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NAFCILLIN SODIUM SALT

NAFCILLIN SODIUM SALT Structure
NAFCILLIN SODIUM SALT structure
CAS No.
985-16-0
Chemical Name:
NAFCILLIN SODIUM SALT
Synonyms
NAFCILLIN;wy3277;unipen;Nafcil;brl1383;naftopen;Nafcil-d5;Wy 3277-d5;BRL 1383-d5;Naftopen-d5
CBNumber:
CB6181365
Molecular Formula:
C21H21N2NaO5S
Molecular Weight:
436.46
MDL Number:
MFCD00056863
MOL File:
985-16-0.mol
MSDS File:
SDS
Last updated:2023-05-04 17:34:44
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NAFCILLIN SODIUM SALT Properties

Melting point >167°C (dec.)
storage temp. Store at 0-5°C
solubility DMSO (Slightly), Methanol (Slightly)
pka pKa 2.65(H2O,t = 25±0.1,c=0.006) (Uncertain)
color Off-White to Pale Yellow
FDA UNII SY07234TTS
ATC code J01CF06

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS08
Signal word  Danger
Hazard statements  H317-H334
Precautionary statements  P261-P280-P342+P311
Hazard Codes  Xn
Risk Statements  42/43
Safety Statements  22-36/37-45
WGK Germany  3
RTECS  XI0175000

NAFCILLIN SODIUM SALT price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 32071 Nafcillin sodium salt VETRANAL 985-16-0 100mg $86 2024-03-01 Buy
Usbiological 240836 Nafcillin 985-16-0 1g $184 2021-12-16 Buy
Usbiological 257354 Nafcillin sodium salt 985-16-0 50mg $460 2021-12-16 Buy
TRC N211500 Nafcillin sodium salt 985-16-0 250mg $640 2021-12-16 Buy
AK Scientific J98226 Nafcillin Sodium 985-16-0 25g $380 2021-12-16 Buy
Product number Packaging Price Buy
32071 100mg $86 Buy
240836 1g $184 Buy
257354 50mg $460 Buy
N211500 250mg $640 Buy
J98226 25g $380 Buy

NAFCILLIN SODIUM SALT Chemical Properties,Uses,Production

Originator

Unipen,Wyeth,US,1964

Uses

Nafcillin Sodium Salt is an antibiotic of the penicillin class that is resistant to beta-lactamase. It can also be used as analyte for biological study and analytical study of hybrid quadrupole-orbitrap mass spectrometry analysis for high-throughput screening and quantification of multi-xenobiotics in honey.

Uses

Nafcillin SodiuM Salt can be used as narcotic antagonist

Uses

As a synthetic beta-lactamase-resistant penicillin, Nafcillin SodiuM Salt can be used to treat infections caused by Gram-positive bacteria, in particular, species of staphylococci that are resistant to other penicillins.

Definition

ChEBI: Nafcillin sodium is an organic sodium salt. It contains a nafcillin(1-).

Indications

It is effective against Gram-positive cocci and staphylococci that produce penicillinase. It is used for the same indications as methicillin. Synonyms of this drug are nafcil, nalpen, unipen, and others.
Another type of semisynthetic penicillin that should undoubtedly be considered is penicillin derivatives of heteroylcarboxylic acids (as a rule an isoxazol) in the third position of which is present a substituted or nonsubstituted phenyl radical (oxacillin, cloxacillin, dicloxacillin), which plays the role of the radical in the acyl side group. These penicillins (oxacillin, cloxacillin, dicloxacillin), which are resistant to penicillinase, are active with respect to penicillin-G-resistant staphylococci. Their antimicrobial spectrum is restricted to Gram-positive microorganisms.
Penicillins that are resistant to penicillinase are the drug of choice for infections resistant to penicillin G, Staph. aureus, or coagulase-negative staphylococci. They are also effective for infections caused by nonenterococcus types of streptococci, such as streptococci groups A, B, C, and G, as well as pneumococci.

Manufacturing Process

A stirred suspension of 12.6 grams 6-aminopenicillanic acid in 130 ml dry alcohol-free chloroform was treated with 16 ml triethylamine and then with 13.8 grams of a solution of 2-ethoxy-1-naphthoyl chloride in 95 ml chloroform. After being washed successively with 58 ml each of 1 N and then 0.1 N hydrochloric acid the chloroform solution was extracted with N aqueous sodium bicarbonate (58 ml + 6 ml). The combined bicarbonate extracts were washed with 20 ml ether and then evaporated at low temperature and pressure to give the crude sodium salt of 2-ethoxy-1-naphthylpenicillin [also called sodium 6-(2-ethoxy-1-naphthamido)penicillinate] as a yellow powder (20.3 grams). This was dissolved in 20 ml water at 30°C and diluted with 180 ml n-butanol, also at 30°C, with stirring. Slow cooling to 0°C gave colorless needles of the product.

brand name

Nallpen (GlaxoSmithKline).

Therapeutic Function

Antibacterial

Antimicrobial activity

The antibacterial spectrum is similar to that of the isoxazolylpenicillins but it is more active against streptococci and pneumococci. Activity in vitro is depressed in the presence of serum. It is more stable than the isoxazolylpenicillins to staphylococcal β-lactamase. There is complete cross-resistance with other group 3 penicillins.

Pharmacokinetics

Oral absorption: c. 35%
Cmax 1 g intramuscular:8 mg/L after 1 h
500 mg intravenous:30 mg/L after 5 min
Plasma half-life: 0.5 h
Plasma protein binding: 90%
Absorption and distribution
Nafcillin is poorly absorbed after oral administration, and absorption is further depressed if the drug is given with food. Most dosing is now intravenous. Penetration into tissues is similar to that of the isoxazolylpenicillins. Penetration into normal meninges is low, but is higher in inflamed meninges.
Metabolism and excretion
About 60–70% is inactivated in the liver. Following intramuscular administration, about 30% appears in the urine, producing concentrations up to 1000 mg/L. Administration of probenecid reduces the urinary excretion and raises and prolongs the plasma level. About 8% of the dose is excreted in the bile.

Clinical Use

Uses are those of group 3 penicillins . Nafcillin has been particularly recommended for the treatment of staphylococcal bacteremia caused by susceptible strains.

Side effects

There is cross-allergenicity with other penicillins. Its side effects are similar to the penicillins. Pseudomembranous colitis has been reported.

Synthesis

Nafcillin, [2S-(2α,5α,6β)]-3,3-dimethyl-7-oxo-6-(2-ethoxy-1-naphthamido)-4- thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.4), is synthesized by acylating 6-APA with 2-ethoxy-1-naphthoic acid chloride in the presence of triethylamine.

NAFCILLIN SODIUM SALT Preparation Products And Raw materials

Raw materials

2-Ethoxynaphthalene-1-carbonyl chloride 6-Aminopenicillanic acid Sodium bicarbonate

Preparation Products

NAFCILLIN SODIUM SALT Suppliers

Global( 73)Suppliers
Supplier Tel Email Country ProdList Advantage
career henan chemical co 		+86-0371-86658258 15093356674; factory@coreychem.com China 29826 58
Shaanxi Dideu Medichem Co. Ltd 		+86-029-81138252 +86-18789408387 1057@dideu.com China 3834 58
Zhengzhou Alfa Chemical Co.,Ltd 		+8618530059196 sale04@alfachem.cn China 12439 58
Hefei TNJ Chemical Industry Co.,Ltd. 		0551-65418671 sales@tnjchem.com China 34572 58
ANHUI WITOP BIOTECH CO., LTD 		+8615255079626 eric@witopchemical.com China 23556 58
Shaanxi Dideu Medichem Co. Ltd 		+86-029-89586680 +86-18192503167 1026@dideu.com China 9604 58
Dideu Industries Group Limited 		+86-29-89586680 +86-15129568250 1026@dideu.com China 29525 58
AFINE CHEMICALS LIMITED 		0571-85134551 info@afinechem.com CHINA 15377 58
Alfa Chemistry 		info@alfa-chemistry.com United States 2344 58
Aston Chemical 		13000000000 sales@astonchem.com United States 1634 58
Supplier Advantage
career henan chemical co 		58
Shaanxi Dideu Medichem Co. Ltd 		58
Zhengzhou Alfa Chemical Co.,Ltd 		58
Hefei TNJ Chemical Industry Co.,Ltd. 		58
ANHUI WITOP BIOTECH CO., LTD 		58
Shaanxi Dideu Medichem Co. Ltd 		58
Dideu Industries Group Limited 		58
AFINE CHEMICALS LIMITED 		58
Alfa Chemistry 		58
Aston Chemical 		58

