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 244.2444
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBIDOPA

SMILES

O.C[C@@](CC1=CC(O)=C(O)C=C1)(NN)C(O)=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 H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C10H14N2O4
Molecular Weight 226.2292
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
L-dopa induces dyskinesia in normal monkeys: behavioural and pharmacokinetic observations.
2001 Aug
L-DOPA and glia-conditioned medium have additive effects on tyrosine hydroxylase expression in human catecholamine-rich neuroblastoma NB69 cells.
2001 Aug
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.
2001 Feb
Molecular analysis and long-term follow-up of patients with different forms of 6-pyruvoyl-tetrahydropterin synthase deficiency.
2001 May
Blood-brain barrier and neuronal membrane transport of 6-[18F]fluoro-L-DOPA.
2001 Nov 15
[The use of amantadine sulfate in combined therapy of Parkinson's disease].
2002
Chronic high dose L-DOPA alone or in combination with the COMT inhibitor entacapone does not increase oxidative damage or impair the function of the nigro-striatal pathway in normal cynomologus monkeys.
2002
Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition.
2002 Apr
[Rhabdomyolysis as a complication of Parkinson's disease].
2002 Jan-Feb
Entacapone in restless legs syndrome.
2002 Mar
Parkinson's disease. Therapeutic strategies to improve patient function and quality of life.
2002 Mar
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
Olanzapine: a proarrhythmic drug?
2002 Sep
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
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition.
2003 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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:14:20 GMT 2023
Edited
by admin
on Fri Dec 15 15:14:20 GMT 2023
Record UNII
MNX7R8C5VO
Record Status Validated (UNII)
Record Version
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Name Type Language
CARBIDOPA
EMA EPAR   EP   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
Carbidopa monohydrate [WHO-DD]
Common 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
DHIVY COMPONENT CARBIDOPA
Brand Name English
CARBIDOPA [ORANGE BOOK]
Common Name English
CARBIDOPA COMPONENT OF CARBILEV
Common Name English
CARBIDOPA COMPONENT OF DHIVY
Brand 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 Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
LIVERTOX NBK548734
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
NCI_THESAURUS C38149
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
NDF-RT N0000175755
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: NERVOUS SYSTEM DISEASES)
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
EMA ASSESSMENT REPORTS STALEVO (AUTHORIZED: PARKINSON DIEASE)
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 09 (LEV/CAR)
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
EMA ASSESSMENT REPORTS CORBILTA (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
EMA ASSESSMENT REPORTS LEVODOPA/CARBIDOPA/ENTACAPONE ORION (AUTHORIZED: PARKINSON DISEASE)
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
NDF-RT N0000175754
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
WHO-ATC N04BA05
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
FDA ORPHAN DRUG 129499
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
Code System Code Type Description
EVMPD
SUB21619
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID50904589
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
CHEBI
3395
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
FDA UNII
MNX7R8C5VO
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
MESH
D002230
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
PUBCHEM
38101
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
RS_ITEM_NUM
1095506
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
CAS
38821-49-7
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
IUPHAR
5159
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
DRUG CENTRAL
496
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
NCI_THESAURUS
C47431
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
DAILYMED
MNX7R8C5VO
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
MERCK INDEX
m3068
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
CARBIDOPA
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
DRUG BANK
DB00190
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
CARBIDOPA
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
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 Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL1201236
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
NSC
758190
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
NSC
751137
Created by admin on Fri Dec 15 15:14:20 GMT 2023 , Edited by admin on Fri Dec 15 15:14:20 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
BINDER->LIGAND
BINDING
ANHYDROUS->SOLVATE
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
IMPURITY -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC