(4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride

• ChemBase ID: 73266
• Molecular Formular: C22H25ClN2O8
• Molecular Mass: 480.8955
• Monoisotopic Mass: 480.12994345
• SMILES: c1ccc2c(c1O)C(=O)C1=C([C@]3([C@@H](C[C@@H]1[C@]2(C)O)[C@@H](C(=C(C3=O)C(=O)N)O)N(C)C)O)O.Cl
• Canonical SMILES: CN([C@@H]1C(=C(C(=O)N)C(=O)[C@@]2([C@H]1C[C@H]1C(=C2O)C(=O)c2c([C@@]1(C)O)cccc2O)O)O)C.Cl
• InChI: InChI=1S/C22H24N2O8.ClH/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28;/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30);1H/t9-,10-,15-,21+,22-;/m0./s1
• InChIKey: XMEVHPAGJVLHIG-FMZCEJRJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,4aS,5aS,6S,12aS)-4-(dimethylamino)-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide hydrochloride
• IUPAC Traditional name: tetracycline hydrochloride
• Synonyms: Tetracycline hydrochloride; Tetracycline hydrochloride; [4S-(4α,4aα,5aα,6β,12aα]-4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-2-Naphthacenecarboxamide Hydrochloride; (-)-Tetracycline Hydrochloride; Achromycin; Imex; Tetracyn; 四环素 盐酸盐; 四环素盐酸盐

Database IDs

• CAS Number: 64-75-5
• EC Number: 200-593-8
• MDL Number: MFCD00078142
• Beilstein Number: 3844873
• Merck Index: 149196
• PubChem SID: 24900468; 24900192; 24900607; 24900135; 162038186; 24870588; 24900496
• PubChem CID: 54704426
• E Number: E701

CALCULATED PROPERTIES

• Acid pKa: 2.9185581
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -3.4724553
• LogD (pH = 7.4): -3.695556
• Log P: -3.4722908
• Molar Refractivity: 114.1883 cm^3
• Polarizability: 43.205765 Å^3
• Polar Surface Area: 181.62 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble10 mg/mL (as a stock solution. Stock solutions should be filtered sterilized and stored at -20°C. Stable at 37°C for 4 days.); Methanol; Water
• Apperance: powder; Yellow Solid
• Melting Point: >215°C (dec.); 215-220 °C (dec.); 220-223 °C(lit.); 220-223°C
• Optical Rotation: [α]20/D -245±9°, c = 1% in methanol; -247 (c=1, 0.1M HCl)

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: Air & Light Sensitive
• RTECS: QI9100000
• European Hazard Symbols: X; Irritant (Xi); Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38; 36-63; 63-36/37/38-64
• Safety Statements: 26-36; 26-36/37-60
• TSCA Listed: 是
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H361-H362; H361-H319
• GHS Precautionary statements: P261-P263-P281-P305 + P351 + P338; P261-P305 + P351 + P338; P280-P281-P305+P351+P338-P308+P313-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥95%; ≥95% (European Pharmacopoeia HPLC assay); ≥96.0% (HPLC); 96%
• Grade: Biotechnology Performance Certified; VETRANAL™, analytical standard
• Salt Data: HCl; hydrochloride
• Suitability: cell culture tested; meets USP testing specifications; suitable for cell culture
• Impurities: endotoxin, tested
• Sterility: γ-irradiated
• Pharmacopeia Traceability: traceable to BP 480; traceable to PhEur T060000; traceable to USP 1651009
• Empirical Formula (Hill Notation): C22H24N2O8 · HCl
• Classification: Genuine Natural Compounds

DETAILS

Selleck Chemicals - S2574

Research Area: Infection
Biological Activity:
Tetracycline hydrochloride is a hydrochloride salt of tetracycline that is a broad-spectrum polyketide antibiotic. Tetracycline binds to the 30S subunit of microbial ribosomes. Tetracycline inhibits protein synthesis by blocking the attachment of charged aminoacyl-tRNA. Thus tetracycline prevents introduction of new amino acids to the nascent peptide chain. The action is usually inhibitory and reversible upon withdrawal of the drug. Resistance to the tetracycline results from changes in permeability of the microbial cell envelope. In susceptible cells, the tetracycline is concentrated from the environment and does not readily leave the cell. In resistant cells, the drug is not actively transported into the cell or leaves it so rapidly that inhibitory concentrations are not maintained. Tetracycline hydrochloride is used in the treatment of bacterial infections, such as urinary tract infections, acne, gonorrhea, chlamydia, and others.[1]References on Tetracycline HCl[1] http://en.wikipedia.org/wiki/Tetracycline, ,

Sigma Aldrich - T9823

Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Loss of cell wall permeability.
Tetracycline inhibits bacterial protein synthesis elongation at the level of aminoacyl-tRNA binding to the 30S ribosome. Tetracycline passively diffuses through porin channels in the bacterial cell membrane. It also binds to the bacterial 50S ribosomal subunit which may alter the cytoplasmic membrane, causing intracellular components to leak from bacterial cells1. Mode of resistance is loss of cell wall permeability.
Application
Tetracycline is a broad spectrum polyketide antibiotic. It is used clinically to treat bacterial infections such as Rocky Mountain spotted fever, typhus fever, tick fevers, Q fever and Brill-Zinsser disease. It is used to treat upper respiratory infections and acne1. It is used to study multidrug resistance2 as well as potential side effects such as acute pancreatitis3. It has been used in target and resistance based mechanistic studies of novel antibiotics4.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - T7660

Application
Used in tetracycline controlled gene expression systems (gene switches) such a the tet-on and tet-off systems. Recommended for use in cell culture applications at 10 mg/L.
Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Loss of cell wall permeability.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - 74749

Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Loss of cell wall permeability.

Sigma Aldrich - 87130

Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Loss of cell wall permeability.

Sigma Aldrich - 31741

Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Loss of cell wall permeability.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - T4062

Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Loss of cell wall permeability.
Mode of Action: inhbit bacterial protein synthesis elongation at the level of aminoacyl-tRNA binding to the 30S ribosome. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria. Mode of Resistance: Loss of cell wall permeability.

Sigma Aldrich - T3383

Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Loss of cell wall permeability.
包装
25, 100 g in poly bottle

Sigma Aldrich - T8032

Application
建议以 10-20μg/ml 的量用于分子生物学应用。
Biochem/physiol Actions
Mode of Action: Inhibits protein synthesis (elongation) by preventing binding of aminoacyl-tRNA to the 30S subunit. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.Mode of Resistance: Loss of cell wall permeability.
Reconstitution
直接在样品瓶中用无菌水 (10mg/ml) 制备储存液。储存液在 2-8°C 下保存不应超过一周；四环素在水溶液中会发生水解。

Toronto Research Chemicals - T291400

Antibiotic substance produced by Streptomyces spp. Antiamebic; antibacterial; antirickettsial.

REFERENCES

• Weiss, et al.: Antibiot. Chemother., 7, 374 (1957)
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1957)