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

• ChemBase ID: 6228
• Molecular Formular: C12H15Cl2NO5S
• Molecular Mass: 356.2222
• Monoisotopic Mass: 355.00479895
• SMILES: C(Cl)(Cl)C(=O)N[C@H](CO)[C@H](O)c1ccc(cc1)S(=O)(=O)C
• Canonical SMILES: OC[C@H]([C@@H](c1ccc(cc1)S(=O)(=O)C)O)NC(=O)C(Cl)Cl
• 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
• InChIKey: OTVAEFIXJLOWRX-NXEZZACHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
• IUPAC Traditional name: thiamphenicol
• Synonyms: D-threo-2,2-Dichloro-N-(β-hydroxy-α-[hydroxymethyl]-4-[methylsulfonyl]phenethyl)acetamide; Thiamphenicol; THIAMPHENICOL; Thiophenicol; 2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide; D-d-threo-2-Dichloroacetamido-1-(4-methylsulfonylphenyl)-1,3-propanediol; Dextrosulphenidol; NSC 522822; Thiocymetin; Win 5063-2

Database IDs

• CAS Number: 15318-45-3
• EC Number: 239-355-3
• MDL Number: MFCD00467983
• Beilstein Number: 2819542
• PubChem SID: 160969653; 24899874; 99445092
• PubChem CID: 27200

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.6499147
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.22368595
• LogD (pH = 7.4): -0.38777936
• Log P: -0.22097217
• Molar Refractivity: 79.8796 cm^3
• Polarizability: 31.870874 Å^3
• Polar Surface Area: 103.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.33
• LOG S: -2.2
• Solubility (Water): 2.27e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; ethanol: soluble50 mg/mL, clear, colorless; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 163-166 °C; 165-168°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer, Under Inert Atmosphere
• RTECS: AB6680000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (TLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C12H15Cl2NO5S

DETAILS

DrugBank - DB08621

Drug information: experimental

Selleck Chemicals - S2583

Research Area: Infection
Biological Activity:
Thiamphenicol (Thiophenicol) is an antimicrobial antibiotic and a methyl-sulfonyl analogue of chloramphenicol. Thiamphenicol (Thiophenicol) has a similar antibacterial spectrum to chloramphenicol. Thiamphenicol (Thiophenicol) inhibits protein synthesis in bacteria. Thiamphenicol (Thiophenicol) has a bacteriostatic action against a broad range of microorganisms, although it may be bactericidal for some species under some conditions, and in concentrations 3 to 5 times higher than the bacteriostatic concentrations. Thiamphenicol (Thiophenicol) is particularly used for the treatment of sexually transmitted infections and pelvic inflammatory disease. [1][2]References on Thiamphenicol (Thiophenicol)[1] Chemotherapy. , 1975, 21(2):73-81[2] http://en.wikipedia.org/wiki/Thiamphenicol, ,

Sigma Aldrich - T0261

Application
Thiamphenicol is an antibiotic that has been used to treat chancroid in men and uncomplicated gonorrhea1,2. It is used in studies of bacterial protein synthesis at the level of peptidyl transferase activity associated with the 23S rRNA of the 50S ribosomal subunit. It is used to study chloraniphenicol-thiamphenicol-resistance and the use of fluorinated analogs when resistance is encountered3.
Biochem/physiol Actions
Thiamphenicol inhibits mitochondrial protein synthesis of proteins such as cytochrome c oxidase.

Toronto Research Chemicals - T344160

Thiamphenicol is an antibiotic. Thiamphenicol is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Thiamphenicol is used particularly for the treatment of sexually transmitted infectio

REFERENCES

• Tikhonova, E., et al.: J. Biol. Chem., 279, 32116 (2004)
• Baucheron, S., et al.: J. Antimicrob. Chemother., 55, 707 (2004)
• Pages, J., et al.: Trends. Mol. Med., 11, 382 (2004)
• Lomovskaya, O., et al.: Biochem. Pharmacol., 71, 910 (2004)
• Samosorn, S.,