SQ109
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MedKoo CAT#: 522649

CAS#: 502487-67-4

Description: SQ109 is a drug undergoing development for treatment of tuberculosis. SQ109 showed activity against both drug susceptible and Multi-drug-resistant tuberculosis bacteria, including Extensively drug-resistant tuberculosis strains. In preclinical studies SQ109 enhanced the activity of anti-tubercular drugs isoniazid and rifampin and reduced by >30% the time required to cure mice of experimental TB.


Chemical Structure

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SQ109
CAS# 502487-67-4

Theoretical Analysis

MedKoo Cat#: 522649
Name: SQ109
CAS#: 502487-67-4
Chemical Formula: C22H38N2
Exact Mass: 330.3035
Molecular Weight: 330.56
Elemental Analysis: C, 79.94; H, 11.59; N, 8.47

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Ready to Ship
25.0mg USD 250.0 Ready to Ship
50.0mg USD 450.0 Ready to Ship
100.0mg USD 750.0 Ready to Ship
200.0mg USD 1350.0 Ready to Ship
500.0mg USD 2450.0 Ready to Ship
1.0g USD 3650.0 Ready to Ship
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Synonym: SQ109; SQ-109; SQ 109; NSC 722041; NSC-722041; NSC722041.

IUPAC/Chemical Name: N1-((1r,5R,7S)-adamantan-2-yl)-N2-((E)-3,7-dimethylocta-2,6-dien-1-yl)ethane-1,2-diamine

InChi Key: JFIBVDBTCDTBRH-WUROFCERSA-N

InChi Code: InChI=1S/C22H38N2/c1-16(2)5-4-6-17(3)7-8-23-9-10-24-22-20-12-18-11-19(14-20)15-21(22)13-18/h5,7,18-24H,4,6,8-15H2,1-3H3/b17-7+/t18-,19+,20-,21?,22?

SMILES Code: C/C(CC/C=C(C)\C)=C\CNCCNC1[C@H]2C[C@@H]3C[C@H](C2)CC1C3

Appearance: Oily liquid

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: SQ109 is a potent inhibitor of the trypomastigote form of the parasite, with IC50 for cell killing of 50±8 nM. SQ109, targets MmpL3, is an antitubercular agent.
In vitro activity: SQ109 was found to be a potent inhibitor of the trypomastigote form of the parasite, with a 50% inhibitory concentration (IC50) for cell killing of 50 ± 8 nM, but it had little effect (50% effective concentration [EC50], ∼80 μM) in a red blood cell hemolysis assay. It also inhibited extracellular epimastigotes (IC50, 4.6 ± 1 μM) and the clinically relevant intracellular amastigotes (IC50, ∼0.5 to 1 μM), with a selectivity index of ∼10 to 20. Reference: Antimicrob Agents Chemother. 2015 Apr;59(4):1950-61. https://pubmed.ncbi.nlm.nih.gov/25583723/
In vivo activity: To explore this aspect, this study infected C57BL/6 mice with a low dose of M.tb H37Rv (~110 CFU) via the aerosol route and treated the animals daily with SQ109 (10 mg/kg body weight) starting from the 15th day of post infection until sacrifice (Fig. 1a). These observations were further supported by histological analysis of lungs, which revealed that a reduced numbers of inflammatory granulomatous and necrotic lesions in SQ109-treated mice (Fig. 1f, g). These data confirm the anti-microbial activity of SQ109. Reference: Commun Biol. 2022 Jul 28;5(1):759. https://pubmed.ncbi.nlm.nih.gov/35902694/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 25.0 75.63

