talampicillin
Description
Talampicillin is a semisynthetic penicillin antibiotic that is a prodrug of ampicillin. It is absorbed more readily than ampicillin from the gastrointestinal tract, resulting in higher serum levels of ampicillin. Talampicillin is hydrolyzed to ampicillin in the body, and has the same spectrum of antibacterial activity as ampicillin. It is used to treat a variety of bacterial infections, including respiratory tract infections, urinary tract infections, and skin infections. Talampicillin is typically administered orally, and is available in both tablet and capsule form. Talampicillin is an important antibiotic because it is effective against a wide range of bacteria, and it is well tolerated by most patients. It is studied to understand its mechanism of action, its pharmacokinetic properties, and its clinical efficacy.'
Talampicillin: An ester of AMPICILLIN which is readily hydrolyzed on absorption to release ampicillin. It is well absorbed from the gastrointestinal tract resulting in a greater bioavailability of ampicillin than can be achieved with equivalent doses of ampicillin. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
talampicillin : A penicillanic acid ester that is the 1-phthalidyl ester of ampicillin. It is a prodrug of ampicillin. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
Cross-References
ID Source | ID |
---|---|
PubMed CID | 71447 |
CHEMBL ID | 1619785 |
CHEBI ID | 9391 |
SCHEMBL ID | 34338 |
MeSH ID | M0021018 |
Synonyms (42)
Synonym |
---|
PRESTWICK3_001010 |
PRESTWICK2_001010 |
BSPBIO_001139 |
AB00514716 |
talampicillin |
BPBIO1_001253 |
brl 8988 |
einecs 256-332-3 |
brl-8988 |
talampicillinum [inn-latin] |
talampicilline [inn-french] |
talampicillin [inn:ban] |
3-phthalidyl (2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carboxylat |
phthalidyl-((1)-6-(2-amino-2-phenylacetamido)penicillanat) |
pc 183 |
talampicilina [inn-spanish] |
SPBIO_003020 |
PRESTWICK0_001010 |
PRESTWICK1_001010 |
CHEBI:9391 , |
3-oxo-1,3-dihydro-2-benzofuran-1-yl (2s,5r,6r)-6-{[(2r)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate |
(3-oxo-1h-2-benzofuran-1-yl) (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate |
D08557 |
talampicillin (inn) |
29oji73dpc , |
talampicilina |
talampicillinum |
unii-29oji73dpc |
ampicillin phthalidyl ester |
talampicilline |
talampicillin [mi] |
(2s,5r,6r)-6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid ester with 3-hydroxyphthalide |
talampicillin hydrochloride [jan] |
talampicillin [inn] |
talampicillin [who-dd] |
SCHEMBL34338 |
CHEMBL1619785 |
(2s,6r)-3-oxo-1,3-dihydroisobenzofuran-1-yl 6-((r)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate |
Q3980350 |
DB13814 |
gtpl12289 |
AKOS040754136 |
Research Excerpts
Overview
Talampicillin is an ester of ampicillin. It is readily hydrolysed on absorption to release ampicillillin.
Excerpt | Reference | Relevance |
---|---|---|
"Talampicillin is an ester of ampicillin which is readily hydrolysed on absorption to release ampicillin. " | ( Bioavailability and metabolism of talampicillin. Jones, KH; Langley, PF; Lees, LJ, 1978) | 1.98 |
Pharmacokinetics
Excerpt | Reference | Relevance |
---|---|---|
" In order to calculate the pharmacokinetic parameters, plasma levels were analyzed using an one-compartment open model, as well as area under the plasma concentration curve (AUC) and urinary excretion." | ( [Talampicillin hydrochloride: Comparison with amoxicillin and ampicillin in the antibacterial activity and pharmacokinetics (author's transl)]. Komiya, M; Naito, S; Ohtani, K; Shimizu, C; Tachibana, A; Yano, K, 1978) | 1.17 |
Bioavailability
Absolute oral bioavailability was 31, 39, 23, and 2% for pivampicillin, bacampicisin, talampicin, and ampicillin sodium, respectively. A 200-mg amount of bacampsicillin showed a significantly higher relative extent of bioavailability than did a 250- mg amount of talampiillin.
