Tolterodine

HCID 443879

Basic information

CAS
124937-51-5
Standard SMILES
Cc1ccc(O)c([C@H](CCN(C(C)C)C(C)C)c2ccccc2)c1
InChIKey
OOGJQPCLVADCPB-HXUWFJFHSA-N
Molecular formula
C22H31NO
Average molar mass
325.5 g/mol
Monoisotopic mass
325.24056461

Overview

Tolterodine is a tertiary amine. It has a role as a muscarinic antagonist, a muscle relaxant and an antispasmodic drug. It is functionally related to a p-cresol.

Names & identifiers

Preferred name
Tolterodine
IUPAC
2-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
English name
Tolterodine
Molecular formula
C22H31NO
Molecular weight
325.49

Names & synonyms

tolterodine124937-51-5(+)-TolterodineTolterodinumKabi 2234TolterodinaKabi-22342-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenolWHE7A56U7K(+)-(R)-2-(alpha-(2-(Diisopropylamino)ethyl)benzyl)-p-cresolCHEBI:96222-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
Show more names
DETROLTOLTERODINE L-TARTRATEPNU-20058EDETRUSITOLPNU 200583Tolterodine-d6TolterodineBaseTolterodine-d14
Detrusitol xlEfflosomyl xlMariosea xlPreblacon xlSantizor xl2-((1R)-3-(bis(propan-2-yl)amino)-1-phenylpropyl)-4-methylphenol2-((1R)-3-(di(propan-2-yl)amino)-1-phenylpropyl)-4-methylphenol2-[(1R)-3-(di(propan-2-yl)amino)-1-phenylpropyl]-4-methylphenol

Database identifiers

CAS
124937-51-5
PubChem CID
443879
DTXSID
DTXSID3023687
ChEMBL
CHEMBL1382
ChEBI
CHEBI:9622
UNII
WHE7A56U7K
EC Number
805-304-4
Nikkaji
J561.859B

Properties

Computed structural properties

XLogP
5.6
Topological polar surface area
23.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
7
Heavy atoms
24

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP5.6
Solubility5.34e-03 g/L
Human DrugsBreast Feeding; Lactation; Milk, Human; Muscarinic Antagonists; Parasympatholytics
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

Physicochemical properties

alpha
25 · D25 +72° (c = 1.0 in CH2Cl2)
Boiling point
442.2 · 442.2±45.0 °C(Predicted)
Density
1.003 · 1.003±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C Freezer
solubility
20 mg/mL · DMSO: ≥20mg/mL
pka
9.8 · pKa 9.8 (Uncertain)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P264, P270, P280, P301+P316, P318, P321, P330, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Hepatotoxicity · 1 item

In multiple randomized controlled trials of tolterodine in patients with overactive bladder syndrome, serum aminotransferase and alkaline phosphatase elevations were not common, arising in less than 1% of treated subjects and in a similar proportion of placebo recipients. In these clinical trials there were no reports of clinically apparent liver injury or jaundice. Since the approval of tolterodine in 1998 and its widescale use (with more than 1 million prescriptions filled yearly in the United States), there has been only one published case report of liver injury with symptoms and jaundice attributed to its use (Case 1). Thus, acute symptomatic liver injury due to tolterodine must be very rare, if it occurs at all.

Adverse EffectsAdverse effects of tolterodine are significantly lower than that of other antimuscarinic drugs indicated for the same use.
Toxicity Summary · 1 item

To prevent toxicity, patients with hepatic impairment should be given a lower dose since the drug's elimination is lower than that of healthy patients. Additionally, tolterodine demonstrated higher concentrations in patients with renal impairment. Therefore, recommendations include a decrease in drug dosage in both patients with hepatic or renal impairment.

Drug Induced Liver Injury · 5 items

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

tolterodine

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

wgk
3
risk_code
63-51/53
Signal word
Danger
Symbol(GHS)
GHS06,GHS08
hazard_code
Xn,N
safety_code
22-36/37-57

Chemistry & industry

Pharmacology

ATC Code · 3 items

G04BD07

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Protein BindingApproximately 96.3%.
Pharmacodynamics · 1 item

Tolterodine is a competitive muscarinic receptor antagonist. Both urinary bladder contraction and salivation are mediated via cholinergic muscarinic receptors. After oral administration, tolterodine is metabolized in the liver, resulting in the formation of the 5-hydroxymethyl derivative, a major pharmacologically active metabolite. The 5-hydroxymethyl metabolite, which exhibits an antimuscarinic activity similar to that of tolterodine, contributes significantly to the therapeutic effect. Both tolterodine and the 5-hydroxymethyl metabolite exhibit a high specificity for muscarinic receptors, since both show negligible activity or affinity for other neurotransmitter receptors and other potential cellular targets, such as calcium channels. Tolterodine has a pronounced effect on bladder function. The main effects of tolterodine are an increase in residual urine, reflecting an incomplete emptying of the bladder, and a decrease in detrusor pressure, consistent with an antimuscarinic action on the lower urinary tract.

Mechanism of Action · 1 item

Both tolterodine and its active metabolite, 5-hydroxymethyltolterodine, act as competitive antagonists at muscarinic receptors. This antagonism results in inhibition of bladder contraction, decrease in detrusor pressure, and an incomplete emptying of the bladder.

Biological Half-Life1.9-3.7 hours
Metabolism/MetabolitesTolterodine has known human metabolites that include 5-Hydroxymethyl tolterodine and N-Dealkylated tolterodine.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >50
Applications · 2 items

UsesA muscarinic receptor antagonist. Used in the treatment of urinary incontinence.

General DescriptionTolterodine (Detrol), 2-[3-[bis(1-methylethyl)amino]-1-phenyl-propyl]-4-methyl-phenol, is an antimuscarinicagent that acts on M2 and M3 muscarinic subtypereceptors. By competitively blocking of the muscarinicreceptors results in a reduction of the smooth muscle tone,allowing for greater volume of urine to be stored in the bladder.This results in less urinary incontinence, urgency, andfrequency.

Suppliers83 total

北京华美互利生物化工010-56205725 · [email protected]
陕西科贝莱药物研发有限公司13119135307 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

Additional notes

DefinitionChEBI: Tolterodine is a tertiary amine. It has a role as a muscarinic antagonist, a muscle relaxant and an antispasmodic drug. It is functionally related to a p-cresol.

Related reactions

26 records

Compound notes

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