MELEVODOPA

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H13NO4
Molecular Weight	211.2145
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC(=O)[C@@H](N)CC1=CC(O)=C(O)C=C1

InChI

InChIKey=XBBDACCLCFWBSI-ZETCQYMHSA-N

InChI=1S/C10H13NO4/c1-15-10(14)7(11)4-6-2-3-8(12)9(13)5-6/h2-3,5,7,12-13H,4,11H2,1H3/t7-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C10H13NO4
Molecular Weight	211.2145
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21080185
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23948989 http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021485s20lbl.pdf

Levodopa (L-DOPA) was first isolated from seedlings of Vicia faba by Marcus Guggenheim in 1913. Levodopa, a dopamine precursor, is an effective and well-tolerated dopamine replacement agent used to treat Parkinson's disease. Oral levodopa has been widely used for over 40 years, often in combination with a dopa-decarboxylase inhibitor carbidopa, which reduces many treatment complications, extending its half-life and increasing levodopa availability to the brain. Entacapone, a catechol-O-methyltransferase inhibitor, can also be used to improve the bioavailability of levodopa, especially when used in conjunction with a carbidopa.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine D1 receptor 101 Target ID: CHEMBL2056 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18851961	Agonist 2678
Dopamine receptor 60 Target ID: CHEMBL2096905 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017555s056s068s071lbl.pdf	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/021485s20lbl.pdf	Primary		Approved 8429	Stalevo Approved Use Stalevo® (carbidopa, levodopa and entacapone) is indicated to treat patients with idiopathic Parkinson’s disease. Launch Date 2003

C_max

Value	Dose	Co-administered	Analyte	Population
0.946 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22549097	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA, DL-	CARBIDOPA, DL-	LEVODOPA plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
84.8 μg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22549097	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA, DL-	CARBIDOPA, DL-	LEVODOPA plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
78.7 min EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/22549097	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: CARBIDOPA, DL-	CARBIDOPA, DL-	LEVODOPA plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
80% DRUG LABEL https://www.drugs.com/monograph/levodopa-carbidopa.html			LEVODOPA plasma	Homo sapiens

Doses

Dose	Population	Adverse events
3 g 1 times / day multiple, oral Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5550880	unhealthy, 54 years n = 1 Health Status: unhealthy Condition: idiopathic Parkinson's disease Age Group: 54 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5550880	Disc. AE: Alopecia... AEs leading to discontinuation/dose reduction: Alopecia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/5550880
420 mg 1 times / day multiple, respiratory Recommended Dose: 420 mg, 1 times / day Route: respiratory Route: multiple Dose: 420 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209184s000lbl.pdf	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209184s000lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209184s000lbl.pdf
84 mg 2 times / day multiple, respiratory Recommended Dose: 84 mg, 2 times / day Route: respiratory Route: multiple Dose: 84 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209184s000lbl.pdf	unhealthy, adult n = 114 Health Status: unhealthy Condition: Parkinson’s disease Age Group: adult Population Size: 114 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209184s000lbl.pdf	Disc. AE: Cough... AEs leading to discontinuation/dose reduction: Cough (2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209184s000lbl.pdf
0.51 mg/kg 3 times / day steady, oral Dose: 0.51 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.51 mg/kg, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	unhealthy, child\|adult n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child\|adult Population Size: 15 Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	Other AEs: Headache, Nausea... Other AEs: Headache (below serious, 2 patients) Nausea (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01176435
0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	unhealthy, child\|adult n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child\|adult Population Size: 15 Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	Other AEs: Headache, Dry mouth... Other AEs: Headache (below serious, 1 patient) Dry mouth (below serious, 2 patients) Nausea (below serious, 1 patient) Fatigue (below serious, 2 patients) Sources: https://clinicaltrials.gov/ct2/show/NCT01176435

AEs

AE	Significance	Dose	Population
Alopecia	1 patient Disc. AE	3 g 1 times / day multiple, oral Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5550880	unhealthy, 54 years n = 1 Health Status: unhealthy Condition: idiopathic Parkinson's disease Age Group: 54 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/5550880
Cough	2% Disc. AE	84 mg 2 times / day multiple, respiratory Recommended Dose: 84 mg, 2 times / day Route: respiratory Route: multiple Dose: 84 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209184s000lbl.pdf	unhealthy, adult n = 114 Health Status: unhealthy Condition: Parkinson’s disease Age Group: adult Population Size: 114 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/209184s000lbl.pdf
Headache	below serious, 2 patients	0.51 mg/kg 3 times / day steady, oral Dose: 0.51 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.51 mg/kg, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	unhealthy, child\|adult n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child\|adult Population Size: 15 Sources: https://clinicaltrials.gov/ct2/show/NCT01176435
Nausea	below serious, 2 patients	0.51 mg/kg 3 times / day steady, oral Dose: 0.51 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.51 mg/kg, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	unhealthy, child\|adult n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child\|adult Population Size: 15 Sources: https://clinicaltrials.gov/ct2/show/NCT01176435
Headache	below serious, 1 patient	0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	unhealthy, child\|adult n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child\|adult Population Size: 15 Sources: https://clinicaltrials.gov/ct2/show/NCT01176435
Nausea	below serious, 1 patient	0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	unhealthy, child\|adult n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child\|adult Population Size: 15 Sources: https://clinicaltrials.gov/ct2/show/NCT01176435
Dry mouth	below serious, 2 patients	0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	unhealthy, child\|adult n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child\|adult Population Size: 15 Sources: https://clinicaltrials.gov/ct2/show/NCT01176435
Fatigue	below serious, 2 patients	0.76 mg/kg 3 times / day steady, oral Dose: 0.76 mg/kg, 3 times / day Route: oral Route: steady Dose: 0.76 mg/kg, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/NCT01176435	unhealthy, child\|adult n = 15 Health Status: unhealthy Condition: Vision Impairment Age Group: child\|adult Population Size: 15 Sources: https://clinicaltrials.gov/ct2/show/NCT01176435

