2,2-Dichloro-N-[1,3-Dihydroxy-1-(4-Nitrophenyl)-2-Propanyl]Acetamide
[CAS# 125440-98-4]

Identification

• Name: 2,2-Dichloro-N-[1,3-Dihydroxy-1-(4-Nitrophenyl)-2-Propanyl]Acetamide
• Synonyms: (-)-Chloramphenicol
• Molecular Formula: C₁₁H₁₂Cl₂N₂O₅
• Molecular Weight: 323.13
• CAS Registry Number: 125440-98-4
• SMILES: C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• 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)
• InChIKey: WIIZWVCIJKGZOK-UHFFFAOYSA-N

Properties

• Density: 1.5±0.1g/cm³ (Cal.)
• Melting point: 149-152°C (Expl.)
• Boiling point: 644.9±55.0°C at 760 mmHg (Cal.)
• Flash point: 343.8±31.5°C (Cal.)
• Refractive index: 1.612 (Cal.)

Safety Data

• Safety Code: S53;S20;S36/37;S45
• Risk Code: R45;R63
• Hazard Symbol: T
• Safety Description: DANGER: POISON, cancer risk, causes cyanosis, irritation

References

• (1): Anneli Nordqvist, Jonas Nilsson, Tuulikki Lindmark, Alf Eriksson, Per Garberg, Mats Kihlén . A General Model for Prediction of Caco-2 Cell Permeability, QSAR Comb. Sci. 2004, 23(5), 303-31046 compounds and their Observed logPapp values have been given in paper. "L-alanine" was retrieved as "Alanine", "AZT" as "Zidovudine", "L-Dopa" as "Levodopa" and "Methyl scopolamine" as "N-Methyl scopolamine" from ChemIDplus.
• (2): Manfred Kansy, Frank Senner, and Klaus Gubernator. Physicochemical High Throughput Screening: Parallel Artificial Membrane Permeation Assay in the Description of Passive Absorption Processes, J. Med. Chem., 1998, 41(7), 1007-101025 compounds and their % Absorption values (humans) are given in the paper. These have been provided here.
• (3): Oprea, T. I. and Gottfries, J.. Toward Minimalistic Modeling of Oral Drug Absorption, J. Mol. Graphics Modell. 1999, 17 (5-6), 261-274"The data set consists of 85 compounds, for which Wessel and co-workers gathered %HIA values from the literature. Sixteen of these 85 structures have Caco-2 cell permeability data, originating from Artursson and Karlsson that were used in the QSAR models proposed by Van de Waterbeemd et. al. and by Norinder et. al. In addition, Yazdanian et. al. reported Caco-2 cell permeability data for 29 of these 85 structures. Thus, three experimental measures were used to derive our QSAR model".
• (4): David E. Clark. Rapid calculation of polar molecular surface area and its application to the prediction of transport phenomena. 1. Prediction of intestinal absorption, J. Pharm. Sci. 1999, 88 (8), 807-8143 tables with %FA values are given in this paper. One is from Palm et. al. (20 compounds, available on this web-page). Other is from Wessel et. al. (86 compounds, available on this web-page). The third dataset is from Kansy et. al. and is made available here. A total of 24 drugs and their oral drug absorption in humans (FA) values taken from the 3rd table given in the paper. Compound "acetylsalicylic acid" was retrieved as "aspirin" from ChemIDplus.
• (5): Oleg A. Raevsky, Klaus-J. Schaper, Per Artursson, James W. McFarland. A Novel Approach for Prediction of Intestinal Absorption of Drugs in Humans based on Hydrogen Bond Descriptors and Structural Similarity, Quant. Struct.-Act. Relat. 2002, 20(5-6), 402-413.