Terodiline

Terodiline
Clinical data
ATC code	G04BD05 (WHO) ;
Identifiers
	IUPAC name N-tert-butyl-4,4-di(phenyl)butan-2-amine;
CAS Number	15793-40-5 ; 7082-21-5 (hydrochloride);
PubChem CID	23480;
ChemSpider	21952 ;
UNII	70KG06964W;
ChEMBL	ChEMBL363295 ;
CompTox Dashboard (EPA)	DTXSID60860001 ;
Chemical and physical data
Formula	C20H27N
Molar mass	281.443 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1ccccc1C(c2ccccc2)CC(NC(C)(C)C)C;
	InChI InChI=1S/C20H27N/c1-16(21-20(2,3)4)15-19(17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14,16,19,21H,15H2,1-4H3 ; Key:UISARWKNNNHPGI-UHFFFAOYSA-N ;

Terodiline is a drug used in urology as an antispasmodic.

It relaxes the smooth muscle and used to reduce bladder tone in treatment of urinary frequency and incontinence. Muscle relaxation caused by terodiline, is probably due to its anticholinergic and calcium antagonist activity.

However, it also blocks IKr (Kv11.1) channels (see hERG gene) so can pose a risk for torsades de pointes. This cardiotoxicity is concentration dependent.^[1]

References[]

^ Thomas SH, Higham PD, Hartigan-Go K, Kamali F, Wood P, Campbell RW, Ford GA (1995). "Concentration dependent cardiotoxicity of terodiline in patients treated for urinary incontinence". Br Heart J. 74 (1): 53–6. doi:10.1136/hrt.74.1.53. PMC 483946. PMID 7662454.

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[1] Thomas SH, Higham PD, Hartigan-Go K, Kamali F, Wood P, Campbell RW, Ford GA (1995). "Concentration dependent cardiotoxicity of terodiline in patients treated for urinary incontinence". Br Heart J. 74 (1): 53–6. doi:10.1136/hrt.74.1.53. PMC 483946. PMID 7662454.

[1]

v t Urologicals, including antispasmodics (G04B)
Acidifiers	Ammonium chloride Calcium chloride
Urinary antispasmodics (primarily antimuscarinics)	Darifenacin Desfesoterodine Emepronium Fesoterodine Flavoxate Imidafenacin Meladrazine Mirabegron Oxybutynin Propiverine Solifenacin Terodiline Tolterodine Trospium chloride Vibegron
Other urologicals	Urea analogues: Acetohydroxamic acid Salicylhydroxamic acid Other: Collagen Dapoxetine Dimethyl sulfoxide Magnesium hydroxide Pentosan polysulfate Phenazopyridine Phenyl salicylate Succinimide Tiopronin

Clinical data

ATC code	G04BD05 (WHO)
Identifiers
IUPAC name N-tert-butyl-4,4-di(phenyl)butan-2-amine
CAS Number	15793-40-5^Y 7082-21-5 (hydrochloride)
PubChem CID	23480
ChemSpider	21952^Y
UNII	70KG06964W
ChEMBL	ChEMBL363295^Y
CompTox Dashboard (EPA)	DTXSID60860001
Chemical and physical data
Formula	C₂₀H₂₇N
Molar mass	281.443 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c1ccccc1C(c2ccccc2)CC(NC(C)(C)C)C
InChI InChI=1S/C20H27N/c1-16(21-20(2,3)4)15-19(17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14,16,19,21H,15H2,1-4H3^Y Key:UISARWKNNNHPGI-UHFFFAOYSA-N^Y