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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H21FINO2
Molecular Weight 429.2677
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ALTROPANE

SMILES

COC(=O)[C@@H]1[C@H]2CC[C@@H](C[C@@H]1C3=CC=C(F)C=C3)N2C\C=C\I

InChI

InChIKey=GTQLIPQFXVKRKJ-UNSMHXHVSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H21FINO2
Molecular Weight 429.2677
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

Alseres Pharmaceuticals is developing an 123I-labelled imaging agent, Altropane®, as a diagnostic aid in Parkinson's disease and other movement disorders. 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. The E isomer of (123)I-2beta-carbomethoxy-3beta-(4-fluorophenyl)-N-(1-iodoprop-1-en-3-yl)nortropane (Altropane(R)) shows high affinity (IC(50) = 6.62 +/- 0.78 nmol) and selectivity (DA/5-HT = 25) for DAT sites in the striatum. Altropane is presently in Phase III clinical development for the diagnosis of Parkinson's disease.

Approval Year

PubMed

PubMed

TitleDatePubMed
Rapid detection of Parkinson's disease by SPECT with altropane: a selective ligand for dopamine transporters.
1998 Jun
Altropane, a SPECT or PET imaging probe for dopamine neurons: III. Human dopamine transporter in postmortem normal and Parkinson's diseased brain.
1998 Jun
Altropane, a SPECT or PET imaging probe for dopamine neurons: II. Distribution to dopamine-rich regions of primate brain.
1998 Jun
Altropane, a SPECT or PET imaging probe for dopamine neurons: I. Dopamine transporter binding in primate brain.
1998 Jun
Altropane (Boston Life Science).
2002 Nov
Cerebellar vermis involvement in cocaine-related behaviors.
2006 Jun
Patents

Sample Use Guides

Parkinsonian Syndromes: 8.0 mCi (±1.0 mCi) are administered intravenously to each subject.
Route of Administration: Intravenous
In Vitro Use Guide
In homogenates of human brain putamen, [125I]altropane bound with high affinity (KD: 4.96 +/- 0.38 nM, n = 4) and site density (BMAX: 212 +/- 41.1 pmol/g original wet tissue weight) well within the density range reported previously for the dopamine transporter in this brain region. In postmortem Parkinson's diseased brain, bound [125I]altropane (1 nM) was markedly reduced (89%, 99% in putamen, depending on measures of nonspecific binding) compared with normal aged-matched controls (normal putamen: 49.2 +/- 8.1 pmol/g; Parkinson's diseased putamen: 0.48 +/- 0.33 pmol/g; n = 4).
Substance Class Chemical
Created
by admin
on Fri Dec 15 19:27:55 GMT 2023
Edited
by admin
on Fri Dec 15 19:27:55 GMT 2023
Record UNII
1Q4092099O
Record Status Validated (UNII)
Record Version
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Name Type Language
ALTROPANE
Common Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(4-FLUOROPHENYL)-8-((2E)-3-IODO-2-PROPEN-1-YL)-, METHYL ESTER, (1R,2S,3S,5S)-
Common Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(4-FLUOROPHENYL)-8-(3-IODO-2-PROPENYL)-, METHYL ESTER, (1R-(1.ALPHA.,2.ALPHA.,3.ALPHA.,5.ALPHA.,8(E)))-
Common Name English
IACFT [MI]
Common Name English
8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, 3-(4-FLUOROPHENYL)-8-((2E)-3-IODO-2-PROPENYL)-, METHYL ESTER, (1R,2S,3S,5S)-
Common Name English
Code System Code Type Description
PUBCHEM
6440180
Created by admin on Fri Dec 15 19:27:55 GMT 2023 , Edited by admin on Fri Dec 15 19:27:55 GMT 2023
PRIMARY
FDA UNII
1Q4092099O
Created by admin on Fri Dec 15 19:27:55 GMT 2023 , Edited by admin on Fri Dec 15 19:27:55 GMT 2023
PRIMARY
EPA CompTox
DTXSID901027571
Created by admin on Fri Dec 15 19:27:55 GMT 2023 , Edited by admin on Fri Dec 15 19:27:55 GMT 2023
PRIMARY
MERCK INDEX
m6180
Created by admin on Fri Dec 15 19:27:55 GMT 2023 , Edited by admin on Fri Dec 15 19:27:55 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB04947
Created by admin on Fri Dec 15 19:27:55 GMT 2023 , Edited by admin on Fri Dec 15 19:27:55 GMT 2023
PRIMARY
WIKIPEDIA
ALTROPANE
Created by admin on Fri Dec 15 19:27:55 GMT 2023 , Edited by admin on Fri Dec 15 19:27:55 GMT 2023
PRIMARY
DRUG CENTRAL
3292
Created by admin on Fri Dec 15 19:27:55 GMT 2023 , Edited by admin on Fri Dec 15 19:27:55 GMT 2023
PRIMARY
CAS
180468-34-2
Created by admin on Fri Dec 15 19:27:55 GMT 2023 , Edited by admin on Fri Dec 15 19:27:55 GMT 2023
PRIMARY
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ACTIVE MOIETY