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0948	http://www.3bsc.com/index/pro_info.php?id=41853
AA Blocks	AA0036Y3	http://www.aablocks.com/goods/Goods/detail?id=AA0036Y3
AHH Chemical co.,ltd	MB-00616	http://www.ahhchemical.com/product/MB-00616.html
AHH Chemical co.,ltd	MT-53193	http://www.ahhchemical.com/product/MT-53193.html
AHH Chemical co.,ltd	NP-1030	http://www.ahhchemical.com/product/NP-1030.html
AK Scientific, Inc. (AKSCI)	H813	http://www.aksci.com/item_detail.php?cat=H813
AK Scientific, Inc. (AKSCI)	J10404	http://www.aksci.com/item_detail.php?cat=J10404
Aaron Chemicals	AR0037PV	http://www.aaronchem.com/59-92-7
AbMole Bioscience	M3255	http://www.abmole.com/products/levodopa.html
Acadechem	ACDS-070481	http://www.acadechemical.com/product/145180
Achemtek	0104-004095	http://www.achemtek.com/59-92-7
Acorn PharmaTech	ACN-038322	http://www.acornpharmatech.com/
Acros Organics	AC167530050	https://www.fishersci.com/shop/products/3-3-4-dihydroxyphenyl-l-alanine-99-acros-organics-2/AC167530050
Acros Organics	AC167530250	https://www.fishersci.com/shop/products/3-3-4-dihydroxyphenyl-l-alanine-99-acros-organics-2/AC167530250
Acros Organics	AC167531000	https://www.fishersci.com/shop/products/3-3-4-dihydroxyphenyl-l-alanine-99-acros-organics/AC167531000
Acros Organics	AC167535000	https://www.fishersci.com/shop/products/3-3-4-dihydroxyphenyl-l-alanine-99-acros-organics/AC167535000
Alfa Aesar	A11311	https://www.alfa.com/en/catalog/A11311/
Alfa Chemistry	AP59927	https://reagents.alfa-chemistry.com/product/3-4-dihydroxy-l-phenylalanine-cas-59-92-7-13808.html
Alfa Chemistry	AP59927-A	https://reagents.alfa-chemistry.com/product/levodopa-cas-59-92-7-13809.html
Alfa Chemistry	AP59927-B	https://reagents.alfa-chemistry.com/product/levodopa-cas-59-92-7-13810.html
Angene	AGN-PC-0WADKI	http://www.angenechemical.com/productshow/AGN-PC-0WADKI.html
Anward	ANW-33396	http://www.anward.com/pro_result/10378
ApexBio Technology	A8460	http://www.apexbt.com/levodopa-22206.html
ApexBio Technology	N1648	http://www.apexbt.com/levodopa.html
Ark Pharm	AK187821	http://www.arkpharminc.com/products/59-92-7.html
Aurum Pharmatech LLC	KM0355	http://www.Aurumpharmatech.com/Product/ProductDetails/KM0355
AvaChem Scientific	3015	http://www.avachem.com/productSearch.asp?3015
Avantor Inc	101095-322	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101095-322
BioSynth	Q-201294	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-201294.html
Boerchem	BC677906	http://www.boerchem.com/?product_39610.html
BroadPharm	BP-12850	http://www.broadpharm.com/web/product.php?catalog=BP-12850
Chem Scene	CS-1945	http://www.chemscene.com/59-92-7.html
ChemFaces	CFN99800	http://www.chemfaces.com/natural/Levodopa-CFN99800.html
ChemMol	30101553	http://www.chemmol.com/chemmol/30101553.html
ChemMol	44009509	http://www.chemmol.com/chemmol/44009509.html
ChemMol	83602606	http://www.chemmol.com/chemmol/83602606.html
Chemodex	D0465	http://www.chemodex.com/products/D0465
Chemspace	CSSB00000743922	https://chem-space.com/CSSB00000743922
DC Chemicals	DCZ-030	http://www.dcchemicals.com//product_show-Levodopa.html
Enamine	Z1762772338	https://www.enaminestore.com/catalog/Z1762772338
Glentham Life Sciences	GM9724	http://www.glentham.com/products/product/GM9724/
Hairui	HR127040	http://www.hairuichem.com/en/product/59-92-7.html
Hello Bio	HB1925	https://www.hellobio.com/l-dopa.html
LGC Standards	LGCFOR0262.00	https://www.lgcstandards.com/US/en/p/LGCFOR0262.00
LGC Standards	MM0262.00	https://www.lgcstandards.com/US/en/p/MM0262.00
Lab Network	LN00235827	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00235827
MedChem Express	HY-N0304	https://www.medchemexpress.com/L-DOPA.html
OChem	3792	http://www.ocheminc.com/index.php?act=psearch&pid=59L927
Oakwood	358380	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=168845&ExtHyperLink=1
Selleck Chemicals	S1726	http://www.selleckchem.com/products/Levodopa(Sinemet).html
Sigma-Aldrich	72816_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/72816?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP213_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp213?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	L0400000_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/l0400000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	D9628_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/d9628?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1361009_USP	https://www.sigmaaldrich.com/catalog/product/usp/1361009?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S054824	http://www.sinfoobiotech.com/product/1058222
Smolecule	S532941	http://www.smolecule.com/products/s532941
Smolecule	S772657	https://www.smolecule.com/products/s772657
Synthink Research Chemicals	SA31801	https://synthinkchemicals.com/product/carbidopa-ep-impurity-a/
TCI (Tokyo Chemical Industry)	D0600	http://www.tcichemicals.com/eshop/en/us/commodity/D0600/index.html
THE BioTek	bt-273342	https://www.thebiotek.com/product/inhibitors/bt-273342
Tocris	3788	https://www.tocris.com/products/l-dopa_3788
Vesino Industrial Co Ltd	VA11170	http://www.vsnchem.com/goto/product/22521/
VladaChem	VL141956	https://www.vladachem.com/product.php?products=59-92-7
VladaChem	VL162882	https://www.vladachem.com/product.php?products=59-92-7
VladaChem	VL261104-100G	https://www.vladachem.com/product.php?products=59-92-7
Watanabe Chemical Ind.	G00130	https://www.watanabechem.co.jp/en/search/details.php?code=G00130
Yuhao Chemical	LL0046	http://www.chemyuhao.com/59-92-7.html
abcr GmbH	AB110351	http://www.abcr.com/shop/en/AB110351
abcr GmbH	AB518194	http://www.abcr.com/shop/en/AB518194
eNovation Chemicals	D404611	https://www.enovationchem.com/ProductDetails.asp?ProductID=D404611
eNovation Chemicals	D954464	https://www.enovationchem.com/ProductDetails.asp?ProductID=D954464
iChemical	EBD21212	http://www.ichemical.com/products/59-92-7.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-4743781842	https://mcule.com/MCULE-4743781842/

