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PIVMECILLINAM

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PIVMECILLINAM Basic information

Product Name:
PIVMECILLINAM
Synonyms:
  • PIVMECILLINAM
  • PIVAMDINOCILLIN
  • AMDINOCILLIN PIVOXIL
  • PIVMECILLINAM IMPURITY CMETHYLENE 2,2-DIMETHYLPROPANOATE (2RS,4S)-2-[[[(HEXAHYDO-1H-AZEPIN-1-YL)METHYLENE]AMINO]METHYL]-5,5-DIMETHYLTHIAZOLIDIN-4-CARBOXYLATE EPP(CRM STANDARD)
  • (2S,5β)-6α-[[(Hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2β-carboxylic acid [2,2-dimethyl-1-oxopropoxy]methyl ester
  • [(2,2-Dimethylpropanoyl)oxy]methyl (2S,5R,6R)-6-[(1-azepanylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (2S,5R,6R)-
  • PIVMECILLINAM USP/EP/BP
CAS:
32886-97-8
MF:
C21H33N3O5S
MW:
439.57
EINECS:
251-276-6
Mol File:
32886-97-8.mol
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PIVMECILLINAM Chemical Properties

Melting point:
118-119 C
alpha 
D20 +231° (c = 1 in 96% ethanol)
Boiling point:
581.0±60.0 °C(Predicted)
Density 
1.30±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: soluble5mg/mL, clear (warmed)
pka
8.11±0.60(Predicted)
form 
powder
color 
white to beige
optical activity
[α]/D +215 to +245°, c = 1 in ethanol
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39
WGK Germany 
3
RTECS 
XI0185000
Toxicity
LD50 in mice, rats (mg/kg): 475-480, 465 i.v.; 1736-1930, 1935-2100 s.c.; 3020, 9500-10000 orally (Sato)
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PIVMECILLINAM Usage And Synthesis

Description

Pivmecillinam was found by a series of studies at Leo in 1969. It is a derivative of 6βformamidinopenicillanic acid and shows strong activity against gram-negative bacilli. Pivmecillinam is hydrolyzed by intestinal esterase and acts similarly to mecillinam after oral administration. Mecillinam shows weaker activity than ampicillin against gram-positive cocci but much stronger activity against a wide range of gramnegative bacilli.

Originator

Selexid, Leo ,UK ,1977

Uses

Antibacterial.

Definition

ChEBI: Pivmecillinam is a penicillanic acid ester that is the [(2,2-dimethylpropanoyl)oxy]methyl ester and prodrug of mecillinam. It has a role as an antiinfective agent, an antibacterial drug and a prodrug. It is a penicillanic acid ester, a penicillin and a pivaloyloxymethyl ester. It is functionally related to a mecillinam.

Manufacturing Process

The starting material N-formylhexamethyleneimine was prepared from hexamethyleneimine and chloral.
12.7 g of N-formylhexamethyleneimine were dissolved in 250 ml of dry ether. While stirring and cooling, 8.5 ml of oxalyl chloride in 50 ml of dry ether were added dropwise, whereafter the mixture was stirred overnight at room temperature. The precipitated amide chloride was filtered off and washed with dry ether, and was placed in an exsiccator.
27.5 g of pivaloyloxymethyl 6-aminopenicillinate tosylate was suspended in 1,500 ml of ethyl acetate with continuous stirring and cooling in an ice bath and 950 ml of ice-cold aqueous sodium bicarbonate (2%) were added. The ethyl acetate layer was separated and was shaken with 750 ml of ice-water containing 25 ml of aqueous sodium bicarbonate (2%), whereafter it was dried over magnesium sulfate at 0°C. After filtration, the solution was evaporated to dryness in vacuo. The residue was dissolved in a solution of 15.5 ml of dry triethylamine in 75 ml of dry alcohol-free chloroform. To this solution, 10 g of the above prepared amide chloride dissolved in 75 ml of dry alcohol-free chloroform were added dropwise at a temperature of about 20°C. After standing for half an hour at -20°C, the temperature was raised to 0°C within 15 minutes and the solution was evaporated to dryness in vacuo. The residue was stirred with 750 ml of ether. Undissolved triethylamine hydrochloride was filtered off, and the filtrate was again evaporated to dryness in vacuo. The residue was reprecipitated from acetone (200 ml) - water (150 ml). After recrystallization from cyclohexane an analytically pure product was obtained with a melting point of 118.5°C to 119.5°C.

brand name

Coactabs (Hoffmann-LaRoche).

Therapeutic Function

Antibacterial

PIVMECILLINAMSupplier

Shanghai Holy Biohemdeviser Co., Ltd
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021-61551100
MedChemexpress LLC
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021-58955995
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Nanjing EnMing Pharmaceutical Technology Co., Ltd.
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025-58894663 13305188663
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Suzhou ChemWe Chemical Co., Ltd.
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512-62706911 13401923197
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SPIRO PHARMA
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