quinacillin

CHEBI:192379 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A semisynthetic penicillase-resistant penicillin with antibacterial activity; it binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:17334 CHEBI:17334
CHEBI:38771 CHEBI:38771

Chemical structure

Computed structure properties
Molecular formula	C18H16N4O6S
Charge	0
Average mass	416.415 Da
Monoisotopic mass	416.07906 Da
Source	ChEBI
InChIKey	GPMSLJIYNWBYEL-TYNCELHUSA-N

SMILES

[H][C@]12SC(C)(C)[C@H](C(=O)O)N1C(=O)[C@H]2NC(=O)c1nc2ccccc2nc1C(=O)O

InChI

InChI=1S/C18H16N4O6S/c1-18(2)12(17(27)28)22-14(24)11(15(22)29-18)21-13(23)9-10(16(25)26)20-8-6-4-3-5-7(8)19-9/h3-6,11-12,15H,1-2H3,(H,21,23)(H,25,26)(H,27,28)/t11-,12+,15-/m1/s1

Also called

quinacilina (INN)— chebi
quinacilline (INN)— chebi
quinacillinum (INN)— chebi
3-{[(2S,5R,6R)-2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]carbamoyl}quinoxaline-2-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-[(3-carboxyquinoxaline-2-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
(3-carboxy-2-quinoxalinyl)penicillin (EXACT_SYNONYM)— chebi
3-carboxy-2-quinoxalinylpenicillanic acid (EXACT_SYNONYM)— chebi
6-(3-Carboxy-2-chinoxalinecarboxamido)-3,3-dimethyl-7-oxo-4-thia-azabicyclo(3.2.0)heptan-2-carbonsaeure (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:1596-63-0
wikipedia.en:Quinacillin

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
CHEBI	`CHEBI:192379`	quinacillin	`antibioticmech:chebi-76418de2e8`	2026-08-30

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
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.