Preparing Stock Solutions

The following data is based on the product molecular weight 330.56 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Veiga-Santos P, Li K, Lameira L, de Carvalho TM, Huang G, Galizzi M, Shang N, Li Q, Gonzalez-Pacanowska D, Hernandez-Rodriguez V, Benaim G, Guo RT, Urbina JA, Docampo R, de Souza W, Oldfield E. SQ109, a new drug lead for Chagas disease. Antimicrob Agents Chemother. 2015 Apr;59(4):1950-61. doi: 10.1128/AAC.03972-14. Epub 2015 Jan 12. PMID: 25583723; PMCID: PMC4356821. 2. Jia L, Noker PE, Coward L, Gorman GS, Protopopova M, Tomaszewski JE. Interspecies pharmacokinetics and in vitro metabolism of SQ109. Br J Pharmacol. 2006 Mar;147(5):476-85. doi: 10.1038/sj.bjp.0706650. PMID: 16432511; PMCID: PMC1616981. 3. Singh M, Kumar S, Singh B, Jain P, Kumari A, Pahuja I, Chaturvedi S, Prasad DVR, Dwivedi VP, Das G. The 1, 2-ethylenediamine SQ109 protects against tuberculosis by promoting M1 macrophage polarization through the p38 MAPK pathway. Commun Biol. 2022 Jul 28;5(1):759. doi: 10.1038/s42003-022-03693-2. PMID: 35902694; PMCID: PMC9334294. 4. Jia L, Tomaszewski JE, Hanrahan C, Coward L, Noker P, Gorman G, Nikonenko B, Protopopova M. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug. Br J Pharmacol. 2005 Jan;144(1):80-7. doi: 10.1038/sj.bjp.0705984. PMID: 15644871; PMCID: PMC1575972.
In vitro protocol: 1. Veiga-Santos P, Li K, Lameira L, de Carvalho TM, Huang G, Galizzi M, Shang N, Li Q, Gonzalez-Pacanowska D, Hernandez-Rodriguez V, Benaim G, Guo RT, Urbina JA, Docampo R, de Souza W, Oldfield E. SQ109, a new drug lead for Chagas disease. Antimicrob Agents Chemother. 2015 Apr;59(4):1950-61. doi: 10.1128/AAC.03972-14. Epub 2015 Jan 12. PMID: 25583723; PMCID: PMC4356821. 2. Jia L, Noker PE, Coward L, Gorman GS, Protopopova M, Tomaszewski JE. Interspecies pharmacokinetics and in vitro metabolism of SQ109. Br J Pharmacol. 2006 Mar;147(5):476-85. doi: 10.1038/sj.bjp.0706650. PMID: 16432511; PMCID: PMC1616981.
In vivo protocol: 1. Singh M, Kumar S, Singh B, Jain P, Kumari A, Pahuja I, Chaturvedi S, Prasad DVR, Dwivedi VP, Das G. The 1, 2-ethylenediamine SQ109 protects against tuberculosis by promoting M1 macrophage polarization through the p38 MAPK pathway. Commun Biol. 2022 Jul 28;5(1):759. doi: 10.1038/s42003-022-03693-2. PMID: 35902694; PMCID: PMC9334294. 2. Jia L, Tomaszewski JE, Hanrahan C, Coward L, Noker P, Gorman G, Nikonenko B, Protopopova M. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug. Br J Pharmacol. 2005 Jan;144(1):80-7. doi: 10.1038/sj.bjp.0705984. PMID: 15644871; PMCID: PMC1575972.

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1: Bhakta S, Scalacci N, Maitra A, Brown AK, Dasugari S, Evangelopoulos D, McHugh TD, Mortazavi PN, Twist A, Petricci E, Manetti F, Castagnolo D. Design and synthesis of 1-((1,5-bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)-4-methylpiperazine (BM212) and N-Adamantan-2-yl-N'-((E)-3,7-dimethyl-octa-2,6-dienyl)-ethane-1,2-diamine (SQ109) pyrrole hybrid derivatives: discovery of potent anti-tubercular agents effective against multi-drug resistant mycobacteria. J Med Chem. 2016 Feb 23. [Epub ahead of print] PubMed PMID: 26907951.

2: Li K, Wang Y, Yang G, Byun S, Rao G, Shoen C, Yang H, Gulati A, Crick DC, Cynamon M, Huang G, Docampo R, No JH, Oldfield E. Oxa, Thia, Heterocycle, and Carborane Analogues of SQ109: Bacterial and Protozoal Cell Growth Inhibitors. ACS Infect Dis. 2015 May 8;1(5):215-221. PubMed PMID: 26258172; PubMed Central PMCID: PMC4527605.

3: Heinrich N, Dawson R, du Bois J, Narunsky K, Horwith G, Phipps AJ, Nacy CA, Aarnoutse RE, Boeree MJ, Gillespie SH, Venter A, Henne S, Rachow A, Phillips PP, Hoelscher M, Diacon AH; Pan African Consortium for the Evaluation of Antituberculosis Antibiotics (PanACEA); Pan African Consortium for the Evaluation of Antituberculosis Antibiotics PanACEA. Early phase evaluation of SQ109 alone and in combination with rifampicin in pulmonary TB patients. J Antimicrob Chemother. 2015 May;70(5):1558-66. doi: 10.1093/jac/dku553. Epub 2015 Jan 27. PubMed PMID: 25630641.

4: Veiga-Santos P, Li K, Lameira L, de Carvalho TM, Huang G, Galizzi M, Shang N, Li Q, Gonzalez-Pacanowska D, Hernandez-Rodriguez V, Benaim G, Guo RT, Urbina JA, Docampo R, de Souza W, Oldfield E. SQ109, a new drug lead for Chagas disease. Antimicrob Agents Chemother. 2015 Apr;59(4):1950-61. doi: 10.1128/AAC.03972-14. Epub 2015 Jan 12. PubMed PMID: 25583723; PubMed Central PMCID: PMC4356821.

5: Makobongo MO, Einck L, Peek RM Jr, Merrell DS. In vitro characterization of the anti-bacterial activity of SQ109 against Helicobacter pylori. PLoS One. 2013 Jul 25;8(7):e68917. doi: 10.1371/journal.pone.0068917. Print 2013. PubMed PMID: 23935905; PubMed Central PMCID: PMC3723868.

