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Substance Name: Thiamphenicol [USAN:INN:BAN:JAN]
RN: 15318-45-3
UNII: FLQ7571NPM
InChIKey: OTVAEFIXJLOWRX-NXEZZACHSA-N

Note

  • A methylsulfonyl analog of CHLORAMPHENICOL. It is an antibiotic and immunosuppressive agent.

Molecular Formula

  • C12-H15-Cl2-N-O5-S

Molecular Weight

  • 356.2245
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Human Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Thiamphenicol
  • Thiamphenicol [USAN:INN:BAN:JAN]

MeSH Heading

  • Thiamphenicol

Synonyms

  • (+)-Thiamphenicol
  • 8065 C.B.
  • Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)ethyl)-, (R-(R*,R*))-
  • CCRIS 8588
  • D-(+)-threo-2,2-Dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)acetamide
  • D-d-threo-2-Dichloroacetamido-1-(4-methylsulfonylphenyl)-1,3-propanediol
  • D-Thiocymetin
  • D-Thiophenicol
  • D-threo-(1R,2R)-1-(p-Methylsulfonylphenyl)-2-dichloroacetamido-1,3-propanediol
  • Descocin
  • Dexawin
  • Dextrosulphenidol
  • Efnicol
  • EINECS 239-355-3
  • Hyrazin
  • Igralin
  • Macphenicol
  • Masatirin
  • Methylsulfonylchloramphenicol
  • Neomyson
  • NSC 522822
  • Rincrol
  • SW 5063
  • Thiamcol
  • Thiamphenicol
  • Thiamphenicolum
  • Thiamphenicolum [INN-Latin]
  • Thiocymetin
  • Thiophenicol
  • Tiamfenicol
  • Tiamfenicol [INN-Spanish]
  • Tiamfenicolo
  • Tiamfenicolo [DCIT]
  • Unaseran-D
  • UNII-FLQ7571NPM
  • Urfamicina
  • Urfamycine
  • Urophenyl
  • Win 5063-2
  • WIN-5063-2

Systematic Names

  • Acetamide, 2,2-dichloro-N-((1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)ethyl)-
  • Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsulfonyl)phenyl)ethyl)-, (R-(R*,R*))-
  • Acetamide, 2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-(methylsulfonyl)phenethyl)-, D-threo-(+)
  • Thiamphenicol

Registry Numbers

CAS Registry Number

  • 15318-45-3

FDA UNII

  • FLQ7571NPM

Other Registry Numbers

  • 14786-51-7
  • 32430-04-9
  • 3785-14-6
  • 90-91-5

System Generated Number

  • 0015318453

Structure Descriptors

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

InChIKey

OTVAEFIXJLOWRX-NXEZZACHSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo unreported 214mg/kg/10D (214mg/kg) BEHAVIORAL: SLEEP

GASTROINTESTINAL: NAUSEA OR VOMITING

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 944, 1974.
mouse LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 390, 1969.
mouse LD50 intravenous 368mg/kg (368mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 390, 1969.
mouse LD50 oral > 7gm/kg (7000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 390, 1969.
rat LD50 intraperitoneal > 5gm/kg (5000mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 390, 1969.
rat LD50 intravenous 339mg/kg (339mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 3, Pg. 390, 1969.
rat LD50 oral > 5gm/kg (5000mg/kg)   Drugs in Japan Vol. -, Pg. 740, 1995.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 165.3 deg C   EXP
log P (octanol-water) -0.330 (none)   EST
Atmospheric OH Rate Constant 3.24E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.