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Prulifloxacin

Abstract Quinolone antibiotics Indication Pharmacokinetics Prulifloxacin Intermediate Side effects References
Prulifloxacin
Prulifloxacin structure
CAS No.
123447-62-1
Chemical Name:
Prulifloxacin
Synonyms
nm441;Sword;Pruvel;CS-1352;Quisnon;AF 3012;PRULIFLOXACIN;Prulifloxacine;Prulioxacin-d8;Prulifloxacin>
CBNumber:
CB5474525
Molecular Formula:
C21H20FN3O6S
Formula Weight:
461.46
MOL File:
123447-62-1.mol

Prulifloxacin Properties

Melting point:
211-214°C
Boiling point:
633.2±65.0 °C(Predicted)
Density 
1.62±0.1 g/cm3(Predicted)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
1 M NaOH: soluble25ML, clear, colorless (Solvent: 1 mg + 25 mL of NaOH)
pka
5.85±0.40(Predicted)
form 
White to yellow crystalline solid.
λmax
276nm(H2O)(lit.)
Merck 
14,7908
CAS DataBase Reference
123447-62-1(CAS DataBase Reference)
FDA UNII
J42298IESW
ATC code
J01MA17
SAFETY
  • Risk and Safety Statements
RTECS  XJ0600000

Prulifloxacin price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TCI Chemical P2058 Prulifloxacin >98.0%(HPLC)(T) 123447-62-1 1g $148 2021-03-22 Buy
TCI Chemical P2058 Prulifloxacin >98.0%(HPLC)(T) 123447-62-1 5g $443 2021-03-22 Buy

Prulifloxacin Chemical Properties,Uses,Production

Abstract

Prulifloxacin, a prodrug of Ulifloxacin inhibits replication of bacterial DNA (nuclear material) by inhibition of DNA-gyrase in microbes, is a newer class of fluoroquinolone exerts broad-spectrum anti-bacterial activity against several Gram-positive and Gram-negative organisms. Prulifloxacin is generally prescribed for the treatment of uncomplicated lower urinary tract infections, acute exacerbations of chronic bronchitis and complicated lower urinary tract infections.

Quinolone antibiotics

Prulifloxacin is a quinolone antibiotic, a fluoroquinolone antibiotics prodrug NM394 by the Japan Pharmaceutical Co. and Meiji Seika Kaisha, Ltd. joint research and development in the late eighties, and it was first approved for marketing in December 2002 in Japan. the dosage form is 100mg tablets, by inhibiting bacterial DNA topoisomerase ⅱ and ⅳ activity and bacterial DNA synthesis, completing sterilization, which is different from the traditional model, without drug resistance to other classes of antibiotics. It is used for the treatment of respiratory gram-positive bacteria and negative bacteria clinically, which is caused by infections, urogenital infections, otolaryngology infection, biliary tract infections, enteritis, skin and soft tissue infections and surgical infections. Notable features are as follows:

Indication

It is used for the treatment of prulifloxacin sensitive staphylococcus, streptococcus, Neisseria gonorrhoeae, (except typhoid, paratyphoid) pneumoniae, Enterococcus, Moraxella Alex Salmonella, E. coli, Shigella, Salmonella, lemon acid bacteria, Klebsiella pneumoniae, Serratia, Proteus, Vibrio cholerae, Pseudomonas aeruginosa, Streptococcus digestion, they can cause the following infections:

Pharmacokinetics

After oral administration, Prulifloxacin is rapidly metabolized as an active form of drug, Ulifloxacin. The drug exerts good penetration into the target tissue with prolonged elimination half-life with once-daily administration.
After absorption, Cmax is generally achieved within one hour, and apparent Vss is 1231 L. About 45% of the administered drug is bound to plasma proteins. The drug is extensively metabolized by first-pass metabolism into active metabolites. The terminal half-life of Ulifloxacin is 10.6-12.1 hours. The drug is mainly excreted via the urine as unmetabolized drug.

Prulifloxacin Intermediate

Prulifloxacin Intermediate PL-7
Appearance: white to light yellow powder
Chemical name: 6,7-difluoro-2-mercapto-ethyl-4-hydroxy-quinoline-3-carboxylic acid ethyl ester CAS: 154330-68-4
 Molecular Formula: C14H13F2NO3S
Prulifloxacin intermediate PL-9
Appearance: white to light yellow powder
Chemical name: 6,7-difluoro-1-methyl-4-oxo--4H-(1,3) thiazine (3,2a) and quinoline-3-carboxylate CAS: 113046-72-
Molecular Formula:C14H11F2NO3S
Prulifloxacin Intermediate PL-10
Appearance: white to light yellow powder
Chemical Name: 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl) 4H-(1,3) thiazine (3,2a) and quinoline-3-carboxylate CAS: 113028-17-4
 Molecular Formula:C18H20FN3O3S
Prulifloxacin Intermediate PL-11
Appearance: white to light yellow powder
Chemical Name: 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3) thiazine (3,2a) and quinoline-3-carboxylic acid CAS : 112984-60-8
Molecular Formula:C16H16FN3O3S
Application:For the total synthesis of gatifloxacin antibacterials

Side effects

Abdominal cramp, Confusion, Diarrhoea, Drowsiness, Altered taste, Epigastric pain, Gastritis, Headache, Hot flashes, Increased bilirubin in the blood, Itching, Loss of appetite, Sedation, Skin rash, Sleep disorder, Vomiting, Nausea.

References

https://www.ncbi.nlm.nih.gov/pubmed/15456336
http://www.drugsupdate.com/generic/view/1110/Prulifloxacin

Description

Prulifloxacin was launched as the third fluoroquinone. It was introduced in Japan as an oral treatment for urinary tract infections (UTls), respiratory tract infections (RTls) and bacterial pneumoniae. It can be synthesized in 10 steps from commercially available 3,4-difluoroaniline. Key steps involve the cyclization of 6,7-difluoro-rl-hydroxy-2- thioquinoline-3carboxylic acid ethyl ester with 1 ,I-dibromomethane to give the corresponding thiazeto-[3,2a]quinoline. Aromatic nucleophilic substitution of the 7-fluoro atom with piperazine followed by hydrolysis of the ethyl ester and finally alkylation of the piperazinyl moiety with 4-(bromomethyl)-5-methyl-l ,bdioxol-Bone complete the synthesis. Prulifloxacin is a lipophilic prodrug, which is rapidly hydrolyzed to the corresponding Ndealkylated piperazine, NM 394, by paraoxonase type enzymes in blood and liver following intestinal absorption. The DNA gyrase inhibitor NM 394 accounts for all antimicrobial activity: it shows a similar or greater activity against gram-positive bacteria compared to ciprofloxacin, and a greater activity in the case of gram-negative bacteria. In clinical studies, prulifloxacin has shown good efficacy against UTls and RTls. The drug is mainly excreted in the urine and in the feces as unchanged NM 394, which has a plasma half-life of approximately 8 h. Phototoxicity in animal models is less severe than with other quinolones. Prulifloxacin is well tolerated with an adverse effect profile similar to that of other fluoroquinolones.

Chemical Properties

Off-White Solid

Originator

Nippon Shinyaku (Japan)

Uses

Prulifloxacin is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class. Prulifloxacin is a prodrug for active metabolite, Ulifloxacin. Antibacterial.

Uses

Fluoroquinoline antibacterial; prodrug for active metabolite, Ulifloxacin. Antibacterial.

brand name

Sword

Pharmaceutical Applications

A lipophilic prodrug which is very rapidly metabolized by esterase into ulifloxacin, a 6-fluoro, 7-piperazinyl thiazetoquinoline.
Ulifloxacin is moderately active against Staph. aureus (MIC 0.4–0.8 mg/L) and inactive against Str. pneumoniae (MIC 2–8 mg/L) as well as against Enterococcus spp. Against Enterobacteriaceae (MIC 0.05–0.8 mg/L) and Ps. aeruginosa (MIC 0.2–0.8 mg/L) activity is similar to that of ciprofloxacin. It is active against fastidious Gram-negative bacilli, but not against anaerobes and non-fermentative Gram-negative bacilli. Activity against Acinetobacter spp. is modest.
Prulifloxacin is rapidly converted into ulifloxacin and after 3 h is no longer detected in blood. In volunteers receiving a single oral dose, peak plasma concentrations of 0.68 mg/L (300 mg dose) to 1.88 mg/L (for 400 mg dose) were attained between 0.67 and 1.25 h. The mean apparent elimination half-life was 8 h and the mean cumulative elimination rate in urine within 48 h was 31–46%. Other inactive metabolites account for 7% of the dose. Half the administered dose is eliminated in feces within 72 h as ulifloxacin and 4% as prulifloxacin. Protein binding is 45%.

Chemical Synthesis

The synthesis of prulifloxacin (22)started with the treatment of 3,4- difluoroaniline (183) with carbon disulfide in the presence of TEA to give the triethylammonium dithiocarbamate, which by reaction with ethyl chloroformate and TEA in chloroform, was converted into isothiocyanate 184 in 74% yield. Reaction of 184 with diethyl malonate in the presence of KOH in dioxane yielded methylenemalonate 185 potassium salt, which was ethylated with ethyl sulfate in ethanol to give compound 186 in excellent yield. 6,7- Difluoroquinoline 187 was obtained with the highest yield and regioselectivity when precursor 186 was heated in refluxing xylene. To suppress the side reaction in the subsequent chlorination, quinoline 187 was acylated to give 188 with acetyl chloride in chloroform. Chlorination of 188 with sulfuryl chloride gave compound 189 in 79% yield. Compound 189 was treated with sodium acetate in THF to afford cyclized compound 190, which was condensed with piperazine in DMF to give compound 191. The hydrolysis of ester 191 with KOH in hot t-butanol gave free acid 192, which was finally condensed with 4-(bromomethyl)-5- methyl-1, 3-dioxol-2-one (163) by treatment of potassium bicarbonate in DMF to give prulifloxacin (22).

Prulifloxacin Preparation Products And Raw materials

Raw materials

Preparation Products


Prulifloxacin Suppliers

Global( 244)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
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Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
career henan chemical co
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Shaanxi Yikanglong Biotechnology Co., Ltd.
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Hubei Jusheng Technology Co.,Ltd.
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Xiamen AmoyChem Co., Ltd
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Shanghai Longyu Biotechnology Co., Ltd.
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+86 15821988213 info@longyupharma.com China 2473 58
Chongqing Chemdad Co., Ltd
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CONIER CHEM AND PHARMA LIMITED
86-18523575427
sales@conier.com CHINA 47498 58
Shaanxi Dideu Medichem Co. Ltd
18192627656
+86-29-88380327 1012@dideu.com CHINA 3949 58

View Lastest Price from Prulifloxacin manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-21 Prulifloxacin
123447-62-1
US $100.00 / Kg/Drum 1KG 99% 1000tons Hebei Mojin Biotechnology Co., Ltd
2021-10-20 Prulifloxacin
123447-62-1
US $2950.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biological Technology Co., Ltd
2021-10-20 Prulifloxacin
123447-62-1
US $2940.00 / KG 1KG 99% 9000kg/per week Hebei Lingding Biological Technology Co., Ltd

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