DT-Web

DB00739 - Hetacillin


Identification
Name Hetacillin
Accession Number DB00739 (APRD01012)
Type small molecule
Description Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs).
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 389.469
Groups approved
Monoisotopic Weight 389.140926929
Pharmacology
Indication Hetacillin is a beta-lactam antibiotic prodrug used to treat bacterial infections. In the body it gets converted to ampicillin.
Mechanism of action Hetacillin is a semisynthetic penicillin prodrug which itself has no antibacterial activity, but is converted in the body to ampicillin and has actions and uses similar to those of ampicillin. Hetacillin is prepared by reacting ampicillin with acetone. Ampicillin rapidly decomposes because of the intramolecular attack of the side chain amino group on the lactam ring. Hetacillin locks up the offending amino group and prevents the decompolsition Hetacillin, once hydrolyzed to ampicillin (and acetone) binds to the penicillin binding proteins found in susceptible bacteria. This inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. Targets below reflect ampicillin targets.
Absorption Not Available
Protein binding Not Available
Biotransformation Hydrolyzed to active ampicillin via esterases
Route of elimination Not Available
Toxicity Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Interactions
Drug Interactions
Drug Mechanism of interaction
Demeclocycline Possible antagonism of action
Doxycycline Possible antagonism of action
Ethinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptive
Minocycline Possible antagonism of action
Tetracycline Possible antagonism of action
Food Interactions Not Available

Targets


Penicillin-binding protein 2a
Name Penicillin-binding protein 2a
Gene Name pbp2a
Pharmacological action yes
Actions inhibitor
References
  • Neu HC: Aminopenicillins - clinical pharmacology and use in disease states. Int J Clin Pharmacol Biopharm. 1975 Mar;11(2):132-44. - Pubmed
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score Not Available
Penicillin-binding protein 1b
Name Penicillin-binding protein 1b
Gene Name pbp1b
Pharmacological action yes
Actions inhibitor
References
  • Neu HC: Aminopenicillins - clinical pharmacology and use in disease states. Int J Clin Pharmacol Biopharm. 1975 Mar;11(2):132-44. - Pubmed
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score 0.0305
Penicillin-binding protein 3
Name Penicillin-binding protein 3
Gene Name pbp3
Pharmacological action yes
Actions inhibitor
References
  • Neu HC: Aminopenicillins - clinical pharmacology and use in disease states. Int J Clin Pharmacol Biopharm. 1975 Mar;11(2):132-44. - Pubmed
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score 0.0287
Penicillin-binding protein 1A
Name Penicillin-binding protein 1A
Gene Name pbpA
Pharmacological action yes
Actions inhibitor
References
  • Neu HC: Aminopenicillins - clinical pharmacology and use in disease states. Int J Clin Pharmacol Biopharm. 1975 Mar;11(2):132-44. - Pubmed
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score 0.03
Penicillin-binding protein 2B
Name Penicillin-binding protein 2B
Gene Name penA
Pharmacological action yes
Actions inhibitor
References
  • Neu HC: Aminopenicillins - clinical pharmacology and use in disease states. Int J Clin Pharmacol Biopharm. 1975 Mar;11(2):132-44. - Pubmed
  • Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. - Pubmed
DTHybrid score 0.7184

Predictions


Id Partner name Gene Name Score
159 Penicillin-binding protein 2B penA 0.7184
1974 Oligopeptide transporter, kidney isoform SLC15A2 0.2024
1539 Oligopeptide transporter, small intestine isoform SLC15A1 0.1927
1729 Solute carrier family 22 member 6 SLC22A6 0.1157
118 Organic cation/carnitine transporter 2 SLC22A5 0.1066
633 Penicillin-binding proteins 1A/1B pbpA 0.0999
6113 MecA PBP2' (penicillin binding protein 2') mecA 0.0796
2461 D-alanyl-D-alanine carboxypeptidase Not Available 0.0747
5756 D-alanyl-D-alanine carboxypeptidase dac 0.0747
6142 Solute carrier family 22 member 8 SLC22A8 0.0624
587 Serum albumin ALB 0.0425
4512 Cytochrome P450 3A4 CYP3A4 0.0409
1024 Solute carrier family 22 member 11 SLC22A11 0.0367
3195 Beta-lactamase Toho-1 bla 0.0357
332 Beta-lactamase blaZ 0.0334
2478 Beta-lactamase ampC 0.0334
2613 Beta-lactamase ampC 0.0334
2635 Beta-lactamase ampC 0.0334
2700 Beta-lactamase penP 0.0334
5445 Beta-lactamase blaB 0.0334
6019 Beta-lactamase SHV-7 0.0334
6701 Beta-lactamase cphA 0.0334
543 Penicillin-binding protein 1B mrcB 0.0305
6186 Penicillin-binding protein 1B ponB 0.0305
6822 Penicillin-binding protein 1b pbp1b 0.0305
1 Peptidoglycan synthetase ftsI ftsI 0.0304
4155 Peptidoglycan synthetase ftsI ftsI 0.0304
645 Penicillin-binding protein 1A mrcA 0.03
5805 Penicillin-binding protein 1A ponA 0.03
6185 Penicillin-binding protein 1A mrcA 0.03
3760 Penicillin-binding protein 5 precursor dacA 0.0291
867 Penicillin-binding protein 3 pbpC 0.0287
6119 Penicillin-binding protein 3 pbp3 0.0287
7157 Penicillin-binding protein 3 LMHCC_2184 0.0287
7162 Penicillin-binding protein 3 pbpB 0.0287
7172 Penicillin-binding protein 3 pbp3 0.0287
6143 Solute carrier family 22 member 7 SLC22A7 0.0285
6184 D-alanyl-D-alanine carboxypeptidase dacC dacC 0.0275
819 Penicillin-binding protein 4 dacB 0.0258
738 Monocarboxylate transporter 1 SLC16A1 0.0238
6154 Multidrug and toxin extrusion protein 1 SLC47A1 0.0198
4200 Cytochrome P450 1A2 CYP1A2 0.0193
6067 Penicillin binding protein 2a mecA 0.0162
3426 Glutamine synthetase glnA 0.0097
3987 Glutamine synthetase GLUL 0.0097
4119 Cytochrome P450 2D6 CYP2D6 0.0091
115 Penicillin-binding protein 2 mrdA 0.008
6069 Penicillin-binding protein 2 mrdA 0.008
6118 Penicillin-binding protein 2 penA 0.008
6187 Penicillin-binding protein 2 pbpA 0.008
6686 Penicillin-binding protein 2 pbp2 0.008
6939 Penicillin-binding protein 2 mrdA 0.008
7163 Penicillin-binding protein 2 pbpA 0.008
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