For research use only. Not for therapeutic Use.
SQ109 (CAS 502487-67-4) (Cat.No:I003772) is an investigational antimycobacterial drug that targets multiple components of the mycobacterial cell envelope. It shows promise in the treatment of tuberculosis (TB) and multidrug-resistant TB (MDR-TB). SQ109 is being evaluated in clinical trials as a potential novel therapy to combat TB and improve treatment outcomes.
| Catalog Number | I003772 |
| CAS Number | 502487-67-4 |
| Synonyms | N/’-(2-adamantyl)-N-[(2E)-3,7-dimethylocta-2,6-dienyl]ethane-1,2-diamine |
| Molecular Formula | C22H38N2 |
| Purity | ≥95% |
| Target | Antibiotic |
| Solubility | 10 mM in DMSO |
| Storage | Store at -20°C |
| IUPAC Name | N'-(2-adamantyl)-N-[(2E)-3,7-dimethylocta-2,6-dienyl]ethane-1,2-diamine |
| InChI | 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? |
| InChIKey | JFIBVDBTCDTBRH-WUROFCERSA-N |
| SMILES | C/C(CC/C=C(C)C)=CCNCCNC1[C@H]2C[C@@H]3C[C@H](C2)CC1C3 |
| Reference | </br>1:Activity of moxifloxacin and linezolid against Mycobacterium tuberculosis in combination with potentiator drugs verapamil, timcodar, colistin and SQ109. de Knegt GJ, van der Meijden A, de Vogel CP, Aarnoutse RE, de Steenwinkel JE.Int J Antimicrob Agents. 2017 Mar;49(3):302-307. doi: 10.1016/j.ijantimicag.2016.11.027. Epub 2017 Feb 2. PMID: 28162983 </br>2:High-dose rifampicin, moxifloxacin, and SQ109 for treating tuberculosis: a multi-arm, multi-stage randomised controlled trial. Boeree MJ, Heinrich N, Aarnoutse R, Diacon AH, Dawson R, Rehal S, Kibiki GS, Churchyard G, Sanne I, Ntinginya NE, Minja LT, Hunt RD, Charalambous S, Hanekom M, Semvua HH, Mpagama SG, Manyama C, Mtafya B, Reither K, Wallis RS, Venter A, Narunsky K, Mekota A, Henne S, Colbers A, van Balen GP, Gillespie SH, Phillips PP, Hoelscher M; PanACEA consortium..Lancet Infect Dis. 2017 Jan;17(1):39-49. doi: 10.1016/S1473-3099(16)30274-2. Epub 2016 Oct 26. PMID: 28100438 Free PMC Article</br>3:Inhibition of Leishmania mexicana Growth by the Tuberculosis Drug SQ109. García-García V, Oldfield E, Benaim G.Antimicrob Agents Chemother. 2016 Sep 23;60(10):6386-9. doi: 10.1128/AAC.00945-16. Print 2016 Oct. PMID: 27458218 Free PMC Article</br>4: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-dimethylocta-2,6-dienyl)ethane-1,2-diamine (SQ109) Pyrrole Hybrid Derivatives: Discovery of Potent Antitubercular Agents Effective against Multidrug-Resistant Mycobacteria. Bhakta S, Scalacci N, Maitra A, Brown AK, Dasugari S, Evangelopoulos D, McHugh TD, Mortazavi PN, Twist A, Petricci E, Manetti F, Castagnolo D.J Med Chem. 2016 Mar 24;59(6):2780-93. doi: 10.1021/acs.jmedchem.6b00031. Epub 2016 Mar 8. PMID: 26907951 </br>5:Oxa, Thia, Heterocycle, and Carborane Analogues of SQ109: Bacterial and Protozoal Cell Growth Inhibitors. 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.ACS Infect Dis. 2015 May 8;1(5):215-221. PMID: 26258172 Free PMC Article</br>6:Early phase evaluation of SQ109 alone and in combination with rifampicin in pulmonary TB patients. 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..J Antimicrob Chemother. 2015 May;70(5):1558-66. doi: 10.1093/jac/dku553. Epub 2015 Jan 27. PMID: 25630641 </br>7:SQ109, a new drug lead for Chagas disease. 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.Antimicrob Agents Chemother. 2015 Apr;59(4):1950-61. doi: 10.1128/AAC.03972-14. Epub 2015 Jan 12. PMID: 25583723 Free PMC Article</br>8:In vitro characterization of the anti-bacterial activity of SQ109 against Helicobacter pylori. Makobongo MO, Einck L, Peek RM Jr, Merrell DS.PLoS One. 2013 Jul 25;8(7):e68917. doi: 10.1371/journal.pone.0068917. Print 2013. PMID: 23935905 Free PMC Article</br>9:Discovery and development of SQ109: a new antitubercular drug with a novel mechanism of action. Sacksteder KA, Protopopova M, Barry CE 3rd, Andries K, Nacy CA.Future Microbiol. 2012 Jul;7(7):823-37. doi: 10.2217/fmb.12.56. Review. PMID: 22827305 Free PMC Article</br>10:Rapid evaluation in whole blood culture of regimens for XDR-TB containing PNU-100480 (sutezolid), TMC207, PA-824, SQ109, and pyrazinamide. Wallis RS, Jakubiec W, Mitton-Fry M, Ladutko L, Campbell S, Paige D, Silvia A, Miller PF.PLoS One. 2012;7(1):e30479. doi: 10.1371/journal.pone.0030479. Epub 2012 Jan 18. PMID: 22279595 Free PMC Article |
