clarithromycin
The 6-O-methyl ether of erythromycin A, clarithromycin is a macrolide antibiotic used in the treatment of respiratory-tract, skin and soft-tissue infections. It is also used to eradicate Helicobacter pylori in the treatment of peptic ulcer disease. It prevents bacteria from growing by interfering with their protein synthesis.
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
macrolide antibioticARO:0000000
- macrolide antibiotic
CHEBI:25105 - macrolide antibiotic
ARO:0000000
Chemical structure
| Molecular formula | C38H69NO13 |
|---|---|
| Charge | 0 |
| Average mass | 747.964 Da |
| Monoisotopic mass | 747.47689 Da |
| Source | ChEBI |
| InChIKey | AGOYDEPGAOXOCK-KCBOHYOISA-N |
[H][C@]1(O[C@H]2[C@H](C)[C@@H](O[C@]3([H])O[C@H](C)C[C@H](N(C)C)[C@H]3O)[C@](C)(OC)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@@H]2C)C[C@@](C)(OC)[C@@H](O)[C@H](C)O1
InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
Also called
- clarithromycina
- clarithromycine
- clarithromycinum
- O6-methylerythromycin
- 6-O-methylerythromycin
- 6-O-methylerythromycin A
- CLA
- CLARITHROMYCIN
- Clarithromycin
- Biaxin
- CLR
- Clambiotic
- Clarith
- Clathromycin
- Klacid
- Klaricid
- Macladin
- Naxy
- Veclam
Cross-references
- clarithromycin
ARO:0000065 - cas:81103-11-9
- kegg.compound:C06912
- lincs.smallmolecule:LSM-5606
- lipidmaps:LMPK04000014
- pdb-ccd:CTY
- reaxys:3581974
- chembl:CHEMBL1741
- pubchem.compound:84029
Drug registries
Patents and articles
Activity roles
- antimicrobial agent
CHEBI:33281 - antibacterial drug
CHEBI:36047
Source concepts
| Source | Native ID | Label | Minted CURIE | Version |
|---|---|---|---|---|
| ARO | ARO:0000065 |
clarithromycin | antibioticmech:aro-5c92a4ddc8 |
2026-08-30 |
| CHEBI | CHEBI:3732 |
clarithromycin | antibioticmech:chebi-e63133b2eb |
2026-08-30 |
Molecular targets
50S ribosomal subunit P-site RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET
Mechanism summary
- Mode of action
- PROTEIN_SYNTHESIS_INHIBITION microbial target
- Clinical status
- APPROVED
Activity spectrum
| Organism | Activity | MIC | Disk diffusion | Assay | Strain | Sample/genome | Evidence |
|---|---|---|---|---|---|---|---|
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; CLIRES2020; not specified | — |
1 source isolates 1 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; SEQTREAT2020; liquid media; microdilution plate; MYCOTB; critical concentration 0.5 mg/L | — |
6 source isolates 6 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; SEQTREAT2020; liquid media; microdilution plate; MYCOTB; critical concentration 0.5 mg/L | — |
6 source isolates 6 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | — | — | — | CRyPTIC DST; SEQTREAT2020; liquid media; microdilution plate; MYCOTB; critical concentration 0.5 mg/L | — |
451 source isolates 451 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | RESISTANT | — | — | CRyPTIC DST; SEQTREAT2020; solid media; middlebrook; 7H10; critical concentration 3.0 mg/L | — |
52 source isolates 52 measurements |
EvidencePage data (JSON.gz) |
| Mycobacterium tuberculosis complex | SUSCEPTIBLE | — | — | CRyPTIC DST; SEQTREAT2020; solid media; middlebrook; 7H10; critical concentration 3.0 mg/L | — |
21 source isolates 21 measurements |
EvidencePage data (JSON.gz) |
Resistance mechanisms
ANTIBIOTIC_TARGET_ALTERATION 35
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| Erm(33) | ARO:3000599 | — | ||
| Erm(34) | ARO:3000600 | — | ||
| Erm(35) | ARO:3000604 | — | ||
| Erm(36) | ARO:3000605 | — | ||
| Erm(37) | ARO:3000392 | — | ||
| Erm(38) | ARO:3000601 | — | ||
| Erm(39) | ARO:3000602 | — | ||
| Erm(41) | ARO:3000603 | — | ||
| Erm(50) | ARO:3007032 | — | ||
| Erm(51) | ARO:3007033 | — | ||
| ErmA | ARO:3000347 | — | ||
| ErmB | ARO:3000375 | — | ||
| ErmC | ARO:3000250 | — | ||
| ErmD | ARO:3000495 | — | ||
| ErmE | ARO:3000326 | — | ||
| ErmF | ARO:3000498 | — | ||
| ErmG | ARO:3000522 | — | ||
| ErmN | ARO:3000592 | — | ||
| ErmQ | ARO:3000593 | — | ||
| ErmR | ARO:3000594 | — | ||
| ErmT | ARO:3000595 | — | ||
| ErmX | ARO:3000596 | — | ||
| Escherichia coli 23S rRNA with mutation conferring resistance to clarithromycin | ARO:3004160 | — | ||
| Helicobacter pylori 23S rRNA with mutation conferring resistance to clarithromycin | ARO:3004134 | — | ||
| Mycobacterium avium 23S rRNA with mutation conferring resistance to clarithromycin | ARO:3004164 | — | ||
| Mycobacterium intracellulare 23S rRNA with mutation conferring resistance to clarithromycin | ARO:3004166 | — | ||
| Mycobacterium kansasii 23S rRNA with mutation conferring resistance to clarithromycin | ARO:3004168 | — | ||
