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 8228

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 8360	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

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
Centrally mediated increased reflex vagal bradycardia after L-dopa in monoamine oxidase-inhibited anesthetized dogs.	1976 Feb	1255483
Effect of dopamine agonists and antagonists on the lorazepam withdrawal syndrome in rats.	2000 Mar	10744342
Chronic akinetic mutism after mesencephalic-diencephalic infarction: remediated with dopaminergic medications.	2001	11811256
Benserazide decreases central AADC activity, extracellular dopamine levels and levodopa decarboxylation in striatum of the rat.	2001	11459076
L-dopa induces dyskinesia in normal monkeys: behavioural and pharmacokinetic observations.	2001 Aug	11498717
Periodic limb movement disorder : a clinical and polysomnographic study.	2001 Dec	11799409
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
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
Role of adenosine in drug-induced catatonia in mice.	2002 Aug	12597016
Selegiline: a second look. Six years later: too risky in Parkinson's disease.	2002 Aug	12199263
Acute dopaminergic challenge tests to assess postural/kinetic tremor of different origin: a case report.	2002 Aug	12122189
[Hallucinations caused by paroxetine taken together with a levodopa-carbidopa preparation].	2002 Aug 31	12233164
Semicarbazide-sensitive amine oxidase (SSAO) gene expression in alloxan-induced diabetes in mice.	2002 Dec	12606817
Life-threatening parkinsonism induced by kava-kava.	2002 Jan	11835463
A double-blind crossover, placebo-controlled study of the adenosine A2A antagonist theophylline in Parkinson's disease.	2002 Jan-Feb	11852293
Gateways to Clinical Trials. June 2002.	2002 Jun	12168506
Parkinsonism associated with interferon alpha therapy for chronic myelogenous leukemia.	2002 Mar	11965836
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
[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
Entacapone improves the availability of L-dopa in plasma by decreasing its peripheral metabolism independent of L-dopa/carbidopa dose.	2002 Oct	12392583
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
Olanzapine: a proarrhythmic drug?	2002 Sep	12355682
Leg muscle strength is reduced in Parkinson's disease and relates to the ability to rise from a chair.	2003 Feb	12539208
Reversal of parkinsonism following liver transplantation.	2003 Feb 11	12578945
Novel levodopa gastroretentive dosage form: in-vivo evaluation in dogs.	2003 Feb 14	12586509
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
Binding site of salsolinol: its properties in different regions of the brain and the pituitary gland of the rat.	2003 Jan	12441164
Neonatal dopa-responsive extrapyramidal syndrome in twins with recessive GTPCH deficiency.	2003 Jan 28	12552057
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	12722161
Parkinsonian speech disfluencies: effects of L-dopa-related fluctuations.	2003 Spring	12706913

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 `Wed Jul 05 22:45:43 UTC 2023` Edited by `admin` on `Wed Jul 05 22:45:43 UTC 2023`
Record UNII	MNX7R8C5VO
Record Status	`Validated (UNII)`
Record Version

Download

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