hetacillin   Click here for help

GtoPdb Ligand ID: 12263

Approved drug
hetacillin is an approved drug (FDA (1971))
Compound class: Synthetic organic
Comment: Hetacillin is a β-lactam antimicrobial compound. It is an inactive prodrug that is converted to ampicillin in vivo.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 115.25
Molecular weight 389.14
XLogP 1.77
No. Lipinski's rules broken 0
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Canonical SMILES OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)N1C(=O)[C@H](NC1(C)C)c1ccccc1
Isomeric SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)N1C(=O)[C@H](NC1(C)C)c1ccccc1)C(=O)O)C
InChI InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1971))
Withdrawn drug? Yes
Is prodrug? Yes
Active form ampicillin
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
1924 hetacillin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Hetacillin
Other databases
CAS Registry No. 3511-16-8 (source: Scifinder)
ChEMBL Ligand CHEMBL1201116
DrugBank Ligand DB00739
DrugCentral Ligand 1363
GtoPdb PubChem SID 473153851
PubChem CID 443387
Search Google for chemical match using the InChIKey DXVUYOAEDJXBPY-NFFDBFGFSA-N
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UniChem Compound Search for chemical match using the InChIKey DXVUYOAEDJXBPY-NFFDBFGFSA-N
UniChem Connectivity Search for chemical match using the InChIKey DXVUYOAEDJXBPY-NFFDBFGFSA-N