U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2O4
Molecular Weight 226.2292
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBIDOPA ANHYDROUS

SMILES

C[C@@](CC1=CC(O)=C(O)C=C1)(NN)C(O)=O

InChI

InChIKey=TZFNLOMSOLWIDK-JTQLQIEISA-N
InChI=1S/C10H14N2O4/c1-10(12-11,9(15)16)5-6-2-3-7(13)8(14)4-6/h2-4,12-14H,5,11H2,1H3,(H,15,16)/t10-/m0/s1

HIDE SMILES / InChI
Carbidopa is a competitive inhibitor of aromatic L-amino acid decarboxylase that does not cross the blood-brain barrier, is routinely administered with levodopa (LD) for the treatment of the symptoms of idiopathic Parkinson’s disease (paralysis agitans), postencephalitic parkinsonism, and symptomatic parkinsonism, which may follow injury to the nervous system by carbon monoxide intoxication and/or manganese intoxication. Current evidence indicates that symptoms of Parkinson’s disease are related to depletion of dopamine in the corpus striatum. Administration of dopamine is ineffective in the treatment of Parkinson’s disease apparently because it does not cross the blood-brain barrier. However, levodopa, the metabolic precursor of dopamine, does cross the blood- brain barrier, and presumably is converted to dopamine in the brain. When levodopa is administered orally it is rapidly decarboxylated to dopamine in extracerebral tissues so that only a small portion of a given dose is transported unchanged to the central nervous system. For this reason, large doses of levodopa are required for adequate therapeutic effect and these may often be accompanied by nausea and other adverse reactions, some of which are attributable to dopamine formed in extracerebral tissues. Carbidopa inhibits decarboxylation of peripheral levodopa. Carbidopa has not been demonstrated to have any overt pharmacodynamic actions in the recommended doses.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
LODOSYN

Approved Use

LODOSYN is indicated for use with carbidopa-levodopa or with levodopa in the treatment of the symptoms of idiopathic Parkinson’s disease (paralysis agitans), postencephalitic parkinsonism, and symptomatic parkinsonism, which may follow injury to the nervous system by carbon monoxide intoxication and/or manganese intoxication. LODOSYN is for use with carbidopa-levodopa in patients for whom the dosage of carbidopa-levodopa provides less than adequate daily dosage (usually 70 mg daily) of carbidopa. LODOSYN is for use with levodopa in the occasional patient whose dosage requirement of carbidopa and levodopa necessitates separate titration of each medication. LODOSYN is used with carbidopa-levodopa or with levodopa to permit the administration of lower doses of levodopa with reduced nausea and vomiting, more rapid dosage titration, and with a somewhat smoother response. However, patients with markedly irregular (“on-off”) responses to levodopa have not been shown to benefit from the addition of carbidopa. Since carbidopa prevents the reversal of levodopa effects caused by pyridoxine, supplemental pyridoxine (vitamin B6), can be given to patients when they are receiving carbidopa and levodopa concomitantly or as carbidopa-levodopa.

