thiamphenicol

CHEBI:32215 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

Derivative of Chloramphenicol. The nitro group (-NO2) is substituted by a sulfomethyl group (-SO2CH3). — PMID:15539072

Classification

phenicol antibioticARO:3000387

Strictly broader compounds or drug classes this molecule belongs to.

• Label unavailable CHEBI:29347
• Label unavailable CHEBI:35850
• phenicol antibiotic ARO:3000387

Chemical structure

SMILES

CS(=O)(=O)c1ccc([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)cc1

InChI

InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1

Also called

• 2,2-dichloro-N-{(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl}acetamide (EXACT_SYNONYM)— chebi
• (+)-Thiamphenicol (EXACT_SYNONYM)— chebi
• Armai (TN) (EXACT_SYNONYM)— chebi
• D-(+)-threo-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)acetamide (EXACT_SYNONYM)— chebi
• Thiamphenicol (EXACT_SYNONYM)— chebi
• Thiocymetin (TN) (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.

• thiamphenicolARO:3000456
• cas:15318-45-3
• kegg.compound:C12853
• lincs.smallmolecule:LSM-5858
• pdb-ccd:TH8
• vsdb:1911
• chembl:CHEMBL1236282
• pubchem.compound:27200

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:DB08621
• drugcentral:2624
• kegg.drug:D01407

Activity roles

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

• antimicrobial agent 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.

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:3000456 (thiamphenicol); database assertion, not a primary citation.)

Resistance mechanisms

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

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. 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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