PubMed

Title	Date	PubMed
The effects of combining carbidopa with levodopa for Parkinson's disease.	1975 Dec	1104406
Persistent parkinsonism following neuroleptanalgesia.	1975 May	1130732
Levodopa-induced myoclonus.	1975 May	1079721
Reduction of dyskinesia and induction of akinesia induced by morphine in two parkinsonian patients with severe sciatica.	1999	10907730
The anticataleptic effect of 7-OH-DPAT: are dopamine D3 receptors involved?	1999	10651103
A wide variety of mutations in the parkin gene are responsible for autosomal recessive parkinsonism in Europe. French Parkinson's Disease Genetics Study Group and the European Consortium on Genetic Susceptibility in Parkinson's Disease.	1999 Apr	10072423
Levodopa-induced dyskinesias treated by pallidotomy.	1999 Aug 1	10500264
[Levodopa-induced psychosis in patients with idiopathic Parkinson disease].	1999 Feb 27	10220750
Pharmacokinetics and pharmacodynamics of L-Dopa after acute and 6-week tolcapone administration in patients with Parkinson's disease.	1999 Jan-Feb	10047930
Selective inhibition of cocaine-seeking behaviour by a partial dopamine D3 receptor agonist.	1999 Jul 22	10432116
Modulation of gastrin processing by vesicular monoamine transporter type 1 (VMAT1) in rat gastrin cells.	1999 Jun 1	10332097
Worsening of levodopa-induced dyskinesias by motor and mental tasks.	1999 Mar	10091616
[Amantadine for the treatment of levodopa dyskinesias in Parkinson's disease].	2000	11050808
Effects of oligonucleotide antisense to dopamine D(1A) receptor messenger RNA in a rodent model of levodopa-induced dyskinesia.	2000	10858612
Investigating levodopa-induced dyskinesias in the parkinsonian primate.	2000 Apr	10762135
Bilateral subthalamic stimulation for Parkinson's disease by using three-dimensional stereotactic magnetic resonance imaging and electrophysiological guidance.	2000 Apr	10761650
Combined use of the adenosine A(2A) antagonist KW-6002 with L-DOPA or with selective D1 or D2 dopamine agonists increases antiparkinsonian activity but not dyskinesia in MPTP-treated monkeys.	2000 Apr	10739638
L-Dopa uptake and dopamine production in proximal tubular cells are regulated by beta(2)-adrenergic receptors.	2000 Jul	10894789
Relationship among nigrostriatal denervation, parkinsonism, and dyskinesias in the MPTP primate model.	2000 May	10830409
Centrally initiated postural adjustments in parkinsonian patients on and off levodopa.	2000 Nov	11067986
The 4F2hc/LAT1 complex transports L-DOPA across the blood-brain barrier.	2000 Oct 6	11011012
Workshop IV: drug treatment guidelines for the long-term management of Parkinson's disease.	2000 Sep	11199819
Levodopa-induced drowsiness in healthy volunteers: results of a choice reaction time test combined with a subjective evaluation of sedation.	2001 Mar-Apr	11307043
Intravenous amantadine improves levadopa-induced dyskinesias: an acute double-blind placebo-controlled study.	2001 May	11391748
Coadministration of (-)-OSU6162 with l-DOPA normalizes preproenkephalin mRNA expression in the sensorimotor striatum of primates with unilateral 6-OHDA lesions.	2001 May	11312565

Patents

Sample Use Guides

In Vivo Use Guide

Maximum dosage in a 24-hour period is eight tablets (Stalevo 50, containing 12.5 mg of carbidopa, 50 mg of levodopa and 200 mg of entacapone; Stalevo 75, containing 18.75 mg of carbidopa, 75 mg of levodopa and 200 mg of entacapone; Stalevo 100, containing 25 mg of carbidopa, 100 mg of levodopa and 200 mg of entacapone; Stalevo 125, containing 31.25 mg of carbidopa, 125 mg of levodopa and 200 mg of entacapone; Stalevo 150, containing 37.5 mg of carbidopa, 150 mg of levodopa and 200 mg of entacapone; Stalevo 200, containing 50 mg of carbidopa, 200 mg of levodopa and 200 mg of entacapone). The optimum daily dosage must be determined by careful titration in each patient.

Route of Administration: Oral

In Vitro Use Guide

Low dose (<30 uM) Levodopa protects PC12 cells against oxidative stress which might be related to the up-regulation of CD39 and pCREB expression.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:46:28 GMT 2023` Edited by `admin` on `Fri Dec 15 16:46:28 GMT 2023`
Record UNII	M30686U4X4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MELEVODOPA

Official Name

English

CHF-1301

Code

English

(-)-3,4-DIHYDROXY-L-PHENYLALANINE, METHYL ESTER

Common Name

English

Melevodopa [WHO-DD]

Common Name

English

melevodopa [INN]

Common Name

English

LEVOMET

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QN04BA04