BENZTROPINE MESYLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H25NO.CH4O3S
Molecular Weight	403.535
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(O)(=O)=O.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(C3=CC=CC=C3)C4=CC=CC=C4

InChI

InChIKey=CPFJLLXFNPCTDW-BWSPSPBFSA-N

InChI=1S/C21H25NO.CH4O3S/c1-22-18-12-13-19(22)15-20(14-18)23-21(16-8-4-2-5-9-16)17-10-6-3-7-11-17;1-5(2,3)4/h2-11,18-21H,12-15H2,1H3;1H3,(H,2,3,4)/t18-,19+,20+;

HIDE SMILES / InChI

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H25NO
Molecular Weight	307.4293
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB00245

Benztropine is an anticholinergic used in the symptomatic treatment of all etiologic groups of parkinsonism and drug-induced extrapyramidal reactions (except tardive dyskinesia). Benztropine possesses both anticholinergic and antihistaminic effects, although only the former has been established as therapeutically significant in the management of parkinsonism. Benztropine's anticholinergic activity is about equal to that of atropine. Benztropine also inhibits dopamine reuptake via the dopamine transporter at nerve terminals. Benztropine is a selective M1 muscarinic acetylcholine receptor antagonist. It is able to discriminate between the M1 (cortical or neuronal) and the peripheral muscarinic subtypes (cardiac and glandular). Benztropine partially blocks cholinergic activity in the CNS, which is responsible for the symptoms of Parkinson's disease. It is also thought to increase the availability of dopamine, a brain chemical that is critical in the initiation and smooth control of voluntary muscle movement. Used as an adjunct in the therapy of all forms of parkinsonism and also for use in the control of extrapyramidal disorders due to neuroleptic drugs.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB00245	Antagonist 2778
Dopamine transporter 180 Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8558504	Inhibitor 8297		312.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinsonism 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	Primary		Approved 8429	COGENTIN Approved Use For use as an adjunct in the therapy of all forms of parkinsonism Useful also in the control of extrapyramidal disorders (except tardive dyskinesia) due to neuroleptic drugs (e.g., phenothiazines). Launch Date 1959
Extrapyramidal disorders 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	Secondary		Approved 8429	COGENTIN Approved Use For use as an adjunct in the therapy of all forms of parkinsonism Useful also in the control of extrapyramidal disorders (except tardive dyskinesia) due to neuroleptic drugs (e.g., phenothiazines). Launch Date 1959

C_max

Value	Dose	Co-administered	Analyte	Population
2.5 ng/mL OTHER GOV https://pdf.hres.ca/dpd_pm/00029138.PDF	1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered:		BENZTROPINE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
7 h OTHER GOV https://pdf.hres.ca/dpd_pm/00029138.PDF	1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered:		BENZTROPINE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
5% OTHER GOV https://pdf.hres.ca/dpd_pm/00029138.PDF	1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered:		BENZTROPINE unknown	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 mg 3 times / day multiple, oral Recommended Dose: 2 mg, 3 times / day Route: oral Route: multiple Dose: 2 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/791573	unhealthy, 20-66 n = 19 Health Status: unhealthy Condition: neuroleptic-induced extrapyramidal symptoms Age Group: 20-66 Sex: M+F Population Size: 19 Sources: https://pubmed.ncbi.nlm.nih.gov/791573	Other AEs: Dry mouth, Visual disturbance... Other AEs: Dry mouth (grade 1-2, 26%) Visual disturbance (grade 1-2, 32%) Constipation (grade 1-2, 10.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/791573
2.25 mg 2 times / day multiple, oral (max) Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9109903	unhealthy, 21 - 80 n = 19 Health Status: unhealthy Condition: Parkinson's disease Age Group: 21 - 80 Sex: M+F Population Size: 19 Sources: https://pubmed.ncbi.nlm.nih.gov/9109903	Other AEs: Confusion, Memory disturbance... Other AEs: Confusion (32%) Memory disturbance (26%) Lightheadedness (16%) Blurred vision (10.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/9109903
2.25 mg 2 times / day multiple, oral (max) Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9109903	unhealthy, 21 - 80 n = 19 Health Status: unhealthy Condition: Parkinson's disease Age Group: 21 - 80 Sex: M+F Population Size: 19 Sources: https://pubmed.ncbi.nlm.nih.gov/9109903	Other AEs: Dry mouth... Other AEs: Dry mouth (63%) Sources: https://pubmed.ncbi.nlm.nih.gov/9109903
2 mg 1 times / day multiple, parenteral (max) Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Co-administed with:: phenothiazines Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	unhealthy Health Status: unhealthy Condition: Parkinsonism\|Extrapyramidal disorders due to neuroleptic drugs Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	Disc. AE: Paralytic ileus... AEs leading to discontinuation/dose reduction: Paralytic ileus (grade 3-5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf
2 mg 1 times / day multiple, parenteral (max) Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Co-administed with:: tricyclic antidepressants Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	unhealthy Health Status: unhealthy Condition: Parkinsonism\|Extrapyramidal disorders due to neuroleptic drugs Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	Disc. AE: Paralytic ileus... AEs leading to discontinuation/dose reduction: Paralytic ileus (grade 3-5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf
2 mg 1 times / day multiple, parenteral (max) Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	unhealthy Health Status: unhealthy Condition: Parkinsonism\|Extrapyramidal disorders due to neuroleptic drugs Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	Other AEs: Mental impairment... Other AEs: Mental impairment Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf
2 mg 2 times / day steady, oral Recommended Dose: 2 mg, 2 times / day Route: oral Route: steady Dose: 2 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5066	unhealthy n = 21 Health Status: unhealthy Condition: Schizophrenia\|Drug-Induced Extrapyramidal Disorders Sex: M+F Population Size: 21 Sources: https://pubmed.ncbi.nlm.nih.gov/5066	Other AEs: Appetite lost, Dry mouth... Other AEs: Appetite lost (33%) Dry mouth (24%) Constipation (29%) Listlessness (24%) Urinary retention (19%) Blurred vision (19%) Muscle weakness (19%) Excitement (10.5%) Sweating decreased (14%) Mental confusion (10.5%) Skin rash (10.5%) Nausea (10.5%) Vomiting (10.5%) Nervousness (10.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/5066
6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Co-administed with:: phenothiazines Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	unhealthy Health Status: unhealthy Condition: Parkinsonism\|Extrapyramidal disorders due to neuroleptic drugs Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	Other AEs: Hyperthermia, Heat stroke... Other AEs: Hyperthermia (grade 3-5) Heat stroke (grade 3-5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf
6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Co-administed with:: tricyclic antidepressants Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	unhealthy Health Status: unhealthy Condition: Parkinsonism\|Extrapyramidal disorders due to neuroleptic drugs Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	Other AEs: Hyperthermia, Heat stroke... Other AEs: Hyperthermia (grade 3-5) Heat stroke (grade 3-5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf
6 mg 1 times / day multiple, parenteral (max) Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	unhealthy Health Status: unhealthy Condition: Parkinsonism\|Extrapyramidal disorders due to neuroleptic drugs Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf	Other AEs: Physical impairment, Anhidrosis... Other AEs: Physical impairment Anhidrosis (grade 3-5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/012015s027lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C19 991

