CAS 28860-95-9|Carbidopa|Lodosyn|(2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid|carbidopa|N-Aminomethyldopa|Lodosin|HMD|Atamet|MK-486|Carbidopa Monohydrate|Carbidopum [INN-Latin]|L...

General Information

Structure

Molecular Formula

C₁₀H₁₄N₂O₄

Molecular Mass

226.22916

Exact Mass

226.09535694

Charge

InChI

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

InChIKey

TZFNLOMSOLWIDK-JTQLQIEISA-N

Canonic Smiles

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

Isomeric Smiles

OC(=O)[C@@](NN)(Cc1cc(O)c(O)cc1)C

Calculated Properties

JChem

LogD (pH = 7.4)

-1.69

LogD (pH = 5.5)

-1.66

Log P

-1.66

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-1.52

Polar Surface Area

115.81

Polarizability

21.81

Molar Refractivity

68.77

LOG S

-0.85

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

CarbidopaLodosynN-AminomethyldopaMK-486Carbidopa MonohydrateCarbidopum [INN-Latin]C-DOPAAlpha-MethyldopahydrazineCarbidopa AnhydrousL-3-(3,4-dihydroxyphenyl)-2-methyl-2-hydrazinopropionic acid(alphaS)-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid(S)-carbidopacarbidopa (anhydrous)(-)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylhydrocinnamic acid(S)-(-)-carbidopaL-alpha-methyldopahydrazine

IUPAC name

(2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid

IUPAC Traditional name

carbidopa

Brand Name

LodosinHMDAtametLodosyn

API Name

(S)-Carbidopa

International Nonproprietary Name (INN)

carbidopum

Names and Identifiers

Registration numbers

PubChem SID

16096353892741027

PubChem CID

34359

CAS Number

28860-95-9

BRENDA Database

3.5.4.12.6.1.572.1.1.62.5.1.72.6.1.493.5.4.B94.1.1.28

BRENDA Ligand Database

869335137204537

PDBeChem Database

142

Drug Central Database

496

LINCS Database

LSM-5850

Protein Data Bank

1js37cx0

ACToR Database

27925-91-328860-95-914585-65-0

MetaboLights Database

MTBLS4820MTBLS751MTBLS417

BKMS React Database

SABIO-RK Database

CHEBI ID

SureChEMBL Database

DrugBank ID

Beilstein Number

CompTox Database

CHEMBL

Wikipedia Title

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

-1.9

Solubility

3.8 mg/L

Product Information

Salt Data

Free Base

Safety Information

Storage Condition

-20°C

Properties

Related Proteins

PDB Bank

1JS3

7CX0

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00190

Drug Groups

approved

Description

An inhibitor of DOPA decarboxylase, preventing conversion of levodopa to dopamine. It is used in parkinson disease to reduce peripheral adverse effects of levodopa. It has no antiparkinson actions by itself. [PubChem]

Indication

For treatment of the symptoms of idiopathic Parkinson's disease (paralysis agitans), post-encephalitic parkinsonism

Pharmacology

Carbidopa, a noncompetitive decarboxylase inhibitor, is used in combination with levodopa for the treatment of Parkinson's disease.

Toxicity

Symptoms of a carbidopa toxicity include muscle spasms or weakness, spasms of the eyelid, nausea, vomiting, diarrhea, an irregular heartbeat, confusion, agitation, hallucinations, and unconsciousness.

Affected Organisms

Humans and other mammals

Biotransformation

The loss of the hydrazine functional group (probably as molecular nitrogen) represents the major metabolic pathway for carbidopa. There are several metabolites of carbidopa metabolism including 3-(3,4-dihydroxyphenyl)-2-methylpropionic acid, 3-(4-hydroxy-3-methoxyphenyl)-2-methylpropionic acid, 3-(3-hydroxyphenyl)-2-methylpropionic acid, 3-(4-hydroxy-3-methoxyphenyl)-2-methyllactic acid, 3-(3-hydroxyphenyl)-2-methyllactic acid, and 3,4-dihydroxyphenylacetone (1,2). [PMID: 4150141]

Absorption

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.

