation data, this impurity was named as N-[(2S)-2-carboxy-2-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}ethylidene]-3-({N-[ (2-ethoxynaphthalen-1-yl)carbonyl]glycyl}sulfanyl)-D-valine. This impurity was prepared by isolation and was co-injected into the HPLC system to confirm the retention time. To the best of our knowledge, this impurity has not been reported elsewhere. The identification and structural elucidation of this degradant impurity has been discussed in detail.
