SOLIFENACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H26N2O2
Molecular Weight	362.4647
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=FBOUYBDGKBSUES-VXKWHMMOSA-N

InChI=1S/C23H26N2O2/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/h1-9,18,21-22H,10-16H2/t21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H26N2O2
Molecular Weight	362.4647
Charge	0
Count

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/vesicare-drug.htm https://www.drugs.com/mtm/solifenacin.html http://www.wikidoc.org/index.php/Solifenacin

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 158 Target ID: CHEMBL245 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/15190387 \| https://www.ncbi.nlm.nih.gov/pubmed/16465186 \| https://www.ncbi.nlm.nih.gov/pubmed/19446545 \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2760	10.0 nM [Ki]
Muscarinic acetylcholine receptor M2 120 Target ID: CHEMBL211 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/16465186 \| https://www.ncbi.nlm.nih.gov/pubmed/19446545 \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2760	125.0 nM [Ki]
Muscarinic acetylcholine receptor M1 168 Target ID: CHEMBL216 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/16465186 \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2760	25.0 nM [Ki]
Muscarinic acetylcholine receptor M4 85 Target ID: CHEMBL1821 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2760	7.73 null [pKi]
Muscarinic acetylcholine receptor M5 61 Target ID: CHEMBL2035 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/19029429 \| http://www.drugbank.ca/drugs/DB01591	Antagonist 2760	7.46 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021518s016lbl.pdf	Primary		Approved 8360	VESICARE Approved Use VESIcare is a muscarinic antagonist indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency. VESIcare is a muscarinic antagonist indicated for the treatment of overactive bladder with symptoms of urge urinary incontinence, urgency, and urinary frequency (1) Launch Date 1.10082235E12

C_max

Value	Dose	Co-administered	Analyte	Population
14.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15206986	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		SOLIFENACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
820 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15206986	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		SOLIFENACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
50.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15206986	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		SOLIFENACIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf			SOLIFENACIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15317830 Page: p.1028	healthy, 19-40 n = 6 Health Status: healthy Age Group: 19-40 Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/15317830 Page: p.1028	Sources: https://pubmed.ncbi.nlm.nih.gov/15317830 Page: p.1028
30 mg 1 times / day multiple, oral Highest studied dose Dose: 30 mg, 1 times / day Route: oral Route: multiple Dose: 30 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15317830 Page: p.1029	healthy, 20-35 n = 8 Health Status: healthy Age Group: 20-35 Sex: M Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/15317830 Page: p.1029	Sources: https://pubmed.ncbi.nlm.nih.gov/15317830 Page: p.1029
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.4	unhealthy n = 1233 Health Status: unhealthy Condition: Overactive bladder Population Size: 1233 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.4	Disc. AE: Dry mouth... AEs leading to discontinuation/dose reduction: Dry mouth (1.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.4
10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Overactive bladder Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.1	Disc. AE: Angioedema, Anaphylactic reaction... AEs leading to discontinuation/dose reduction: Angioedema Anaphylactic reaction (rare) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.1

AEs

AE	Significance	Dose	Population
Dry mouth	1.5% Disc. AE	10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.4	unhealthy n = 1233 Health Status: unhealthy Condition: Overactive bladder Population Size: 1233 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.4
Angioedema	Disc. AE	10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Overactive bladder Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.1
Anaphylactic reaction	rare Disc. AE	10 mg 1 times / day multiple, oral Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Overactive bladder Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021518s012lbl.pdf Page: p.1

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1709 inhibitor 1579	inhibitor 1752	substrate 1193 inhibitor 1837	inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 72 CYP2C19 1463	CYP2C19 985 CYP3A5 391 CYP2C8 688 CYP1A1 348 P-gp 1527