Half Life

1-2 hours

Protein Binding

76%

Elimination

In clinical pharmacologic studies, simultaneous administration of separate tablets of carbidopa and levodopa produced greater urinary excretion of levodopa in proportion to the excretion of dopamine when compared to the two drugs administered at separate times.

References

• Vickers S, Stuart EK, Bianchine JR, Hucker HB, Jaffe ME, Rhodes RE, Vandenheuvel WJ: Metabolism of carbidopa (1-(-)-alpha-hydrazino-3,4-dihydroxy-alpha-methylhydrocinnamic acid monohydrate), an aromatic amino acid decarboxylase inhibitor, in the rat, rhesus monkey, and man. Drug Metab Dispos. 1974 Jan-Feb;2(1):9-22. [Pubmed]

• Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1891

Research Area: Neurological Disease
Biological Activity:
Carbidopa is an aromatic-L-amino-acid decarboxylase inhibitor with an IC50 of 29 ± 2 μM. [1] It increases the plasma half-life of levodopa from 50 minutes to 1½ hours. CarbiDOPA cannot cross the blood brain barrier, so it inhibits only peripheral DDC. It thus prevents the conversion of L-DOPA to dopamine peripherally. This reduces the side effects caused by dopamine on the periphery,besides, it increases the concentration of L-DOPA and dopamine in the brain. [2]

ChEBI

CHEBI:39585

3-(3,4-Dihydroxyphenyl)propanoic acid in which the hydrogens alpha- to the carboxyl group are substituted by hydrazinyl and methyl groups (S-configuration). Carbidopa is a dopa decarboxylase inhibitor, so prevents conversion of levodopa to dopamine. It has no antiparkinson activity by itself, but is used (commonly as its hydrate) in the management of Parkinson's disease to reduce peripheral adverse effects of levodopa.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Carbidopa

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

Data Source

• Academic Data

• Commercial Catalog

Names and Identifiers

• Synonyms

• IUPAC name

• IUPAC Traditional name

• Brand Name

• API Name

• International Nonproprietary Name (INN)

Names and Identifiers

Registration numbers

• PubChem SID

• PubChem CID

• CAS Number

• BRENDA Database

• BRENDA Ligand Database

• PDBeChem Database

• Drug Central Database

• LINCS Database

• Protein Data Bank

• ACToR Database

• MetaboLights Database

• BKMS React Database

• SABIO-RK Database

• CHEBI ID

• SureChEMBL Database

• DrugBank ID

• Beilstein Number

• CompTox Database

• CHEMBL

• Wikipedia Title

Registration numbers

Properties

• Physical Property

• Product Information

• Safety Information

Related Proteins

• PDB Bank

Molecular Spectra

Molecule Details

• DrugBank

• Selleck Chemicals

• ChEBI

Molecule Details

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

PubChem SID

16096353892741027

CAS Number

28860-95-9

BRENDA Ligand Database

869335137204537

PDBeChem Database

142

Drug Central Database

496

LINCS Database

LSM-5850

Protein Data Bank

1js37cx0

MetaboLights Database

MTBLS4820MTBLS751MTBLS417

BKMS React Database

SABIO-RK Database

CHEBI ID

SureChEMBL Database

Beilstein Number

CompTox Database

Wikipedia Title

Physical Property

Hydrophobicity(logP)

-1.9

Solubility

3.8 mg/L

Product Information

Salt Data

Free Base

Safety Information

Storage Condition

-20°C

From Data Sources

• http://en.wikipedia.org/wiki/Carbidopa

Synonyms

IUPAC name

(2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid

IUPAC Traditional name

carbidopa

Brand Name

LodosinHMDAtametLodosyn

API Name

(S)-Carbidopa

International Nonproprietary Name (INN)

carbidopum

DrugBank

DB00190

Drug Groups

approved

Description

Indication

For treatment of the symptoms of idiopathic Parkinson's disease (paralysis agitans), post-encephalitic parkinsonism

Pharmacology

Carbidopa, a noncompetitive decarboxylase inhibitor, is used in combination with levodopa for the treatment of Parkinson's disease.

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Absorption

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.

Half Life

1-2 hours

Protein Binding

76%

Elimination

References

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1891

ChEBI

CHEBI:39585

Molecule

ID:75