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

• ChemBase编号: 53504
• 分子式: C11H12Cl2N2O5
• 平均质量: 323.12938
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• IUPAC传统名: chloromycetin
• 别名: 氯霉素; 氯霉素; 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

登记号

• CAS号: 56-75-7
• EC号: 200-287-4
• MDL号: MFCD00078159; MFCD00007360
• Beilstein号: 2225532
• PubChem SID: 24892989; 24853926; 162058267; 24867881; 24892278; 24892448; 24869808; 24892441; 24892250
• PubChem CID: 5959; 298
• CHEBI ID: 17698
• ATC码: S03AA08; D06AX02; J01BA01; G01AA05; D10AF03; S02AA01; QJ51BA01; S01AA01
• CHEMBL: 130
• Chemspider ID: 5744
• DrugBank ID: DB00446
• KEGG ID: D00104
• 美国药典/FDA物质标识码: 66974FR9Q1
• 维基百科标题: Chloramphenicol
• Medline Plus: a608008

理论计算性质

• Acid pKa: 7.4943175
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 0.87482697
• LogD (pH = 7.4): 0.66041094
• Log P: 0.8787035
• 摩尔折射率: 73.2007 cm^3
• 极化性: 27.817905 Å^3
• 极化表面积: 115.38 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: absolute ethanol: soluble5-20 mg/mL (as a stock solution); DMSO; Ethanol; Methanol; methanol: soluble (as a stock solution)
• 外观: White Solid
• 熔点: 147-149°C; 148-150 °C(lit.); 149-151 °C; 149-153°C
• 比旋光度: [α]20/D +19.5±1°, c = 5% in ethanol

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存注意事项: IRRITANT
• RTECS编号: AB6825000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 德国WGK号: 3
• 危险公开号: 45; R:45
• 安全公开号: 53-45; S:28-36/37/39-45-53
• TSCA收录: false
• GHS危险品标识: GHS08
• GHS警示词: Danger
• GHS危险声明: H350
• GHS警示性声明: P201-P308 + P313
• 个人保护装置: 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
• 保存温度: 2-8°C

药理学性质

• 给药途径: Topical (ocular), oral, IV, IM
• 生物利用度: 75–90%
• 排泄: Renal
• 半衰期: 1.5–4.0 hours
• 代谢: Hepatic
• 法定药品分级: Ocular P, else POM (UK)
• 妊娠期药物分类: C (systemic), A (topical)
• 相关基因信息: human ... CYP1A2(1544)

产品相关信息

• 纯度: ≥98% (TLC); ≥99.0% (HPLC)
• 级别: analytical standard; Biotechnology Performance Certified; Ph Eur; VETRANAL™, analytical standard
• 成盐信息: Free Base
• 包装: ampule of 1000 mg
• 适用性: meets USP testing specifications; suitable for plant cell culture
• 杂质: endotoxin, tested; Endotoxin, tested
• 无菌消毒: γ-irradiated
• 产品质量级别: PREMIUM
• 产品线: BioReagent
• 线性分子式: Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2

详细说明

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
直接用小瓶配制推荐范围内任意浓度的储存液。储存液应在 2-8°C 下保存。在 37°C 下可稳定 5 天。
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
Supelco MIP SPE 滤筒标准品。更多信息，请参阅 Supelco 文献 T407075 和 T706024。
法律信息
VETRANAL 商标 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
Supelco MIP SPE 滤筒标准品。更多信息，请参阅 Supelco 文献 T407075 和 T706024。
法律信息
VETRANAL 商标 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
通过结合到细菌核糖体的大亚基上以及通过阻断肽基转移从而抑制蛋白质的生物合成；氯霉素抗性是一种用于筛选真核细胞的有用遗传标记；1抗性通常由氯霉素乙酰转移酶介导，但也存在例外；2综述。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).
包装
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.

参考文献

• 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