Thiamphenicol (CED0006306)

Record Information

Version

1.0

Creation Date

2016-05-22 03:31:15 UTC

Update Date

2026-08-18 18:04:03 UTC

Accession Number

CHEM016423

Identification

Common Name

Thiamphenicol

Class

Small Molecule

Description

Thiamphenicol is an organic compound with the chemical formula C12H15Cl2NO5S and an average molecular weight of 356.22 g/mol. Thiamphenicol belongs to the benzenesulfonyl compounds, a subclass of benzene and substituted derivatives within the organic compounds. This compound is identified as being found in or released from 11 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an antibiotic. Other sources include food, food processing, and cookware, specifically in the processing of meats, as well as household cleaning and consumer products such as tobacco smoke filters. Additionally, it is associated with electrical and electronic equipment, including antennas, electric switches, electrically stimulated smoking devices, fixed capacitors and their manufacture, and line transmission systems, among three other sources. Recorded routes of exposure for thiamphenicol include oral and inhalation. Regarding its biological activity, one protein target has been recorded: the Dr hemagglutinin structural subunit (draA).

Contaminant Type

Human Neurotoxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Thiamphenicol	ChEBI
Armai	ChEBI
D-(+)-Threo-2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)acetamide	ChEBI
Thiocymetin	ChEBI
Dexawin	Kegg
D-(+)-Threo-2,2-dichloro-N-(b-hydroxy-a-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)acetamide	Generator
D-(+)-Threo-2,2-dichloro-N-(b-hydroxy-a-(hydroxymethyl)-p-(methylsulphonyl)phenethyl)acetamide	Generator
D-(+)-Threo-2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulphonyl)phenethyl)acetamide	Generator
D-(+)-Threo-2,2-dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)acetamide	Generator
D-(+)-Threo-2,2-dichloro-N-(β-hydroxy-α-(hydroxymethyl)-p-(methylsulphonyl)phenethyl)acetamide	Generator
Vicemycetin	MeSH
Thiomycetin	MeSH
Dextrosulfenidol	MeSH
Thiophenicol	MeSH
Urfamycin	MeSH
Raceophenidol	MeSH
Thiamcol	MeSH
Sanofi brand OF thiamphenicol	MeSH
Zambon brand OF thiamphenicol	MeSH

Chemical Formula

C₁₂H₁₅Cl₂NO₅S

Average Molecular Mass

356.222 g/mol

Monoisotopic Mass

355.005 g/mol

CAS Registry Number

15318-45-3

IUPAC Name

2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide

Traditional Name

thiamphenicol

SMILES

[H][C@](CO)(NC(=O)C(Cl)Cl)[C@]([H])(O)C1=CC=C(C=C1)S(C)(=O)=O

InChI Identifier

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

InChI Key

OTVAEFIXJLOWRX-NXEZZACHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonyl compounds

Direct Parent

Benzenesulfonyl compounds

Alternative Parents

Substituents

Benzenesulfonyl group
Sulfone
Sulfonyl
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Alcohol
Aromatic alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Primary alcohol
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

sulfone (CHEBI:32215 )
monocarboxylic acid amide (CHEBI:32215 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.27 g/L	ALOGPS
logP	0.33	ALOGPS
logP	-0.22	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.65	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	79.88 m³·mol⁻¹	ChemAxon
Polarizability	32.29 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0649000000-3f7e62d09a29a445c8a6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-2931000000-1f1691e17ae627c7d762	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0649000000-3f7e62d09a29a445c8a6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-2931000000-1f1691e17ae627c7d762	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-0119000000-d79b9cd923b41085e791	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-0697000000-5d2f4906b775ca05b56a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-2930000000-c1620ac7ed346ef97c7d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1249000000-15a531c5279040580bd0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-6945000000-a470bfa27bf9e1406426	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9600000000-631e16b07c1556c258ad	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2587.0	Log mg/kg	[1500:4600]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
306	Antibiotics	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
517	Electric Switches	Electrical & Electronic Equipment	Not Available
518	Electrically Stimulated Smoking Devices	Electrical & Electronic Equipment	Not Available
521	Fixed Capacitors And Their Manufacture	Electrical & Electronic Equipment	Not Available
525	Line Transmission Systems	Electrical & Electronic Equipment	Not Available
531	Relays	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
552	Processing Meats	Food, food processing & cookware	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
592	Marine Propulsion Or Steering	Marine, shipping & aquaculture	Not Available
603	Nematocides	Agriculture & land management	Not Available
605	Pest Repellants	Agriculture & land management	Not Available
613	Depilatories	Personal care & cosmetics	Not Available
617	Lip Care Products	Personal care & cosmetics	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available

Pathways

0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Methionine--tRNA ligase, mitochondrial	Q96GW9	Humans	Predicted (SEA)	0.233548
Click to view 3D structure	Procathepsin L	P07711	Humans	Predicted (SEA)	215.02
Click to view 3D structure	Cathepsin B	P07858	Humans	Predicted (SEA)	205.833
Click to view 3D structure	Streptokinase A	P10520	Streptococcus pyogenes serotype M1	Predicted (SEA)	195.402
Click to view 3D structure	Cathepsin S	P25774	Humans	Predicted (SEA)	234.56
Click to view 3D structure	Cathepsin K	P43235	Humans	Predicted (SEA)	243.668
Click to view 3D structure	Cathepsin F	Q9UBX1	Humans	Predicted (SEA)	9.49761
Click to view 3D structure	Prostaglandin G/H synthase 2	P79208	Ovis aries	Predicted (SEA)	51.2248
Click to view 3D structure	Alkaline ceramidase 2	Q5QJU3	Humans	Predicted (SEA)	45.8532
Click to view 3D structure	Cruzipain	P25779	Trypanosoma cruzi	Predicted (SEA)	165.585
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	922.591
Click to view 3D structure	Prostaglandin G/H synthase 1	P05979	Ovis aries	Predicted (SEA)	198.516
Click to view 3D structure	5-lipoxygenase	O49150	Solanum tuberosum	Predicted (SEA)	3.19182
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	3491.38
Click to view 3D structure	Macrophage colony-stimulating factor 1 receptor	P07333	Humans	Predicted (SEA)	2381.64
Click to view 3D structure	Prostaglandin G/H synthase 1	P22437	Mus musculus	Predicted (SEA)	20.0072
Click to view 3D structure	Seed linoleate 13S-lipoxygenase-1	P08170	Glycine max	Predicted (SEA)	11.8331
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	1175.52
Click to view 3D structure	Matrix metalloproteinase-9	P14780	Humans	Predicted (SEA)	1020.37
Click to view 3D structure	Vascular endothelial growth factor receptor 2	P35968	Humans	Predicted (SEA)	3421.47
Click to view 3D structure	Prostaglandin G/H synthase 2	P35354	Humans	Predicted (SEA)	657.281
Click to view 3D structure	Cyclin-dependent kinase 2	P24941	Humans	Predicted (SEA)	2817.21
Click to view 3D structure	Cyclin-dependent kinase 1	P06493	Humans	Predicted (SEA)	2317.88
Click to view 3D structure	Ceramide transfer protein	Q9Y5P4	Humans	Predicted (SEA)	51.3026
Click to view 3D structure	Mitogen-activated protein kinase 9	P45984	Humans	Predicted (SEA)	2597.59