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Ioflupane I-123

Ioflupane I-123 structure

CAS No:
155798-07-5
Formula:
C18H23FINO2
Chemical Name:
Ioflupane I-123
Synonyms:
8-Azabicyclo[3.2.1]octane-2-carboxylic acid,8-(3-fluoropropyl)-3-[4-(iodo-123I)phenyl]-,methyl ester,(1R,2S,3S,5S)-;8-Azabicyclo[3.2.1]octane-2-carboxylic acid,8-(3-fluoropropyl)-3-[4-(iodo-123I)phenyl]-,methyl ester,[1R-(exo,exo)]-;Ioflupane (123I);123I-FP-CIT;DaTSCAN;V 09AB03;123I-Ioflupane;Ioflupane I-123;Striascan
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Loflupane was launched as a new imaging agent for investigation of the dopaminergic neurons and the early diagnosis of Parkinson’s disease and related syndromes. This (123I) iodine-labeled agent was developed for imaging with single-photon emission computed tomography (SPECT); it binds to dopamine transporters on cerebral neurons, enabling the detection of an eventual loss of functional neurons, particularly in the striatal region.

Ioflupane I(123) is an azabicycloalkane that is ecgonine methyl ester in which the N-methyl group is replaced by 3-fluoropropyl and the 3beta-hydroxy group is replaced by 4-((123)I)iodophenyl. Used for the imaging of dopamine transporters in the brain of adult patients with potential Parkinsonian Syndromes. It has a role as a radioactive imaging agent and a radiopharmaceutical. It is an azabicycloalkane, an organofluorine compound and a methyl ester. It derives from an ecgonine.|Ioflupane (I-123) is a radiopharmaceutical used to image dopamine neurons and diagnose Parkinsonian syndromes.|Ioflupane i-123 is a Radioactive Diagnostic Agent. The mechanism of action of ioflupane i-123 is as a Radiopharmaceutical Activity.

Ioflupane I-123 Basic Attributes

Molecular Weight：

431.283

Exact Mass：

427.077

UNII：

3MM99T8R5Q

ATC Code：

V09AB03|V - Various

Characteristics

PSA：

29.5

XLogP3：

Melting Point：

82-83°

Water Solubility：

Soluble in water

Specific rotation：

D24 -12.8°

Drug Information

Drug Indication：

Ioflupane I-123 is a SPECT (single photon emission computerized tomography) agent used to distinguish between Parkinson’s syndrome tremors and essential tremor.|FDA Label|This medicinal product is for diagnostic use only.DaTSCAN is indicated for detecting loss of functional dopaminergic neuron terminals in the striatum:In adult patients with clinically uncertain Parkinsonian syndromes, for example those with early symptoms, in order to help differentiate essential tremor from Parkinsonian syndromes related to idiopathic Parkinson's disease, multiple system atrophy and progressive supranuclear palsy. DaTSCAN is unable to discriminate between Parkinson's disease, multiple system atrophy and progressive supranuclear palsy.In adult patients, to help differentiate probable dementia with Lewy bodies from Alzheimer's disease. DaTSCAN is unable to discriminate between dementia with Lewy bodies and Parkinson's disease dementia.|This medicinal product is for diagnostic use only.Celsunax is indicated for detecting loss of functional dopaminergic neuron terminals in the striatum:In adult patients with clinically uncertain parkinsonian syndromes, for example those with early symptoms, in order to help differentiate essential tremor from parkinsonian syndromes related to idiopathic Parkinson's disease, multiple system atrophy and progressive supranuclear palsy. Celsunax is unable to discriminate between Parkinson's disease, multiple system atrophy and progressive supranuclear palsy.In adult patients, to help differentiate probable dementia with Lewy bodies from Alzheimer's disease. Celsunax is unable to discriminate between dementia with Lewy bodies and Parkinson's disease dementia.

Pharmacology：

iodine-123 labeled ioflupanebinds selectively to striatal presynaptic dopamine neurons by binding reversibly to presynaptic dopamine transporters.

MeSH：

Chemicals administered to patients in order to diagnose or study the pathology of medical conditions, diseases, or syndromes. (See all compounds classified as Diagnostic Uses of Chemicals.)

Absorption：

Absorption is 100% because administered I.V.|About 60% is excreted in the urine and 14% in the feces after 48 hours.|Compared to the entire brain, about 30% of radioactivity is taken up by the striatum.

Biological Half-Life：

Half life is 13.2 hours.

Mechanism of Action：

Iodine-123 labeled ioflupane binds to presynaptic dopamine transporters. When Iodine-123 decays, a gammay ray is emmitted and detected through SPECT.

MeSH Entry Terms：

(18F)FP-CIT|(1R,2S,3S,5S)-8-(3-fluoropropyl)-3-(4-iodophenyl)-8-azabicyclo(3,2,1)octane-2-carboxylic acid methyl ester

Ioflupane I-123 Use and Manufacturing

Use Classification：

Human drugs -> DaTSCAN -> EMA Drug Category|Diagnostic radiopharmaceuticals -> Human pharmacotherapeutic group|Human drugs -> Celsunax -> EMA Drug Category|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:427.3
XLogP3:4
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:6
Exact Mass:427.07687
Monoisotopic Mass:427.07687
Topological Polar Surface Area:29.5
Heavy Atom Count:23
Complexity:414
Isotope Atom Count:1
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes