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Pipracil

Pipracil
Pipracil structure
CAS No.
61477-96-1
Chemical Name:
Pipracil
Synonyms
PIPC;C14034;Pipraci;Pipracil;(N-CD2CD3);Pipercillin;PIPERAILLIN;Piperacillin;PIPERACILLIN NA;Piperacilin Acid
CBNumber:
CB0181853
Molecular Formula:
C23H27N5O7S
Formula Weight:
517.55
MOL File:
61477-96-1.mol

Pipracil Properties

Melting point:
183-185?C (dec.)
Density 
1.51±0.1 g/cm3(Predicted)
RTECS 
XH8952200
storage temp. 
Sealed in dry,2-8°C
solubility 
Freely soluble in methanol. Only sparingly soluble in aqueous solution at 0.119 mg/mL
pka
2.44±0.50(Predicted)
CAS DataBase Reference
61477-96-1(CAS DataBase Reference)
NCI Drug Dictionary
piperacillin sodium
ATC code
J01CA12
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS08
Hazard statements  H317-H334
Precautionary statements  P261-P280g-P284-P304+P340-P342+P311a-P501a
Hazard Codes  Xi
Risk Statements  42/43
Safety Statements  36/37

Pipracil price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Alfa Aesar J66143 Piperacillin, 95% 61477-96-1 500mg $107 2021-03-22 Buy
Alfa Aesar J66143 Piperacillin, 95% 61477-96-1 1g $152 2021-03-22 Buy

Pipracil Chemical Properties,Uses,Production

Chemical Properties

Crystalline Solid

Originator

Pentcillin, Toyama ,Japan ,1980

Uses

antibactierial

Uses

Broad spectrum semi-synthetic antibiotic related to Penicillin. Antibacterial.

Definition

ChEBI: A penicillin in which the substituent at position 6 of the penam ring is a 2-[(4-ethyl-2,3-dioxopiperazin-1-yl)carboxamido]-2-phenylacetamido group.

Manufacturing Process

To a suspension of 0.9 g of 6-[D(-)-α-aminophenylacetamido]penicillanic acid in 30 ml of anhydrous ethyl acetate were added at 5°C to 10°C 0.55 g of triethylamine and 0.6 g of trimethylsilyl chloride. The resulting mixture was reacted at 15°C to 20°C for 3 hours to form trimethylsilylated 6-[D(-)-αaminophenylacetamido]penicillanic acid.
To this acid was then added 1 g of 4-ethyl-2,3-dioxo-1-piperazinocarbonyl chloride (from the reaction of N-ethylethylenediamine and diethyl oxalate to give 2,3-dioxo-4-ethyl-piperazine which is then reacted with phosgene) and the resulting mixture was reacted at 15°C to 20°C for 2 hours. After the reaction, a deposited triethylamine hydrochloride was separated by filtration, and the filtrate was incorporated with 0.4 g of n-butanol to deposit crystals. The deposited crystals were collected by filtration to obtain l.25 g of white crystals of 6-[D(-)α-(4-ethyl-2,3-dioxo-1-piperazinocarbonylamino) phenylacetamido]penicillanic acid. Into a solution of these crystals in 30 ml of tetrahydrofuran was dropped a solution of 0.38 g of a sodium salt of 2-ethylhexanoic acid in 10 ml of tetrahydrofuran, upon which white crystals were deposited. The deposited crystals were collected by filtration, sufficiently washed with tetrahydrofuran and then dried to obtain 1.25 g of sodium salt of 6-[D(-)-α-(4-ethyl-2,3-dioxo-1-piperazinocarbonylamino)phenylacetamido] penicillanic acid, melting point 183°C to 185°C (decomposition), yield 90%.

brand name

Pipracil (Wyeth).

Therapeutic Function

Antibiotic

Antimicrobial activity

It displays good activity against non-β-lactamaseproducing strains of N. gonorrhoeae, ampicillin-susceptible H. influenzae and many Enterobacteriaceae. It is the most active of the antipseudomonal penicillins against Ps. aeruginosa and retains its activity in the absence of a β-lactamase inhibitor. Synergy with aminoglycosides has been demonstrated against many strains of Enterobacteriaceae and Ps. aeruginosa.

Acquired resistance

There is complete cross-resistance with other ureidopenicillins, but ticarcillin-resistant strains of Ps. aeruginosa may be susceptible. Piperacillin-resistant strains of B. fragilis and other Bacteroides spp. are common. Because piperacillin is hydrolyzed by most β-lactamases, many β-lactamaseproducing isolates are resistant unless it is protected by β-lactamase inhibitors.

