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

• ChemBase ID: 53504
• Molecular Formular: C11H12Cl2N2O5
• Molecular Mass: 323.12938
• Monoisotopic Mass: 322.01232685
• SMILES: [N+](=O)(c1ccc([C@H]([C@H](NC(=O)C(Cl)Cl)CO)O)cc1)[O-]
• Canonical SMILES: OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
• InChIKey: WIIZWVCIJKGZOK-RKDXNWHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• IUPAC Traditional name: chloromycetin
• Synonyms: 2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]Acetamide; D-threo-N-Dichloroacetyl-1-p-nitrophenyl-2-amino-1,3-propanediol; Anacetin; Aquamycetin; Chlorocid; Chloroptic; Fenicol; Pantovernil; Paraxin; 2,2-Dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide; Chloramphenicolum; D(-)-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethyl]acetamide; D-(-)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol; D-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]acetamide; D-(-)-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethyl]acetamide; Chloramphenicol; D-2-DICHLOROACETAMIDO-1-p-NITROPHENYL-1,3-PROPANEDIOL; Alficetyn; Chlornitromycin; Chloromycetin; Chloramphenicol; 氯霉素; 氯霉素

Database IDs

• CAS Number: 56-75-7
• EC Number: 200-287-4
• MDL Number: MFCD00078159; MFCD00007360
• Beilstein Number: 2225532
• PubChem SID: 24867881; 24892278; 24892448; 24869808; 24853926; 162058267; 24892989; 24892441; 24892250
• PubChem CID: 298; 5959
• CHEBI ID: 17698
• ATC CODE: D06AX02; J01BA01; G01AA05; S03AA08; D10AF03; S02AA01; QJ51BA01; S01AA01
• CHEMBL: 130
• Chemspider ID: 5744
• DrugBank ID: DB00446
• KEGG ID: D00104
• Unique Ingredient Identifier: 66974FR9Q1
• Wikipedia Title: Chloramphenicol
• Medline Plus: a608008

CALCULATED PROPERTIES

• Acid pKa: 7.4943175
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.87482697
• LogD (pH = 7.4): 0.66041094
• Log P: 0.8787035
• Molar Refractivity: 73.2007 cm^3
• Polarizability: 27.817905 Å^3
• Polar Surface Area: 115.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: absolute ethanol: soluble5-20 mg/mL (as a stock solution); DMSO; Ethanol; Methanol; methanol: soluble (as a stock solution)
• Apperance: White Solid
• Melting Point: 147-149°C; 148-150 °C(lit.); 149-151 °C; 149-153°C
• Optical Rotation: [α]20/D +19.5±1°, c = 5% in ethanol

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: AB6825000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45; R:45
• Safety Statements: 53-45; S:28-36/37/39-45-53
• TSCA Listed: false
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H350
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Topical (ocular), oral, IV, IM
• Bioavailability: 75–90%
• Excretion: Renal
• Half Life: 1.5–4.0 hours
• Metabolism: Hepatic
• Legal Status: Ocular P, else POM (UK)
• Pregnancy Category: C (systemic), A (topical)
• Gene Information: human ... CYP1A2(1544)

Product Information

• Purity: ≥98% (TLC); ≥99.0% (HPLC)
• Grade: analytical standard; Biotechnology Performance Certified; Ph Eur; VETRANAL™, analytical standard
• Salt Data: Free Base
• Packaging: ampule of 1000 mg
• Suitability: meets USP testing specifications; suitable for plant cell culture
• Impurities: endotoxin, tested; Endotoxin, tested
• Sterility: γ-irradiated
• Quality Level: PREMIUM
• Product Line: BioReagent
• Linear Formula: Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2

DETAILS

MP Biomedicals - 05204959

MP Biomedicals Rare Chemical collection

Selleck Chemicals - S1677

Research Area: Infection
Biological Activity:
Chloramphenicol(Chloromycetin) is a bacteriostatic antimicrobial. It is considered as a prototypical broad-spectrum antibiotic. It is effective against a wide variety of Gram-positive and Gram-negative bacteria, including most of anaerobic organisms. It is bacteriostatic (that is, it stops bacterial growth). It is a protein synthesis inhibitor, inhibiting peptidyl transferase activity of the bacterial ribosome, binding to A2451 and A2452 residues in the 23S rRNA of the 50S ribosomal subunit, preventing peptide bond formation. [1]

Sigma Aldrich - C7795

Application
Use as a seletion agent for transformed cells containing chloramphenicol resistance genes. Recommended for use in molecular biology applications at 10-20 μg/ml.
Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).
Reconstitution
Prepare stock solutions directly in the vial at any concentration in the recommended range. Stock solutions should be stored at 2-8 °C. Stable at 37 °C for 5 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - C1863

Application
Used as a seletion agent for transformed cells containing chloramphenicol resistance genes.
Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - C1919

Application
Used as a seletion agent for transformed cells containing chloramphenicol resistance genes.
Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 31667

Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).
General description
Standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706024
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 23276

Application
Used as a seletion agent for transformed cells containing chloramphenicol resistance genes.
Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).

Sigma Aldrich - C0857

Application
Used as a seletion agent for transformed cells containing chloramphenicol resistance genes. Recommended for use in cell culture applications at 10 ml/L.
Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).

Sigma Aldrich - 46110

Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).
General description
Standard for Supelco MIP SPE cartridges. For more information request Supelco Literature T407075, T706024
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 23275

Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).
Other Notes
Inhibits protein biosynthesis by binding to the large subunit of the bacterial ribosome and by blocking the peptidyl transfer; chloramphenicol-resistance is a useful genetic marker for the selection of eukaryotic cells;1 Resistance is usually mediated by a chloramphenicol-acetyl-transferase, but there are exceptions;2 Review.3

Sigma Aldrich - C0378

Application
Used as a seletion agent for transformed cells containing chloramphenicol resistance genes.
Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).
Packaging
1 kg in poly bottle
5, 25, 100, 500 g in poly bottle
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 442513

Biochem/physiol Actions
Mode of Action: Inhibits translation on the 50S ribosomal subunit at the peptidyltransferase step (elongation inhibition). Bacteriostatic.Mode of Resistance: Acetylation by chloramphenicol acetyltransferase (cat gene).

Toronto Research Chemicals - 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.

REFERENCES

• http://en.wikipedia.org/wiki/Chloramphenicol
• Bartz, et al.: J. Biol. Chem., et al.: 172, 445 (1948)
• Gottlieb, et al.: J. Bacteriol., 55, 409 (1948)
• Szulczewski, D., et al.: Anal. Profiles Drug Subs., 4, 47 (1948)
• Price, A., et al.: J. Antibiot., 43, 118 (1948)
• Shalit, I., et al.: Drugs, 28, 281