6: 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.

7: Wallis RS, Jakubiec W, Mitton-Fry M, Ladutko L, Campbell S, Paige D, Silvia A, Miller PF. Rapid evaluation in whole blood culture of regimens for XDR-TB containing PNU-100480 (sutezolid), TMC207, PA-824, SQ109, and pyrazinamide. PLoS One. 2012;7(1):e30479. doi: 10.1371/journal.pone.0030479. Epub 2012 Jan 18. PubMed PMID: 22279595; PubMed Central PMCID: PMC3261206.

8: Reddy VM, Dubuisson T, Einck L, Wallis RS, Jakubiec W, Ladukto L, Campbell S, Nacy CA. SQ109 and PNU-100480 interact to kill Mycobacterium tuberculosis in vitro. J Antimicrob Chemother. 2012 May;67(5):1163-6. doi: 10.1093/jac/dkr589. Epub 2012 Jan 17. PubMed PMID: 22258923.

9: Tahlan K, Wilson R, Kastrinsky DB, Arora K, Nair V, Fischer E, Barnes SW, Walker JR, Alland D, Barry CE 3rd, Boshoff HI. SQ109 targets MmpL3, a membrane transporter of trehalose monomycolate involved in mycolic acid donation to the cell wall core of Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2012 Apr;56(4):1797-809. doi: 10.1128/AAC.05708-11. Epub 2012 Jan 17. PubMed PMID: 22252828; PubMed Central PMCID: PMC3318387.

10: Reddy VM, Einck L, Andries K, Nacy CA. In vitro interactions between new antitubercular drug candidates SQ109 and TMC207. Antimicrob Agents Chemother. 2010 Jul;54(7):2840-6. doi: 10.1128/AAC.01601-09. Epub 2010 Apr 12. PubMed PMID: 20385864; PubMed Central PMCID: PMC2897281.

11: Onajole OK, Govender P, van Helden PD, Kruger HG, Maguire GE, Wiid I, Govender T. Synthesis and evaluation of SQ109 analogues as potential anti-tuberculosis candidates. Eur J Med Chem. 2010 May;45(5):2075-9. doi: 10.1016/j.ejmech.2010.01.046. Epub 2010 Jan 28. PubMed PMID: 20149497.

12: Meng Q, Luo H, Liu Y, Li W, Zhang W, Yao Q. Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents. Bioorg Med Chem Lett. 2009 May 15;19(10):2808-10. doi: 10.1016/j.bmcl.2009.03.091. Epub 2009 Mar 26. PubMed PMID: 19362471.

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

14: Nikonenko BV, Protopopova M, Samala R, Einck L, Nacy CA. Drug therapy of experimental tuberculosis (TB): improved outcome by combining SQ109, a new diamine antibiotic, with existing TB drugs. Antimicrob Agents Chemother. 2007 Apr;51(4):1563-5. Epub 2007 Jan 22. PubMed PMID: 17242141; PubMed Central PMCID: PMC1855523.

15: Chen P, Gearhart J, Protopopova M, Einck L, Nacy CA. Synergistic interactions of SQ109, a new ethylene diamine, with front-line antitubercular drugs in vitro. J Antimicrob Chemother. 2006 Aug;58(2):332-7. Epub 2006 Jun 3. PubMed PMID: 16751637.

16: Jia L, Noker PE, Coward L, Gorman GS, Protopopova M, Tomaszewski JE. Interspecies pharmacokinetics and in vitro metabolism of SQ109. Br J Pharmacol. 2006 Mar;147(5):476-85. PubMed PMID: 16432511; PubMed Central PMCID: PMC1616981.

17: Protopopova M, Hanrahan C, Nikonenko B, Samala R, Chen P, Gearhart J, Einck L, Nacy CA. Identification of a new antitubercular drug candidate, SQ109, from a combinatorial library of 1,2-ethylenediamines. J Antimicrob Chemother. 2005 Nov;56(5):968-74. Epub 2005 Sep 19. PubMed PMID: 16172107.

18: Jia L, Coward L, Gorman GS, Noker PE, Tomaszewski JE. Pharmacoproteomic effects of isoniazid, ethambutol, and N-geranyl-N'-(2-adamantyl)ethane-1,2-diamine (SQ109) on Mycobacterium tuberculosis H37Rv. J Pharmacol Exp Ther. 2005 Nov;315(2):905-11. Epub 2005 Aug 5. PubMed PMID: 16085758.

19: Jia L, Tomaszewski JE, Hanrahan C, Coward L, Noker P, Gorman G, Nikonenko B, Protopopova M. Pharmacodynamics and pharmacokinetics of SQ109, a new diamine-based antitubercular drug. Br J Pharmacol. 2005 Jan;144(1):80-7. PubMed PMID: 15644871; PubMed Central PMCID: PMC1575972.

SQ109

10.0mg / USD 150.0