Lortalamine
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Explore a selection of our essential drug information below, or:
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
- Weight
- Average: 292.76
Monoisotopic: 292.0978555 - Chemical Formula
- C15H17ClN2O2
- Synonyms
- Lortalamine
- External IDs
- LM-1404
Pharmacology
- Indication
Not Available
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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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Lortalamine is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Lortalamine is combined with Acenocoumarol. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Lortalamine. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Lortalamine. Agomelatine The 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
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Ding YS, Lin KS, Logan J: PET imaging of norepinephrine transporters. Curr Pharm Des. 2006;12(30):3831-45. [Article]
- External Links
- KEGG Drug
- D04781
- PubChem Compound
- 3053755
- PubChem Substance
- 310265095
- ChemSpider
- 2315437
- ChEMBL
- CHEMBL2218922
- Wikipedia
- Lortalamine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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
Property Value Source Water Solubility 0.654 mg/mL ALOGPS logP 1.93 ALOGPS logP 1.9 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 10.2 Chemaxon pKa (Strongest Basic) 8.28 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 41.57 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 75.95 m3·mol-1 Chemaxon Polarizability 30.05 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0aba-4090000000-b160c7f7c93a285d4555 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-067477b90f939a75716d Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-de3ae918649860fa4156 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-738b93174957f7e59cbd Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-2090000000-ab5383f83436420c25aa Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-2190000000-7f9c5ae9813bb66429d0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-067i-0390000000-cd6ff88636fb16b00061 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 158.44524 predictedDeepCCS 1.0 (2019) [M+H]+ 160.80324 predictedDeepCCS 1.0 (2019) [M+Na]+ 166.8964 predictedDeepCCS 1.0 (2019)
Drug created at October 16, 2015 19:41 / Updated at February 21, 2021 18:52