Repositioning Candidate Details
| Candidate ID: | R0260 |
| Source ID: | DB00739 |
| Source Type: | approved; vet_approved; withdrawn |
| Compound Type: | small molecule |
| Compound Name: | Hetacillin |
| Synonyms: | (2S,5R,6R)-6-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6β-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid; Hetacillin |
| Molecular Formula: | C19H23N3O4S |
| SMILES: | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C(O)=O |
| Structure: |
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| DrugBank 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). Hetacillin has been withdrawn from the market since it has been discovered that it has no therapeutic advantage compared to non-ester derivatives like ampicillin. |
| CAS Number: | 3511-16-8 |
| Molecular Weight: | 389.469 |
| DrugBank Indication: | Hetacillin is a beta-lactam antibiotic prodrug used to treat bacterial infections. In the body it gets converted to ampicillin. |
| DrugBank Pharmacology: | 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). |
| DrugBank MoA: | 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. _In vitro_ studies have shown that hetacillin is resistant to beta lactamase activity. However, this effect is transient, as the hydrolysis product, ampicillin, is readily inactivated by beta lactamase. Hetacillin locks up the offending amino group and prevents the decomposition of Hetacillin. Once hydrolyzed to ampicillin (and acetone), ampicillin 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: | Penicillin-binding protein 2a inhibitor; Penicillin-binding protein 1b inhibitor; Penicillin-binding protein 3 inhibitor; Penicillin-binding protein 1A inhibitor; Penicillin-binding protein 2B inhibitor |
| Inclusion Criteria: | Indication associated |
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