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Mezlocillin

CAS No.
51481-65-3
Chemical Name:
Mezlocillin
Synonyms
Melocin;Bay-f 1353;Multocillin;MEZLOCILLIN;Meslocillin;Meloxacam acid;Mezlocillin acid;Melocillin sodium;Meloxicillin acid;antibioticbay-f1353
CBNumber:
CB9268151
Molecular Formula:
C21H25N5O8S2
Molecular Weight:
539.58
MDL Number:
MFCD00056866
MOL File:
51481-65-3.mol
MSDS File:
SDS
Last updated:2023-06-30 17:01:55

Mezlocillin Properties

Density 1.63±0.1 g/cm3(Predicted)
storage temp. 2-8°C
pka pKa 2.7 (Uncertain)
CAS DataBase Reference 51481-65-3(CAS DataBase Reference)
FDA UNII OH2O403D1G
ATC code J01CA10

Mezlocillin price More Price(11)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Usbiological 283562 Mezlocillin 51481-65-3 25mg $410 2021-12-16 Buy
TRC M340853 Mezlocillin 51481-65-3 500mg $550 2021-12-16 Buy
TRC M340853 Mezlocillin 51481-65-3 1000mg $880 2021-12-16 Buy
Matrix Scientific 099565 Mezlocillin 95+% 51481-65-3 250mg $284 2021-12-16 Buy
Matrix Scientific 099565 Mezlocillin 95+% 51481-65-3 1g $639 2021-12-16 Buy
Product number Packaging Price Buy
283562 25mg $410 Buy
M340853 500mg $550 Buy
M340853 1000mg $880 Buy
099565 250mg $284 Buy
099565 1g $639 Buy

Mezlocillin Chemical Properties,Uses,Production

Description

Mezlocilin is an acylaminopenicillin, which has been shown to cause both immediate and delayed hypersensitivity in a nurse.

Originator

Baypen,Bayer,W. Germany,1977

Uses

Like azlocillin, mezlocillin is used for infections of the urinary tract, gynecological infections, intraabdominal infections, skin infections, and respiratory tract infections. Synonyms of this drug are baypen, mezlin, and optocillin.

Uses

Antibacterial.

Uses

Mezlocillin is a broad spectrum penicillin antibiotic.

Definition

ChEBI: A penicillin in which the substituent at position 6 of the penam ring is a (2R)-2-[3-(methanesulfonyl)-2-oxoimidazolidine-1-carboxamido]-2-phenylacetamido group.

Manufacturing Process

9.3 parts by weight of ampicillin were suspended in 80% strength aqueous tetrahydrofuran (140 parts by volume) and sufficient triethylamine (approximately 6.3 parts by volume) was added dropwise while stirring at 20°C, just to produce a clear solution and to give a pH value of between 7.5 and 8.2 (glass electrode). The mixture was cooled to 0°C and 5.1 parts by weight of 3-methylsulfonyl-imidazolidin-2-one-1-carbonyl chloride were added gradually in portions over the course of 30 minutes, while the mixture was stirred and kept at a pH value of between 7 and 8 by simultaneous addition of triethylamine.
The carbonyl chloride reactant was prepared by reacting 2-imidazolidone with methanesulfonyl chloride then that product with phosgene. The mixture was stirred for 10 minutes at 0°C and subsequently further stirred at room temperature until no further addition of triethylamine was necessary to maintain a pH value of 7 to 8. 150 parts by volume of water were added andthe tetrahydrofuran was largely removed in a rotary evaporator at room temperature.
The residual aqueous solution was extracted once by shaking with ethyl acetate, covered with 250 parts by volume of fresh ethyl acetate and acidified to pH 1.5 to 2.0 with dilute hydrochloric acid while being cooled with ice. The organic phase was separated off, washed twice with 50 parts by volume of water at a time and dried for 1 hour over anhydrous MgSO4 in a refrigerator. After filtration, about 45 parts by volume of a 1 molar solution of sodium 2- ethylhexanoate in ether containing methanol were added to the solution of the penicillin. The mixture was concentrated on a rotary evaporator until it had an oily consistency and was dissolved in a sufficient amount of methanol by vigorous shaking, and the solution was rapidly added dropwise, with vigorous stirring, to 500 parts by volume of ether which contained 10% of methanol.
The precipitate was allowed to settle for 30 minutes, the solution was decanted from the precipitate, and the latter was again suspended in ether, filtered off and washed with anhydrous ether. After drying over P2O5 in a vacuum desiccator, the sodium salt of the mezlocillin was obtained in the form of a white solid substance.

brand name

Multocillin (Bayer).

Therapeutic Function

Antibiotic

Antimicrobial activity

A semisynthetic acylureidopenicillin supplied as the sodium salt for parenteral administration.
Ampicillin-susceptible strains of H. influenzae and Neisseria spp. are very susceptible, but β-lactamase-producing organisms are usually resistant. It is less active than azlocillin and piperacillin against Ps. aeruginosa and has variable activity against B. fragilis, independent of β-lactamase production. It exhibits typical β-lactam synergy with aminoglycosides against Ps. aeruginosa and enterobacteria.
It attains peak concentrations of 250 mg/L after a 2 g intravenous infusion, with a plasma half-life of 55 min. Protein binding is 20–30%. It distributes into multiple tissues and human body fluids at therapeutically useful concentrations. Up to 60% of the dose is recoverable unchanged from the urine, with up to 2.5% excreted in the bile.
Toxicity and side effects are similar to those associated with carboxypenicillins. Its clinical use is for serious infections with susceptible organisms, including lower respiratory tract, intra-abdominal, urinary tract and gynecological infections. Commercial availability is quite limited.

