AntibioticMech

hetacillin

CHEBI:5683 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Hetacillin is a semi-synthetic penicillin compound with bactericidal properties. Hetacillin is a prodrug that is converted to ampicillin via esterases. — PMID:5907864

Classification

penicillin beta-lactamARO:3000008

Strictly broader compounds or drug classes this molecule belongs to.

• CHEBI:17334 CHEBI:17334
• ARO:3000008 ARO:3000008

Chemical structure

Computed structure properties

Molecular formula	C19H23N3O4S
Charge	0
Average mass	389.477 Da
Monoisotopic mass	389.14093 Da
Source	ChEBI
InChIKey	DXVUYOAEDJXBPY-NFFDBFGFSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2N1C(=O)[C@@H](c2ccccc2)NC1(C)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

Also called

• hetacilina (INN)— chebi
• hetacilline (INN)— chebi
• hetacillinum (INN)— chebi
• 6β-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
• (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 (EXACT_SYNONYM)— chebi
• 6β-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid (EXACT_SYNONYM)— chebi
• Hetacillin (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

• ARO:3009132
• beilstein:5405483
• cas:3511-16-8
• drugbank:DB00739
• drugcentral:1363
• kegg.compound:C11729
• kegg.drug:D01074
• patent:US3198804
• wikipedia.en:Hetacillin
• chembl:CHEMBL1201116
• pubchem.compound:443387

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

• CHEBI:33281 CHEBI:33281
• CHEBI:36047 CHEBI:36047

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record

Source	Native ID	Label	Minted CURIE	Version
ARO	ARO:3009132	hetacillin	antibioticmech:aro-712b258082	2026-08-30
CHEBI	CHEBI:5683	hetacillin	antibioticmech:chebi-d47f6da68e	2026-08-30

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.