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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

1977
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
The effects of combining carbidopa with levodopa for Parkinson's disease.
1975 Dec
Centrally mediated increased reflex vagal bradycardia after L-dopa in monoamine oxidase-inhibited anesthetized dogs.
1976 Feb
Benserazide decreases central AADC activity, extracellular dopamine levels and levodopa decarboxylation in striatum of the rat.
2001
The central catechol-O-methyltransferase inhibitor tolcapone increases striatal hydroxyl radical production in L-DOPA/carbidopa treated rats.
2001
Levodopa induces dyskinesias in normal squirrel monkeys.
2001 Aug
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
Amelioration of frozen gait by tandospirone, a serotonin 1A agonist, in a patient with pure akinesia developing resistance to L-threo-3,4-dihydroxyphenylserine.
2001 Jul-Aug
The pharmacokinetic profile of the "first ever" oral dose of levodopa in de novo patients with Parkinson's disease.
2001 Mar-Apr
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
Semicarbazide-sensitive amine oxidase (SSAO) gene expression in alloxan-induced diabetes in mice.
2002 Dec
[Benefit of L-DOPA-without-DCI (decarboxylase inhibitor) therapy on wearing-off phenomenon in advanced stages of Parkinson's disease patients].
2002 Feb
Nitecapone and selegiline as effective adjuncts to L-DOPA in reserpine-induced catatonia in mice.
2002 Jan-Feb
[Atypical phenylketonuria treatment effectiveness].
2002 Jul-Sep
Gateways to Clinical Trials. June 2002.
2002 Jun
[Hallucinations caused by paroxetine in combined usage of levodopa-carbidopa].
2002 Jun 1
In vivo metabolism and partitioning of 6-[18F]fluoro-L-meta-tyrosine in whole blood: a unified compartment model.
2002 Jun 7
Effects of entacapone and tolcapone on mitochondrial membrane potential.
2002 Oct 18
The role of PET in localization of neuroendocrine and adrenocortical tumors.
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
Reversal of parkinsonism following liver transplantation.
2003 Feb 11
Novel levodopa gastroretentive dosage form: in-vivo evaluation in dogs.
2003 Feb 14
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition.
2003 Jun
Selegiline in the treatment of Parkinson's disease: its impact on orthostatic hypotension.
2003 Mar
Randomized trial of pallidotomy versus medical therapy for Parkinson's disease.
2003 May
Effect of pulsatile administration of levodopa on dyskinesia induction in drug-naïve MPTP-treated common marmosets: effect of dose, frequency of administration, and brain exposure.
2003 May
Optimizing levodopa pharmacokinetics: intestinal infusion versus oral sustained-release tablets.
2003 May-Jun
Parkinsonian speech disfluencies: effects of L-dopa-related fluctuations.
2003 Spring
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 Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
NCI_THESAURUS C66884
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
Code System Code Type Description
RXCUI
1545982
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00190
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
CAS
28860-95-9
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
DAILYMED
KR87B45RGH
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
PUBCHEM
34359
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
249-271-9
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
INN
3258
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
EVMPD
SUB06126MIG
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
NCI_THESAURUS
C61803
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
EVMPD
SUB22639
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID4022735
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
MERCK INDEX
m3068
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY
FDA UNII
KR87B45RGH
Created by admin on Fri Dec 15 15:23:25 GMT 2023 , Edited by admin on Fri Dec 15 15:23:25 GMT 2023
PRIMARY