Related articles

View Lastest Price from NAFCILLIN SODIUM SALT manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
NAFCILLIN SODIUM SALT USP/EP/BP pictures 2021-06-28 NAFCILLIN SODIUM SALT USP/EP/BP
985-16-0
 US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
Nafcillin SodiuM Salt pictures 2020-05-10 Nafcillin SodiuM Salt
985-16-0
 US $1.00 / KG 1KG 99% 20T Shaanxi Dideu Medichem Co. Ltd
NAFCILLIN SODIUM SALT pictures 2019-12-26 NAFCILLIN SODIUM SALT
985-16-0
 US $1.00 / g 1g ≥98% g/kg/Ton Career Henan Chemical Co

985-16-0(NAFCILLIN SODIUM SALT)Related Search:

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naftopen sodium6-(2-ethoxy-1-naphthamido)penicillanate sodiumnafcillin unipen wy3277 NAFCILLIN SODIUM SALT sodium [2S-(2alpha,5alpha,6beta)]-6-[[(2-ethoxy-1-naphthyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-Thia-1-azabicyclo3.2.0heptane-2-carboxylic acid, 6-(2-ethoxy-1-naphthalenyl)carbonylamino-3,3-dimethyl-7-oxo-, monosodium salt, (2S,5R,6R)- NAFCILLIN SODIUM ANHYDROUS (2S,5β)-6α-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid sodium salt 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amido)-3,3-dimethyl-7-oxo-, monosodium salt, (2S,5R,6R)- 3-dimethyl-7-oxo--monosodiumsalt 6-(2-ethoxy-1-naphthamido)penicillinsodium brl1383 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-, monosodium salt Einecs 213-574-4 (2S,5R,6R)-6-[[(2-Ethoxy-1-naphthalenyl)carbonyl]aMino]-3,3-diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid SodiuM Salt 6-(2-Ethoxy-1-naphthaMido)-3,3-diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid SodiuM Salt Nafcil Naphthicillin SodiuM 6-(2-ethoxy-1-naphthaMido)-3,3-diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (2S,5R,6R)-6-[[(2-(Ethoxy-d5)-1-naphthalenyl)carbonyl]aMino]-3,3-diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid SodiuM Salt 6-(2-(Ethoxy-d5)-1-naphthaMido)-3,3-diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid SodiuM Salt 6-(2-(Ethoxy-d5)-1-naphthaMido)penicillin SodiuM Salt BRL 1383-d5 Nafcil-d5 Naftopen-d5 Naphthicillin-d5 SodiuM 6-(2-(ethoxy-d5)-1-naphthaMido)-3,3-diMethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate SodiuM 6-(2-(ethoxy-d5)-1-naphthaMido)penicillanate SodiuM Nafcillin-d5 Wy 3277-d5 Nafcillin sodium salt solution,100ppm 6-[2-ETHOXY-1-NAPHTHAMIDO]-PENICILLIN SODIUM SALT NAFCILLIN SODIUM SALT USP/EP/BP 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2-ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, sodiumsalt (1:1), (2S,5R,6R)- Nafcillin sodium sal NAFCILLIN 985-16-0 C21H21N2NaO5S C21H21N2O5SNa C21H22N2NaO5S Amines Aromatics Chiral Reagents Heterocycles Intermediates & Fine Chemicals Pharmaceuticals NARCAN