SQ-109

Identification

Name
SQ-109
Accession Number
DB05186
Type
Small Molecule
Groups
Investigational
Description

SQ-109 is an orally active, small molecule antibiotic for treatment of pulmonary TB. Currently in Phase I clinical trials, SQ-109 could replace one or more drugs in the current first-line TB drug regimen, simplify therapy, and shorten the TB treatment regimen.

Structure
Thumb
Synonyms
Not Available
External IDs
SQ-109 / SQ109
Categories
UNII
9AU7XUV31A
CAS number
502487-67-4
Weight
Average: 330.5505
Monoisotopic: 330.303499226
Chemical Formula
C22H38N2
InChI Key
JFIBVDBTCDTBRH-REZTVBANSA-N
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+
IUPAC Name
N-(2-{[(2E)-3,7-dimethylocta-2,6-dien-1-yl]amino}ethyl)adamantan-2-amine
SMILES
CC(C)=CCC\C(C)=C\CNCCNC1C2CC3CC(C2)CC1C3

Pharmacology

Indication

Investigated for use/treatment in bacterial infection, infectious and parasitic disease (unspecified), and tuberculosis.

Pharmacodynamics
Not Available
Mechanism of action

With a mechanism of action distinct from other antibiotics used in TB therapy, SQ109 inhibits cell wall synthesis and acts on multiple cellular pathways in a select group of microorganisms.

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

References

General References
  1. Barry PJ, O'Connor TM: Novel agents in the management of Mycobacterium tuberculosis disease. Curr Med Chem. 2007;14(18):2000-8. [PubMed:17691942]
  2. Nikonenko BV, Protopopova M, Samala R, Einck L, Nacy CA: Drug therapy of experimental tuberculosis (TB): improved outcome by combining SQ109, a new diamine antibiotic, with existing TB drugs. Antimicrob Agents Chemother. 2007 Apr;51(4):1563-5. Epub 2007 Jan 22. [PubMed:17242141]
  3. Chen P, Gearhart J, Protopopova M, Einck L, Nacy CA: Synergistic interactions of SQ109, a new ethylene diamine, with front-line antitubercular drugs in vitro. J Antimicrob Chemother. 2006 Aug;58(2):332-7. Epub 2006 Jun 3. [PubMed:16751637]
  4. 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. [PubMed:16432511]
External Links
PubChem Compound
5274428
PubChem Substance
175426955
ChemSpider
4438718
BindingDB
50388398
ChEMBL
CHEMBL561057
ZINC
ZINC000039959796

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentMulti-Drug Resistant Tuberculosis1
1CompletedTreatmentTuberculosis Infection2
1WithdrawnTreatmentTuberculosis Infection1
2CompletedTreatmentPulmonary Tuberculosis (TB)2
2WithdrawnTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00171 mg/mLALOGPS
logP4.42ALOGPS
logP4.64ChemAxon
logS-5.3ALOGPS
pKa (Strongest Basic)10.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area24.06 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity105.79 m3·mol-1ChemAxon
Polarizability42.83 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9822
Blood Brain Barrier+0.7427
Caco-2 permeable+0.5298
P-glycoprotein substrateSubstrate0.9108
P-glycoprotein inhibitor IInhibitor0.7106
P-glycoprotein inhibitor IIInhibitor0.5677
Renal organic cation transporterNon-inhibitor0.5551
CYP450 2C9 substrateNon-substrate0.8496
CYP450 2D6 substrateNon-substrate0.5432
CYP450 3A4 substrateSubstrate0.5181
CYP450 1A2 substrateNon-inhibitor0.7403
CYP450 2C9 inhibitorNon-inhibitor0.8328
CYP450 2D6 inhibitorNon-inhibitor0.7825
CYP450 2C19 inhibitorNon-inhibitor0.8088
CYP450 3A4 inhibitorNon-inhibitor0.9093
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9082
Ames testNon AMES toxic0.6855
CarcinogenicityNon-carcinogens0.8187
BiodegradationNot ready biodegradable0.9243
Rat acute toxicity2.4283 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5971
hERG inhibition (predictor II)Inhibitor0.5841
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as monoterpenoids. These are compounds containing a chain of two isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Monoterpenoids
Alternative Parents
Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Monoterpenoid / Secondary amine / Secondary aliphatic amine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Amine / Aliphatic homopolycyclic compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available

Drug created on October 21, 2007 16:24 / Updated on March 01, 2020 19:31

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