Drug as perpetrator

Target	Modality	Activity
CYP1A 121	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0	not significant
CYP2C9 1803	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0	not significant
CYP2D6 1875	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0	not significant
CYP3A4 1909	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0	not significant
CYP2C19 1537	inhibitor 3240 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=51 Page: 51.0	yes [Inhibition 1.04 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP3A4 1709	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=22 Page: 22,52	major	yes (co-administration study) Comment: Label: coadministration with ketoconazole increased the mean Cmax and AUC of solifenacin by 1.5 and 2.7 fold, respectively; Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=22 Page: 22,52
CYP1A1 348	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=27 Page: 27.0	minor
CYP2C19 985	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=22 Page: 22,27	minor
CYP2C8 688	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=27 Page: 27.0	minor
CYP2D6 1193	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=27 Page: 27.0	minor
CYP3A5 391	substrate 3326 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_biopharmr.pdf#page=27 Page: 27.0	minor
P-gp 1527	substrate 3326 Sources: https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1111/j.1365-2125.2011.03961.x	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1632	inhibitor 1613 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2004/21-518_VESIcare_pharmr.pdf#page=35 Page: 35.0

Sourcing

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
AK Scientific, Inc. (AKSCI)	X4689	http://www.aksci.com/item_detail.php?cat=X4689
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
Achemtek	0102-022129	http://www.achemtek.com/242478-37-1
Acorn PharmaTech	ACN-037989	http://www.acornpharmatech.com/
Adooq BioScience	A16947	https://www.adooq.com/solifenacin.html
Alfa Chemistry	242478-37-1	https://www.alfa-chemistry.com/cas_242478-37-1.htm
Alfa Chemistry	ACM180272144	https://www.alfa-chemistry.com/solifenacin-cas-180272-14-4-item-285040.htm
Alichem	189007421	http://www.alichem.com/en/products/180272-14-4.html
Ambinter	Amb20241303	http://www.ambinter.com/reference/20241303
Aurora Fine Chemicals LLC	K16.645.638	http://online.aurorafinechemicals.com/info?ID=K16.645.638
AvaChem Scientific	2557B	http://www.avachem.com/productSearch.asp?2557B
BLD Pharm	BD764111	http://www.bldpharm.com/products/180272-14-4.html
BLD Pharm	BD151698	http://www.bldpharm.com/products/242478-37-1.html
CSNpharm	CSN21835	https://www.csnpharm.com/products/solifenacin.html
Capot Chemical	23264	http://www.capotchem.com/en/23264.htm
Capot Chemical	PubChem23264	http://www.capotchem.com/en/23264.htm
Chem Scene	CS-8096	http://www.chemscene.com/242478-37-1.html
ChemMol	49419563	http://www.chemmol.com/chemmol/49419563.html
Chemenu	CM126714	http://www.chemenu.com/products/CM126714
Chemspace	CSSB00138412639	https://chem-space.com/CSSB00138412639
Chemspace	CSSS00020667699	https://chem-space.com/CSSS00020667699
Chemspace	CSSS00102523311	https://chem-space.com/CSSS00102523311
Chemspace	CSSS00116206880	https://chem-space.com/CSSS00116206880
DC Chemicals	DC9214	http://www.dcchemicals.com/product_show-Solifenacin.html
Debye Scientific	DB-001095	http://www.debyesci.com/DB-001095.html
Excenen	EX-A4180	https://www.excenen.com/searchresultlist.php?id=EX-A4180
Finetech	FT-0698075	http://www.finetechnology-ind.com/prod/detail/pub/242478-37-1.html
Finetech	FT-0778252	https://www.finetechnology-ind.com/prod/detail/pub/180272-14-4.html
Hairui	HR112258	http://www.hairuichem.com/en/product/242478-37-1.html
Lab Network	LN01345685	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01345685
MedChem Express	HY-A0034	https://www.medchemexpress.com/Solifenacin.html
MolPort	MolPort-023-220-809	https://www.molport.com/shop/molecule-link/MolPort-023-220-809
MolPort	MolPort-046-871-055	https://www.molport.com/shop/molecule-link/MolPort-046-871-055
Molcore	MC543715	https://www.molcore.com/product/242478-37-1
MuseChem	I012990	https://www.musechem.com/product/I012990.html
