Altropane
Identification
- Name
- Altropane
- Accession Number
- DB04947
- Description
Boston Life Sciences (BLS) is developing Altropane as a potential radio-imaging agent to be used with single photon emission tomography (SPECT), for the early diagnosis of Parkinson's disease (PD) and attention deficit hyperactivity disorder (ADHD).
- Type
- Small Molecule
- Groups
- Investigational
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Learn More- Structure
Structure for Altropane (DB04947)
- Weight
- Average: 429.2677
Monoisotopic: 429.060100546 - Chemical Formula
- C18H21FINO2
- Synonyms
- Not Available
Pharmacology
- Indication
Investigated for use/treatment in attention deficit/hyperactivity disorder (ADHD), parkinson's disease, and pediatric indications.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Altropane is a molecular-imaging agent that specifically binds to the dopamine transporter (DAT) protein found on the surface of dopamine-producing neurons, making it visible during SPECT imaging. Since most forms of Parkinsonian Syndromes result in a decreased number of dopamine-producing cells, it would be expected that these patients also have fewer DATs than do patients without PS. Thus, it is believed that altropane used in conjunction with SPECT imaging could be a useful test to distinguish Parkinsonian Syndrome tremors from non-Parkinsonian tremor: non-Parkinsonian patients would have more altropane-binding visible in the SPECT image, while Parkinsonian patients would have less.
- Mechanism of action
Positron emission tomography (PET) cameras are expensive and scarce, and the tests are non-reimbursable. A less costly and more available test such as a single photon emission computed tomography (SPECT) may be helpful in the diagnosis of early or atypical Parkinson's disease (PD) if its sensitivity is comparable to a PET scan. Altropane is an iodinated form of the N-allyl analog of WIN 35,428 which acts as a dopamine transport inhibitor. When radiolabeled with the gamma emitting isotope [123I], altropane serves as a SPECT ligand with high affinity and selectivity for the dopamine transporter. It is a good marker for dopamine neurons and is useful in detecting PD.
Target Actions Organism USodium-dependent dopamine transporter Not Available Humans - 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
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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 phenyltropanes. These are compounds containing a phenyl group linked to a tropane moiety. Tropane is an organonitrogenous [3.2.1] bicyclic organic compound.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Tropane alkaloids
- Sub Class
- Phenyltropanes
- Direct Parent
- Phenyltropanes
- Alternative Parents
- Phenylpiperidines / Piperidinecarboxylic acids / Aralkylamines / Fluorobenzenes / Aryl fluorides / N-alkylpyrrolidines / Methyl esters / Trialkylamines / Amino acids and derivatives / Vinyl iodides show 9 more
- Substituents
- Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative show 29 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 1Q4092099O
- CAS number
- 180468-34-2
- InChI Key
- GTQLIPQFXVKRKJ-UNSMHXHVSA-N
- InChI
- InChI=1S/C18H21FINO2/c1-23-18(22)17-15(12-3-5-13(19)6-4-12)11-14-7-8-16(17)21(14)10-2-9-20/h2-6,9,14-17H,7-8,10-11H2,1H3/b9-2+/t14-,15+,16+,17-/m0/s1
- IUPAC Name
- methyl (1R,2S,3S,5S)-3-(4-fluorophenyl)-8-[(2E)-3-iodoprop-2-en-1-yl]-8-azabicyclo[3.2.1]octane-2-carboxylate
- SMILES
- [H][[email protected]]12CC[[email protected]]([H])([[email protected]]([[email protected]](C1)C1=CC=C(F)C=C1)C(=O)OC)N2C\C=C\I
References
- General References
- Cattabeni F: Altropane (Boston Life Science). Curr Opin Investig Drugs. 2002 Nov;3(11):1647-51. [PubMed:12476968]