Pharmacokinetics

Oral absorption: Negligible
Cmax 2 g (2–3 min intravenous injection): 305 mg/L after 5 min
Plasma half-life: 0.9 h
Volume of distribution: 16–24 L/1.73 m2
Plasma protein binding: 16%
In patients with meningitis, mean CSF penetration of 30% has been found. The urine is the principal route of excretion, 50–70% of the dose appearing over 12 h, most in the first 4 h. Most is excreted via the tubules, 75–90% in active form. The half-life is prolonged in renal failure but much less than is the case with carboxypenicillins. There is substantial biliary excretion, levels in the common duct bile after a 1 g intravenous dose commonly reaching 500 mg/L or more. During hemodialysis the plasma half-life remains elevated and only 10–15% of the dose is removed.

Clinical Use

Piperacillin (Pipracil) is the most generally useful of the extended-spectrum acylureidopenicillins. It is more active thanmezlocillin against susceptible strains of Gram-negativeaerobic bacilli, such as Serratia marcescens, Proteus,Enterobacter, Citrobacter spp., and P. aeruginosa.Mezlocillin, however, appears to be more active againstProvidencia spp. and K. pneumoniae. Piperacillin is alsoactive against anaerobic bacteria, especially B. fragilis andS. faecalis (enterococcus). β-Lactamase–producing strainsof these organisms are, however, resistant to piperacillin,which is hydrolyzed by S. aureus β-lactamase. The β-lactamase susceptibility of piperacillin is not absolute becauseβ-lactamase–producing, ampicillin-resistant strainsof N. gonorrhoeae and H. influenzae are susceptible topiperacillin.
Piperacillin is destroyed rapidly by stomach acid; therefore,it is active only by intramuscular or intravenousadministration. The injectable form is provided as the white,crystalline, water-soluble sodium salt. Its pharmacokineticproperties are very similar to those of the other acylureidopenicillins.

Clinical Use

Intra-abdominal infection
Urinary tract infections
Gynecological and gonococcal infections
Septicemia
Lower respiratory infections
Skin and skin structure infections
Bone and joint infections

Side effects

Piperacillin is generally well tolerated, with mild to moderate pain on injection, thrombophlebitis and diarrhea in some patients. It otherwise exhibits side effects common to the group, including hypersensitivity, leukopenia and abnormalities of platelet aggregation without coagulation defect, except on prolonged treatment.

Chemical Synthesis

Piperacillin, (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2R)-2-[(4-ethyl-2,3-dioxo- 1-piperazinyl)formamido]-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.30), is also synthesized by acylating ampicillin (32.1.1.16), but with 1-chlorocarbonyl-4-ethylpiperazin-2,3-dione (32.1.1.29). The necessary 1-chlorocarbonyl-4- ethylpiperazin-2,3-dione (32.1.1.29) is synthesized by reacting N-ethylethylenediamine with diethyloxalate, forming 4-ethylpiperazin-2,3-dione (32.1.1.28), and then acylating this with phosgene after initial silylation of the product at the nitrogen atom with trimethylchlorosilane.

Pipracil Preparation Products And Raw materials

Raw materials

Preparation Products


Pipracil Suppliers

Global( 196)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 20918 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Guangzhou PI PI Biotech Inc
+8618371201331
020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Nanjing ChemLin Chemical Industry Co., Ltd.
025-83697070
product@chemlin.com.cn CHINA 3013 60
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418679
86-0551-65418697 info@tnjchem.com China 3000 55
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
Hubei Jusheng Technology Co.,Ltd.
86-18871470254
027-59599243 linda@hubeijusheng.com CHINA 28229 58
Xiamen AmoyChem Co., Ltd
+86 592-605 1114
sales@amoychem.com CHINA 6369 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460
faith@widelychemical.com CHINA 743 58
BOC Sciences
1-631-485-4226
1-631-614-7828 inquiry@bocsci.com United States 19752 58

View Lastest Price from Pipracil manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-08-12 Pipracil
61477-96-1
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
2021-06-25 Pipracil USP/EP/BP
61477-96-1
US $1.10 / g 1g 99.9% 100 Tons Min Dideu Industries Group Limited
2020-11-16 Pipracil
61477-96-1
US $50.00 / KG 1KG 99% 1000kg Longyan Tianhua Biological Technology Co., Ltd

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