Tigecycline

Base Information

• Chemical Name: Tigecycline
• CAS No.: 220620-09-7
• Molecular Formula: C29H39N5O8
• Molecular Weight: 585.657
• Hs Code.: 29419090
• Mol file: 220620-09-7.mol

Synonyms:2-Naphthacenecarboxamide, 4,7-bis(dimethylamino)-9-((((1,1-dimethylethyl)amino)acetyl)amino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-, (4S,4aS,5aR,12aS)-;N-[(5aR,6aS,7S,9Z,10aS)-9-(amino-hydroxy-methylidene)-4,7-bis(dimethylamino)-1,10a,12-trihydroxy-8,10,11-trioxo-5a,6,6a,7-tetrahydro-5H-tetracen-2-yl]-2-(tert-butylamino)acetamide;Tygacil (TN);Tygacil;(4S,4aS,5aR,12aS)-9-(2-(tert-butylamino)acetamido)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;

Chemical Property of Tigecycline

Chemical Property:

• Appearance/Colour: Powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 164-166°C
• Refractive Index: 1.675
• Boiling Point: 890.922 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 492.612 °C
• PSA: 205.76000
• Density: 1.455 g/cm³
• LogP: 1.67740
• Storage Temp.: Amber Vial, -20°C Freezer
• Solubility.: Soluble in DMSO (up to at least 25 mg/ml).

Purity/Quality:

99% ^*data from raw suppliers

Tigecycline 99+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: The emergence of drug-resistant bacteria has diminished the clinical utility of the tetracyclines. Research to circumvent the efflux and ribosomal protection mechanisms of bacteria has led to the development of the glycylcyclines. Tigecycline is the first glycylcycline antibiotic to launch for the parenteral treatment of baterial infection, including complicated intra-abdominal and skin infections. Its mechanism of action involves inhibiting protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome to effectively prevent incorporation of amino acid residues into elongating peptide chains. Presumably, ribosomal protection proteins are ineffective against tigecycline due to its higher affinity for ribosomal binding compared to tetracyclines (approximately 16-fold). In addition, tigecycline may be resistant to efflux mechanisms by either their inability to translocate it across the cytoplasmic membrane due to steric complications or simply by their failure to recognize the molecule. Tigecycline is a broad-spectrum glycylcycline antibiotic that binds to the bacterial 30S ribosome, blocking the entry of transfer RNA, which halts protein synthesis and inhibits bacterial growth. It is active against a panel of 1,924 European clinical bacterial isolates including S. aureus, S. epidermidis, S. pneumoniae, E. faecalis, E. faecium, E. coli, K. pneumoniae, P. aeruginosa, and P. mirabilis strains (MICs = <1-32 μg/ml). In vivo, tigecycline (6.25 mg/kg twice daily for 5 days) decreases levels of C. difficile cytotoxin activity and spore formation in cecum and colon in a mouse model of C. difficile infection. Formulations containing tigecycline have been used in the treatment of a variety of bacterial infections.
• Uses: antineoplastic Tigecycline is a semi-synthetic tetracycline prepared by the introduction of a tert-butylaminoacetamido group into a previously unexplored and un-substituted region of existing tetracyclines. Like other tetracyclines, tigecycline acts by reversibly binding to the 30S ribosomal subunit and inhibits protein translation by blocking entry of aminoacyl-tRNA into the ribosome A site. The enhanced activity can be attributed to stronger binding affinity, thus minimising the impact of existing mechanisms of resistance. Tigecycline is regarded as the first of a new class of glycylcyline antibiotics. Critical comparison to the tetracycline class appears to be lacking in the literature. A broad spectrum glycylcycline antibiotic A glycylcycline antibiotic, used to treat infection by drug resistant bacteria such as Staphylococcus aureus (Staph aureus) and Acinetobacter baumannii.
• Clinical Use: Complicated skin and skin structure infections Complicated intra-abdominal infections Community-acquired bacterial pneumonia Recommended principally for the treatment of infections with multiresistant organisms.
• Drug interactions: Potentially hazardous interactions with other drugs Anticoagulants: possibly enhanced anticoagulant effect of coumarins. Oestrogens: possibly reduced contraceptive effects of oestrogens (risk probably small).

Technology Process of Tigecycline

There total 19 articles about Tigecycline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

9-chloroacetamidominocycline (156263-28-4) + tert-butylamine (75-64-9) → tigecycline (220620-09-7)

Guidance literature:

With sodium iodide; In N,N-dimethyl acetamide; at 50 ℃; for 2h;

Reference yield: 90.0%

2-tert-butylaminoacetylchloride hydrochloride + 9-amino-7-(dimethylamino)doxycycline hydrochloride → tigecycline (220620-09-7)

Guidance literature:

In water; at 0 - 5 ℃; for 2h;

Reference yield: 89.1%

→ tigecycline (220620-09-7)

Guidance literature:

In methanol; acetic acid methyl ester; at 0 - 35 ℃; Purification / work up;

upstream raw materials:

3,3-dimethylbutanoic acid chloride

[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

9-chloroacetamidominocycline

tert-butylamine

Downstream raw materials:

tigecycline hydrochloride

Refernces

• 1、 -. "Purification method of tigecycline". Paragraph 0019-0029. . Retrieved 2020/12/08.
• 2、 -. "Synthetic method of minocycline and derivative of minocycline". Paragraph 0026; 0027. . Retrieved 2019/09/13.