PIVMECILLINAM
Synonym(s):Amdinocillin pivoxil
- CAS NO.:32886-97-8
- Empirical Formula: C21H33N3O5S
- Molecular Weight: 439.57
- MDL number: MFCD00865080
- EINECS: 251-276-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-10-28 23:16:16
What is PIVMECILLINAM?
Absorption
Well absorbed following oral administration.
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
The Uses of PIVMECILLINAM
Antibacterial.
Indications
Used to treat infections due to mecillinam-sensitive organisms such as urinary tract infections, salmonellosis and typhoid fever.
Background
Pivmecillinam is a mecillinam prodrug, a pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin. [PubChem]
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
Pharmacokinetics
Pivmecillinam is a pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin.
Metabolism
Not Available
Properties of PIVMECILLINAM
Melting point: | 118-119 C |
Boiling point: | 581.0±60.0 °C(Predicted) |
alpha | D20 +231° (c = 1 in 96% ethanol) |
Density | 1.30±0.1 g/cm3(Predicted) |
storage temp. | -20°C |
solubility | DMSO: soluble5mg/mL, clear (warmed) |
form | powder |
pka | 8.11±0.60(Predicted) |
color | white to beige |
optical activity | [α]/D +215 to +245°, c = 1 in ethanol |
Safety information for PIVMECILLINAM
Computed Descriptors for PIVMECILLINAM
Abamectin manufacturer
Medec Dragon Private Limited
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