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Fesoterodine Maleate

Fesoterodine Maleate

Synopsis, Chemistry

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Also known as: 286930-02-7, (r) fesoterodine, Fesoterodine (inn), [2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate, Fesoterodine [inn], (r)-2-(3-(diisopropylamino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl isobutyrate

Molecular Formula

C₂₆H₃₇NO₃

Molecular Weight

411.6 g/mol

InChI Key

DCCSDBARQIPTGU-HSZRJFAPSA-N

FDA UNII

621G617227

Fesoterodine is 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 Maleate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate

2.1.2 InChI

InChI=1S/C26H37NO3/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/h7-13,16,18-20,23,28H,14-15,17H2,1-6H3/t23-/m1/s1

2.1.3 InChI Key

DCCSDBARQIPTGU-HSZRJFAPSA-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

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

2.2 Other Identifiers

2.2.1 UNII

621G617227

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fesoterodine Fumarate

2. Toviaz

2.3.2 Depositor-Supplied Synonyms

1. 286930-02-7

2. (r) Fesoterodine

3. Fesoterodine (inn)

4. [2-[(1r)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate

5. Fesoterodine [inn]

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

7. 621g617227

8. Propanoic Acid, 2-methyl-, 2-((1r)-3-(bis(1-methylethyl)amino)-1-phenylpropyl)-4-(hydroxymethyl)phenyl Ester

9. Fesoterodine [inn:ban]

10. [2-[(1r)-3-(di(propan-2-yl)amino)-1-phenylpropyl]-4-(hydroxymethyl)phenyl] 2-methylpropanoate

11. Unii-621g617227

12. Feso

13. Starbld0000599

14. Fesoterodine [mi]

15. Fesoterodine [vandf]

16. Fesoterodine [mart.]

17. Fesoterodine [who-dd]

18. Schembl121127

19. Gtpl7473

20. Chembl1201764

21. Dtxsid80182853

22. Chebi:135920

23. Cs-m2392

24. Zinc1552908

25. Akos015841710

26. Db06702

27. Ncgc00346540-01

28. Ncgc00346540-02

29. Ncgc00346540-03

30. Ac-32493

31. Hy-70053

32. D07226

33. Ab01274866-01

34. Ab01274866_02

35. 930f027

36. Q4482372

37. 2-[(1r)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenyl 2-methylpropanoate

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₇NO₃
Molecular Weight	411.6 g/mol
XLogP3	5.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	11
Exact Mass	411.27734404 g/mol
Monoisotopic Mass	411.27734404 g/mol
Topological Polar Surface Area	49.8 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	491
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 1
Drug Name	TOVIAZ
Active Ingredient	FESOTERODINE FUMARATE
Company	PFIZER (Application Number: N022030. Patents: 6858650, 7384980, 7807715, 7855230, 7985772, 8088398, 8338478, 8501723)

4.2 Drug Indication

For the treatment of overactive bladder (with symptoms of urinary frequency, urgency, or urge incontinence).

FDA Label

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 Pharmacology

In-vivo the fesoteridine prodrug is broken down into its active metabolite, 5-hydroxymethyl tolterodine (5-HMT), by plasma esterases. The 5-hydroxymethyl metabolite, which exhibits an antimuscarinic activity. Both urinary bladder contraction and salivation are mediated via cholinergic muscarinic receptors. Therefore, acting as a competitive muscarinic receptor antagonist, fesoterodine ultimately acts to decrease the detrusor pressure by its muscarinic antagonism, thereby decreasing bladder contraction and consequently, the urge to urinate.

5.2 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.)

5.3 ATC Code

G04BD11

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

G - Genito urinary system and sex hormones

G04 - Urologicals

G04B - Urologicals

G04BD - Drugs for urinary frequency and incontinence

G04BD11 - Fesoterodine

5.4 Absorption, Distribution and Excretion

Absorption

Tmax (5-HMT): 5 hours post-adminitration of fesoterodine. AUC (0,)= 49.5 ngh/ ml Bioavailability, 5-HMT = 52%

Route of Elimination

Renal: 70% of fesoterodine was recovered in urine as 5-HMT; 35% carboxy metabolite; 18% carboxy-N-desisopropylmetabolite, and 1% N-desisopropyl metabolite Fecal: 7% Hepatic: fesoterodine elimination via CYP2D6 and CYP3A4

Volume of Distribution

IV, 5-HMT: 169 L

Clearance

5-HMT, healthy subjects: 14.4 L/h 5-HMT is also secreted into the nephron.

5.5 Metabolism/Metabolites

Metabolized by ubiquitous, nonspecific esterases to transform fesoterodine into 5-HMT Extensive metabolism via CYP2D6 and CYP3A4 into inactive metabolites

5.6 Biological Half-Life

7-8 hours for the active metabolite 5-hydroxymethyl tolterodine

5.7 Mechanism of Action

Fesoterodine, once converted to its active metabolite, 5-hydroxymethyltolterodine, acts as a competitive antagonists at muscarinic receptors. This results in the inhibition of bladder contraction, decrease in detrusor pressure, and an incomplete emptying of the bladder.