- Fernandez HH, Friedman JH, Fischman AJ, Noto RB, Lannon MC: Is altropane SPECT more sensitive to fluoroDOPA PET for detecting early Parkinson's disease? Med Sci Monit. 2001 Nov-Dec;7(6):1339-43. [PubMed:11687754]
- Madras BK, Gracz LM, Fahey MA, Elmaleh D, Meltzer PC, Liang AY, Stopa EG, Babich J, Fischman AJ: Altropane, a SPECT or PET imaging probe for dopamine neurons: III. Human dopamine transporter in postmortem normal and Parkinson's diseased brain. Synapse. 1998 Jun;29(2):116-27. [PubMed:9593102]
- Fischman AJ, Bonab AA, Babich JW, Livni E, Alpert NM, Meltzer PC, Madras BK: [(11)C, (127)I] Altropane: a highly selective ligand for PET imaging of dopamine transporter sites. Synapse. 2001 Mar 15;39(4):332-42. [PubMed:11169784]
- Madras BK, Meltzer PC, Liang AY, Elmaleh DR, Babich J, Fischman AJ: Altropane, a SPECT or PET imaging probe for dopamine neurons: I. Dopamine transporter binding in primate brain. Synapse. 1998 Jun;29(2):93-104. [PubMed:9593100]
- Madras BK, Gracz LM, Meltzer PC, Liang AY, Elmaleh DR, Kaufman MJ, Fischman AJ: Altropane, a SPECT or PET imaging probe for dopamine neurons: II. Distribution to dopamine-rich regions of primate brain. Synapse. 1998 Jun;29(2):105-15. [PubMed:9593101]
- Fischman AJ, Bonab AA, Babich JW, Palmer EP, Alpert NM, Elmaleh DR, Callahan RJ, Barrow SA, Graham W, Meltzer PC, Hanson RN, Madras BK: Rapid detection of Parkinson's disease by SPECT with altropane: a selective ligand for dopamine transporters. Synapse. 1998 Jun;29(2):128-41. [PubMed:9593103]
- External Links
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Unknown Status Diagnostic Parkinsonian Syndromes 1 2 Completed Diagnostic Parkinson's Disease (PD) 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
Property Value Source Water Solubility 0.0081 mg/mL ALOGPS logP 4.05 ALOGPS logP 3.95 ChemAxon logS -4.7 ALOGPS pKa (Strongest Basic) 7.59 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 29.54 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 97.34 m3·mol-1 ChemAxon Polarizability 37.12 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9925 Blood Brain Barrier + 0.9807 Caco-2 permeable + 0.5405 P-glycoprotein substrate Non-substrate 0.5265 P-glycoprotein inhibitor I Inhibitor 0.8581 P-glycoprotein inhibitor II Inhibitor 0.756 Renal organic cation transporter Inhibitor 0.6782 CYP450 2C9 substrate Non-substrate 0.7524 CYP450 2D6 substrate Non-substrate 0.6614 CYP450 3A4 substrate Substrate 0.6347 CYP450 1A2 substrate Inhibitor 0.5323 CYP450 2C9 inhibitor Non-inhibitor 0.6098 CYP450 2D6 inhibitor Non-inhibitor 0.6468 CYP450 2C19 inhibitor Inhibitor 0.5619 CYP450 3A4 inhibitor Non-inhibitor 0.8397 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6144 Ames test Non AMES toxic 0.7037 Carcinogenicity Non-carcinogens 0.9281 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.8285 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7373 hERG inhibition (predictor II) Inhibitor 0.5528
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Monoamine transmembrane transporter activity
- Specific Function
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name
- SLC6A3
- Uniprot ID
- Q01959
- Uniprot Name
- Sodium-dependent dopamine transporter
- Molecular Weight
- 68494.255 Da
References
- Spencer TJ, Biederman J, Madras BK, Dougherty DD, Bonab AA, Livni E, Meltzer PC, Martin J, Rauch S, Fischman AJ: Further evidence of dopamine transporter dysregulation in ADHD: a controlled PET imaging study using altropane. Biol Psychiatry. 2007 Nov 1;62(9):1059-61. Epub 2007 May 23. [PubMed:17511972]
Drug created on October 21, 2007 16:23 / Updated on June 12, 2020 10:52
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