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/23565891/ Page: 3.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1Q3XL3
Amadis Chemical	A806390
Angene	AGN-PC-0V2SW3	http://www.angenechemical.com/productshow/AGN-PC-0V2SW3.html
Bide Pharmatech	BD1513
BioSynth	Q-200694
Chemieliva Pharmaceutical Co., Ltd	PBCM1439177
Hairui	HR143302	http://www.hairuichem.com/en/product/86-13-5.html
IBScreen	BB_NC-02710
IBScreen	Bio-0891
MuseChem	R044799	https://www.musechem.com/product/R044799.html
NCI Diversity	42199
NCI Plated 2007	169913
NCI Plated 2007	42199
NCI Plated 2007	63912
Pharmeks	PHAR266808
TimTec	ST50997629
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0814AA
ZINC	ZINC000000968360	http://zinc15.docking.org/substances/ZINC000000968360
eNovation Chemicals	D671977	https://www.enovationchem.com/ProductDetails.asp?ProductID=D671977
iChemical	EBD71620	http://www.ichemical.com/products/86-13-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Novel 4'-substituted and 4',4"-disubstituted 3 alpha-(diphenylmethoxy)tropane analogs as potent and selective dopamine uptake inhibitors.	1995 Sep 29	7562926
Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curaçao Extrapyramidal Syndromes Study III.	1998 Apr	9546009

Patents

Sample Use Guides

In Vivo Use Guide

The usual daily dose is 1 to 2 mg, with a range of 0.5 to 6 mg parenterally.

Route of Administration: Parenteral

In Vitro Use Guide

Benztropine inhibited veratridine-induced efflux of K+, membrane depolarization and release of amino acid neurotransmitters with Kd of 2 uM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 04:54:44 GMT 2023` Edited by `admin` on `Sat Dec 16 04:54:44 GMT 2023`
Record UNII	WMJ8TL7510
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BENZTROPINE MESYLATE

Common Name

English

BENZTROPINE MESYLATE [VANDF]

Common Name

English

3.ALPHA.-(DIPHENYLMETHOXY)-1.ALPHA.H,5.ALPHA.H-TROPANE METHANESULPHONATE

Common Name

English

3α-(Diphenylmethoxy)-1αH,5αH-tropane methanesulfonate

Common Name

English

8-AZABICYCLO(3.2.1)OCTANE, 3-(DIPHENYLMETHOXY)-, ENDO, METHANESULPHONATE

Common Name

English

8-AZABICYCLO(3.2.1)OCTANE, 3-(DIPHENYLMETHOXY)-8-METHYL-, (3-ENDO)-, METHANESULFONATE (1:1)

Common Name

English

BENZTROPINE MESYLATE [USP MONOGRAPH]

Common Name

English

BENZTROPINE METHANESULFONATE [MI]

Common Name

English

8-AZABICYCLO(3.2.1)OCTANE, 3-(DIPHENYLMETHOXY)-, ENDO, METHANESULFONATE

Common Name

English

BENZTROPINE MESILATE

Common Name

English

BENZATROPINE MESILATE [MART.]

Common Name

English

BENZATROPINE MESILATE

Common Name

English

Benzatropine mesilate [WHO-DD]

Common Name

English

BENZTROPINE MESYLATE [USP IMPURITY]

Common Name

English

BENZTROPINE MESYLATE [ORANGE BOOK]

Common Name

English

NSC-169913

Code

English

BENZTROPINE MESYLATE [USP-RS]

Common Name

English

BENZTROPINE MESILATE [JAN]

Common Name

English

COGENTIN

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704