SQ-109

Investigational

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22827305
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dehydrosqualene synthase 1 Target ID: CHEMBL5440 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22486710	Inhibitor 8297		0.36 µM [Ki]
Trehalose monomycolate exporter MmpL3 1 Target ID: P9WJV5 Gene ID: 886752.0 Gene Symbol: mmpL3 Target Organism: Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22252828/	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25630641	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
43.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25630641	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25630641	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25630641	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16432511	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

Value	Dose	Analyte	Population
183.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25630641	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25630641	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25630641	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16432511	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
11.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16432511	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
91.6% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/16432511	unknown, unknown		SQ-109 plasma	Rattus norvegicus population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/25630641 Page: p.3	unhealthy, ADULT Health Status: unhealthy Condition: tuberculosis Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/25630641 Page: p.3	Sources: https://pubmed.ncbi.nlm.nih.gov/25630641 Page: p.3

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00DBO8	https://www.1pchem.com/search?query=1P00DBO8
ApexBio Technology	A3834	https://www.apexbt.com/catalogsearch/result/?q=A3834
AstaTech	40681	http://astatechinc.com/CPSResult.php?CRNO=40681
AstaTech	94478	http://astatechinc.com/CPSResult.php?CRNO=94478
BLD Pharm	BD630736	http://www.bldpharm.com/search/Search.html?keyword=BD630736
Chem Scene	CS-1188	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-1188
ChemShuttle	141241	https://www.chemshuttle.com/catalogsearch/result/?q=141241
Excenen	EX-A764	http://www.excenen.com/searchresultlist.php?id=EX-A764
Hairui	SQJB016	http://www.hairuichem.com/en/product/search.do?q=SQJB016
Lab Network	LN01341990	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01341990
MedChem Express	HY-14989	https://www.medchemexpress.com/search.html?q=HY-14989&ft=&fa=&fp=
MolPort	MolPort-005-932-895	https://www.molport.com/shop/molecule-link/MolPort-005-932-895
MuseChem	I003772	https://www.musechem.com/product/I003772.html
eMolecules	195275714	https://orderbb.emolecules.com/search/#?query=195275714
eMolecules	266610522	https://orderbb.emolecules.com/search/#?query=266610522
eMolecules	275119232	https://orderbb.emolecules.com/search/#?query=275119232
eMolecules	300768302	https://orderbb.emolecules.com/search/#?query=300768302
eMolecules	45475557	https://orderbb.emolecules.com/search/#?query=45475557
mcule	MCULE-1061812051	https://mcule.com/MCULE-1061812051/

PubMed

Title	Date	PubMed
Interspecies pharmacokinetics and in vitro metabolism of SQ109.	2006 Mar	16432511
Design, synthesis, and biological evaluation of novel fluorinated ethanolamines.	2011 Dec 23	22113787
Head-to-head prenyl tranferases: anti-infective drug targets.	2012 May 10	22486710

Patents

Sample Use Guides

In Vivo Use Guide

In clinical trials against tuberculosis, SQ-109 was administered orally at doses 75-300 mg daily

Route of Administration: Oral

In Vitro Use Guide

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

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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