37661-08-8 Usage
Chemical Properties
White or almost white powder or granules, hygroscopic.
Originator
Penglobe,Astra,W. Germany,1977
Uses
Bacampicillin is a penicillin class of antibiotic. Bacampicillin is a prodrug of ampicillin (A634300) with improved oral bioavailability.
Definition
ChEBI: The hydrochloride salt of bacampicillin.
Manufacturing Process
1'-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 name
Spectrobid (Pfizer).
Therapeutic Function
Antibacterial
Clinical Use
Bacampicillin 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 Profile
Poison by intraperitoneal andintravenous routes. Mildly toxic by ingestion andsubcutaneous routes. When heated to decomposition itemits very toxic fumes of NOx, SOx, and HCl.
Check Digit Verification of cas no
The CAS Registry Mumber 37661-08-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,7,6,6 and 1 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 37661-08:
(7*3)+(6*7)+(5*6)+(4*6)+(3*1)+(2*0)+(1*8)=128
128 % 10 = 8
So 37661-08-8 is a valid CAS Registry Number.
InChI:InChI=1/C21H27N3O7S.ClH/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12;/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25);1H/t11?,13-,14?,15?,18?;/m1./s1
37661-08-8Relevant articles and documents
Preparation of 1'-ethoxycarbonyl-oxyethyl esters of penicillins
-
, (2008/06/13)
Process for the preparation of 1'-ethoxy carbonyloxy ethyl esters of penicillins, wherein a compound of the formula STR1 in which A is phenyl, phenoxy or 4-hydroxyphenyl, B is hydrogen, an amino group or a protected amino group and Z is hydrogen or a cation selected from the group of alkali metal, tri (lower alkyl ) ammonium and tetra (lower alkyl) ammonium, is reacted with 1-bromoethyl ethyl carbonate in an organic solvent and when B is a protected amino group the protecting group is split off to yield a primary amino group. There are also provided novel compounds of the formula STR2 in which Ph is phenyl and R is CH3 -- or C2 H5 --.
Studies on prodrugs. III. A convenient and practical preparation of ampicillin prodrugs
Ikeda,Sakamoto,Kondo,et al.
, p. 4316 - 4322 (2007/10/02)
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