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Chemistry

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Also known as: Ioflupane i 123, Ioflupane (123i), 123i-ioflupane, Datscan, 123i-fp-cit, Ioflupane i(123)
Molecular Formula
C18H23FINO2
Molecular Weight
427.3  g/mol
InChI Key
HXWLAJVUJSVENX-HFIFKADTSA-N
FDA UNII
3MM99T8R5Q

Ioflupane
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.
1 2D Structure

Ioflupane

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl (1R,2S,3S,5S)-8-(3-fluoropropyl)-3-(4-(123I)iodanylphenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate
2.1.2 InChI
InChI=1S/C18H23FINO2/c1-23-18(22)17-15(12-3-5-13(20)6-4-12)11-14-7-8-16(17)21(14)10-2-9-19/h3-6,14-17H,2,7-11H2,1H3/t14-,15+,16+,17-/m0/s1/i20-4
2.1.3 InChI Key
HXWLAJVUJSVENX-HFIFKADTSA-N
2.1.4 Canonical SMILES
COC(=O)C1C2CCC(N2CCCF)CC1C3=CC=C(C=C3)I
2.1.5 Isomeric SMILES
COC(=O)[C@@H]1[C@H]2CC[C@H](N2CCCF)C[C@@H]1C3=CC=C(C=C3)[123I]
2.2 Other Identifiers
2.2.1 UNII
3MM99T8R5Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (18f)fp-cit

2. (o-methyl-11c)beta-cit-fp

3. 123i-fp-cit

4. 2-carbomethoxy-8-(3-fluoropropyl)-3-(4-iodophenyl)tropane

5. Beta-cit-fp

6. Fluoropropylcarbomethoxyiodophenylnortropane

7. Fp-cit

8. Fpcit

9. I(123)-n-fluoropropyl-2-beta-carbomethoxy-3-(4-iodophenyl)nortropane

10. I(123)-n-omega-fluoropropyl-2-beta-carbomethoxy-3-beta(4-iodophenyl)nortropane

11. N-omega-fluoropropyl-2beta-carbomethoxy-3beta-(4-iodophenyl)tropane

12. (1r,2s,3s,5s)-8-(3-fluoropropyl)-3-(4-iodophenyl)-8-azabicyclo(3,2,1)octane-2-carboxylic Acid Methyl Ester

13. 123i-ioflupane

14. Ioflupane

15. Rti 313

16. Rti-313

2.3.2 Depositor-Supplied Synonyms

1. Ioflupane I 123

2. Ioflupane (123i)

3. 123i-ioflupane

4. Datscan

5. 123i-fp-cit

6. Ioflupane I(123)

7. V09ab03

8. Ioflupane ((123)i)

9. Ioflupane

10. V-09ab03

11. (123i)fp-cit

12. 155798-07-5

13. Ioflupane (123l)

14. Ioflupane, I-123

15. Fp-cit I-123

16. Ioflupane (sup 123)i

17. Iodine Ioflupane (123i)

18. Ioflupane (123i) [inn]

19. 3mm99t8r5q

20. Ioflupane I 123 [usan]

21. Methyl (1r,2s,3s,5s)-8-(3-fluoropropyl)-3-[4-((123)i)iodophenyl]-8-azabicyclo[3.2.1]octane-2-carboxylate

22. Methyl 8-(3-fluoropropyl)-3beta-(p-iodo-i(sup 123)-phenyl)-1alphah, 5alphah-nortropane-2beta-carboxylate

23. 123i-beta-cit-fp)

24. Unii-3mm99t8r5q

25. Ioflupane I-123 And Iodine

26. V 09ab03

27. Ioflupane I 123 [usan:inn:ban]

28. Ioflupano (123i)

29. Ioflupanum (123i)

30. Ioflupane ((sup 123)i)

31. Gtpl7653

32. Chembl3989517

33. Schembl16472968

34. Chebi:68855

35. Dtxsid90935291

36. Ioflupane I 123 [mi]

37. Ioflupane I-123 [vandf]

38. Ioflupane (123i) [who-dd]

39. Db08824

40. Ioflupane (123l) [ema Epar]

41. Ioflupane I-123 [orange Book]

42. Methyl (1s,3s,4s,5r)-8-(3-fluoropropyl)-3-(4-iodanylphenyl)-8-azabicyclo[3.2.1]octane-4-carboxylate

43. Ioflupane (sup 123)i [ema Epar]

44. Q3801359

45. 8-azabicyclo(3.2.1)octane-2-carboxylic Acid, 8-(3-fluoropropyl)-3-(4-(iodo-(sup 123)i)phenyl)-, Methyl Ester, (1r,2s,3s,5s)-

46. Methyl (1r,2s,3s,5s)-8-(3-fluoropropyl)-3-(4-(123i)iodanylphenyl)-8-azabicyclo[3.2.1]octane-2-carboxylate

47. Methyl 8-(3-fluoropropyl)-3.beta.-(p-iodo-(sup 123)i-phenyl)-1.alpha.h,5.alpha.h-nortropane-2.beta.-carboxylate

48. Methyl 8-(3-fluoropropyl)-3beta-(p-iodo-(sup 123)i-phenyl)-1alphah,5alphah-nortropane-2beta-carboxylate

2.4 Create Date
2005-08-09
3 Chemical and Physical Properties
Molecular Weight 427.3 g/mol
Molecular Formula C18H23FINO2
XLogP34
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Exact Mass427.07687 g/mol
Monoisotopic Mass427.07687 g/mol
Topological Polar Surface Area29.5 Ų
Heavy Atom Count23
Formal Charge0
Complexity414
Isotope Atom Count1
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Ioflupane I-123 is a SPECT (single photon emission computerized tomography) agent used to distinguish between Parkinsons syndrome tremors and essential tremor.


FDA Label


This medicinal product is for diagnostic use only.

Striascan 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 Parkinsons disease, multiple system atrophy and progressive supranuclear palsy. Striascan 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 Alzheimers disease. Striascan is unable to discriminate between dementia with Lewy bodies and Parkinsons disease dementia.


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 Parkinsons 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 Alzheimers disease. DaTSCAN is unable to discriminate between dementia with Lewy bodies and Parkinsons 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 Parkinsons 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 Alzheimers disease. Celsunax is unable to discriminate between dementia with Lewy bodies and Parkinsons disease dementia.


5 Pharmacology and Biochemistry
5.1 Pharmacology

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


5.2 MeSH Pharmacological Classification

Diagnostic Uses of Chemicals

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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
IOFLUPANE I-123
5.3.2 FDA UNII
3MM99T8R5Q
5.3.3 Pharmacological Classes
Radiopharmaceutical Activity [MoA]; Radioactive Diagnostic Agent [EPC]
5.4 ATC Code

V09AB03


V09AB03


V09AB03


V - Various

V09 - Diagnostic radiopharmaceuticals

V09A - Central nervous system

V09AB - Iodine (123i) compounds

V09AB03 - Iodine ioflupane (123I)


5.5 Absorption, Distribution and Excretion

Absorption

Absorption is 100% because administered I.V.


Route of Elimination

About 60% is excreted in the urine and 14% in the feces after 48 hours.


Volume of Distribution

Compared to the entire brain, about 30% of radioactivity is taken up by the striatum.


5.6 Biological Half-Life

Half life is 13.2 hours.


5.7 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.


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