Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C10H15N3O5 |
| Molecular Weight | 257.2432 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(CO)C(=O)NNCC1=C(O)C(O)=C(O)C=C1
InChI
InChIKey=BNQDCRGUHNALGH-UHFFFAOYSA-N
InChI=1S/C10H15N3O5/c11-6(4-14)10(18)13-12-3-5-1-2-7(15)9(17)8(5)16/h1-2,6,12,14-17H,3-4,11H2,(H,13,18)
| Molecular Formula | C10H15N3O5 |
| Molecular Weight | 257.2432 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Benserazide is a peripherally-acting aromatic L-amino acid decarboxylase (AADC) or DOPA decarboxylase inhibitor. Benserazide is only used in conjunction with L-dopa for the treatment of Parkinson's disease under the brand name Madopar in the UK. Madopar HBS (125 mg) is a controlled-release dosage form with 100 mg L-dopa and 25 mg benserazide.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12703659
Curator's Comment: Benserazide is unable to cross the blood–brain barrier.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1843 |
550.0 nM [IC50] | ||
Target ID: CHEMBL3399911 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27521834 |
30.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | MADOPAR Approved UseMADOPAR is indicated for the treatment of all forms of Parkinson's syndrome with the exception of
medicine-induced parkinsonism. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
620.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31378952/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
LEVODOPA plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
627.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31378952/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
LEVODOPA plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
0.287 μM |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
BENSERAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
8.37 μM |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
LEVODOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10053234/ |
25 mg 3 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: LEVODOPA |
BENSERAZIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10053234/ |
50 mg 3 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: LEVODOPA |
BENSERAZIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10053234/ |
50 mg 3 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: LEVODOPA |
BENSERAZIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2784.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31378952/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
LEVODOPA plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
2753.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31378952/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
LEVODOPA plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
511 μM × h |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
LEVODOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10053234/ |
25 mg 3 times / day steady-state, oral dose: 25 mg route of administration: Oral experiment type: STEADY-STATE co-administered: LEVODOPA |
BENSERAZIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10053234/ |
50 mg 3 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: LEVODOPA |
BENSERAZIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10053234/ |
50 mg 3 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered: LEVODOPA |
BENSERAZIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.28 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31378952/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
LEVODOPA plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
1.79 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31378952/ |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
LEVODOPA plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
|
48.6 min |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
BENSERAZIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
72 min |
25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA |
LEVODOPA plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Anxiety, Restlessness... Other AEs: Vomiting... AEs leading to discontinuation/dose reduction: Anxiety (2.2%) Other AEs:Restlessness (2.2%) Sleepiness (2.2%) Nausea (4.4%) Confusion (2.2%) Hallucinations (2.2%) Vomiting (4.4%) Sources: |
200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Anxiety | 2.2% Disc. AE |
200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Confusion | 2.2% Disc. AE |
200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Hallucinations | 2.2% Disc. AE |
200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Restlessness | 2.2% Disc. AE |
200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Sleepiness | 2.2% Disc. AE |
200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Vomiting | 4.4% | 200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Nausea | 4.4% Disc. AE |
200 mg 1 times / day multiple, oral Highest studied dose Dose: 200 mg, 1 times / day Route: oral Route: multiple Dose: 200 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| weak [IC50 116.6 uM] | ||||
| yes [Inhibition 10 uM] | ||||
| yes [Inhibition 10 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 87 | 90 |
no |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Paraphilic behaviours in a parkinsonian patient with hedonistic homeostatic dysregulation. | 2006-12 |
|
| Levodopa availability improves with progression of Parkinson's disease. | 2006-09 |
|
| Increased slow oscillatory activity in substantia nigra pars reticulata triggers abnormal involuntary movements in the 6-OHDA-lesioned rat in the presence of excessive extracellular striatal dopamine. | 2006-06 |
|
| L-3,4-dihydroxyphenylalanine-induced c-Fos expression in the CNS under inhibition of central aromatic L-amino acid decarboxylase. | 2006-06 |
|
| Electrophysiological characterization of substantia nigra dopaminergic neurons in partially lesioned rats: effects of subthalamotomy and levodopa treatment. | 2006-04-21 |
|
| Prevention of levodopa-induced dyskinesias by a selective NR1A/2B N-methyl-D-aspartate receptor antagonist in parkinsonian monkeys: implication of preproenkephalin. | 2006-01 |
|
| Effect of L-dopa decarboxylase inhibitor benserazide on renal function in streptozotocin-diabetic rats. | 2006 |
|
| A spectroscopic study on applicability of spectral analysis for simultaneous quantification of l-dopa, benserazide and ascorbic acid in batch and flow systems. | 2005-11 |
|
| Impact of levodopa on reduced nerve growth factor levels in patients with Parkinson disease. | 2005-10-22 |
