| Identification | Back Directory | [Name]
TALAMPICILLIN | [CAS]
47747-56-8 | [Synonyms]
C11751
TALAMPICILLIN
TALAMPICILLIN USP/EP/BP
Ampicillin phthalidyl ester
3-Phthalidyl D-2-amino-2-phenylacetamidopenicillanic acid
(6R)-6-[[(R)-2-Amino-2-phenylacetyl]amino]penicillanic acid 1,3-dihydro-3-oxoisobenzofuran-1-yl ester
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester, [2S-[2a,5a,6b(S*)]]-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester, (2S,5R,6R)-
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-, 1,3-dihydro-3-oxo-1-isobenzofuranyl ester, (2S,5R,6R)- (9CI) | [EINECS(EC#)]
256-332-3 | [Molecular Formula]
C24H23N3O6S | [MDL Number]
MFCD00869410 | [MOL File]
47747-56-8.mol | [Molecular Weight]
481.52 |
| Hazard Information | Back Directory | [Originator]
Talpen,Beecham,US,1975 | [Uses]
Antibacterial. | [Definition]
ChEBI: Talampicillin is a penicillanic acid ester that is the 1-phthalidyl ester of ampicillin. It is a prodrug of ampicillin. It has a role as a prodrug. It is functionally related to an ampicillin and an o-phthalaldehydic acid. | [Manufacturing Process]
A fine suspension of 25.18 grams (0.05 mol) of potassium salt of enamine
protected ampicillin and 10.65 grams (0.05 mol) 3-bromophthalide were
reacted in a 1:2 mixture of acetone/ethyl acetate (1,500 ml) for 24 hours.
After filtration the organic layer was washed twice with 250 ml portions of 1 N
sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and
concentrated in vacuo. Addition of ether crystallized the phthalide enamine
protected α-aminophenylacetamido penicillanate in 85% yield. | [Therapeutic Function]
Antibacterial |
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