NAV

Lortalamine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Lortalamine
DrugBank Accession Number
DB09187
Background

Lortalamine (LM-1404) is a selective norepinephrine reuptake inhibitor developed in the 1980s. This drug never made it past clinical trials, likely due to ocular toxicity in animals, but has been used in positron emission tomography studies to label norepinephrine transporters.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 292.76
Monoisotopic: 292.0978555
Chemical Formula
C15H17ClN2O2
Synonyms
  • Lortalamine
External IDs
  • LM-1404
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Lortalamine is combined with 1,2-Benzodiazepine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Lortalamine is combined with Acenocoumarol.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Lortalamine.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Lortalamine.
AgomelatineThe risk or severity of CNS depression can be increased when Agomelatine is combined with Lortalamine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as naphthyridines. These are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Naphthyridines
Direct Parent
Naphthyridines
Alternative Parents
1-benzopyrans / Piperidinones / Aralkylamines / Delta lactams / Aryl chlorides / Benzenoids / Trialkylamines / Secondary carboxylic acid amides / Amino acids and derivatives / Oxacyclic compounds
show 6 more
Substituents
1-benzopyran / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzenoid / Benzopyran
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
9GIR4SV22T
CAS number
70384-91-7
InChI Key
MJRPHRMGEKCADU-UHFFFAOYSA-N
InChI
InChI=1S/C15H17ClN2O2/c1-18-5-4-15-12(8-18)10(7-14(19)17-15)11-6-9(16)2-3-13(11)20-15/h2-3,6,10,12H,4-5,7-8H2,1H3,(H,17,19)
IUPAC Name
6-chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.0¹,¹⁰.0³,⁸]heptadeca-3,5,7-trien-16-one
SMILES
CN1CCC23NC(=O)CC(C2C1)C1=CC(Cl)=CC=C1O3

References

General References
  1. Belleville M, Grand M, Briet P: Plasma levels, elimination and metabolic fate of 4a-amino-8-chloro-2-methyl-1,2,3,4,4a,10a-hexahydro-10H-benzopyrano[3,2-c]pyridin -10-ylacetic acid lactam, a new antidepressive agent, in rats and dogs. Drug Metab Dispos. 1981 May-Jun;9(3):233-9. [Article]
  2. Depin JC, Betbeder-Matibet A, Bonhomme Y, Muller AJ, Berthelon JJ: Pharmacology of lortalamine, a new potent non-tricyclic antidepressant. Arzneimittelforschung. 1985;35(11):1655-62. [Article]
  3. Lin KS, Ding YS: Synthesis and C-11 labeling of three potent norepinephrine transporter selective ligands ((R)-nisoxetine, lortalamine, and oxaprotiline) for comparative PET studies in baboons. Bioorg Med Chem. 2005 Aug 1;13(15):4658-66. [Article]
  4. Elsom LF, Biggs SR, Chasseaud LF, Hawkins DR, Pulsford J, Darragh A: Metabolism of the anti-depressant lortalamine. Eur J Drug Metab Pharmacokinet. 1985 Jul-Sep;10(3):209-15. [Article]
  5. Mally C, Thiebault JJ: Ocular toxicity in beagle dogs with lortalamine, a non tricyclic antidepressant compound. Drug Chem Toxicol. 1990;13(4):309-23. [Article]
  6. Ding YS, Lin KS, Logan J, Benveniste H, Carter P: Comparative evaluation of positron emission tomography radiotracers for imaging the norepinephrine transporter: (S,S) and (R,R) enantiomers of reboxetine analogs ([11C]methylreboxetine, 3-Cl-[11C]methylreboxetine and [18F]fluororeboxetine), (R)-[11C]nisoxetine, [11C]oxaprotiline and [11C]lortalamine. J Neurochem. 2005 Jul;94(2):337-51. [Article]
  7. Ding YS, Lin KS, Logan J: PET imaging of norepinephrine transporters. Curr Pharm Des. 2006;12(30):3831-45. [Article]
KEGG Drug
D04781
PubChem Compound
3053755
PubChem Substance
310265095
ChemSpider
2315437
ChEMBL
CHEMBL2218922
Wikipedia
Lortalamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.654 mg/mLALOGPS
logP1.93ALOGPS
logP1.9Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)10.2Chemaxon
pKa (Strongest Basic)8.28Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area41.57 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity75.95 m3·mol-1Chemaxon
Polarizability30.05 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0aba-4090000000-b160c7f7c93a285d4555
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-067477b90f939a75716d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-de3ae918649860fa4156
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-738b93174957f7e59cbd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-2090000000-ab5383f83436420c25aa
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-2190000000-7f9c5ae9813bb66429d0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-067i-0390000000-cd6ff88636fb16b00061
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]-158.44524
predicted
DeepCCS 1.0 (2019)
[M+H]+160.80324
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.8964
predicted
DeepCCS 1.0 (2019)

Drug created at October 16, 2015 19:41 / Updated at February 21, 2021 18:52