|
| Uptake and decarboxylation of L-3,4-dihydroxyphenylalanine in cultured monkey placenta amniotic epithelial cells. | 2005-09-06 |
|
| Enhanced cortical dopamine output and antipsychotic-like effect of raclopride with adjunctive low-dose L-dopa. | 2005-08-15 |
|
| [Idiopathic Parkinson's disease: practical hints for the treatment]. | 2005-07-27 |
|
| Pharmacological validation of a mouse model of l-DOPA-induced dyskinesia. | 2005-07 |
|
| Genetic polymorphism of catechol-O-methyltransferase and levodopa pharmacokinetic-pharmacodynamic pattern in patients with Parkinson's disease. | 2005-06 |
|
| Levodopa + carbidopa + entacapone. Entacapone: a second look: new preparations. Parkinson's disease: a modest effect. | 2005-04 |
|
| Localized pemphigoid on the soles of both feet. | 2005-04 |
|
| Cross talk between the intrarenal dopaminergic and cyclooxygenase-2 systems. | 2005-04 |
|
| Cholinopositive effect of dilept (neurotensin peptidomimetic) as the basis of its mnemotropic effect. | 2005-03 |
|
| DOPA-sensitive dystonia-plus syndrome. | 2005-03 |
|
| Early administration of entacapone prevents levodopa-induced motor fluctuations in hemiparkinsonian rats. | 2005-03 |
|
| 3,4-dihydroxyphenylalanine reverses the motor deficits in Pitx3-deficient aphakia mice: behavioral characterization of a novel genetic model of Parkinson's disease. | 2005-02-23 |
|
| [Madopar in the complex therapy of ischemic insult]. | 2005-01 |
|
| [Six months treatment of restless legs syndrome with levodopa/benserazide in domiciliary practice]. | 2004-12-09 |
|
| Simultaneous determination of levodopa and benserazide by stopped-flow injection analysis and three-way multivariate calibration of kinetic-spectrophotometric data. | 2004-11-15 |
|
| [What helps in the treatment of restless legs?]. | 2004-11-11 |
|
| L-DOPA reverses the hypokinetic behaviour and rigidity in rotenone-treated rats. | 2004-08-31 |
|
| Influence of dipeptidyl peptidase inhibitors on growth, peptidase activity, and ammonia production by ruminal microorganisms. | 2004-08 |
|
| Antinociceptive mechanism of L-DOPA. | 2004-07 |
|
| Chronic levodopa intake increases levodopa plasma bioavailability in patients with Parkinson's disease. | 2004-06-17 |
|
| The neurobehavioral changes induced by bilateral rotenone lesion in medial forebrain bundle of rats are reversed by L-DOPA. | 2004-05-05 |
|
| Treatment of idiopathic restless legs syndrome (RLS) with slow-release valproic acid compared with slow-release levodopa/benserazid. | 2004-05 |
|
| Parkinsonism following anterior choroidal artery stroke. | 2004-04 |
|
| Comparison between dopaminergic agents and physical exercise as treatment for periodic limb movements in patients with spinal cord injury. | 2004-04 |
|
| Static mechanical hyperalgesia without dynamic tactile allodynia in patients with restless legs syndrome. | 2004-04 |
|
| Augmentation of endogenous dopamine production increases lung liquid clearance. | 2004-03-15 |
|
| Phenotypic heterogeneity of dopa-responsive dystonia in monozygotic twins. | 2004-02-24 |
|
| Effect of the adenosine A2A receptor antagonist 8-(3-chlorostyryl)caffeine on L-DOPA biotransformation in rat striatum. | 2004-02-20 |
|
| [Influence of L-DOPA on rat brain depending on individual behavioral features]. | 2004 |
|
| Depletion and restoration of endogenous monoamines affects beta-CIT binding to serotonin but not dopamine transporters in non-human primates. | 2004 |
|
| Gas chromatography/mass spectrometric identification of dopaminergic metabolites in striata of rats treated with L-DOPA. | 2004 |
|
| Improvement of sleep hypopnea by antiparkinsonian drugs in a patient with Parkinson's disease: a polysomnographic study. | 2003-11 |
|
| Pharmacokinetic-pharmacodynamic interaction between BIA 3-202, a novel COMT inhibitor, and levodopa/benserazide. | 2003-11 |
|
| Levodopa pharmacokinetics and dyskinesias: are there sex-related differences? | 2003-10 |
|
| One-year treatment with standard and sustained-release levodopa: appropriate long-term treatment of restless legs syndrome? | 2003-10 |
|
| Hyperleptinemia elicited by the 5-HT precursor, 5-hydroxytryptophan in mice: involvement of insulin. | 2003-09-19 |
|
| Effect of acute and chronic administration of U50,488, a kappa opioid receptor agonist, in 6-OHDA-lesioned rats chronically treated with levodopa. | 2003-09 |
|
| Catechol-O-methyltransferase inhibition in erythrocytes and liver by BIA 3-202 (1-[3,4-dibydroxy-5-nitrophenyl]-2-phenyl-ethanone). | 2003-06 |
|
| [The effect of shourong compound formula on levels of dopamine and its metabolites in brain of Parkinson's disease mice induced by reserpine]. | 2002-05 |
|
| A case report of dopa-responsive dystonia. | 2001-06 |
|
| Effects of brain serotonin alterations on prostaglandin E1-induced bradycardia in rats. | 1979-02 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/PIL.3212.latest.pdf
Patients NOT already treated with levodopa:
The usual starting dose is one 50 mg/12.5 mg tablet (50 mg levodopa), three or four times a day.
Your doctor will then increase your dose every 2 to 3 days until they find the right dose for you.
Patients already treated with levodopa:
Your starting dose of Madopar will be one less 100 mg/25 mg tablet than the number of levodopa
500 mg capsules or tablets you take each day. For example if you take four levodopa tablets (2000 mg
levodopa) each day, your doctor will start by giving you three Madopar 100 mg/25 mg tablets daily.
After one week your doctor may then start to increase your dose every 2 to 3 days until they find the
right dose for you.
Patients already treated with a combined levodopa/decarboxylase inhibitor:
The usual starting dose is one 50 mg/12.5 mg tablet (50 mg levodopa), three or four times a day.
Your doctor will then increase your dose every 2 to 3 days until they find the right dose for you.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2289048
Benserazide inhibited AADC with IC50 550 and 530 nM in the
presence and absence of 1 mM pargyline, respectively.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 08:56:07 GMT 2025
by
admin
on
Wed Apr 02 08:56:07 GMT 2025
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| Record UNII |
762OS3ZEJU
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Validated (UNII)
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C38149
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C471
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C81109
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ACTIVE MOIETY |