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Fesoterodine

Synopsis, Chemistry

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TABLET, EXTENDED RELEASE;ORAL - 4MG
TABLET, EXTENDED RELEASE;ORAL - 8MG

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Also known as: 286930-03-8, Toviaz, (r)-fesoterodine fumarate, Spm 907, Spm 8272, Spm-907

Molecular Formula

C₃₀H₄₁NO₇

Molecular Weight

527.6 g/mol

InChI Key

MWHXMIASLKXGBU-RNCYCKTQSA-N

FDA UNII

EOS72165S7

Fesoterodine Fumarate is the fumarate salt form of fesoterodine, a competitive muscarinic receptor antagonist with muscle relaxant and urinary antispasmodic properties. Fesoterodine is rapidly hydrolyzed in vivo into its active metabolite 5-hydroxy methyl tolterodine, which binds and inhibits muscarinic receptors on the bladder detrusor muscle, thereby preventing bladder contractions or spasms caused by acetylcholine. This results in the relaxation of bladder smooth muscle and greater bladder capacity, in addition to a reduction in involuntary muscle contractions and involuntary loss of urine. The active metabolite does not interact with alpha-adrenergic, serotonergic, histaminergic and excitatory amino acid receptors and is eliminated via renal excretion.

1 2D Structure

Fesoterodine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(E)-but-2-enedioic acid;[2-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate

2.1.2 InChI

InChI=1S/C26H37NO3.C4H4O4/c1-18(2)26(29)30-25-13-12-21(17-28)16-24(25)23(22-10-8-7-9-11-22)14-15-27(19(3)4)20(5)6;5-3(6)1-2-4(7)8/h7-13,16,18-20,23,28H,14-15,17H2,1-6H3;1-2H,(H,5,6)(H,7,8)/b;2-1+/t23-;/m1./s1

2.1.3 InChI Key

MWHXMIASLKXGBU-RNCYCKTQSA-N

2.1.4 Canonical SMILES

CC(C)C(=O)OC1=C(C=C(C=C1)CO)C(CCN(C(C)C)C(C)C)C2=CC=CC=C2.C(=CC(=O)O)C(=O)O

2.1.5 Isomeric SMILES

CC(C)C(=O)OC1=C(C=C(C=C1)CO)[C@H](CCN(C(C)C)C(C)C)C2=CC=CC=C2.C(=C/C(=O)O)\C(=O)O

2.2 Other Identifiers

2.2.1 UNII

EOS72165S7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fesoterodine

2. Toviaz

2.3.2 Depositor-Supplied Synonyms

1. 286930-03-8

2. Toviaz

3. (r)-fesoterodine Fumarate

4. Spm 907

5. Spm 8272

6. Spm-907

7. Spm-8272

8. Fesoterodine Maleate

9. Fesoterodine (fumarate)

10. Eos72165s7

11. (e)-but-2-enedioic Acid;[2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate

12. Propanoic Acid, 2-methyl-, 2-[(1r)-3-[bis(1-methylethyl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl Ester, (2e)-2-butenedioate (1:1)

13. 286930-03-8 (fumarate); 286930-02-7 (free Base)

14. Fesoterodine Fumarate [usan]

15. Unii-eos72165s7

16. Fesoterodine Fumarate [usan:jan]

17. (e)-but-2-enedioic Acid,[2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate

18. Toviaz (tn)

19. (r)-fesoterodinefumarate

20. Mls003915638

21. Schembl814971

22. Fesoterodine Fumarate - Toviaz

23. Schembl1993632

24. Chembl1201765

25. Dtxsid00904655

26. Bcpp000231

27. Fesoterodine Fumarate (jan/usan)

28. Fesoterodine Fumarate [mi]

29. Hms3884d11

30. Fesoterodine Fumarate [jan]

31. Amy37611

32. Hy-a0030

33. Bdbm50248002

34. Fesoterodine Fumarate [vandf]

35. Mfcd12756004

36. S2240

37. Fesoterodine Fumarate [mart.]

38. Akos005146248

39. Akos015855886

40. Fesoterodine Fumarate [who-dd]

41. Ac-3486

42. Bcp9000682

43. Ccg-269901

44. Cs-0822

45. Ks-1298

46. 2-((1r)-3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl Isobutyrate

47. Fesoterodine Fumarate [ema Epar]

48. 2-((1r)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl 2-methylpropanoate Hydrogen (2e)-butenedioate (salt)

49. Propanoic Acid, 2-methyl-, 2-((1r)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl Ester, (2e)-2-butenedioate (1:1) (salt)

50. Smr002544691

51. Fesoterodine Fumarate [orange Book]

52. Pf-00695838

53. D08923

54. 930f038

55. A846296

56. Q27277274

57. 2-((1r)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl 2-methylpropanoate Hydrogen(2e)-butenedioate (salt)

58. Fesoterodinefumarate;(r)-fesoterodine Fumarate;2-methylpropanoic Acid 2-[(1r)-3-[bis(1-methylethyl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl Ester (2e)-2-butenedioate

59. Propanoic Acid,2-methyl ,2-((1r)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl Ester,(2e)-2-butenedioate (1:1)(salt)

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₄₁NO₇
Molecular Weight	527.6 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	13
Exact Mass	527.28830265 g/mol
Monoisotopic Mass	527.28830265 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	610
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Toviaz
PubMed Health	Fesoterodine (By mouth)
Drug Classes	Urinary Antispasmodic
Drug Label	Toviaz contains fesoterodine fumarate and is an extended-release tablet. Fesoterodine is rapidly de-esterified to its active metabolite (R)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol, or 5-hydroxymethyl tolterodine, which is a musca...
Active Ingredient	Fesoterodine fumarate
Dosage Form	Tablet, extended release
Route	Oral
Strength	8mg; 4mg
Market Status	Prescription
Company	Pfizer

2 of 2
Drug Name	Toviaz
PubMed Health	Fesoterodine (By mouth)
Drug Classes	Urinary Antispasmodic
Drug Label	Toviaz contains fesoterodine fumarate and is an extended-release tablet. Fesoterodine is rapidly de-esterified to its active metabolite (R)-2-(3-diisopropylamino-1-phenylpropyl)-4-hydroxymethyl-phenol, or 5-hydroxymethyl tolterodine, which is a musca...
Active Ingredient	Fesoterodine fumarate
Dosage Form	Tablet, extended release
Route	Oral
Strength	8mg; 4mg
Market Status	Prescription
Company	Pfizer

4.2 Drug Indication

Treatment of the symptoms (increased urinary frequency and / or urgency and / or urgency incontinence) that may occur in patients with overactive-bladder syndrome.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Muscarinic Antagonists

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

Urological Agents

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)

5.2 ATC Code

G04BD11

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