ceftriaxone

CHEBI:29007 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A third-generation cephalosporin compound having 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetylamino and [(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl side-groups. — 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:36816 CHEBI:36816
CHEBI:38418 CHEBI:38418
CHEBI:39410 CHEBI:39410
ARO:0000032 ARO:0000032

Chemical structure

Computed structure properties
Molecular formula	C18H18N8O7S3
Charge	0
Average mass	554.592 Da
Monoisotopic mass	554.04606 Da
Source	ChEBI
InChIKey	VAAUVRVFOQPIGI-SPQHTLEESA-N

SMILES

[H][C@]12SCC(CSc3nc(=O)c(=O)nn3C)=C(C(=O)O)N1C(=O)[C@H]2NC(=O)/C(=N\OC)c1csc(N)n1

InChI

InChI=1S/C18H18N8O7S3/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7/h5,9,15H,3-4H2,1-2H3,(H2,19,20)(H,21,27)(H,23,29)(H,31,32)/b24-8-/t9-,15-/m1/s1

Also called

ceftriaxona (INN)— chebi
ceftriaxonum (INN)— chebi
7β-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-3,4-didehydrocepham-4-carboxylic acid (EXACT_SYNONYM)— chebi
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (EXACT_SYNONYM)— chebi
rocephin (EXACT_SYNONYM)— chebi
Biotrakson (EXACT_SYNONYM)— aro
CRO (EXACT_SYNONYM)— aro
Cefatriaxone (EXACT_SYNONYM)— aro
Ceftriaxon (EXACT_SYNONYM)— aro
Ceftriaxona (EXACT_SYNONYM)— aro
Ceftriaxonum (EXACT_SYNONYM)— aro
Ceftriazone (EXACT_SYNONYM)— aro
Longacef (EXACT_SYNONYM)— aro
Longaceph (EXACT_SYNONYM)— aro
Rocephin (EXACT_SYNONYM)— aro

Cross-references

Equivalent identifiers for this same structure in other resources.

ARO:0000062
cas:73384-59-5
drugbank:DB01212
drugcentral:564
hmdb:HMDB0015343
kegg.compound:C06683
kegg.drug:D07659
metacyc.compound:CPD-12294
patent:GB2022090
patent:US4327210
reaxys:6495519
wikipedia.en:Ceftriaxone
chembl:CHEMBL161
pubchem.compound:5479530

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:0000062`	ceftriaxone	`antibioticmech:aro-f34c32c3a8`	2026-08-30
CHEBI	`CHEBI:29007`	ceftriaxone	`antibioticmech:chebi-ef2d0c9777`	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:0000062 (ceftriaxone); database assertion, not a primary citation.)

Resistance mechanisms

23 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 12

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
CAE-1	ARO:3007635	not organism-specific	—	ARO:3007635 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
CMY-2	ARO:3002013	not organism-specific	—	ARO:3002013 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
CTX-M-15	ARO:3001878	not organism-specific	—	ARO:3001878 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
CTX-M-3	ARO:3001866	not organism-specific	—	ARO:3001866 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
CTX-M-55	ARO:3001917	not organism-specific	—	ARO:3001917 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
PDC-3	ARO:3002500	not organism-specific	—	ARO:3002500 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
PDC-5	ARO:3002502	not organism-specific	—	ARO:3002502 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
PRC-1	ARO:3007085	not organism-specific	—	ARO:3007085 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
SHV-12	ARO:3001071	not organism-specific	—	ARO:3001071 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
VAM-1	ARO:3007062	not organism-specific	—	ARO:3007062 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
VMB-1	ARO:3005015	not organism-specific	—	ARO:3005015 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
blaS1	ARO:3005111	not organism-specific	—	ARO:3005111 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 4

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
Haemophilus influenzae PBP3 conferring resistance to beta-lactam antibiotics	ARO:3004446	not organism-specific	—	ARO:3004446 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
Neisseria gonorrhoeae PBP2 conferring resistance to beta-lactam antibiotics	ARO:3004832	not organism-specific	—	ARO:3004832 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
Neisseria gonorrhoeae pilQ gene conferring resistance to beta-lactam	ARO:3004835	not organism-specific	—	ARO:3004835 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
Neisseria meningititis PBP2 conferring resistance to beta-lactam	ARO:3003937	not organism-specific	—	ARO:3003937 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)

REDUCED_PERMEABILITY 4

REDUCED_PERMEABILITY
Determinant	ARO ID	Organism	Gene families	Evidence
IreK	ARO:3007678	not organism-specific	—	ARO:3007678 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
Klebsiella pneumoniae OmpK35	ARO:3003966	not organism-specific	—	ARO:3003966 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
Klebsiella pneumoniae OmpK36	ARO:3003968	not organism-specific	—	ARO:3003968 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
Serratia marcescens Omp1	ARO:3004128	not organism-specific	—	ARO:3004128 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 3

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Acinetobacter baumannii AbuO	ARO:3004578	not organism-specific	—	ARO:3004578 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
Klebsiella pneumoniae KpnEF	ARO:3004585	not organism-specific	—	ARO:3004585 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); database assertion, not a primary citation.)
MexAB-OprM	ARO:3000386	not organism-specific	—	ARO:3000386 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:0000062 (ceftriaxone); 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.