General Description

Mezlocillin was synthesized by Bayer in 1974. The NH2 residue of ampicillin was acylated. Mezlocillin is a member of the so-called ureidopenicillins and shows two- to eightfold greater activity against Citrobacter, Enterobacter, Klebsiella, Escherichia coli, and Haemophilus influenzae than ampicillin, carbenicillin, or sulbenicillin. Its activity against gram-positive bacteria is almost the same as that of carbenicillin. Mezlocillin is used by intravenous administration for therapy of sepsis, meningitis, and respiratory tract, urinary tract, and abdominal infections.

Synthesis

Mezlocillin, (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(R)-2-[(3-methylsulfonyl)-2- oxoimidazolidin-1-carboxamido]-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]-heptan-2- carboxylic acid (32.1.1.27), is synthesized by acylating ampicillin (32.1.1.16) with 3-chlorocarbonyl-1-methansulfonyl-2-imidazolidinone (32.1.1.26) in the presence of triethylamine. The necessary 3-chlorocarbonyl-1-methansulfonyl-2-imidazolidinone (32.1.1.26) is synthesized by sulfonating 2-imidazolidinone with methanesulfonyl chloride, which forms 1-methanesulfonyl-2-imidazolidinone (32.1.1.25) and its subsequent reaction with phosgene.

Synthesis_51481-65-3

69-53-4
41762-76-9
51481-65-3
Synthesis of Mezlocillin from Ampicillin and 3-Chlorocarbonyl-1-methanesulfonyl-2-imidazolidinone

Mezlocillin Preparation Products And Raw materials

Global( 132)Suppliers
Supplier Tel Email Country ProdList Advantage
Hebei Mojin Biotechnology Co., Ltd
+8613288715578 sales@hbmojin.com China 12452 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21700 55
Hebei Guanlang Biotechnology Co., Ltd.
+86-19930503282 alice@crovellbio.com China 8823 58
Xiamen AmoyChem Co., Ltd
+86-592-6051114 +8618959220845 sales@amoychem.com China 6387 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460 faith@widelychemical.com CHINA 742 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 47465 58
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 3979 58
SIMAGCHEM CORP
+86-13806087780 sale@simagchem.com China 17368 58
Hefei TNJ Chemical Industry Co.,Ltd.
0551-65418671 sales@tnjchem.com China 34572 58

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Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Mezlocillin pictures 2023-07-01 Mezlocillin
51481-65-3
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd
Mezlocillin Acid pictures 2023-03-19 Mezlocillin Acid
51481-65-3
US $10.00 / KG 1KG 99% 10 mt Hebei Guanlang Biotechnology Co., Ltd.
Mezlocillin pictures 2022-09-28 Mezlocillin
51481-65-3
US $0.00-0.00 / kg 1kg 98% 1Ton Henan Aochuang Chemical Co.,Ltd.
  • Mezlocillin pictures
  • Mezlocillin
    51481-65-3
  • US $0.00 / KG
  • 99%
  • Hebei Mojin Biotechnology Co., Ltd
  • Mezlocillin Acid pictures
  • Mezlocillin Acid
    51481-65-3
  • US $10.00 / KG
  • 99%
  • Hebei Guanlang Biotechnology Co., Ltd.
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  • Mezlocillin
    51481-65-3
  • US $0.00-0.00 / kg
  • 98%
  • Henan Aochuang Chemical Co.,Ltd.
(2s-(2-alpha,5-alpha,6-beta)(s*))-sodiumsal 4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylicacid,3,3-dimethyl-6-(((((3-(met antibioticbay-f1353 3,3-dimethyl-7-[[2-[(3-methylsulfonyl-2-oxo-imidazolidin-1-yl)carbonylamino]-2-phenyl-acetyl]amino]-6-oxo-2-thia-5-azabicyclo[3.2.0]heptane-4-carboxylic acid Melocillin sodium Meloxacam acid Mezlocillin acid MEZLOCILLIN SODIUM USP(CRM STANDARD) 6α-[[(R)-[[[3-(Methylsulfonyl)-2-oxoimidazolidin-1-yl]carbonyl]amino]phenylacetyl]amino]penicillanic acid Multocillin Mezlocillin(Mezlocillin sodium) MEZLOCILLIN Mezlocillin Solution, 100ppm (2S,5R,6R)-3,3-dimethyl-6-[[(2R)-2-[[(3-methylsulfonyl-2-oxo-1-imidazolidinyl)-oxomethyl]amino]-1-oxo-2-phenylethyl]amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 3,3-dimethyl-6-[[(2R)-2-[[[3-(methylsulfonyl)-2-oxo-1-imidazolidinyl]carbonyl]amino]-2-phenylacetyl]amino]-7-oxo-, (2S,5R,6R)- Mezlocillin USP/EP/BP Meloxicillin acid Bay-f 1353 Melocin Meslocillin 51481-65-3 51484-65-3