| Mycobacteroides abscessus 23S rRNA with mutation conferring resistance to clarithromycin | ARO:3004163 | — | ||
| Mycobacteroides chelonae 23S rRNA with mutation conferring resistance to clarithromycin | ARO:3004165 | — | ||
| Mycolicibacterium smegmatis 23S rRNA with mutation conferring resistance to clarithromycin | ARO:3004169 | — | ||
| Mycoplasma hominis 23S rRNA with mutation conferring resistance to macrolide antibiotics | ARO:3004176 | — | ||
| Mycoplasmopsis fermentans 23S rRNA with mutation conferring resistance to macrolide antibiotics | ARO:3004177 | — | ||
| erm(40) | ARO:3004606 | — | ||
| erm(46) | ARO:3004596 | — | ||
| erm(55) | ARO:3009647 | — |
UNKNOWN 10
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| erm(55)-associated clarithromycin resistance in clinical isolate 18:60630 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) | |
| erm(55)-associated clarithromycin resistance in clinical isolate 18:62378 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) | |
| erm(55)-associated clarithromycin resistance in clinical isolate 19:64973 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) | |
| erm(55)-associated clarithromycin resistance in clinical isolate 20:67831 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) | |
| erm(55)-associated clarithromycin resistance in clinical isolate 20:69984 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) | |
| erm(55)-associated clarithromycin resistance in clinical isolate 21:70135 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) | |
| erm(55)-associated clarithromycin resistance in clinical isolate 21:70968 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) | |
| erm(55)-associated clarithromycin resistance in clinical isolate 21:71627 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) | |
| erm(55)-associated clarithromycin resistance in clinical isolate 21:73373 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) | |
| erm(55)-associated clarithromycin resistance in clinical isolate MC6 22:74950 |
— | Mycobacteroides chelonae NCBITaxon:1774 |
erm(55) |
ANTIBIOTIC_INACTIVATION 8
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| EreA | ARO:3000361 | — | ||
| EreB | ARO:3000363 | — | ||
| mphA | ARO:3000316 | — | ||
| mphB | ARO:3000318 | — | ||
| mphC | ARO:3000319 | — | ||
| mphF | ARO:3003071 | — | ||
| mphG | ARO:3003742 | — | ||
| mphL | ARO:3003072 | — |
ANTIBIOTIC_EFFLUX 1
| Determinant | ARO ID | Organism | Gene families | Evidence |
|---|---|---|---|---|
| lmrP | ARO:3003969 | — |
Causal graphs
Clarithromycin blocks the bacterial 50S exit tunnel MECHANISTIC
Clarithromycin binds the macrolide site in the bacterial 50S nascent-peptide exit tunnel, restricting translation elongation and reducing protein synthesis.
| Node | Label | Type | Grounding |
|---|---|---|---|
clarithromycin |
clarithromycin | COMPOUND | CHEBI:3732 |
ribosomal_50s_macrolide_site |
bacterial 50S nascent-peptide exit tunnel macrolide site | RNA | REVIEWED_LABEL_ONLY |
clarithromycin_bound_50s |
clarithromycin-bound 50S exit tunnel | STATE | REVIEWED_LABEL_ONLY |
translation_elongation |
bacterial translation elongation | BIOLOGICAL_PROCESS | REVIEWED_LABEL_ONLY |
protein_synthesis |
bacterial protein synthesis | BIOLOGICAL_PROCESS | REVIEWED_LABEL_ONLY |
| Subject | Predicate | Object | Evidence |
|---|---|---|---|
clarithromycin |
binds | clarithromycin_bound_50s |
|
ribosomal_50s_macrolide_site |
participates in | clarithromycin_bound_50s |
|
clarithromycin_bound_50s |
decreases | translation_elongation |
|
translation_elongation |
supports | protein_synthesis |
Curation history
-
SEEDED_FROM_SOURCES
Seeded from data/raw/ inventories (ARO, CHEBI)
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
CURATED_CAUSAL_GRAPH
Added a PMID-supported causal graph for clarithromycin binding to the bacterial 50S macrolide site.
-
RESEEDED_FROM_SOURCES
Re-seeded from updated data/raw/ inventories
-
RESEEDED_FROM_SOURCES
Re-seeded; changed: activity_spectrum (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
-
RESEEDED_FROM_SOURCES
Re-seeded; changed: activity_membership_collections (CRYPTIC 3.4.0). Upstream retrieval date 2026-08-30, unchanged.
-
CURATED_RESISTANCE_EVIDENCE
Added ten clinical-isolate erm(55)/clarithromycin co-occurrence claims using corrected primary Table 2; grounded the verified species synonym while withholding exact alleles and protein identifiers. Preserved all source-owned content and negative-comparator distinctions. Whole-record review remains open.