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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)]-

Basic information Safety Supplier Related

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)]- Basic information

Product Name:
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)]-
Synonyms:
  • 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-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,5R,6R)- (9CI)
  • 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-(2a,5a,6b)]-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, hydroxymethyl ester pivalate (ester), monohydrochloride, (+)- (8CI)
  • Selexid
  • PIVMECILLINUMHYDROCHLORIDE
  • Amidinocillin Pivoxil
  • Melysin
CAS:
32887-03-9
MF:
C21H34ClN3O5S
MW:
476.02976
EINECS:
251-278-7
Mol File:
32887-03-9.mol
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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)]- Chemical Properties

Melting point:
172-173°
alpha 
D20 +219° (c = 1 in 0.1N HCl)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Freely soluble in water, in anhydrous ethanol and in methanol, slightly soluble in acetone.
form 
Solid
color 
White to off-white
CAS DataBase Reference
32887-03-9
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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)]- Usage And Synthesis

Chemical Properties

White or almost white, crystalline powder.

Uses

Pivmecillinam is an orally active prodrug of Amdinocillin (A576300), an broad spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2.

in vivo

Pivmecillinam (0.5 and 1 mg per mouse, subcutaneous injection, three times daily for four days) can effectively inhibit urinary tract infections caused by multidrug-resistant E. coli in a mouse model of urinary tract infection induced by catheter injection of E. coli[4].

Animal Model:Mouse urinary tract infection (UTI) model? (OF1 female mice were inoculated with approximately 109 CFU/mL E. coli bacterial suspension through a catheter)[4]
Dosage:0.5 and 1 mg/mouse
Administration:Subcutaneous injection? (s.c.), three times daily for 4 days
Result:Significantly reduced the number of E. coli strains in the urine, bladder, and kidneys, especially in the urine.

IC 50

β-lactam

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)]-Supplier

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