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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H14N2O4.H2O
Molecular Weight 244.2448
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBIDOPA

SMILES

C[C@](Cc1ccc(c(c1)O)O)(C(=O)O)NN.O

InChI

InChIKey=QTAOMKOIBXZKND-PPHPATTJSA-N
InChI=1S/C10H14N2O4.H2O/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);1H2/t10-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C10H14N2O4
Molecular Weight 226.2296
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

230774400000
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Centrally mediated increased reflex vagal bradycardia after L-dopa in monoamine oxidase-inhibited anesthetized dogs.
1976 Feb
[Neuroleptic malignant syndrome].
2002
Restless legs syndrome in the older adult: diagnosis and management.
2002
[The use of amantadine sulfate in combined therapy of Parkinson's disease].
2002
Role of adenosine in drug-induced catatonia in mice.
2002 Aug
Selegiline: a second look. Six years later: too risky in Parkinson's disease.
2002 Aug
Two advances in the management of Parkinson disease.
2002 Aug
Acute dopaminergic challenge tests to assess postural/kinetic tremor of different origin: a case report.
2002 Aug
[The usefulness of dopaminergic drugs in traumatic brain injury].
2002 Aug 16-31
[Hallucinations caused by paroxetine taken together with a levodopa-carbidopa preparation].
2002 Aug 31
Semicarbazide-sensitive amine oxidase (SSAO) gene expression in alloxan-induced diabetes in mice.
2002 Dec
Effect of promoters on cellular immune response induced by recombinant fowlpox virus expressing multi-epitope polypeptides from HIV-1.
2002 Dec
Screening for tetrahydrobiopterin deficiency among hyperphenylalaninemia patients in Southern China.
2002 Feb
[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
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
[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
Role of sphingosine synthesis inhibition in transcutaneous delivery of levodopa.
2002 May 15
Levodopa but not ropinirole induces an internalization of D1 dopamine receptors in parkinsonian rats.
2002 Nov
Long-term follow-up of L-dopa treatment in children with amblyopia.
2002 Nov-Dec
Entacapone improves the availability of L-dopa in plasma by decreasing its peripheral metabolism independent of L-dopa/carbidopa dose.
2002 Oct
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
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
Olanzapine: a proarrhythmic drug?
2002 Sep
Dopamine replacement therapy reverses abnormal synchronization of pallidal neurons in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine primate model of parkinsonism.
2002 Sep 15
Viral encephalitis complicated by neuroleptic malignant syndrome in a 7-year-old girl.
2003 Apr
Leg muscle strength is reduced in Parkinson's disease and relates to the ability to rise from a chair.
2003 Feb
Reversal of parkinsonism following liver transplantation.
2003 Feb 11
Novel levodopa gastroretentive dosage form: in-vivo evaluation in dogs.
2003 Feb 14
Protein 4.1N is required for translocation of inositol 1,4,5-trisphosphate receptor type 1 to the basolateral membrane domain in polarized Madin-Darby canine kidney cells.
2003 Feb 7
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
Commonly used L-amino acid decarboxylase inhibitors block monoamine oxidase activity in the rat.
2003 Mar
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:02:47 UTC 2021
Edited
by admin
on Fri Jun 25 21:02:47 UTC 2021
Record UNII
MNX7R8C5VO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBIDOPA
EMA EPAR   EP   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
(-)-L-.ALPHA.-HYDRAZINO-3,4-DIHYDROXY-.ALPHA.-METHYLHYDROCINNAMIC ACID MONOHYDRATE
Common Name English
CARBIDOPA COMPONENT OF PARCOPA
Common Name English
CARBIDOPA [MI]
Common Name English
CARBIDOPA [USP MONOGRAPH]
Common Name English
CARBIDOPA [EMA EPAR]
Common Name English
CARBIDOPA [USP-RS]
Common Name English
MK-486
Code English
CARBIDOPA HYDRATE [JAN]
Common Name English
CARBIDOPUM MONOHYDRATE [WHO-IP LATIN]
Common Name English
