SQ 109
[CAS# 502487-67-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Amine
• Name: SQ 109
• Synonyms: N-[(2E)-3,7-Dimethyl-2,6-octadienyl]-N'-tricyclo[3.3.1.1(3,7)]dec-2-yl-1,2-ethanediamine; NSC 722041
• Molecular Formula: C₂₂H₃₈N₂
• Molecular Weight: 330.55
• CAS Registry Number: 502487-67-4
• SMILES: CC(=CCC/C(=C/CNCCNC1C2CC3CC(C2)CC1C3)/C)C

Properties

• Solubility: Insoluble (9.6E^-3 g/L) (25 ºC), Calc.^*
• Density: 0.97±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.529, Calc.^*
• Boiling Point: 450.0±33.0 ºC (760 mmHg), Calc.^*
• Flash Point: 257.7±17.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302
• Precautionary Statements: P280-P305+P351+P338

Discovory and Applicatios

SQ 109 is a synthetic antibiotic that has garnered attention due to its potential as a treatment for multidrug-resistant tuberculosis (MDR-TB). It was first discovered in the early 2000s by researchers at Sequella, Inc., a biotechnology company focused on the development of therapies for infectious diseases. The compound is derived from a class of antimicrobials known as azoles, and its discovery marked a significant step in the search for new drugs to combat resistant bacterial infections.

The development of SQ 109 was driven by the growing global health threat of drug-resistant tuberculosis, which has become a major public health challenge. Tuberculosis (TB) is caused by *Mycobacterium tuberculosis*, a bacterium that primarily affects the lungs, although it can also spread to other organs. Standard TB treatment requires long courses of antibiotics, and the emergence of resistant strains has complicated treatment regimens. MDR-TB, which is resistant to at least the two most powerful first-line drugs (isoniazid and rifampicin), has led to the need for new and more effective therapeutic options. SQ 109 was identified as a promising candidate through a screening process designed to find compounds that inhibit the growth of *Mycobacterium tuberculosis*.

SQ 109 works by targeting the bacterial cell wall synthesis, a vital process for the survival and replication of *Mycobacterium tuberculosis*. The drug specifically inhibits the function of the enzyme responsible for the biosynthesis of mycolic acids, which are crucial components of the bacterial cell wall. The inhibition of mycolic acid synthesis results in the disruption of the bacterial cell wall, leading to the death of the bacteria. This mechanism is distinct from that of many other anti-TB drugs, which target different components of the bacterial cell, making SQ 109 an attractive candidate for combination therapies. It has shown efficacy against both drug-susceptible and drug-resistant strains of *Mycobacterium tuberculosis*.

In preclinical studies, SQ 109 demonstrated potent activity against *Mycobacterium tuberculosis*, with a favorable pharmacokinetic profile, which means that it is well absorbed and distributed within the body. The compound has been tested in combination with other anti-TB agents to evaluate its potential in multidrug-resistant and extensively drug-resistant tuberculosis. Early clinical trials have shown promising results, and the drug is currently undergoing further clinical testing to determine its safety and efficacy in humans, particularly in individuals with MDR-TB. It is hoped that SQ 109 can be developed into a valuable addition to the existing arsenal of anti-TB drugs, particularly in the context of the growing prevalence of drug-resistant tuberculosis.

The applications of SQ 109 are not limited to tuberculosis. The compound has also shown activity against other bacterial pathogens, and researchers are exploring its potential use in the treatment of other infectious diseases. The ongoing research into its broader spectrum of activity could lead to new indications for SQ 109 beyond tuberculosis. However, its primary application remains in the treatment of drug-resistant TB, a disease that causes millions of deaths each year worldwide.

One of the key advantages of SQ 109 is its relatively low toxicity profile in preclinical studies. Unlike some other tuberculosis drugs, which can cause significant side effects, SQ 109 appears to be well-tolerated, with fewer adverse effects observed in animal models. This makes it an appealing candidate for further development, particularly in the context of the long treatment durations required for TB therapy.

Despite the encouraging results, challenges remain in the development of SQ 109. Like many other antibiotic candidates, the emergence of resistance to SQ 109 could limit its long-term effectiveness. Researchers are continuing to study the mechanisms of resistance to SQ 109 and to identify ways to overcome this challenge, such as by developing combination therapies that incorporate SQ 109 alongside other antibiotics.

In conclusion, SQ 109 represents a promising new compound in the fight against drug-resistant tuberculosis. Its novel mechanism of action, effectiveness against MDR-TB, and relatively low toxicity make it a compelling candidate for further development. As the global health community continues to combat the growing threat of antibiotic resistance, SQ 109 could play a critical role in improving the treatment options available for tuberculosis, particularly in cases where conventional therapies have failed.