(+)-Chloramphenicol
Basic information
- CAS
134-90-7- Standard SMILES
O=C(N[C@@H](CO)[C@@H](O)c1ccc([N+](=O)[O-])cc1)C(Cl)Cl- InChIKey
WIIZWVCIJKGZOK-IUCAKERBSA-N- Molecular formula
- C11H12Cl2N2O5
- Average molar mass
- 323.13 g/mol
- Monoisotopic mass
- 322.0123269
Overview
optic isomer of chloramphenicol which is not an antibiotic
Names & identifiers
- Preferred name
- (+)-Chloramphenicol
- IUPAC
- 2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
- English name
- L-(+)-threo-chloramphenicol
- Molecular formula
- C11H12Cl2N2O5
- Molecular weight
- 323.13
Names & synonyms
Dextramycine134-90-7L-(+)-Threo-chloramphenicolL-threo-Chloramphenicol(+)-ChloramphenicolL-threo-ChloroamphenicolU0PWV2Z3IWL-threo-(1S,2S)-1-p-Nitrophenyl-2-dichloroacetamido-1,3-propanediolDTXSID40158453Acetamide, 2,2-dichloro-N-((1S,2S)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (S-(R*,R*))-RefChem:132408
Show more names
DextromycetinL-threo-ChloraMphenicChloramphenicol Impurity 23L-threo-N-Dichloracetyl-1-p-nitrophenyl-2-amino-1,3-propanediolL-threo-N-Dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol
DTXCID1080944DextramycinL-Chloramphenicol2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide137731-89-6[S-(R*,R*)]-2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamideMFCD01733852C11H12Cl2N2O5
Database identifiers
Properties
Computed structural properties
- XLogP
- 1.1
- Topological polar surface area
- 115 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 5
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 342
Experimental & physicochemical properties
SpringerMaterials PropertiesCrystal structure
Physicochemical properties
- Melting point
- 150 · 150-151 °C
- Boiling point
- 527.51 °C · 527.51°C (rough estimate)
- Density
- 1.2886 · 1.2886 (rough estimate)
- refractive index
- 1.63 · 1.6300 (estimate)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Ethanol (Sparingly, Sonicated), Methanol (Slightly)
- form
- Solid
- pka
- 11.03 · 11.03±0.46(Predicted)
- color
- White to Off-White
- FDA UNII
- 0 PWV2Z3IW · U0PWV2Z3IW
Chemistry & industry
Applications
UsesThe S,S-stereoisomer of Chloramphenicol (C325030). Broad spectrum antibiotic obtained from cultures of the soil bacterium Streptomyces venezuelae. It has a broad spectrum of activity against Gram-positive and gram-negative bacteria. Antibacterial; antirickettsial.
Additional notes
DefinitionChEBI: Chloramphenicol is an organochlorine compound that is dichloro-substituted acetamide containing a nitrobenzene ring, an amide bond and two alcohol functions. It has a role as an antimicrobial agent, an antibacterial drug, a protein synthesis inhibitor, an Escherichia coli metabolite, a Mycoplasma genitalium metabolite and a geroprotector. It is an organochlorine compound, a diol, a C-nitro compound and a carboxamide.
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