OChem	25997	http://www.ocheminc.com/index.php?act=psearch&pid=478S382
Smolecule	S006668	http://www.smolecule.com/products/s006668
Smolecule	S598639	https://www.smolecule.com/products/s598639
Smolecule	S635527	https://www.smolecule.com/products/s635527
Specs	AR-270/43507775	http://www.specs.net/enter.php?specsid=AR-270/43507775
Synblock Inc	SB17427	http://www.synblock.com/product/242478-37-1.html
THE BioTek	bt-255435	https://www.thebiotek.com/product/inhibitors/bt-255435
THE BioTek	bt-339594	https://www.thebiotek.com/product/others/bt-339594
Vitas-M Laboratory	STL484275	http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL484275&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
Yuhao Chemical	YH48847	http://www.chemyuhao.com/242478-37-1.html
eNovation Chemicals	D591419	https://www.enovationchem.com/ProductDetails.asp?ProductID=D591419
eNovation Chemicals	D775303	https://www.enovationchem.com/ProductDetails.asp?ProductID=D775303
eNovation Chemicals	D962251	https://www.enovationchem.com/ProductDetails.asp?ProductID=D962251
iChemical	EBD2197604	http://www.ichemical.com/products/242478-37-1.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Gateways to clinical trials.	2003 Jul-Aug	12949633
Gateways to clinical trials.	2003 Jun	12851663
Food does not affect the pharmacokinetics of solifenacin, a new muscarinic receptor antagonist: results of a randomized crossover trial.	2004 Jul	15206986
[Overactive bladder. New anticholinergic drug controls urinary urge].	2004 Jul 8	15526670
Gateways to clinical trials.	2004 May	15319808
Gateways to clinical trials.	2004 Nov	15632957
The emerging role of solifenacin in the treatment of overactive bladder.	2004 Oct	15461562
Overactive bladder in the elderly: a guide to pharmacological management.	2005	16363885
[Neurological aspect of the hyperactive urinary bladder syndrome].	2005	16117151
Solifenacin and darifenacin for overactive bladder.	2005 Aug	16055596
[Medical therapy of urinary incontinence].	2005 Jan	15609033
The Q-T interval and antimuscarinic drugs.	2005 Nov	16238912
Pharmacokinetic interaction of solifenacin with an oral contraceptive containing ethinyl estradiol and levonorgestrel in healthy women: a double-blind, placebo-controlled study.	2005 Sep	16291413
Gateways to clinical trials.	2006 Apr	16810345
The causes and consequences of overactive bladder.	2006 Apr	16620184
Patient-reported outcomes in overactive bladder: importance for determining clinical effectiveness of treatment.	2006 Aug	16908335
Open-label study of the safety and pharmacokinetics of solifenacin in subjects with hepatic impairment.	2006 Dec	17170513
New drugs 06, part I.	2006 Feb	16462265
Pharmacokinetic effect of ketoconazole on solifenacin in healthy volunteers.	2006 Jul	16867168
Gateways to clinical trials.	2006 Jul-Aug	16894408
Efficacy and tolerability of solifenacin in elderly subjects with overactive bladder syndrome: a pooled analysis.	2006 Mar	16730617
Gateways to clinical trials.	2006 May	16801985
Treatment of the overactive bladder syndrome with muscarinic receptor antagonists: a matter of metabolites?	2006 Nov	17021853
Reductions in overactive bladder-related incontinence from pooled analysis of phase III trials evaluating treatment with solifenacin.	2006 Sep	16625311
Effect of antimuscarinic drugs used for overactive bladder on learning in a rat passive avoidance response test.	2007 Feb 28	17207478
Redefining response in overactive bladder syndrome.	2007 Jan	17227496
Solifenacin for overactive bladder with incontinence: symptom bother and health-related quality of life outcomes.	2007 Mar	17341526
An unusual cause of postoperative detrusor overactivity.	2007 Oct	17333438

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 Created by `admin` on `Wed Jul 05 23:52:46 UTC 2023` Edited by `admin` on `Wed Jul 05 23:52:46 UTC 2023`
Record UNII	A8910SQJ1U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SOLIFENACIN

Official Name

English

solifenacin [INN]

Common Name

English

NSC-759144

Code

English

SOLIFENACIN [MI]

Common Name

English

Solifenacin [WHO-DD]

Common Name

English

SOLIFENACIN [VANDF]

Common Name

English

Classification Tree Code System Code

WHO-ATC

G04CA53