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F8304

Sigma-Aldrich

Flavoxate hydrochloride

≥98% (HPLC), solid

Synonym(s):

3-Methyl-4-oxo-2-phenyl-4H-1-benzopyran-8-carboxylic acid 2-(1-piperidinyl)ethyl ester hydrochloride, DW-61, Rec-7-0040

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About This Item

Empirical Formula (Hill Notation):
C24H25NO4 · HCl
CAS Number:
3717-88-2
Molecular Weight:
427.92
EC Number:
223-066-4
MDL number:
MFCD00072099
UNSPSC Code:
12352200
PubChem Substance ID:
24724484
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

color

white

solubility

H2O: ~6.6 mg/mL

originator

Johnson & Johnson

SMILES string

Cl[H].CC1=C(Oc2c(cccc2C1=O)C(=O)OCCN3CCCCC3)c4ccccc4

InChI

1S/C24H25NO4.ClH/c1-17-21(26)19-11-8-12-20(23(19)29-22(17)18-9-4-2-5-10-18)24(27)28-16-15-25-13-6-3-7-14-25;/h2,4-5,8-12H,3,6-7,13-16H2,1H3;1H

InChI key

XOEVKNFZUQEERE-UHFFFAOYSA-N

Gene Information

human ... PDE4A(5141) , PDE4B(5142) , PDE4C(5143) , PDE4D(5144) , PDE7A(5150) , PDE7B(27115) , PDE8A(5151) , PDE8B(8622)

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Biochem/physiol Actions

Flavoxate, a flavone derivative[1] and a tertiary-amine antimuscarinic[2] possess antispasmodic properties.[2] It is a strong smooth muscle relaxant[1] that selectively acts on the pelvic region[3] and is used in the symptomatic treatment of overactive bladder (OAB)[1] and incontinence.[2] Post-absorption in the gastrointestinal tract, flavoxate is localized in bladder, liver, and kidney tissues.[1] It mediates the inhibition of phosphodiesterase (PDE) in the urinary bladder.[1] Use of flavoxate aids pain relief in inflammatory disorders of the urinary tract.[3]
L-type Ca2+ (Cav1.2) channel inhibitor

Features and Benefits

This compound is featured on the Calcium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H335

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
016K4700

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Erythema and hand edema due to flavoxate.
M C Moreno Escobosa et al.
Journal of investigational allergology & clinical immunology, 22(5), 390-391 (2012-10-30)
Nury Pérez-Hernández et al.
Journal of pharmaceutical and biomedical analysis, 41(2), 603-609 (2006-01-24)
1H and 13C NMR chemical shift assignments for the urinary tract antispasmodic flavoxate (1) and flavoxate hydrochloride (2) were obtained from one- and two-dimensional measurements. A Monte Carlo random search using molecular mechanics, followed by geometry optimization of each minimum
Toshihisa Tomoda et al.
British journal of pharmacology, 146(1), 25-32 (2005-06-21)
The effects of flavoxate hydrochloride (Bladderon, piperidinoethyl-3-methylflavone-8-carboxylate; hereafter referred as flavoxate) on voltage-dependent nifedipine-sensitive inward Ba(2+) currents in human detrusor myocytes were investigated using a conventional whole-cell patch-clamp. Tension measurement was also performed to study the effects of flavoxate on
Johannes Kornhuber et al.
Journal of cellular physiology, 224(1), 152-164 (2010-03-20)
Lysosomes accumulate many drugs several fold higher compared to their extracellular concentration. This mechanism is believed to be responsible for many pharmacological effects. So far, uptake and release kinetics are largely unknown and interactions between concomitantly administered drugs often provoke
Rachna Sehgal et al.
Journal of tropical pediatrics, 53(4), 259-263 (2007-05-15)
A prospective study was done in pediatric out-patient department of a tertiary care hospital to evaluate the role of urodynamics in the management of primary enuresis in the 5-14-year-old children and to compare the effectiveness of multidimensional behavioral therapy with
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