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Ent-Thiamphenicol

CAT: 0804-HY-116974Size: 1 EachDry Ice: NoHazardous: No
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Description
Ent-Thiamphenicol (ent-Dextrosulphenidol) is a enantiomer of Thiamphenicol. Thiamphenicol, a methyl-sulfonyl derivative of Chloramphenicol, is a broad-spectrum antimicrobial antibiotic. Thiamphenicol acts by binding to the 50S ribosomal subunit, leading to inhibition of protein synthesis and bacteriostatic effect (against Gram-negative, Gram-positive aerobic and anaerobic bacteria)[2].
CAS Number
19934-71-5
Product Name Alternative
Ent-Thiophenicol; ent-Dextrosulphenidol
UNSPSC
12352005
Target
Antibiotic
Type
Reference compound
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Others
Assay Protocol
https://www.medchemexpress.com/ent-thiamphenicol.html
Smiles
O[C@H]([C@H](CO)NC(C(Cl)Cl)=O)C1=CC=C(S(C)(=O)=O)C=C1
Molecular Formula
C12H15Cl2NO5S
Molecular Weight
356.22
References & Citations
[1]A Marchese, et al. In vitro activity of thiamphenicol against multiresistant Streptococcus pneumoniae, Haemophilus influenzae and Staphylococcus aureus in Italy. J Chemother. 2002 Dec;14 (6) :554-61.|[2]Marta Tikhomirov, et al. Pharmacokinetics of florfenicol and thiamphenicol in ducks. J Vet Pharmacol Ther. 2019 Jan;42 (1) :116-120.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

ent-Thiamphenicol
CAS Number19934-71-5
PubChem CID146678
IUPAC Name2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
Molecular FormulaC12H15Cl2NO5S
Molecular Weight356.2
XLogP-0.3
Topological Polar Surface Area112
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count6
Heavy Atom Count21
Formal Charge0
Complexity443
SMILES
CS(=O)(=O)C1=CC=C(C=C1)[C@@H]([C@H](CO)NC(=O)C(Cl)Cl)O
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-/m0/s1
InChIKey
OTVAEFIXJLOWRX-UWVGGRQHSA-N
Chemical Structure
2D Structure
2D structure of ent-Thiamphenicol
CAS: 19934-71-5
CID: 146678
Formula: C12H15Cl2NO5S
MW: 356.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight356.2
XLogP3-0.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count6
Exact Mass355.0047991
Monoisotopic Mass355.0047991
Topological Polar Surface Area112 Ų
Heavy Atom Count21
Formal Charge0
Complexity443
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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