98079-51-7 Hazards Identification
Pictogram(s):
Signal:
Warning
GHS Hazard Statements:
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal]
H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]
Precautionary Statement Codes:
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501
Hazard Classes and Categories:
Acute Tox. 4 (100%)
98079-51-7 Usage
Uses
Used in Pharmaceutical Industry:
Lomefloxacin is used as an antibiotic for the treatment of bacterial infections such as bronchitis and urinary tract infections. Its broad-spectrum activity and once-daily dosing make it a convenient and effective option for patients.
Used in Surgical Prophylaxis:
Lomefloxacin is used as a prophylactic agent to prevent urinary tract infections prior to surgery, ensuring a reduced risk of postoperative complications related to bacterial infections.
Used in Resistance Management:
Lomefloxacin is efficacious against pathogens resistant to other common antibiotics such as cephalosporins, penicillins, and aminoglycosides, making it a valuable option for managing antibiotic resistance in clinical settings.
References
https://en.wikipedia.org/wiki/Lomefloxacin
https://www.drugbank.ca/drugs/DB00978
Manufacturing Process
A mixture of 1.00 g of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-
carboxylic acid, 1.10 g of 2-methylpiperazine and 10 ml of pyridine was
heated for 15 minutes under reflux. The reaction mixture was evaporated and
methanol was added to the residue. The precipitate was filtered and
recrystallized from ethanol to give 0.36 g of the 1-ethyl-6,8-difluoro-1,4-
dihydro-7-(3-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid as
colorless needles, melting point 239.0-240.5°C.By the usual manner the hydrochloride was prepared and recrystallized from
water as colorless needles, melting point 290-300°C (decomp.).
Therapeutic Function
Antibacterial
Pharmaceutical Applications
A difluoropiperazinyl quinolone formulated as the hydrochloride salt for oral administration. The in-vitro activity is very similar to that of norfloxacin . It is active against Enterobacteriaceae and fastidious Gram-negative bacilli, including L. pneumophila. Activity against Campylobacter spp., Ps. aeruginosa, Acinetobacter and Chlamydia spp. is poor. It has reduced activity against staphylococci and poor activity against streptococci, L. monocytogenes, anaerobes and Mycobacterium spp.A 400 mg oral dose achieves a concentration of 3–5 mg/L after 1–1.5 h. In escalating oral doses of 100, 400 and 800 mg to volunteers, the AUC was essentially proportional to the dosage, the mean plasma concentrations following 100, 400 and 800 mg doses being approximately 1.1, 4.7 and 7.5 mg/L, respectively.Several metabolites have been described, accounting for <5% of the oral dose. Elimination occurs principally via the kidneys and 50–70% of a dose appears in the urine over 24 h. In patients with impaired renal function given 400 mg orally, the apparent elimination half-life ranged from 8 to 44 h, depending on the degree of renal failure. Non-renal clearance was also impaired, but there was no significant change in other pharmacokinetic parameters. The daily dosage (400 mg) should be reduced to 280 mg when the creatinine clearance falls below 30 mL/min. Hemodialysis has no effect on the plasma concentration. The effect of lomefloxacin on the plasma concentration of theophylline is clinically insignificant and no dosage adjustment is required.The main adverse event is phototoxicity; other adverse events (mainly diarrhea, abdominal pain, skin reactions, dizziness, headache and insomnia) occur in about 10% of patients.It is chiefly used in urinary tract infection, but is no longer widely available.
Clinical Use
1-Ethyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid (Maxaquin) is adifluorinated quinolone with a longer elimination half-life(7–8 hours) than other members of its class. It is the onlyquinolone for which once-daily oral dosing suffices. The oralbioavailability of lomefloxacin is estimated to be 95% to98%. Food slows, but does not prevent, its oral absorption.The extent of biotransformation of lomefloxacin is only about5%, and high concentrations of unchanged drug, rangingfrom 60% to 80%, are excreted in the urine. The comparativelylong half-life of lomefloxacin is apparently because ofits excellent tissue distribution and renal reabsorption and not because of plasma protein binding (only ～10%) or enterohepaticrecycling (biliary excretion is estimated to be ～10%).Lomefloxacin has been approved for two primary indications. First, it is indicated for acute bacterial exacerbations of chronic bronchitis caused by H. influenzae or Moraxella (Branhamella) catarrhalis, but not if Streptococcus pneumoniae is the causative organism. Second, it is used for prophylaxis of infection following transurethral surgery. Lomefloxacin also finds application in the treatment of acute cystitis and chronic urinary tract infections caused by Gram-negative bacilli.
Check Digit Verification of cas no
The CAS Registry Mumber 98079-51-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,8,0,7 and 9 respectively; the second part has 2 digits, 5 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 98079-51:
(7*9)+(6*8)+(5*0)+(4*7)+(3*9)+(2*5)+(1*1)=177
177 % 10 = 7
So 98079-51-7 is a valid CAS Registry Number.
InChI:InChI=1/C17H21F2N3O3/c1-3-21-8-11(17(24)25)16(23)10-6-12(18)15(13(19)14(10)21)22-5-4-20-9(2)7-22/h6,9,11,20H,3-5,7-8H2,1-2H3,(H,24,25)
98079-51-7Relevant academic research and scientific papers
Shu, Zhan,Li, Hai Yan,Ma, Lin Lin,Chen, Wei Liang,Jin, Zhi Min
, p. 384 - 388 (2009)
The DL-lomenfloxacin hydrate is an innersalt, which crystallizes in space group C2/c with cell parameters a = 22.897(10), b = 8.682(1), c = 18.365(2) A, β = 93.6 33(9)°, V = 3,705(3) A3 and Z = 8. The piperazinyl ring adopts a chair conformation, and the quinolone ring is essentially planar. The plane defined by C atoms of the piperazinyl ring is not coplanar with the quinolone ring. The carboxylate group shows two disorder parts, and is not coplanar with the quinolone ring, the dihedral angle between them is 113.8°. The disorder carboxylate group is split into two parts, the planes of which are skewed at the dihedral angles of 24.5 and 21.6° with the plane of the quinolone ring, respectively. The IR of the title compound is measured and studied. Springer Science+Business Media, LLC 2008.
Preparation method of lomefloxacin hydrochloride
-
Paragraph 0025-0029, (2019/12/25)
The invention discloses a preparation method of lomefloxacin hydrochloride. The preparation method comprises the steps: with a lomefloxacin hydrochloride cyclization material as a starting raw material, the lomefloxacin hydrochloride finished product is obtained through ethylation reaction, hydrolysis reaction, condensation reaction with 2-methylpiperazine and salt formation; an ethylation reagentused in the ethylation reaction is bromoethane, and bromoethane is directly added; the ethylation reaction temperature is further divided into two sections, firstly, reaction is carried out for 2 h at the temperature of 80-90 DEG C, and then reaction is carried out for 2 h at the temperature of 100-105 DEG C; the hydrolysis reaction is carried out in the presence of glacial acetic acid and purified water. In the ethylation, the reaction yield can be greatly improved by adjusting the reaction temperature; the hydrolysis reaction adopts a part of purified water instead of glacial acetic acid, the yield not only can be guaranteed, but also the production cost is greatly reduced and the discharge of three wastes is reduced.
NOVEL METHOD OF SYNTHESIS OF FLUOROQUINOLONES
-
Page/Page column 6, (2009/04/24)
The invention relates to a method of preparation of fluoroquinolones of formula (I) from compounds of formula (II): in which R1, R2, R3, R4, R5, R6, R7, and X are as defined in Claim 1.
Regioselective nucleophilic substitution of halogen derivatives of 1-substituted 4-oxo-1,4-dihydroquinoline-3-carboxylic acids
Hermecz, Istvan,Vasvari-Debreczy, Lelle,Podanyi, Benjamin,Kereszturi, Geza,Balogh, Maria,Horvath, Agnes,Varkonyi, Peter
, p. 1111 - 1116 (2007/10/03)
The rate of the nucleophilic displacement of the fluoro atom of 7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate could be enhanced either by the introduction of further fluoro atom(s) into position(s) 6 and/or 8, or by the formation of a boron chelate (e.g. 3). The regioselectivity of the nucleophilic substitution of the chloro atom in 1-substituted 6-fluoro-7-chloro-4-oxo-1,4dihydroquinoline-3-carboxylic acids could also be enhanced by the formation of a boron chelate (e.g. 7).
Synthesis and biological activity of 5-amino- and 5-hydroxyquinolones, and the overwhelming influence of the remote N1-substituent in determining the structure-activity relationship
Domagala,Bridges,Culbertson,Gambino,Hagen,Karrick,Porter,Sanchez,Sesnie,Spense,Szotek,Wemple
, p. 1142 - 1154 (2007/10/02)
A series of 5-amino- and 5-hydroxyquinolone antibacterials substituted at C7 with a select group of common piperazinyl and 3-aminopyrrolidinyl side chains was prepared. These 5-substituted derivatives were compared to the analogous 5-hydrogen compounds for antiinfective activity by using DNA gyrase inhibition, minimum inhibitory concentrations against a variety of bacteria, and in vivo efficacy in the mouse infection model. The influence on the structure-activity relationships of varied substituents at C8 (H, F, Cl) and N1 (ethyl, cyclopropyl, difluorophenyl) was also studied. The results showed that several of the structure-activity conclusions regarding side-chain bulk at C7, the effect of halogen at C8, and the effect of the C5-amino group were greatly influenced by the choice of the N1-substituent. Several outstanding broad spectrum quinolones were identified in this work. In particular, the spectrum and potency of the 7-piperazinyl quinolones could be greatly enhanced by the judicious choice of C5-, C8-, and N1-substitutents.
6-Fluoro-1, 4-dihydro-4-oxo-7-substituted piperazinylquinoline-3-carboxylic acids and the method for preparing the same
-
, (2008/06/13)
The invention is concerned with the novel piperazinylquinoline-3-carboxylic acids represented by formula (I) STR1 or a pharmacologically-acceptable salt thereof, a process for the preparation of them, and a pharmaceutical composition which contains these new compounds as active ingredient and can be used as the therapeutic agent against bacteria.