Launch Date

2.30774407E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
108.57 ng/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered: LEVODOPA
CARBIDOPA plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
559.92 ng × h/mL
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered: LEVODOPA
CARBIDOPA plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.09 h
25 mg single, oral
dose: 25 mg
route of administration: Oral
experiment type: SINGLE
co-administered: LEVODOPA
CARBIDOPA plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
64%
CARBIDOPA plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Centrally mediated increased reflex vagal bradycardia after L-dopa in monoamine oxidase-inhibited anesthetized dogs.
1976 Feb
Switching from pergolide to pramipexole in patients with Parkinson's disease.
2001
L-dopa induces dyskinesia in normal monkeys: behavioural and pharmacokinetic observations.
2001 Aug
Duodenal levodopa infusion in Parkinson's disease--long-term experience.
2001 Dec
Periodic limb movement disorder : a clinical and polysomnographic study.
2001 Dec
Amantadine for dyskinesia in patients affected by severe Parkinson's disease.
2001 Feb
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001 Feb
Aldrin-induced locomotor activity: possible involvement of the central GABAergic-cholinergic-dopaminergic interaction.
2001 Jan-Feb
Blood-brain barrier and neuronal membrane transport of 6-[18F]fluoro-L-DOPA.
2001 Nov 15
Post-stroke violent adventitial movement responsive to levo-dopa/carbi-dopa therapy.
2001 Oct
Dopaminergic therapy with carbidopa L-dopa for left neglect after stroke: a case series.
2001 Sep
Stereoselective effect of (R)- and (S)-1-methyl-1,2,3,4-tetrahydroisoquinolines on a mouse model of Parkinson's disease.
2001 Sep 1
Atypical presentation of dopa-responsive dystonia: generalized hypotonia and proximal weakness.
2001 Sep 25
Restless legs syndrome in the older adult: diagnosis and management.
2002
[Serotonin syndrome: report of a fatal case and review of the literature].
2002 Apr
Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition.
2002 Apr
Selegiline: a second look. Six years later: too risky in Parkinson's disease.
2002 Aug
Levodopa-carbidopa with occlusion in older children with amblyopia.
2002 Dec
Screening for tetrahydrobiopterin deficiency among hyperphenylalaninemia patients in Southern China.
2002 Feb
[Benefit of L-DOPA-without-DCI (decarboxylase inhibitor) therapy on wearing-off phenomenon in advanced stages of Parkinson's disease patients].
2002 Feb
Parkinson disease neuropathology: later-developing dementia and loss of the levodopa response.
2002 Jan
[Rhabdomyolysis as a complication of Parkinson's disease].
2002 Jan-Feb
Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice.
2002 Jan-Feb
The SSRI, citalopram, improves bradykinesia in patients with Parkinson's disease treated with L-dopa.
2002 Jan-Feb
Levodopa-responsive rubral (Holmes') tremor.
2002 Jul
[Atypical phenylketonuria treatment effectiveness].
2002 Jul-Sep
Gateways to Clinical Trials. June 2002.
2002 Jun
In vivo metabolism and partitioning of 6-[18F]fluoro-L-meta-tyrosine in whole blood: a unified compartment model.
2002 Jun 7
Parkinsonism associated with interferon alpha therapy for chronic myelogenous leukemia.
2002 Mar
Bruxism as presenting feature of Parkinson's disease.
2002 Mar
Entacapone in restless legs syndrome.
2002 Mar
Oral solution of levodopa ethylester for treatment of response fluctuations in patients with advanced Parkinson's disease.
2002 Mar
Influence of layer position on in vitro and in vivo release of levodopa methyl ester and carbidopa from three-layer matrix tablets.
2002 Mar
[Hallucinations caused by paroxetine taken together with a levodopa-carbidopa preparation].
2002 Mar 23
Dopaminergic transmission in the rat striatum in vivo in conditions of pharmacological modulation.
2002 Mar-Apr
Gender and pramipexole effects on levodopa pharmacokinetics and pharmacodynamics.
2002 May 14
Role of sphingosine synthesis inhibition in transcutaneous delivery of levodopa.
2002 May 15
Clozapine withdrawal symptoms in a Parkinson's disease patient.
2002 Nov
Levodopa but not ropinirole induces an internalization of D1 dopamine receptors in parkinsonian rats.
2002 Nov
The role of PET in localization of neuroendocrine and adrenocortical tumors.
2002 Sep
Simultaneous determination of dopa and carbidopa enantiomers by capillary zone electrophoresis.
2002 Sep
Quantitative description of loss of clinical benefit following withdrawal of levodopa-carbidopa and bromocriptine in early Parkinson's disease.
2002 Sep
Repeated administration of piribedil induces less dyskinesia than L-dopa in MPTP-treated common marmosets: a behavioural and biochemical investigation.
2002 Sep
Leg muscle strength is reduced in Parkinson's disease and relates to the ability to rise from a chair.
2003 Feb
Binding site of salsolinol: its properties in different regions of the brain and the pituitary gland of the rat.
2003 Jan
Neonatal dopa-responsive extrapyramidal syndrome in twins with recessive GTPCH deficiency.
2003 Jan 28
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition.
2003 Jun
Optimizing levodopa pharmacokinetics: intestinal infusion versus oral sustained-release tablets.
2003 May-Jun
Patents

Sample Use Guides

Whether given with carbidopa-levodopa or with levodopa, the optimal daily dose of LODOSYN (CARBIDOPA tablets) must be determined by careful titration. Most patients respond to a 1:10 proportion of carbidopa and levodopa, provided the daily dosage of carbidopa is 70 mg or more a day. The maximum daily dosage of carbidopa should not exceed 200 mg, since clinical experience with larger dosages is limited. If the patient is taking carbidopa-levodopa, the amount of carbidopa in carbidopa-levodopa should be considered when calculating the total amount of LODOSYN to be administered each day.
Route of Administration: Oral
It was evaluated the effect of carbidopa on 6-18F-fluoro-3,4-dihydroxy-l-phenylalanine (18F-FDOPA) uptake in the murine β-cell line RIN-m5F. Incubation of RIN-m5F cells with 80 μM carbidopa did not significantly affect the cellular accumulation of 18F-FDOPA.
Name Type Language
CARBIDOPA ANHYDROUS
Common Name English
carbidopa [INN]
Common Name English
Carbidopa [WHO-DD]
Common Name English
CARBIDOPA, L- ANHYDROUS
Common Name English
BENZENEPROPANOIC ACID, .ALPHA.-HYDRAZINO-3,4-DIHYDROXY-.ALPHA.-METHYL-, (S)-
Common Name English
CARBIDOPA ANHYDROUS [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C38149
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
NCI_THESAURUS C66884
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
Code System Code Type Description
RXCUI
1545982
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY RxNorm
DRUG BANK
DB00190
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
CAS
28860-95-9
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
DAILYMED
KR87B45RGH
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
PUBCHEM
34359
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
ECHA (EC/EINECS)
249-271-9
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
INN
3258
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
EVMPD
SUB06126MIG
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
NCI_THESAURUS
C61803
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
EVMPD
SUB22639
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID4022735
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
MERCK INDEX
M3068
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY
FDA UNII
KR87B45RGH
Created by admin on Wed Jul 05 22:53:50 UTC 2023 , Edited by admin on Wed Jul 05 22:53:50 UTC 2023
PRIMARY