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Flutemetamol F 18
Also known as: Flutemetamol f 18, Vizamyl, Flutemetamol (18f), 18f-flutemetamol, Flutemetamol f18, Flutemetamol ((sup18)f)
Molecular Formula
C14H11FN2OS
Molecular Weight
273.32  g/mol
InChI Key
VVECGOCJFKTUAX-HUYCHCPVSA-N
FDA UNII
L49M066S0O

Flutemetamol F 18 is a radiopharmaceutical containing flutemetamol, a thioflavin derivative of Pittsburgh compound B (PiB) labeled with the radioisotope fluorine F18 that can be used to detect beta-amyloid deposition upon positron emission tomography (PET). After intravenous administration of flutemetamol F 18, the flutemetamol moiety selectively accumulates in and binds to cerebral fibrillar amyloid-beta in the brain. The fluorine F18 radioisotope moiety is detected using PET, which allows imaging and quantification of amyloid-beta density. Amyloid plaque deposition is linked to cognitive decline, including Alzheimer's disease, and may be linked to chemotherapy-induced cognitive impairment (CICI).
Flutemetamol f-18 is a Radioactive Diagnostic Agent. The mechanism of action of flutemetamol f-18 is as a Radiopharmaceutical Activity.
1 2D Structure

Flutemetamol F 18

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[3-(18F)fluoranyl-4-(methylamino)phenyl]-1,3-benzothiazol-6-ol
2.1.2 InChI
InChI=1S/C14H11FN2OS/c1-16-11-4-2-8(6-10(11)15)14-17-12-5-3-9(18)7-13(12)19-14/h2-7,16,18H,1H3/i15-1
2.1.3 InChI Key
VVECGOCJFKTUAX-HUYCHCPVSA-N
2.1.4 Canonical SMILES
CNC1=C(C=C(C=C1)C2=NC3=C(S2)C=C(C=C3)O)F
2.1.5 Isomeric SMILES
CNC1=C(C=C(C=C1)C2=NC3=C(S2)C=C(C=C3)O)[18F]
2.2 Other Identifiers
2.2.1 UNII
L49M066S0O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (18f)flutemetamol

2. Flutemetamol

3. Vizamyl

2.3.2 Depositor-Supplied Synonyms

1. Flutemetamol F 18

2. Vizamyl

3. Flutemetamol (18f)

4. 18f-flutemetamol

5. Flutemetamol F18

6. Flutemetamol ((sup18)f)

7. 765922-62-1

8. [18f]flutemetamol

9. Flutemetamol F 18 [usan]

10. Flutemetamol (18f) [inn]

11. Chebi:76611

12. L49m066s0o

13. (18f)flutemetamol

14. (18f)ah110690

15. 2-(3-(sup 18)f)fluoro-4-(methylamino)phenyl)-1,3-benzothiazol-6-ol

16. Flutemetamol F 18 (usan)

17. 2-[3-(18f)fluoro-4-(methylamino)phenyl]-1,3-benzothiazol-6-ol

18. 2-[3-(18f)fluoranyl-4-(methylamino)phenyl]-1,3-benzothiazol-6-ol

19. [18f]ah110690

20. Flutemetamol ((sup 18)f)

21. Unii-l49m066s0o

22. Vizamyl (tn)

23. [18f]-flutemetamol

24. Flutemetamol ((18)f)

25. [18f]-flutemetamol F18

26. Gtpl7342

27. Chembl2042122

28. Schembl10032147

29. (18f)flutemetamol [mi]

30. Dtxsid80227394

31. ((18 Sup)f)ah110690

32. Db09151

33. Flutemetamol (18f) [who-dd]

34. Flutemetamol F-18 [orange Book]

35. Ah-110690 F-18

36. D10231

37. Q18355673

38. 2-[3-((18)f)fluoro-4-(methylamino)phenyl]-1,3-benzothiazol-6-ol

39. 2-(3-((18 Sup)f)fluoro-4-(methylamino)phenyl)-1,3-benzothiazol-6-ol

40. 6-benzothiazolol, 2-(3-(fluoro-(sup 18)f)-4-(methylamino)phenyl)-

2.4 Create Date
2007-03-07
3 Chemical and Physical Properties
Molecular Weight 273.32 g/mol
Molecular Formula C14H11FN2OS
XLogP33.8
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Exact Mass273.060146 g/mol
Monoisotopic Mass273.060146 g/mol
Topological Polar Surface Area73.4 Ų
Heavy Atom Count19
Formal Charge0
Complexity320
Isotope Atom Count1
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameVizamyl
PubMed HealthFlutemetamol F 18 (Injection)
Drug ClassesDiagnostic Agent
Drug LabelVizamyl contains flutemetamol F 18, a molecular imaging agent that binds to -amyloid aggregates, and is intended for use with PET imaging of the brain. Chemically, flutemetamol F 18, is described as 2-[3-[18F]fluoro-4-(methylamino) phenyl]-6-benzot...
Active IngredientFlutemetamol f-18
Dosage FormInjectable
RouteIntravenous
Strength40.5mci/10ml (4.05mci/ml); 121.5mci/30ml (4.05mci/ml)
Market StatusPrescription
CompanyGe Healthcare

2 of 2  
Drug NameVizamyl
PubMed HealthFlutemetamol F 18 (Injection)
Drug ClassesDiagnostic Agent
Drug LabelVizamyl contains flutemetamol F 18, a molecular imaging agent that binds to -amyloid aggregates, and is intended for use with PET imaging of the brain. Chemically, flutemetamol F 18, is described as 2-[3-[18F]fluoro-4-(methylamino) phenyl]-6-benzot...
Active IngredientFlutemetamol f-18
Dosage FormInjectable
RouteIntravenous
Strength40.5mci/10ml (4.05mci/ml); 121.5mci/30ml (4.05mci/ml)
Market StatusPrescription
CompanyGe Healthcare

4.2 Drug Indication

Flutemetamol F18 is indicated for Positron Emission Tomography (PET) imaging of the brain to estimate amyloid neuritic plaque density in adult patients with cognitive impairment who are being evaluated for Alzheimer's disease (AD) or other causes of cognitive decline.


FDA Label


This medicinal product is for diagnostic use only.

Vizamyl is a radiopharmaceutical medicinal product indicated for Positron Emission Tomography (PET) imaging of amyloid neuritic plaque density in the brains of adult patients with cognitive impairment who are being evaluated for Alzheimers disease (AD) and other causes of cognitive impairment. Vizamyl should be used in conjunction with a clinical evaluation.

A negative scan indicates sparse or no plaques, which is not consistent with a diagnosis of AD.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Following intravenous injection, flutemetamol F 18 diffuses across the human blood-brain barrier and produces a radioactivity signal detectable throughout the brain. Subsequently, cerebral perfusion decreases the brain flutemetamol F 18 content, with differential retention of the drug in cortical areas that contain -amyloid aggregates compared to areas that lack the aggregates.


5.2 MeSH Pharmacological Classification

Contrast Media

Substances used to allow enhanced visualization of tissues. (See all compounds classified as Contrast Media.)


Radiopharmaceuticals

Compounds that are used in medicine as sources of radiation for radiotherapy and for diagnostic purposes. They have numerous uses in research and industry. (Martindale, The Extra Pharmacopoeia, 30th ed, p1161) (See all compounds classified as Radiopharmaceuticals.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
FLUTEMETAMOL F-18
5.3.2 FDA UNII
L49M066S0O
5.3.3 Pharmacological Classes
Radiopharmaceutical Activity [MoA]; Radioactive Diagnostic Agent [EPC]
5.4 ATC Code

V09AX04


V09AX04

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


V - Various

V09 - Diagnostic radiopharmaceuticals

V09A - Central nervous system

V09AX - Other central nervous system diagnostic radiopharmaceuticals

V09AX04 - Flutemetamol (18F)


5.5 Absorption, Distribution and Excretion

Absorption

The time-activity curves for flutemetamol F 18 in the brain of subjects with positive scans shows continual signal increases from time zero through 30 minutes post administration, with stable values thereafter up to at least 120 minutes post-injection. Following intravenous injection of 185 MBq (5 mCi) of Vizamyl in humans, flutemetamol F 18 plasma concentrations declined by approximately 75% in the first 20 minutes post-injection, and by approximately 90% in the first 180 minutes.


Route of Elimination

Excretion was found to be approximately 37% renal and 52% hepatobiliary.


5.6 Metabolism/Metabolites

The F 18 in circulation during the 30-120 minutes imaging window in plasma was principally associated with flutemetamol metabolites.


5.7 Mechanism of Action

Fluorine-18 (F 18) is a cyclotron-produced radionuclide that decays by positron emission (+ decay, 96.7%) and orbital electron capture (3.3%) to stable oxygen-18 with a physical half-life of 109.8 minutes. The positron can undergo annihilation with an electron to produce two gamma rays; the energy of each gamma ray is 511 keV. After flumetamol F18 is given intravenously, it accumulates in beta amyloid plaques in the brain, and thus becomes visible via positron emission tomography (PET).


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