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SQ109

Catalog No.
A3834
Antibiotic for treatment of pulmonary TB
Grouped product items
SizePriceStock Qty
5mg
$228.00
In stock
10mg
$365.00
In stock
50mg
$1,227.00
Ship with 10-15 days
100mg
$1,890.00
Ship with 10-15 days
For scientific research use only and should not be used for diagnostic or medical purposes.

Tel: +1-832-696-8203

Email: [email protected]

Worldwide Distributors

Background

SQ109 is a novel antitubercular drug with IC50 value of 0.2 μg/ml on XDR [1].
Tuberculosis is a serious infection disease caused by Mycobacterium tuberculosis (Mtb). It is the leading single-agent killer with highest fatality rate. About more than three million lives were killed by tuberculosis every year. Even so, the existed drugs for TB treatment are facing many challenges including the side effects and the development of multidrug-resistant tuberculosis (MDR-TB). As a novel antitubercular drug, SQ109 has a distinguished mechanism of action and improved potency. The target of it is the mycolic acid transporter MmpL3 required for the synthesis of mycolic acid in cell wall of Mtb [1 and 2].  
SQ109 was screened out from a big chemical library designed around the active pharmacophore of ethambutol (EMB). Even so, SQ109 had different chemical structure, potency and mechanism with EMB. Among the top 27 candidates, SQ109 showed the highest selectivity index value and lowest IC50 value in vitro of 16.7 and 0.78 μg/ml, respectively. SQ109 displayed potent activity against all the substrains of Mtb including XDR- and MDR-TB clinical strains with IC50 values of 0.2 μg/ml. Besides that, SQ109 also showed significant effects on other pathogenic Mycobacteria with MIC values in the range of 4 to 16 μg/ml [1].
SQ109 showed low oral bioavailability in PK studies. The carbamate prodrug of it with improved oral bioavailability (from 21.4% to 91.4 %) exerted a high tissue distribution in rats. In the infected mice, treatment of SQ109 at dose of 10 mg/kg significantly attenuated the symptom of weight loss. In the chronic TB model in mice, 10 mg/kg of SQ109 showed better potency than EMB at dose of 100 mg/kg. Besides that, it was reported that the combination treatment of SQ109 and bedaquiline demonstrated a durable cure in infected mice model [1 and 3].
References:
[1] Sacksteder K A, Protopopova M, Barry C E, et al. Discovery and development of SQ109: a new antitubercular drug with a novel mechanism of action. Future microbiology, 2012, 7(7): 823-837.
[2] Meng Q, Luo H, Liu Y, et al. Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents. Bioorganic & medicinal chemistry letters, 2009, 19(10): 2808-2810.
[3] SQ109 (2008) SQ109. Tuberculosis (Edinb) 88, 159–161.
[4] Reddy V M, Dubuisson T, Einck L, et al. SQ109 and PNU-100480 interact to kill Mycobacterium tuberculosis in vitro. Journal of antimicrobial chemotherapy, 2012: dkr589.

Product Citation

Chemical Properties

StorageStore at -20°C
M.Wt330.55
Cas No.502487-67-4
FormulaC22H38N2
SynonymsNSC 722041;SQ-109;SQ 109
SolubilitySoluble in DMSO
Chemical NameN'-(2-adamantyl)-N-[(2E)-3,7-dimethylocta-2,6-dienyl]ethane-1,2-diamine
SDFDownload SDF
Canonical SMILESCC(=CCCC(=CCNCCNC1C2CC3CC(C2)CC1C3)C)C
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

Protocol

Cell experiment [1]:

Model organism

Mycobacteria

Preparation method

The solubility of this compound in DMSO is soluble. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months.

Reacting condition

0.64 μg/ml

Applications

SQ109 has significant in vitro activity against Mycobacteria

Animal experiment [1]:

Animal models

The chronic TB model in mice

Dosage form

10 mg/kg (p.o.), for 20 days

Application

In the chronic TB model in mice, 10 mg/kg of SQ109 showed better potency than EMB at dose of 100 mg/kg. Besides that, it was reported that the combination treatment of SQ109 and bedaquiline demonstrated a durable cure in infected mice model.

Other notes

Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal.

References:

[1]. Sacksteder KA, Protopopova M, Barry CE 3rd, Andries K, Nacy CA. Discovery and development of SQ109: a new antitubercular drug with a novel mechanism of action.Future Microbiol. 2012 Jul;7(7):823-37. doi: 10.2217/fmb.12.56. Review. PubMed PMID: 22827305; PubMed Central PMCID: PMC3480206.

[2]. SQ109. Tuberculosis (Edinb). 2008 Mar;88(2):159-61. doi:10.1016/S1472-9792(08)70026-X. Review. PubMed PMID: 18486060.

Biological Activity

Description SQ109 is an orally active, small molecule antibiotic for treatment of pulmonary T(tuberculosis).
Targets Mycobacterium TB bacteria        
IC50 1-0.5 μM (MIC)          

Quality Control

Chemical structure

SQ109

Related Biological Data

SQ109