thiamphenicol

Also known as D-(+)-threo-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)acetamide, (+)-Thiamphenicol, Armai (TN), Thiocymetin (TN), dextrosulphenidol

Thiamphenicol (also known as thiophenicol and dextrosulphenidol) is an antibiotic. It is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Like chloramphenicol, it is insoluble in water, but highly soluble in lipids. It is used in many countries as a veterinary antibiotic, but is available in China, Taiwan, Brazil, Morocco, and Italy for use in humans. Its main advantage over chloramphenicol is that it has never been associated with aplastic anaemia.

In the Vinony graph

Within Vinony's link graph, thiamphenicol is referenced by 1,206 other articles, and connects out to neomycin, Brazil and International Standard Book Number.

It sits within the topics 4-(Methylsulphonyl)phenyl compounds, Acetamides and Amphenicols.

Its subject is documented across 16 Wikipedia language editions.

Chemical data

Formula: C12H15Cl2NO5S
Molecular weight: 356.2 g/mol
IUPAC name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
SMILES: CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O
InChIKey: OTVAEFIXJLOWRX-NXEZZACHSA-N
XLogP: -0.3
Polar surface area: 112 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 2
Molecule type: Small molecule
Indications: bacterial disease

via ChEMBL · EBI

Research

1,624 papers

Chloramphenicol and thiamphenicol.Antibiotics and chemotherapy · 1982
[Chloramphenicol and thiamphenicol].La Clinica terapeutica · 1978
In vitro activity of thiamphenicol against drug-susceptible and drug-resistant strains of Mycoplasma genitalium.The Journal of antimicrobial chemotherapy · 2025
Failure of thiamphenicol in a penicillin-allergic patient with Listeria meningoencephalitis--delayed cure following penicillin desensitization.Intensive care medicine · 1992
Pharmacokinetics of florfenicol and thiamphenicol in ducks.Journal of veterinary pharmacology and therapeutics · 2019

via PubMed

Wikidata facts

Mass: 355.005

Show 7 more facts

chemical formula: C₁₂H₁₅Cl₂NO₅S
canonical SMILES: CS(=O)(=O)C1=CC=C(C=C1)C(C(CO)NC(=O)C(Cl)Cl)O
isomeric SMILES: CS(=O)(=O)C1=CC=C(C=C1)[C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl
NCI Thesaurus ID: C61969
subject has role: antibiotic
medical condition treated: bacterial infectious disease
Commons category: Thiamphenicol

Sources (5)

via Wikidata · CC0

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Encyclopedic overview

2 sections

Contents

References
Further reading

{{Drugbox | Verifiedfields = changed | verifiedrevid = 470606287 | IUPAC_name = 2,2-dichloro-N-{(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl}acetamide | image = Thiamphenicol.svg | image_class = skin-invert-image | width = 214 | image2 = Thiamphenicol_sf.gif | image_class2 = bg-transparent

Excerpted from Wikipedia’s “thiamphenicol” article, available under the CC BY-SA 4.0 licence.