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MedKoo Cat#: 522649 | Name: SQ109
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

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
10mg USD 150.00 Ready to Ship
25mg USD 250.00 Ready to Ship
50mg USD 450.00 Ready to Ship
100mg USD 750.00 Ready to Ship
200mg USD 1,350.00 Ready to Ship
500mg USD 2,450.00 Ready to Ship
1g USD 3,650.00 Ready to Ship
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Related CAS #
No Data
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
More Info
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/
Solvent mg/mL mM comments
Solubility
DMSO 25.0 75.63
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
1: Jing W, Zhang F, Shang Y, Shi W, Yao C, Zhang X, Chu N, Lu J, Yuan J. Deciphering the possible role of MmpL7 efflux pump in SQ109 resistance in Mycobacterium tuberculosis. Ann Clin Microbiol Antimicrob. 2024 Sep 28;23(1):87. doi: 10.1186/s12941-024-00746-8. PMID: 39342331; PMCID: PMC11439249. 2: Recio-Balsells AI, Carlucci R, Giovannuzzi S, Carta F, Supuran CT, Tekwani BL, Morbidoni HR, Labadie GR. Repurposing antiparasitic N,N'-aliphatic diamine derivatives as promising antimycobacterial agents. Arch Pharm (Weinheim). 2024 Nov;357(11):e2400597. doi: 10.1002/ardp.202400597. Epub 2024 Sep 12. PMID: 39263819. 3: Babii S, Li W, Yang L, Grzegorzewicz AE, Jackson M, Gumbart JC, Zgurskaya HI. Allosteric coupling of substrate binding and proton translocation in MmpL3 transporter from Mycobacterium tuberculosis. mBio. 2024 Oct 16;15(10):e0218324. doi: 10.1128/mbio.02183-24. Epub 2024 Aug 30. PMID: 39212407; PMCID: PMC11481577. 4: Watson SJ, van der Watt ME, Theron A, Reader J, Tshabalala S, Erlank E, Koekemoer LL, Naude M, Stampolaki M, Adewole F, Sadowska K, Pérez-Lozano P, Turcu AL, Vázquez S, Ko J, Mazurek B, Singh D, Malwal SR, Njoroge M, Chibale K, Onajole OK, Kolocouris A, Oldfield E, Birkholtz LM. The Tuberculosis Drug Candidate SQ109 and Its Analogs Have Multistage Activity against Plasmodium falciparum. ACS Infect Dis. 2024 Sep 13;10(9):3358-3367. doi: 10.1021/acsinfecdis.4c00461. Epub 2024 Aug 14. PMID: 39143042; PMCID: PMC11406516. 5: Choksi H, Carbone J, Paradis NJ, Bennett L, Bui-Linh C, Wu C. Novel Inhibitors to MmpL3 Transporter of Mycobacterium tuberculosis by Structure-Based High-Throughput Virtual Screening and Molecular Dynamics Simulations. ACS Omega. 2024 Mar 12;9(12):13782-13796. doi: 10.1021/acsomega.3c08401. PMID: 38559933; PMCID: PMC10976370. 6: Ge Y, Luo Q, Liu L, Shi Q, Zhang Z, Yue X, Tang L, Liang L, Hu J, Ouyang W. S288T mutation altering MmpL3 periplasmic domain channel and H-bond network: a novel dual drug resistance mechanism. J Mol Model. 2024 Jan 15;30(2):39. doi: 10.1007/s00894-023-05814-y. PMID: 38224406. 7: Musisi E, Wyness A, Eldirdiri S, Dombay E, Mtafya B, Ntinginya NE, Heinrich N, Kibiki GS, Hoelscher M, Boeree M, Aarnoutse R, Gillespie SH, Sabiiti W; PanACEA consortium. Effect of seven anti-tuberculosis treatment regimens on sputum microbiome: a retrospective analysis of the HIGHRIF study 2 and PanACEA MAMS-TB clinical trials. Lancet Microbe. 2023 Nov;4(11):e913-e922. doi: 10.1016/S2666-5247(23)00191-X. Epub 2023 Oct 10. PMID: 37832571. 8: Carbone J, Paradis NJ, Bennet L, Alesiani MC, Hausman KR, Wu C. Inhibition Mechanism of Anti-TB Drug SQ109: Allosteric Inhibition of TMM Translocation of Mycobacterium Tuberculosis MmpL3 Transporter. J Chem Inf Model. 2023 Aug 28;63(16):5356-5374. doi: 10.1021/acs.jcim.3c00616. Epub 2023 Aug 17. PMID: 37589273; PMCID: PMC10466384. 9: Malwal SR, Mazurek B, Ko J, Xie P, Barnes C, Varvitsiotis C, Zimmerman MD, Olatunji S, Lee J, Xie M, Sarathy J, Caffrey M, Strynadka NCJ, Dartois V, Dick T, Lee BNR, Russell DG, Oldfield E. Investigation into the Mechanism of Action of the Tuberculosis Drug Candidate SQ109 and Its Metabolites and Analogues in Mycobacteria. J Med Chem. 2023 Jun 8;66(11):7553-7569. doi: 10.1021/acs.jmedchem.3c00398. Epub 2023 May 26. PMID: 37235809; PMCID: PMC10330530. 