NAV

SQ-109

Identification

Generic Name
SQ-109
DrugBank Accession Number
DB05186
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 330.5505
Monoisotopic: 330.303499226
Chemical Formula
C22H38N2
Synonyms
  • N-adamantanyl-N'-geranyl-ethylenediamine
External IDs
  • SQ-109
  • SQ109
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

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

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aliphatic homopolycyclic compound / Amine / Hydrocarbon derivative / Monoterpenoid / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Secondary aliphatic amine / Secondary amine
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
9AU7XUV31A
CAS number
502487-67-4
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

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
PubChem Compound
5274428
PubChem Substance
175426955
ChemSpider
4438718
BindingDB
50388398
ChEMBL
CHEMBL561057
ZINC
ZINC000039959796

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentPulmonary Tuberculosis (TB)2
2WithdrawnTreatmentHelicobacter Pylori Infection1
1CompletedTreatmentMultidrug Resistant Tuberculosis1
1CompletedTreatmentTuberculosis (TB)2
1WithdrawnTreatmentTuberculosis (TB)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
Polarizability42.84 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-MSsplash10-02ti-3910000000-4bb7d19a3ce89f7b78fc
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0229000000-11421164b5f16d82643c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-cdc7b5e80909c2245770
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0109000000-ddf8cd04ec6f29b6fd1f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-003i-2921000000-7dae08e9a646de06c305
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-0910000000-1d21fc210098c31e4081
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-9700000000-5e9761db8db7e1b4259e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.3436
predicted
DeepCCS 1.0 (2019)
[M+H]+181.7016
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.43658
predicted
DeepCCS 1.0 (2019)

Drug created at October 21, 2007 22:24 / Updated at May 13, 2023 04:07