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.

CHEBI:23066 CHEBI:23066
CHEBI:38099 CHEBI:38099
ARO:0000032 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

Equivalent identifiers for this same structure in other resources.

ARO:3003927
cas:689293-68-3
patent:US2017233408
patent:WO2016028670
reaxys:24720344
wikipedia.en:Ceftolozane
chembl:CHEMBL2103872
pubchem.compound:53234134

Activity roles

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

CHEBI:33281 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 known routes by which microbes resist this compound, grounded in ARO where CARD models them. Grouped by mechanism type — expand a group to see its determinants.

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

Provenance

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