PIVMECILLINAM

Product Name: PIVMECILLINAM
CAS No.: 32886-97-8
Chemical Name: PIVMECILLINAM
Synonyms: PIVMECILLINAM;PIVAMDINOCILLIN;AMDINOCILLIN PIVOXIL;PIVMECILLINAM USP/EP/BP;[(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;(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;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 IMPURITY CMETHYLENE 2,2-DIMETHYLPROPANOATE (2RS,4S)-2-[[[(HEXAHYDO-1H-AZEPIN-1-YL)METHYLENE]AMINO]METHYL]-5,5-DIMETHYLTHIAZOLIDIN-4-CARBOXYLATE EPP(CRM STANDARD)
CBNumber: CB8680680
Molecular Formula: C21H33N3O5S
Formula Weight: 439.57
MOL File: 32886-97-8.mol

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PIVMECILLINAM Property

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

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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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0817
Product name: Pivmecillinam
Purity: ≥98% (HPLC)
Packaging: 10mg
Price: $74.1
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0817
Product name: Pivmecillinam
Purity: ≥98% (HPLC)
Packaging: 50mg
Price: $303
Updated: 2024/03/01

American Custom Chemicals Corporation

Product number: API0015830
Product name: PIVMECILLINAM
Purity: 95.00%
Packaging: 25MG
Price: $465.15
Updated: 2021/12/16

Medical Isotopes, Inc.

Product number: D34125
Product name: Pivmecillinam-d9
Packaging: 1mg
Price: $665
Updated: 2021/12/16

AHH

Product number: MT-47025
Product name: Amdinocillinpivoxil
Purity: 98%
Packaging: 0.1g
Price: $380
Updated: 2021/12/16

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PIVMECILLINAM Chemical Properties,Usage,Production

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

PIVMECILLINAM Preparation Products And Raw materials

Raw materials

Preparation Products

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PIVMECILLINAM Suppliers

China 27 Germany 1 India 3 United Kingdom 4 United States 9 Global 44

MedChemexpress LLC

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Musechem

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TargetMol Chemicals Inc.

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American Custom Chemicals Corporation

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View Lastest Price from PIVMECILLINAM manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: Pivmecillinam 32886-97-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

Zhuozhou Wenxi import and Export Co., Ltd

Product: Pivmecillinam 32886-97-8
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-09

32886-97-8, PIVMECILLINAMRelated Search:

Cephalosporin Ampicillin Penicillin G sodium salt PIVMECILLINAM IMPURITY C PIVMECILLINAM HYDROCHLORIDE PIVMECILLINAM HYDROCHLORIDE EPP(CRM STANDARD) 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, monohydrochloride, [2S-(2alpha,5alpha,6beta)]- 4-METHOXY-2-METHYL-2-BUTANETHIOL PIVMECILLINAM pivalyloxymethyl butyrate Mecillinam

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

32886-97-8

C21H33N3O5S