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
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+;
| 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 |
| 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 |
DescriptionCurator's Comment: Description was created based on several sources, including
http://www.drugbank.ca/drugs/DB00245
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL216 Sources: http://www.drugbank.ca/drugs/DB00245 |
|||
Target ID: CHEMBL238 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8558504 |
312.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | COGENTIN Approved UseFor 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 Date1959 |
|||
| Secondary | COGENTIN Approved UseFor 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 Date1959 |
Cmax
| 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 |
T1/2
| 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 |
Funbound
| 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: |
unhealthy, 20-66 |
Other AEs: Dry mouth, Visual disturbance... Other AEs: Dry mouth (grade 1-2, 26%) Sources: Visual disturbance (grade 1-2, 32%) Constipation (grade 1-2, 10.5%) |
2.25 mg 2 times / day multiple, oral Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 |
Other AEs: Confusion, Memory disturbance... Other AEs: Confusion (32%) Sources: Memory disturbance (26%) Lightheadedness (16%) Blurred vision (10.5%) |
2.25 mg 2 times / day multiple, oral Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 |
Other AEs: Dry mouth... |
2 mg 1 times / day multiple, parenteral Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Mental impairment... Other AEs: Mental impairment Sources: |
2 mg 1 times / day multiple, parenteral Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Paralytic ileus... AEs leading to discontinuation/dose reduction: Paralytic ileus (grade 3-5) Sources: |
2 mg 1 times / day multiple, parenteral Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Paralytic ileus... AEs leading to discontinuation/dose reduction: Paralytic ileus (grade 3-5) Sources: |
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: |
unhealthy |
Other AEs: Appetite lost, Dry mouth... Other AEs: Appetite lost (33%) Sources: 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%) |
6 mg 1 times / day multiple, parenteral Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Physical impairment, Anhidrosis... Other AEs: Physical impairment Sources: Anhidrosis (grade 3-5) |
6 mg 1 times / day multiple, parenteral Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Hyperthermia, Heat stroke... Other AEs: Hyperthermia (grade 3-5) Sources: Heat stroke (grade 3-5) |
6 mg 1 times / day multiple, parenteral Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Hyperthermia, Heat stroke... Other AEs: Hyperthermia (grade 3-5) Sources: Heat stroke (grade 3-5) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Constipation | grade 1-2, 10.5% | 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: |
unhealthy, 20-66 |
| Dry mouth | grade 1-2, 26% | 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: |
unhealthy, 20-66 |
| Visual disturbance | grade 1-2, 32% | 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: |
unhealthy, 20-66 |
| Blurred vision | 10.5% | 2.25 mg 2 times / day multiple, oral Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 |
| Lightheadedness | 16% | 2.25 mg 2 times / day multiple, oral Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 |
| Memory disturbance | 26% | 2.25 mg 2 times / day multiple, oral Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 |
| Confusion | 32% | 2.25 mg 2 times / day multiple, oral Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 |
| Dry mouth | 63% | 2.25 mg 2 times / day multiple, oral Studied dose Dose: 2.25 mg, 2 times / day Route: oral Route: multiple Dose: 2.25 mg, 2 times / day Sources: |
unhealthy, 21 - 80 |
| Mental impairment | 2 mg 1 times / day multiple, parenteral Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Paralytic ileus | grade 3-5 Disc. AE |
2 mg 1 times / day multiple, parenteral Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Paralytic ileus | grade 3-5 Disc. AE |
2 mg 1 times / day multiple, parenteral Recommended Dose: 2 mg, 1 times / day Route: parenteral Route: multiple Dose: 2 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Excitement | 10.5% | 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: |
unhealthy |
| Mental confusion | 10.5% | 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: |
unhealthy |
| Nausea | 10.5% | 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: |
unhealthy |
| Nervousness | 10.5% | 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: |
unhealthy |
| Skin rash | 10.5% | 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: |
unhealthy |
| Vomiting | 10.5% | 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: |
unhealthy |
| Sweating decreased | 14% | 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: |
unhealthy |
| Blurred vision | 19% | 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: |
unhealthy |
| Muscle weakness | 19% | 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: |
unhealthy |
| Urinary retention | 19% | 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: |
unhealthy |
| Dry mouth | 24% | 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: |
unhealthy |
| Listlessness | 24% | 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: |
unhealthy |
| Constipation | 29% | 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: |
unhealthy |
| Appetite lost | 33% | 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: |
unhealthy |
| Physical impairment | 6 mg 1 times / day multiple, parenteral Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
| Anhidrosis | grade 3-5 | 6 mg 1 times / day multiple, parenteral Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Heat stroke | grade 3-5 | 6 mg 1 times / day multiple, parenteral Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Hyperthermia | grade 3-5 | 6 mg 1 times / day multiple, parenteral Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Heat stroke | grade 3-5 | 6 mg 1 times / day multiple, parenteral Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
| Hyperthermia | grade 3-5 | 6 mg 1 times / day multiple, parenteral Recommended Dose: 6 mg, 1 times / day Route: parenteral Route: multiple Dose: 6 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/23565891/ Page: 3.0 |
yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Selective inhibition of hepatitis C virus infection by hydroxyzine and benztropine. | 2014-06 |
|
| A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle. | 2010-02-23 |
|
| Synthesis and reactions of some new substituted pyridine and pyrimidine derivatives as analgesic, anticonvulsant and antiparkinsonian agents. | 2005-09 |
|
| Risk factors for tardive dyskinesia in a large population of youths and adults. | 2001-08 |
|
| Intermittent neuroleptic treatment and risk for tardive dyskinesia: Curaçao Extrapyramidal Syndromes Study III. | 1998-04 |
|
| Novel 4'-substituted and 4',4"-disubstituted 3 alpha-(diphenylmethoxy)tropane analogs as potent and selective dopamine uptake inhibitors. | 1995-09-29 |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2902895
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
Edited
Mon Mar 31 21:24:54 GMT 2025
by
admin
on
Mon Mar 31 21:24:54 GMT 2025
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| Record UNII |
WMJ8TL7510
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C29704
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169913
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1061005
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205-048-8
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C28864
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18927
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SUB31964
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m2394
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
An absolute control is imposed over the potential presence as it is included as IPC specification and Intermediate release specification into the Stage-I, Crude benztropine mesylate with a stringent 75-ppm limit.
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ACTIVE MOIETY |