thiamphenicol

CHEBI:32215 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

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

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

phenicol antibioticARO:3000387

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:29347 CHEBI:29347
CHEBI:35850 CHEBI:35850
ARO:3000387 ARO:3000387

Chemical structure

Computed structure properties
Molecular formula	C12H15Cl2NO5S
Charge	0
Average mass	356.227 Da
Monoisotopic mass	355.0048 Da
Source	ChEBI
InChIKey	OTVAEFIXJLOWRX-NXEZZACHSA-N

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

Equivalent identifiers for this same structure in other resources.

ARO:3000456
cas:15318-45-3
drugbank:DB08621
drugcentral:2624
kegg.compound:C12853
kegg.drug:D01407
lincs.smallmolecule:LSM-5858
pdb-ccd:TH8
vsdb:1911
chembl:CHEMBL1236282
pubchem.compound:27200

Activity roles

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

CHEBI:33281 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.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
ARO	`ARO:3000456`	thiamphenicol	`antibioticmech:aro-af60808af7`	2026-08-30
CHEBI	`CHEBI:32215`	thiamphenicol	`antibioticmech:chebi-ad740ea0f4`	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.

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 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 19

ANTIBIOTIC_INACTIVATION
Determinant	ARO ID	Organism	Gene families	Evidence
Bacillus pumilus cat86	ARO:3002672	not organism-specific	—	ARO:3002672 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
CatU	ARO:3003983	not organism-specific	—	ARO:3003983 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
Clostridium butyricum catB	ARO:3002674	not organism-specific	—	ARO:3002674 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
Limosilactobacillus reuteri cat-TC	ARO:3002671	not organism-specific	—	ARO:3002671 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
Plasmid-encoded cat (pp-cat)	ARO:3002689	not organism-specific	—	ARO:3002689 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
Pseudomonas aeruginosa catB6	ARO:3002678	not organism-specific	—	ARO:3002678 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
Pseudomonas aeruginosa catB7	ARO:3002679	not organism-specific	—	ARO:3002679 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catA1	ARO:3002683	not organism-specific	—	ARO:3002683 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catB10	ARO:3003110	not organism-specific	—	ARO:3003110 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catB2	ARO:3002675	not organism-specific	—	ARO:3002675 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catB3	ARO:3002676	not organism-specific	—	ARO:3002676 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catB8	ARO:3002680	not organism-specific	—	ARO:3002680 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catB9	ARO:3002681	not organism-specific	—	ARO:3002681 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catD	ARO:3002682	not organism-specific	—	ARO:3002682 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catII	ARO:3002684	not organism-specific	—	ARO:3002684 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catIII	ARO:3002685	not organism-specific	—	ARO:3002685 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catP	ARO:3002686	not organism-specific	—	ARO:3002686 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catQ	ARO:3002687	not organism-specific	—	ARO:3002687 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
catS	ARO:3002688	not organism-specific	—	ARO:3002688 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)

ANTIBIOTIC_TARGET_ALTERATION 6

ANTIBIOTIC_TARGET_ALTERATION
Determinant	ARO ID	Organism	Gene families	Evidence
cfrA	ARO:3003441	not organism-specific	—	ARO:3003441 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
cfrE	ARO:3005023	not organism-specific	—	ARO:3005023 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
cipA	ARO:3003907	not organism-specific	—	ARO:3003907 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
clbA	ARO:3002814	not organism-specific	—	ARO:3002814 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
clbB	ARO:3002815	not organism-specific	—	ARO:3002815 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
clbC	ARO:3002816	not organism-specific	—	ARO:3002816 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)

ANTIBIOTIC_EFFLUX 3

ANTIBIOTIC_EFFLUX
Determinant	ARO ID	Organism	Gene families	Evidence
Escherichia coli mdfA	ARO:3001328	not organism-specific	—	ARO:3001328 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
MexMN-OprM	ARO:3003703	not organism-specific	—	ARO:3003703 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); database assertion, not a primary citation.)
MexPQ-OpmE	ARO:3003697	not organism-specific	—	ARO:3003697 (CARD/ARO asserts confers_resistance_to_antibiotic ARO:3000456 (thiamphenicol); 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.