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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

Molecular Formula C22H38N2
Molecular Weight 330.5505
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
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
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
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
37.1 ng/mL
15 mg/kg single, oral
dose: 15 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
SQ-109 plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
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
158 ng × h/mL
15 mg/kg single, oral
dose: 15 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
SQ-109 plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
11.6 h
15 mg/kg single, oral
dose: 15 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
SQ-109 plasma
Canis lupus
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
91.6%
unknown, unknown
SQ-109 plasma
Rattus norvegicus
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
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: Page: p.3
unhealthy, ADULT
Health Status: unhealthy
Condition: tuberculosis
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Sources: Page: p.3
PubMed

PubMed

TitleDatePubMed
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:45:50 GMT 2023
Edited
by admin
on Fri Dec 15 17:45:50 GMT 2023
Record UNII
9AU7XUV31A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SQ-109
Common 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
NSC-722041
Code English
Classification Tree Code System Code
EU-Orphan Drug EU/3/07/479
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
FDA ORPHAN DRUG 247307
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
Code System Code Type Description
CAS
502487-67-4
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
PUBCHEM
5274428
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID30964540
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
WIKIPEDIA
SQ109
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
DRUG BANK
DB05186
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
NCI_THESAURUS
C95706
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
FDA UNII
9AU7XUV31A
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
EVMPD
SUB196877
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
NSC
722041
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
SMS_ID
100000182674
Created by admin on Fri Dec 15 17:45:50 GMT 2023 , Edited by admin on Fri Dec 15 17:45:50 GMT 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
Despite its broad structural similarity to EMB retained good activity against EMB-resistant Mtb strains (MIC 2.4 μM, cf. 1.2 μMNagainst H37Rv).
MIC
Related Record Type Details
ACTIVE MOIETY