SOLIFENACIN TARTRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H26N2O2.C4H6O6
Molecular Weight	512.5516
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.O=C(O[C@H]1CN2CCC1CC2)N3CCC4=C(C=CC=C4)[C@@H]3C5=CC=CC=C5

InChI

InChIKey=KTNRTEKPBRTUKA-DWERDEDHSA-N

InChI=1S/C23H26N2O2.C4H6O6/c26-23(27-21-16-24-13-10-18(21)11-14-24)25-15-12-17-6-4-5-9-20(17)22(25)19-7-2-1-3-8-19;5-1(3(7)8)2(6)4(9)10/h1-9,18,21-22H,10-16H2;1-2,5-6H,(H,7,8)(H,9,10)/t21-,22-;1-,2-/m01/s1

HIDE SMILES / InChI

Molecular Formula	C4H6O6
Molecular Weight	150.0868
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C23H26N2O2
Molecular Weight	362.4647
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Solifenacin is a competitive muscarinic acetylcholine receptor antagonist. The binding of acetylcholine to these receptors, particularly the M3 receptor subtype, plays a critical role in the contraction of smooth muscle. By preventing the binding of acetylcholine to these receptors, solifenacin reduces smooth muscle tone in the bladder, allowing the bladder to retain larger volumes of urine. It is FDA approved for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency. Common adverse reactions include constipation, Xerostomia. Inhibitors of CYP3A4 may increase the concentration of Solifenacin. Vice versa, CYP3A4 Inducers decrease concentration.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Muscarinic acetylcholine receptor M3 160	Antagonist 2,849	10.0 nM [Ki]
Muscarinic acetylcholine receptor M2 121	Antagonist 2,849	125.0 nM [Ki]
Muscarinic acetylcholine receptor M1 168	Antagonist 2,849	25.0 nM [Ki]
Muscarinic acetylcholine receptor M4 87	Antagonist 2,849	7.73 null [pKi]
Muscarinic acetylcholine receptor M5 63	Antagonist 2,849	7.46 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency 4	Primary		Approved 8,583	VESICARE

C_max

Value	Dose	Co-administered	Analyte	Population
14.1 ng/mL	10 mg single, oral		SOLIFENACIN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
820 ng × h/mL	10 mg single, oral		SOLIFENACIN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
50.8 h	10 mg single, oral		SOLIFENACIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
2%			SOLIFENACIN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
100 mg single, oral Highest studied dose	healthy, 19-40
30 mg 1 times / day multiple, oral Highest studied dose	healthy, 20-35
10 mg 1 times / day multiple, oral Recommended	unhealthy	Disc. AE: Angioedema, Anaphylactic reaction...
10 mg 1 times / day multiple, oral Recommended	unhealthy	Disc. AE: Dry mouth...

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AEs

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AE	Significance	Dose	Population
Angioedema	Disc. AE	10 mg 1 times / day multiple, oral Recommended	unhealthy
Anaphylactic reaction	rare Disc. AE	10 mg 1 times / day multiple, oral Recommended	unhealthy
Dry mouth	1.5% Disc. AE	10 mg 1 times / day multiple, oral Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inhibitor 2,252	inhibitor 2,438	substrate 1,388 inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 70 CYP2C19 2,057	CYP2C19 1,119 CYP3A5 446 CYP2C8 810 CYP1A1 389 P-gp 2,052

Drug as perpetrator

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Target	Modality	Activity
CYP1A 122	inhibitor 4,027	not significant
CYP2C9 2,497	inhibitor 4,027	not significant
CYP2D6 2,546	inhibitor 4,027	not significant
CYP3A4 2,633	inhibitor 4,027	not significant
CYP2C19 2,141	inhibitor 4,027	yes [Inhibition 1.04 uM]

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP3A4 1,946	substrate 4,014	major	yes (co-administration study)
CYP1A1 389	substrate 4,014	minor
CYP2C19 1,119	substrate 4,014	minor
CYP2C8 810	substrate 4,014	minor
CYP2D6 1,388	substrate 4,014	minor

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	DY543715	https://www.001chemical.com/chem/242478-37-1
AA Blocks	AA019FPZ	https://www.aablocks.com/goods/Goods/detail?id=AA019FPZ
Aaron Chemicals	AR019GHR	http://www.aaronchem.com/242478-37-1
Acadechem	ACDX-012562	http://acadechemical.com/product/87283
Achemo Scientific Limited	AC-63428	http://www.achemo.com/search/?Keyword= 242478-37-1

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PubMed

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Title	Date	PubMed
Effects of YM905, a novel muscarinic M3-receptor antagonist, on experimental models of bowel dysfunction in vivo.	2001 Jul	11488427
Gateways to clinical trials.	2003 Nov	14685303
Solifenacin demonstrates high absolute bioavailability in healthy men.	2004	15293866
Solifenacin: treatment of overactive bladder.	2004 Apr	15190387
Randomized, double-blind placebo- and tolterodine-controlled trial of the once-daily antimuscarinic agent solifenacin in patients with symptomatic overactive bladder.	2004 Feb	14764127

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Patents

Sample Use Guides

In Vivo Use Guide

5 mg tablet taken once daily, and if well tolerated may be increased to 10 mg once daily.

Route of Administration: Oral

In Vitro Use Guide

The inhibitory effect of solifenacin (dose range: 10^-10 - 10^-6 M) for bladder smooth muscle cells (pK(i)=8.12) was 3.6-fold more potent than that for salivary gland cells (pK(i)=7.57).

Substance Class	Chemical
Record UNII	CCM244AP8R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SOLIFENACIN TARTRATE

Common Name

English

SOLIFENACIN BITARTRATE

Preferred Name

English

Solifenacin tartrate [WHO-DD]

Common Name

English

SOLIFENACIN HYDROGEN TARTRATE

Common Name

English

2(1H)-ISOQUINOLINECARBOXYLIC ACID, 3,4-DIHYDRO-1-PHENYL-, (3R)-1-AZABICYCLO(2.2.2)OCT-3-YL ESTER, (1S)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1)

Systematic Name

English

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Code System

Code

Type

Description

FDA UNII

CCM244AP8R

PRIMARY

CAS

1035547-81-9

PRIMARY

PUBCHEM

154731572

PRIMARY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator