Dirithromycin

Summary

Dirithromycin (CHEMBL1237072) is an approved small-molecule prodrug (ATC J01FA13); indicated across 2 conditions including bacterial infectious disease and osteomyelitis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J01FA13
• Indications: 2 conditions
• Chemistry: 835.1 Da · C42H78N2O14

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1237072
Name	Dirithromycin
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	6473883
ChEBI	CHEBI:474014
ATC	J01FA13
Molecular formula	C42H78N2O14
Molecular weight	835.1
InChIKey	WLOHNSSYAXHWNR-DWIOZXRMSA-N

SMILES: CC[C@@H]1[C@@]([C@H]2[C@H]([C@H]([C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C)O)(C)O)C)N[C@H](O2)COCCOC)C)(C)O

IUPAC name: (1R,2R,3R,6R,7S,8S,9R,10R,12R,13S,15R,17S)-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-2,10-dihydroxy-7-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-15-(2-methoxyethoxymethyl)-2,6,8,10,12,17-hexamethyl-4,16-dioxa-14-azabicyclo[11.3.1]heptadecan-5-one

ChEBI definition: The hemi-aminal resulting from the condensation of the erythromycin derivative (9S)-erythromycyclamine with 2-(2-methoxyethoxy)acetaldehyde. As the oxazine ring containing the hemi-aminal group is unstable under both acidic and alkaline conditions, dirithromycin functions as a more lipid-soluble prodrug for (9S)-erythromycyclamine. Administered as enteric coated tablets to protect it from acid catalysed hydrolysis in the stomach, it is used to treat respiratory tract, skin, and soft tissue infections caused by susceptible organisms.

Pharmacological roles (ChEBI): prodrug.

Also known as: Dirithromycin, Dirithromycine, Diritromicina, Dynabac, LY 237216, LY-237216, NSC-758672, dirithromycin, SID11532875, DIRITHROMYCIN, SID56422096, DIRITHROMYCINE

Patent coverage: 34 distinct patent families (64 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: Lysine-specific demethylase 4E, Prelamin-A/C, Menin/Histone-lysine N-methyltransferase MLL, Prostaglandin G/H synthase 1.

Bioactivity

ChEMBL activities: 1 potent at pChembl ≥ 5 of 4 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
PTGS1	5.02	AC50	9630	nM	CHEMBL_ACT_25205274

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

2 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
bacterial infectious disease	4	MONDO:0005113	EFO:0000771
osteomyelitis	0	MONDO:0005246	EFO:0003102

Clinical trials

Total trials: 0.

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).