U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry ACHIRAL
Molecular Formula C22H38N2
Molecular Weight 330.5505
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SQ-109

SMILES

CC(C)=CCC\C(C)=C\CNCCNC1C2CC3CC(C2)CC1C3

InChI

InChIKey=JFIBVDBTCDTBRH-REZTVBANSA-N
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+

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25630641

SQ-109 is a [1,2]-diamine-based ethambutol (EMB) analog developed for the treatment of tuberculosis. SQ109 acts by inhibiting MmpL3, a transporter of trehalose monomyclate, which is an important component of cellular wall. The drug was investigated as a monotherapy or in combination with rifampicin in phase II clinical trials in pulmonary tuberculosis patients. The clinical trials, however, did not demonstrate activity of SQ-109 alone or its ability to enhance the activity of rifampicin.

CNS Activity

Curator's Comment: Known to be CNS non-penetrant in mice. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.36 µM [Ki]
Target ID: P9WJV5
Gene ID: 886752.0
Gene Symbol: mmpL3
Target Organism: Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
39.1 ng/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SQ-109 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
43.3 ng/mL
300 mg 1 times / day single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SQ-109 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
45.9 ng/mL
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SQ-109 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
240.8 ng × h/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SQ-109 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
183.7 ng × h/mL
300 mg 1 times / day single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
SQ-109 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
268.5 ng × h/mL
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SQ-109 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day multiple, oral
Highest studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources:
PubMed

PubMed

TitleDatePubMed
Synergistic interactions of SQ109, a new ethylene diamine, with front-line antitubercular drugs in vitro.
2006 Aug
Interspecies pharmacokinetics and in vitro metabolism of SQ109.
2006 Mar
Novel agents in the management of Mycobacterium tuberculosis disease.
2007
Drug therapy of experimental tuberculosis (TB): improved outcome by combining SQ109, a new diamine antibiotic, with existing TB drugs.
2007 Apr
In vitro interactions between new antitubercular drug candidates SQ109 and TMC207.
2010 Jul
Synthesis and evaluation of SQ109 analogues as potential anti-tuberculosis candidates.
2010 May
Novel linear diamine disubstituted polycyclic 'cage' derivatives as potential antimycobacterial candidates.
2011 Dec
Design, synthesis, and biological evaluation of novel fluorinated ethanolamines.
2011 Dec 23
Head-to-head prenyl tranferases: anti-infective drug targets.
2012 May 10
Patents

Sample Use Guides

In clinical trials against tuberculosis, SQ-109 was administered orally at doses 75-300 mg daily
Route of Administration: Oral
MIC assays were performed in 96-well round-bottom plates for seven-days. SQ-109 was suspended in DMSO at a final concentration of 10 mM and diluted 100-fold into 7H9-OADC liquid medium containing 0.05% Tween-80. This 100 uM stock was diluted by 2-fold serial dilutions in the same medium in microtiter wells, resulting in 50 uL total volume in each well. In addition to a control lacking drug, the lowest concentration of drug assayed was 0.04 uM (11 dilutions total). M. tuberculosis H37Rv was grown to an optical density [600nm] 0.5 and diluted 1:10 before adding 50 uL to each individual well of the 96-well plates. The final optical density at 600nm was 0.025, and there was no visible growth within the wells of the microtiter plate. Upon incubation for 7 days at 37 °C, growth became apparent, and the MIC was determined to be the lowest concentration that prevents visible growth. MIC for SQ-109 in this assay was 0.2 uM.
Name Type Language
SQ-109
Common Name English
NSC-722041
Preferred Name English
1,2-ETHANEDIAMINE, N-((2E)-3,7-DIMETHYL-2,6-OCTADIENYL)-N'-TRICYCLO(3.3.1.13,7)DEC-2-YL-
Systematic Name English
N-ADAMANTANYL-N'-GERANYL-ETHYLENEDIAMINE
Systematic Name English
SQ109
Code English
Classification Tree Code System Code
EU-Orphan Drug EU/3/07/479
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
FDA ORPHAN DRUG 247307
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
Code System Code Type Description
CAS
502487-67-4
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY
PUBCHEM
5274428
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY
EPA CompTox
DTXSID30964540
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY
WIKIPEDIA
SQ109
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY
DRUG BANK
DB05186
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY
NCI_THESAURUS
C95706
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY
FDA UNII
9AU7XUV31A
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY
EVMPD
SUB196877
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY
NSC
722041
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY
SMS_ID
100000182674
Created by admin on Mon Mar 31 18:51:45 GMT 2025 , Edited by admin on Mon Mar 31 18:51:45 GMT 2025
PRIMARY