DUOPA COMPONENT CARBIDOPA
Brand Name English
STALEVO COMPONENT CARBIDOPA
Brand Name English
CORBILTA COMPONENT CARBIDOPA
Brand Name English
CARBIDOPA [VANDF]
Common Name English
NSC-751137
Code English
CARBIDOPA COMPONENT OF STALEVO
Brand Name English
CARBIDOPA COMPONENT OF DOPASNAP
Common Name English
RYTARY COMPONENT CARBIDOPA
Brand Name English
DOPASNAP COMPONENT CARBIDOPA
Common Name English
CARBIDOPA [ORANGE BOOK]
Common Name English
CARBIDOPA MONOHYDRATE [WHO-DD]
Common Name English
CARBIDOPA COMPONENT OF CARBILEV
Common Name English
CARBIDOPA [EP MONOGRAPH]
Common Name English
CARBIDOPA COMPONENT OF DUOPA
Brand Name English
CARBILEV COMPONENT CARBIDOPA
Common Name English
NSC-758190
Code English
BENZENEPROPANOIC ACID, .ALPHA.-HYDRAZINO-3,4-DIHYDROXY-.ALPHA.-METHYL-, MONOHYDRATE, (S)-
Common Name English
IPX-203 COMPONENT CARBIDOPA
Common Name English
CARBIDOPA COMPONENT OF LEVODOPA/CARBIDOPA/ENTACAPONE ORION
Brand Name English
CARBIDOPA COMPONENT OF SINEMET
Common Name English
CARBIDOPA COMPONENT OF RYTARY
Brand Name English
LODOSYN
Brand Name English
PARCOPA COMPONENT CARBIDOPA
Common Name English
CARBIDOPA MONOHYDRATE [WHO-IP]
Common Name English
LEVODOPA/CARBIDOPA/ENTACAPONE ORION COMPONENT CARBIDOPA
Brand Name English
CARBIDOPA COMPONENT OF CORBILTA
Brand Name English
SINEMET COMPONENT CARBIDOPA
Common Name English
CARBIDOPA MONOHYDRATE
WHO-DD   WHO-IP  
Common Name English
CARBIDOPA [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66884
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
LIVERTOX 148
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
NCI_THESAURUS C38149
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
NDF-RT N0000175755
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: NERVOUS SYSTEM DISEASES)
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
EMA ASSESSMENT REPORTS STALEVO (AUTHORIZED: PARKINSON DIEASE)
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 09 (LEV/CAR)
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
EMA ASSESSMENT REPORTS LEVODOPA/CARBIDOPA/ENTACAPONE ORION (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
NDF-RT N0000175754
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
WHO-ATC N04BA05
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
FDA ORPHAN DRUG 129499
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
Code System Code Type Description
EVMPD
SUB21619
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
FDA UNII
MNX7R8C5VO
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
MESH
D002230
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
PUBCHEM
38101
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
CAS
38821-49-7
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
IUPHAR
5159
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
DRUG CENTRAL
496
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
NCI_THESAURUS
C47431
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
MERCK INDEX
M3068
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
CARBIDOPA
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
DRUG BANK
DB00190
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CARBIDOPA
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY Description: A white to creamy white powder; odourless or almost odourless. Solubility: Slightly soluble in water; very slightly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Antiparkinsonism drug. Storage: Carbidopa should be kept in a well-closed container, protected from light. Definition: Carbidopa contains not less than 99.0% and not more than 101.0% of C10H14N2O4, calculated with reference to the anhydrous substance.
RXCUI
2019
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY RxNorm
ChEMBL
CHEMBL1201236
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY
USP_CATALOG
1095506
Created by admin on Fri Jun 25 21:02:47 UTC 2021 , Edited by admin on Fri Jun 25 21:02:47 UTC 2021
PRIMARY USP-RS
Related Record Type Details
PARENT -> SALT/SOLVATE
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
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IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC