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15318-45-3 molecular structure
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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 and InChIs

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

Cite this record

CBID:6228 http://www.chembase.cn/molecule-6228.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 7.6499147  H Acceptors
H Donor LogD (pH = 5.5) -0.22368595 
LogD (pH = 7.4) -0.38777936  Log P -0.22097217 
Molar Refractivity 79.8796 cm3 Polarizability 31.870874 Å3
Polar Surface Area 103.7 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.33  LOG S -2.2 
Solubility (Water) 2.27e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Ethanol expand Show data source
ethanol: soluble50 mg/mL, clear, colorless expand Show data source
Methanol expand Show data source
Apperance
White to Off-White Solid expand Show data source
Melting Point
163-166 °C expand Show data source
165-168°C expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
AB6680000 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥99.0% (TLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C12H15Cl2NO5S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB08621 external link
Drug information: experimental
Selleck Chemicals - S2583 external link
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 external link
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 external link
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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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.,
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PATENTS

PATENTS

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INTERNET

INTERNET

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