51481-65-3 Usage
Uses
Used in Medical Applications:
Mezlocillin is used as an antibiotic for treating a wide range of bacterial infections, including urinary tract infections, gynecological infections, intraabdominal infections, skin infections, and respiratory tract infections. Its broad-spectrum activity makes it a versatile choice for combating various bacterial pathogens.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Mezlocillin is utilized as a key component in the development of antibiotics, contributing to the fight against bacterial infections. Its broad-spectrum nature allows for its use in a variety of formulations and treatments, catering to the diverse needs of patients with different types of infections.
Originator
Baypen,Bayer,W. Germany,1977
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.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 51481-65-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,4,8 and 1 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 51481-65:
(7*5)+(6*1)+(5*4)+(4*8)+(3*1)+(2*6)+(1*5)=113
113 % 10 = 3
So 51481-65-3 is a valid CAS Registry Number.
InChI:InChI=1/C16H26N2O5S/c1-16(2)8-10(16)13(19)18-12(15(22)23)6-4-3-5-7-24-9-11(17)14(20)21/h6,10-11H,3-5,7-9,17H2,1-2H3,(H,18,19)(H,20,21)(H,22,23)/b12-6-/t10-,11+/m0/s1
51481-65-3Relevant articles and documents
Apparatus And Methods For Delivering A Plurality Of Medicaments For Management Of Co-Morbid Diseases, Illnesses Or Conditions
-
, (2010/09/07)
A method and apparatus for delivering a plurality of medicaments in a single delivery vehicle for the management of co-morbid diseases, illnesses and conditions. The present invention provides a novel delivery process for many medicaments. Medicaments may be encapsulated and stored separately within a larger capsule until the time of ingestion, consumption, or the like. Benefits of the present invention include maintaining separation of distinct ingredients within a single capsule and the capability to control the time release of multiple ingredients within the capsule.
Mezlocillin: A Penicillin from the Acylureido Series / Synthesis and chemical properties
Koenig, H.-B.,Metzger, K. G.,Offe, H.-A.,Schroeck, W.
, p. 88 - 90 (2007/10/02)
Mezlocillin, 6--penicillanic acid, is a new semisynthetic acylureido-penicillin with a broad spectrum of antibacterial activity.The synthesis of mezlocillin from ampicillin and the from 6-aminopenicillanic acid and the physico-chemical properties are described.Mezlocillin is cleaved by penicillinase to the penicilloate which is degraded further by acids to the penilloate. - Key words: Acylureido series; Mezlocillin, chemical properties, synthesis; Penicillins
