ceftolozane

CHEBI:134719 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A fifth-generation cephalosporin antibiotic having (5-amino-4-{[(2-aminoethyl)carbamoyl]amino}-1-methyl-1H-pyrazol-2-ium-2-yl)methyl and [(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino side groups located at positions 3 and 7 respectively; developed for the treatment of infections with gram-negative bacteria that have become resistant to conventional antibiotics. — 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

cephalosporinARO:0000032

Strictly broader compounds or drug classes this molecule belongs to.

cephalosporin CHEBI:23066
Label unavailable CHEBI:38099
cephalosporin ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C23H30N12O8S2
Charge	0
Average mass	666.703 Da
Monoisotopic mass	666.1751 Da
Source	ChEBI
InChIKey	JHFNIHVVXRKLEF-DCZLAGFPSA-N

SMILES

[H][C@]12SCC(C[n+]3cc(NC(=O)NCCN)c(N)n3C)=C(C(=O)[O-])N1C(=O)[C@H]2NC(=O)/C(=N\OC(C)(C)C(=O)O)c1nsc(N)n1

InChI

InChI=1S/C23H30N12O8S2/c1-23(2,20(40)41)43-31-11(15-30-21(26)45-32-15)16(36)29-12-17(37)35-13(19(38)39)9(8-44-18(12)35)6-34-7-10(14(25)33(34)3)28-22(42)27-5-4-24/h7,12,18,25H,4-6,8,24H2,1-3H3,(H7,26,27,28,29,30,32,36,38,39,40,41,42)/b31-11-/t12-,18-/m1/s1

Also called

ceftolozano (INN)— chebi
ceftolozanum (INN)— chebi
7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-3-[ (5-amino-4-{[(2-aminoethyl)carbamoyl]amino}-1-methyl-1H-pyrazol-2-ium-2-yl)methyl]-3,4-didehydrocepham-4-carboxylate (EXACT_SYNONYM)— chebi
(6R,7R)-3-[(5-amino-4-{[(2-aminoethyl)carbamoyl]amino}-1-methyl-1H-pyrazol-2-ium-2-yl)methyl]-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-{[(2-carboxypropan-2-yl)oxy]imino}acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (EXACT_SYNONYM)— chebi
CXA-101 (EXACT_SYNONYM)— chebi
Zerbaxa (EXACT_SYNONYM)— aro

Cross-references

Identifiers for this same structure in other resources. An accession that lands on two different structures in this corpus is withheld from both rather than shown here, since it names at most one of them.

Patents and articles

Documents about this compound. A patent covers a class and an article covers a topic; neither identifies a structure.

Activity roles

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

antimicrobial agent CHEBI:33281

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:3003927`	ceftolozane	`antibioticmech:aro-af1946ad8f`	2026-08-30
CHEBI	`CHEBI:134719`	ceftolozane	`antibioticmech:chebi-af6d508119`	2026-08-30

Resistance mechanisms

2 source-backed resistance determinants or associations, with ARO grounding where reported. Grouped by reported mechanism type.

ANTIBIOTIC_INACTIVATION 2

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
CAM-1	ARO:3004559	not organism-specific	—	ARO:3004559 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003927 (ceftolozane); database assertion, not a primary citation.)
CMY-136	ARO:3004854	not organism-specific	—	ARO:3004854 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3003927 (ceftolozane); 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 2026-09-10 · 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 (YAML).

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