10: North EJ, Schwartz CP, Zgurskaya HI, Jackson M. Recent advances in mycobacterial membrane protein large 3 inhibitor drug design for mycobacterial infections. Expert Opin Drug Discov. 2023 Jul;18(7):707-724. doi: 10.1080/17460441.2023.2218082. Epub 2023 Jun 4. PMID: 37226498; PMCID: PMC10330604. 11: de Souza TG, Granado R, Benaim G, de Souza W, Benchimol M. Effects of SQ109 on Trichomonas vaginalis. Exp Parasitol. 2023 Jul;250:108549. doi: 10.1016/j.exppara.2023.108549. Epub 2023 May 16. PMID: 37196704. 12: Stampolaki M, Stylianakis I, Zgurskaya HI, Kolocouris A. Study of SQ109 analogs binding to mycobacterium MmpL3 transporter using MD simulations and alchemical relative binding free energy calculations. J Comput Aided Mol Des. 2023 Jun;37(5-6):245-264. doi: 10.1007/s10822-023-00504-6. Epub 2023 May 2. PMID: 37129848; PMCID: PMC10232594. 13: Stampolaki M, Malwal SR, Alvarez-Cabrera N, Gao Z, Moniruzzaman M, Babii SO, Naziris N, Rey-Cibati A, Valladares-Delgado M, Turcu AL, Baek KH, Phan TN, Lee H, Alcaraz M, Watson S, van der Watt M, Coertzen D, Efstathiou N, Chountoulesi M, Shoen CM, Papanastasiou IP, Brea J, Cynamon MH, Birkholtz LM, Kremer L, No JH, Vázquez S, Benaim G, Demetzos C, Zgurskaya HI, Dick T, Oldfield E, Kolocouris AD. Synthesis and Testing of Analogs of the Tuberculosis Drug Candidate SQ109 against Bacteria and Protozoa: Identification of Lead Compounds against Mycobacterium abscessus and Malaria Parasites. ACS Infect Dis. 2023 Feb 10;9(2):342-364. doi: 10.1021/acsinfecdis.2c00537. Epub 2023 Jan 27. PMID: 36706233; PMCID: PMC10615177. 14: Dhulap A, Banerjee P. Pharmacophore based virtual screening & molecular docking approach for identification of mycobacterial membrane protein large 3 (MmpL3) inhibitors. J Biomol Struct Dyn. 2023 Dec;41(20):11062-11077. doi: 10.1080/07391102.2022.2159876. Epub 2022 Dec 26. PMID: 36571432. 15: Imran M, Arora MK, Chaudhary A, Khan SA, Kamal M, Alshammari MM, Alharbi RM, Althomali NA, Alzimam IM, Alshammari AA, Alharbi BH, Alshengeti A, Alsaleh AA, Alqahtani SA, Rabaan AA. MmpL3 Inhibition as a Promising Approach to Develop Novel Therapies against Tuberculosis: A Spotlight on SQ109, Clinical Studies, and Patents Literature. Biomedicines. 2022 Nov 3;10(11):2793. doi: 10.3390/biomedicines10112793. PMID: 36359313; PMCID: PMC9687596. 16: Nguyen TQ, Hanh BTB, Jeon S, Heo BE, Park Y, Choudhary A, Moon C, Jang J. Synergistic Effect of Q203 Combined with PBTZ169 against Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2022 Dec 20;66(12):e0044822. doi: 10.1128/aac.00448-22. Epub 2022 Nov 2. PMID: 36321819; PMCID: PMC9765072. 17: Coelho RA, Alves GM, Figueiredo-Carvalho MHG, Almeida-Silva F, de Souza GR, Lourenço MCDS, Brito-Santos F, Amaral ACF, Almeida-Paes R. New possibilities for chromoblastomycosis and phaeohyphomycosis treatment: identification of two compounds from the MMV Pathogen Box® that present synergism with itraconazole. Mem Inst Oswaldo Cruz. 2022 Sep 12;117:e220089. doi: 10.1590/0074-02760220089. PMID: 36102413; PMCID: PMC9467274. 18: Kwofie SK, Hanson G, Sasu H, Enninful KS, Mensah FA, Nortey RT, Yeboah OP, Agoni C, Wilson MD. Molecular Modelling and Atomistic Insights into the Binding Mechanism of MmpL3 Mtb. Chem Biodivers. 2022 Sep;19(9):e202200160. doi: 10.1002/cbdv.202200160. Epub 2022 Aug 31. PMID: 35969844. 19: 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. 20: Liu HT, Fu L, Wang B, Wang N, Li DS, Ding YM, Yao R, Qi XT, Lu Y. [Study on the pharmacodynamic activity of combinations with the new anti-tuberculosis drug pyrifazimine in vitro and in vivo in mouse]. Zhonghua Jie He He Hu Xi Za Zhi. 2022 Jun 12;45(6):560-566. Chinese. doi: 10.3760/cma.j.cn112147-20211008-00697. PMID: 35658380.