dalfopristin

CHEBI:4309 ·resolve ·ANTIBACTERIAL ·EXACT REVIEWED

A macrolide that is pristinamycin IIA in which the double bond between positions 26 and 26a of the pyrroline ring has been reduced and position 26R carries a [2-(diethylamino)ethyl]sulfonyl group. It is a semi-synthetic streptogramin antibiotic and often used as a mixture with quinupristin for the treatment of vancomycin-resistant Enterococcus faecium. — ChEBI

Classification

streptogramin antibioticARO:0000026

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:140325
• Label unavailable CHEBI:140326
• macrolide antibiotic CHEBI:25105
• Label unavailable CHEBI:25106
• Label unavailable CHEBI:33308
• Label unavailable CHEBI:35681
• Label unavailable CHEBI:35850
• Label unavailable CHEBI:3992
• Label unavailable CHEBI:46812
• Label unavailable CHEBI:50996
• Label unavailable CHEBI:51751
• streptogramin antibiotic ARO:0000026

Chemical structure

SMILES

[H][C@@]12C(=O)O[C@H](C(C)C)[C@H](C)/C=C/C(=O)NC/C=C/C(C)=C/[C@@H](O)CC(=O)Cc3nc(co3)C(=O)N1CC[C@H]2S(=O)(=O)CCN(CC)CC

InChI

InChI=1S/C34H50N4O9S/c1-7-37(8-2)16-17-48(44,45)28-13-15-38-31(28)34(43)47-32(22(3)4)24(6)11-12-29(41)35-14-9-10-23(5)18-25(39)19-26(40)20-30-36-27(21-46-30)33(38)42/h9-12,18,21-22,24-25,28,31-32,39H,7-8,13-17,19-20H2,1-6H3,(H,35,41)/b10-9+,12-11+,23-18+/t24-,25-,28-,31-,32-/m1/s1

Also called

• dalfopristina (INN)— chebi
• dalfopristine (INN)— chebi
• dalfopristinum (INN)— chebi
• (3R,4R,5E,10E,12E,14S,26R,26aS)-26-{[2-(diethylamino)ethyl]sulfonyl}-14-hydroxy-4,12-dimethyl-3-(propan-2-yl)-8,9,14,15,24,25,26,26a-octahydro-1H,3H,22H-21,18-(azeno)pyrrolo[2,1-c][1,8,4,19]dioxadiazacyclotetracosine-1,7,16,22(4H,17H)-tetrone (EXACT_SYNONYM)— chebi
• RP 54476 (EXACT_SYNONYM)— chebi
• RP-54476 (EXACT_SYNONYM)— chebi
• RP54476 (EXACT_SYNONYM)— chebi

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.

• dalfopristinARO:3000674
• cas:112362-50-2
• hmdb:HMDB0015566
• kegg.compound:C08033
• pdb-ccd:DOL
• chembl:CHEMBL1200937
• pubchem.compound:6323289

Drug registries

Identifiers that name a drug rather than a structure. One of these can cover a parent compound, its salts and its stereoisomers, which this corpus keeps as separate records, so it is not an equivalence of structure.

• drugbank:DB01764
• drugcentral:778
• kegg.drug:D00853

Patents and articles

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

• wikipedia.en:Dalfopristin

Activity roles

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

• antimicrobial agent CHEBI:33281
• antibacterial drug 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.

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

antibiotic sensitive peptidyl transferase (23S rRNA) NUCLEIC_ACID DIRECT_BINDING_TARGET

ARO:3000754

CARD/ARO database assertion; target organism, strain, and assay are not specified. 23S rRNA peptidyl-transferase center is asserted as the target. Evidence status: PRIMARY_EVIDENCE_NEEDED. Source: CARD_ARO 2026-08-30 (retrieved 2026-08-30).

• ARO:3000754 (CARD/ARO asserts targeted_by_antibiotic ARO:3000674 (dalfopristin); database assertion, not a primary citation.)

50S ribosomal peptidyl-transferase center RIBOSOMAL_SUBUNIT DIRECT_BINDING_TARGET

A D. radiodurans 50S cocrystal with dalfopristin and quinupristin localized dalfopristin in the peptidyl-transferase center and showed the synergistic rRNA rearrangement. Evidence status: PRIMARY_EVIDENCE. Source: PRIMARY_LITERATURE 2004-04 (retrieved 2026-09-02).

Deinococcus radiodurans NCBITaxon:1299

• PMID:15059283 (Primary dalfopristin/quinupristin-bound 50S structural mechanism study (DOI:10.1186/1741-7007-2-4).)

Mechanism summary

Mode of action

PROTEIN_SYNTHESIS_INHIBITION host shared target — CURATOR: PMID:15059283 resolved dalfopristin with quinupristin on the Deinococcus radiodurans 50S subunit. Dalfopristin binds in the peptidyl-transferase center, perturbs A- and P-site tRNA occupation, and cooperates with quinupristin to stabilize a nonproductive rRNA conformation. PMID:12771141 also resolved dalfopristin in the resistance acetyltransferase VatD.

Resistance mechanisms

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

Record-level evidence

• PMID:15059283 (Primary ribosome-bound dalfopristin/quinupristin mechanism study.)
• PMID:12771141 (Primary VatD-dalfopristin resistance-enzyme cocrystal study.)

Curation history

1. SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Seeded from data/raw/ inventories (ARO, CHEBI)

2. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

3. RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

4. RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources

   Re-seeded from updated data/raw/ inventories

5. REVIEWED 2026-09-02 · codex · LLM-assisted

   Verified exact ChEBI/CARD identity, structure, roles, class, and the provenance of retained CARD resistance assertions; curator-confirmed protein-synthesis inhibition and added a primary dalfopristin-bound 50S target beside the imported target.

6. 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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