Excerpt | Reference | Relevance |
---|---|---|
" The results obtained showed that talampicillin hydrochloride was well absorbed from the gastro-intestinal tract." | ( [Talampicillin hydrochloride: Comparison with amoxicillin and ampicillin in the antibacterial activity and pharmacokinetics (author's transl)]. Komiya, M; Naito, S; Ohtani, K; Shimizu, C; Tachibana, A; Yano, K, 1978) | 1.45 |
" It is well absorbed from the gastro-intestinal tract resulting in a greater bioavailiability of ampicillin than can be achieved with equivalent doses of ampicillin itself." | ( Bioavailability and metabolism of talampicillin. Jones, KH; Langley, PF; Lees, LJ, 1978) | 0.54 |
"A 200-mg amount of bacampicillin showed a significantly higher relative extent of bioavailability than did a 250-mg amount of talampicillin, possibly due to their different stability in the digestive juices." | ( Bioavailability of bacampicillin and talampicillin, two oral prodrugs of ampicillin. Magni, L; Sjövall, J; Vinnars, E, 1981) | 0.74 |
"Absolute oral bioavailability was 31, 39, 23, and 2% for pivampicillin, bacampicillin, talampicillin, and ampicillin sodium, respectively." | ( Oral bioavailability and in vitro stability of pivampicillin, bacampicillin, talampicillin, and ampicillin in horses. Ensink, JM; Fluitman, MA; Tukker, JJ; van Miert, AS; Vulto, AG; Winkel, MB, 1996) | 0.75 |
Dosage Studied
A smaller dosage of talampicillin than ampicillin is required. The drug is better tolerated by the patient, and the time of nursing staff is saved.
Excerpt | Relevance | Reference |
---|---|---|
" Dosing of ampicillin after food has been shown to adversely affect the total bioavailability of ampicillin." | ( Bioavailability and metabolism of talampicillin. Jones, KH; Langley, PF; Lees, LJ, 1978) | 0.54 |
" The use of a high daily dosage of 3 g per day was neither a cause of more frequent nor more severe side-effects than the usually smaller posology used in other studies published in the literature." | ( [Current aspects of clinical bronchopulmonary and cardiovascular clinical pharmacology. Talampicillin in acute bronchopulmonary diseases in mine workers]. Bruninx, M; Minette, A, 1979) | 0.48 |
" The pattern of radiometabolites was very similar in extracts of the urines of radiometabolites was very similar in extracts of the urines of rat, dog and man dosed orally with [phthalidyl-14C]talampicillin." | ( The metabolism of talampicillin in rat, dog and man. Jeffery, DJ; Jones, KH; Langley, PF, 1978) | 0.78 |
" A smaller dosage of talampicillin than ampicillin is required, the drug is better tolerated by the patient, and the time of nursing staff is saved." | ( Treatment of uncomplicated gonorrhoea in women with talampicillin in a single oral 1.5 g dose. Mohanty, KC; Roy, RB, 1982) | 0.83 |
"The drugs were administered intragastrically to the horses at a dosage equimolar to 15 mg of ampicillin/kg of body weight." | ( Oral bioavailability and in vitro stability of pivampicillin, bacampicillin, talampicillin, and ampicillin in horses. Ensink, JM; Fluitman, MA; Tukker, JJ; van Miert, AS; Vulto, AG; Winkel, MB, 1996) | 0.52 |
Roles (1)
Role | Description |
---|---|
prodrug | A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. |
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Drug Classes (1)
Class | Description |
---|---|
penicillanic acid ester | |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Bioassays (3)
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1678479 | Inhibition of recombinant His6-tagged SARS-CoV-2 main protease using Dabcyl-KTSAVLQ-SGFRKM-E(Edans-NH2) as substrate preincubated for 15 mins followed by substrate addition by FRET based assay | 2020 | ACS medicinal chemistry letters, Dec-10, Volume: 11, Issue:12 | Identification of 14 Known Drugs as Inhibitors of the Main Protease of SARS-CoV-2. |
AID1678478 | Inhibition of recombinant His6-tagged SARS-CoV-2 main protease assessed as residual enzyme activity at 100 uM using Dabcyl-KTSAVLQ-SGFRKM-E(Edans-NH2) as substrate preincubated for 15 mins followed by substrate addition by FRET based assay relative to con | 2020 | ACS medicinal chemistry letters, Dec-10, Volume: 11, Issue:12 | Identification of 14 Known Drugs as Inhibitors of the Main Protease of SARS-CoV-2. |
AID1159607 | Screen for inhibitors of RMI FANCM (MM2) intereaction | 2016 | Journal of biomolecular screening, Jul, Volume: 21, Issue:6 | A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Research
Studies (42)
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 36 (85.71) | 18.7374 |
1990's | 2 (4.76) | 18.2507 |
2000's | 2 (4.76) | 29.6817 |
2010's | 1 (2.38) | 24.3611 |
2020's | 1 (2.38) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Market Indicators
Research Demand Index: 30.14
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (30.14) All Compounds (24.57) |
Study Types
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 10 (22.22%) | 5.53% |
Reviews | 2 (4.44%) | 6.00% |
Case Studies | 2 (4.44%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 31 (68.89%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |