CARBIDOPA

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017830s014s016s017s018s019s030lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/10934669

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DOPA decarboxylase 15 Target ID: CHEMBL1843 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11106255	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Idiopathic Parkinson's disease 19 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017830s014s016s017s018s019s030lbl.pdf	Palliative		Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
108.57 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30295551	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA	LEVODOPA	CARBIDOPA plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
559.92 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30295551	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA	LEVODOPA	CARBIDOPA plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.09 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30295551	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered: LEVODOPA	LEVODOPA	CARBIDOPA plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
64% DRUG LABEL https://www.drugs.com/monograph/levodopa-carbidopa.html			CARBIDOPA plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

PubMed

Title	Date	PubMed
The effects of combining carbidopa with levodopa for Parkinson's disease.	1975 Dec	1104406
Comparison of dopa decarboxylase inhibitor (carbidopa) combined with levodopa and levodopa alone in Parkinson's disease.	1975 Oct	1101099
Chronic akinetic mutism after mesencephalic-diencephalic infarction: remediated with dopaminergic medications.	2001	11811256
Catechol-O-methyltransferase inhibitors in the management of Parkinson's disease.	2001	11346021
L-DOPA and glia-conditioned medium have additive effects on tyrosine hydroxylase expression in human catecholamine-rich neuroblastoma NB69 cells.	2001 Aug	11483656
Duodenal levodopa infusion in Parkinson's disease--long-term experience.	2001 Dec	11903087
Periodic limb movement disorder : a clinical and polysomnographic study.	2001 Dec	11799409
Amantadine for dyskinesia in patients affected by severe Parkinson's disease.	2001 Feb	11487209
[Pharmacological treatments of Parkinson's disease].	2001 Feb	11233302
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.	2001 Feb	11160877
Case report: successful use of rectally administered levodopa-carbidopa.	2001 Jan	11212422
Aldrin-induced locomotor activity: possible involvement of the central GABAergic-cholinergic-dopaminergic interaction.	2001 Jan-Feb	11785907
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	11479395
A novel neurodevelopmental syndrome responsive to 5-hydroxytryptophan and carbidopa.	2001 Jun	11386854
Visual acuities after levodopa administration in amblyopia.	2001 Mar-Apr	11310708
Molecular analysis and long-term follow-up of patients with different forms of 6-pyruvoyl-tetrahydropterin synthase deficiency.	2001 May	11388593
Structural insight into Parkinson's disease treatment from drug-inhibited DOPA decarboxylase.	2001 Nov	11685243
Dopamine mediates striatal malonate toxicity via dopamine transporter-dependent generation of reactive oxygen species and D2 but not D1 receptor activation.	2001 Oct	11595758
Dopaminergic therapy with carbidopa L-dopa for left neglect after stroke: a case series.	2001 Sep	11552204
Atypical presentation of dopa-responsive dystonia: generalized hypotonia and proximal weakness.	2001 Sep 25	11571350
Restless legs syndrome in the older adult: diagnosis and management.	2002	12390051
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	11793162
Placebo-controlled comparison of three dose-regimens of 5-hydroxytryptophan challenge test in healthy volunteers.	2002 Apr	11910264
Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): insights into the mechanisms of substrate recognition.	2002 Apr	11901210
Levodopa-carbidopa with occlusion in older children with amblyopia.	2002 Dec	12506278
Effect of promoters on cellular immune response induced by recombinant fowlpox virus expressing multi-epitope polypeptides from HIV-1.	2002 Dec	12452800
Screening for tetrahydrobiopterin deficiency among hyperphenylalaninemia patients in Southern China.	2002 Feb	11940335
[Benefit of L-DOPA-without-DCI (decarboxylase inhibitor) therapy on wearing-off phenomenon in advanced stages of Parkinson's disease patients].	2002 Feb	11889758
Brain catecholamine metabolism in catechol-O-methyltransferase (COMT)-deficient mice.	2002 Jan	11849292
Levodopa-responsive rubral (Holmes') tremor.	2002 Jul	12210864
Parkinsonism associated with interferon alpha therapy for chronic myelogenous leukemia.	2002 Mar	11965836
Bruxism as presenting feature of Parkinson's disease.	2002 Mar	11922248
Entacapone in restless legs syndrome.	2002 Mar	11921139
Oral solution of levodopa ethylester for treatment of response fluctuations in patients with advanced Parkinson's disease.	2002 Mar	11921115
Parkinson's disease. Therapeutic strategies to improve patient function and quality of life.	2002 Mar	11899548
Influence of layer position on in vitro and in vivo release of levodopa methyl ester and carbidopa from three-layer matrix tablets.	2002 Mar	11880007
[Hallucinations caused by paroxetine taken together with a levodopa-carbidopa preparation].	2002 Mar 23	11938583
Dopaminergic transmission in the rat striatum in vivo in conditions of pharmacological modulation.	2002 Mar-Apr	11942697
Effect of levodopa and carbidopa in human amblyopia.	2002 Mar-Apr	11911549
Levodopa plus carbidopa before physiotherapy increased motor recovery after stroke.	2002 Mar-Apr	11874277
Clozapine withdrawal symptoms in a Parkinson's disease patient.	2002 Nov	12465085
Levodopa but not ropinirole induces an internalization of D1 dopamine receptors in parkinsonian rats.	2002 Nov	12465054
Long-term follow-up of L-dopa treatment in children with amblyopia.	2002 Nov-Dec	12458842
The role of PET in localization of neuroendocrine and adrenocortical tumors.	2002 Sep	12381551
Repeated administration of piribedil induces less dyskinesia than L-dopa in MPTP-treated common marmosets: a behavioural and biochemical investigation.	2002 Sep	12360537
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	12223537
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	12444087
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition.	2003 Jun	12711835
Randomized trial of pallidotomy versus medical therapy for Parkinson's disease.	2003 May	12730989
Optimizing levodopa pharmacokinetics: intestinal infusion versus oral sustained-release tablets.	2003 May-Jun	12782919

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

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

Common Name

English

CARBIDOPA [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C66884