Tolterodine

HCID 178797231CAS 88407-28-7

Grundinformationen

Standard-SMILES
Cc1ccc(O)c([C@H](CCN(C(C)C)C(C)C)c2ccccc2)c1
InChIKey
OOGJQPCLVADCPB-HXUWFJFHSA-N
Summenformel
C22H31NO
Durchschnittliche Molmasse
325,5 g/mol

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Tolterodine
IUPAC
2-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
Englischer Name
Tolterodine Impurity 1
Summenformel
C22H31NO
Molmasse
325.48764

Namen und Synonyme

tolterodine124937-51-5(+)-TolterodineTolterodinumKabi 2234TolterodinaKabi-2234WHE7A56U7K2-[(1R)-3-[di(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol(+)-(R)-2-(alpha-(2-(Diisopropylamino)ethyl)benzyl)-p-cresolCHEBI:96222-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-methylphenol
Weitere Namen anzeigen
Tolterodine Impurity 1
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

Datenbank-Bezeichner

CAS
88407-28-7
ChEMBL
CHEMBL1382
ChEBI
CHEBI:9622
UNII
WHE7A56U7K
EC Number
805-304-4
Nikkaji
J561.859B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,6
Polarare Oberfläche (TPSA)
23,5 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
7
Schwere Atome
24

Experimentelle und physikochemische Eigenschaften

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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 Eintrag

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 Einträge

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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

G04BD07

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Protein BindingApproximately 96.3%.
Pharmacodynamics · 1 Eintrag

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 Eintrag

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.

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >50

Anbieter7 Anbieter

Sinco Pharmachem (ShenZhen) R&D Co., Ltd.+86-18603013401 · [email protected]
杭州云易国科生物科技有限公司18457506494 · [email protected]
深圳菲斯生物科技有限公司0755-83725350 13380397412 · [email protected]
深圳市祥根生物医药有限公司0755-28967200 13631290199 · [email protected]
湖北摩科化学有限公司18627753421; 18627756402 · [email protected]

Zugehörige Reaktionen

0

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

Verknüpfte Notizen

Wird geladen…