BACAMPICILLIN HYDROCHLORIDE

BACAMPICILLIN HYDROCHLORIDE Basic information
Product Name:BACAMPICILLIN HYDROCHLORIDE
Synonyms:BECAMPICILLINHYDROCHLORIDE;Pengood;Bacampicilline Hydrochloride;Bacampicillin Hydrochloride (200 mg);1-[(ethoxycarbonyl)oxy]ethyl [2S-[2alpha,5alpha,6beta(S*)]]-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate monohydrochloride;Bacampicillin HCl;BACAMPICILLIN HYDROCHLORIDE USP STANDARD;BACAMPICILLIN HYDROCHLORIDE EP STANDARD
CAS:37661-08-8
MF:C21H28ClN3O7S
MW:501.98
EINECS:253-580-4
Product Categories:
Mol File:37661-08-8.mol
BACAMPICILLIN HYDROCHLORIDE Structure
BACAMPICILLIN HYDROCHLORIDE Chemical Properties
Melting point 171-176° (dec)
alpha D20 +161.5°
storage temp. Store at -20°C
solubility Soluble in water, freely soluble in ethanol (96 per cent), soluble in methylene chloride.
form neat
color Crystals from Me2CO pet ether
Safety Information
ToxicityLD50 in mice (mg/kg): 8529 orally; 176 i.p.; 9475 s.c.; 184 i.v. (Edanaga)
MSDS Information
BACAMPICILLIN HYDROCHLORIDE Usage And Synthesis
Chemical PropertiesWhite or almost white powder or granules, hygroscopic.
OriginatorPenglobe,Astra,W. Germany,1977
UsesBacampicillin is a penicillin class of antibiotic. Bacampicillin is a prodrug of ampicillin (A634300) with improved oral bioavailability.
DefinitionChEBI: The hydrochloride salt of bacampicillin.
Manufacturing Process1'-Ethoxycarbonyloxyethyl 6-(D-α-azidophenylacetamido)penicillinate (98 g) was prepared from sodium 6-(D-α-azidophenylacetamido)penicillinate (397 g, 1 mol), α-chlorodiethylcarbonate (458 g, 3 mols) and sodium bicarbonate (504 g, 6 mols). The product showed strong IR absorption at 2090 cm-1 and 1780-1750 cm-1 showing the presence of azido group and β-lactam and ester carbonyls.
It was dissolved in ethyl acetate (700 ml) and hydrogenated at ambient conditions over a palladium (5%)on carbon catalyst (18 g). The catalyst was removed by filtration and washed with ethyl acetate. The combined filtrates were extracted with water at pH 2.5 by addition of dilute hydrochloric acid. Lyophilization of the aqueous phase gave the hydrochloride of 1'- ethoxycarbonyloxyethyl 6-(D-α-aminophenylacetarnido)penicillinate (94 g), MP 171°-176°C.
Brand nameSpectrobid (Pfizer).
Therapeutic FunctionAntibacterial
Clinical UseBacampicillin hydrochloride (Spectrobid) is the hydrochloridesalt of the 1-ethoxycarbonyloxyethyl ester of ampicillin.It is a prodrug of ampicillin with no antibacterial activity.After oral absorption, bacampicillin is hydrolyzed rapidly byesterases in the plasma to form ampicillin.
Oral absorption of bacampicillin is more rapid and completethan that of ampicillin and less affected by food.Plasma levels of ampicillin from oral bacampicillin exceedthose of oral ampicillin or amoxicillin for the first 2.5 hoursbut thereafter are the same as for ampicillin and amoxicillin.49 Effective plasma levels are sustained for 12 hours,allowing twice-a-day dosing.
Safety ProfilePoison by intraperitoneal andintravenous routes. Mildly toxic by ingestion andsubcutaneous routes. When heated to decomposition itemits very toxic fumes of NOx, SOx, and HCl.
BACAMPICILLIN HYDROCHLORIDE Preparation Products And Raw materials
Raw materialsHydrogen-->Palladium hydroxide-->Sodium bicarbonate
METHICILLIN SODIUM*) USP(CRM STANDARD) AMPICILINE Arbidol HCl AMpicillin EP IMpurity C (4S)-2-(((R)-2-Amino-2-phenylacetamido)(carboxy)-methyl)-5,5-dimethylthiazolidine-4-carboxylic PIVAMPICILLIN D-2-Phenylglycine BACAMPICILLIN HYDROCHLORIDE EPB(CRM STANDARD) (S)-Bacampicillin hydrochloride BACAMPICILLIN (R)-Bacampicillin hydrochloride

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