mecillinam

CHEBI:51208 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A penicillin in which the 6β substituent is [(azepan-1-yl)methylidene]amino; an extended-spectrum penicillin antibiotic that binds specifically to penicillin binding protein 2 (PBP2), and is only considered to be active against Gram-negative bacteria. — 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

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	C15H23N3O3S
Charge	0
Average mass	325.434 Da
Monoisotopic mass	325.14601 Da
Source	ChEBI
InChIKey	BWWVAEOLVKTZFQ-NTZNESFSSA-N

SMILES

[H]C(=N[C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@]12[H])N1CCCCCC1

InChI

InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/t10-,11+,13-/m1/s1

Also called

Coactin (BRAND_NAME)— chebi
mecilinamo (INN)— chebi
mecillinamum (INN)— chebi
6β-{[(azepan-1-yl)methylidene]amino}-2,2-dimethylpenam-3α-carboxylic acid (EXACT_SYNONYM)— chebi
(2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (EXACT_SYNONYM)— chebi
amdinocillin (EXACT_SYNONYM)— chebi
penicillin HX (EXACT_SYNONYM)— chebi
Selexid (EXACT_SYNONYM)— aro
Selexidin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:3000761
cas:32887-01-7
drugbank:DB01163
lincs.smallmolecule:LSM-5528
patent:DE2055531
patent:US3957764
reaxys:1223657
chembl:CHEMBL530
pubchem.compound:36273

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:3000761`	mecillinam	`antibioticmech:aro-ce23eb8e8c`	2026-08-30
CHEBI	`CHEBI:51208`	mecillinam	`antibioticmech:chebi-a5c2f56674`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

beta-lactam sensitive penicillin-binding protein PROTEIN DIRECT_BINDING_TARGET

ARO:3000749

CARD/ARO database assertion; target organism, strain, and assay are not specified. Penicillin-binding proteins are asserted as inhibited transpeptidases. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

ARO:3000749 (CARD/ARO asserts targeted_by_antibiotic ARO:3000761 (mecillinam); database assertion, not a primary citation.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (ARO, 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
RESEEDED_FROM_SOURCES 2026-08-31 · 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.