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L-DOPA(CAS No. 59-92-7)

L-DOPA C9H11NO4 (cas 59-92-7) Molecular Structure

59-92-7 Structure

Identification and Related Records

【Name】
L-DOPA
【CAS Registry number】
59-92-7
【Synonyms】
L-3-(3,4-Dihydroxyphenyl)alanine
Levodopa
L-DOPA 3,4-L-Dihydroxyphenylalanine
3-Hydroxy-L-tyrosine
H-Tyr(3-OH)-OH
L-3-Hydroxytyrosine
【EINECS(EC#)】
200-445-2
【Molecular Formula】
C9H11NO4 (Products with the same molecular formula)
【Molecular Weight】
197.19
【Inchi】
InChI=1/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
【Canonical SMILES】
C1=CC(=C(C=C1CC(C(=O)O)N)O)O
【Isomers smiles】
C1=CC(=C(C=C1C[C@@H](C(=O)O)N)O)O
【MOL File】
59-92-7.mol

Chemical and Physical Properties

【Appearance】
Colorless Crystalline Powder
【Density】
1.468g/cm3
【Melting Point】
295℃
【Boiling Point】
448.4 °C at 760 mmHg
【Refractive Index】
-12 ° (C=5, 1mol/L HCl)
【Flash Point】
225 °C
【Alpha】
-11.7 o (C=5.3, 1N HCL)
【Solubilities】
1.6 g/L
【Color/Form】
Colorless to white crystals or crystalline powder; needles from water
【Stability】
Stable. Incompatible with strong oxidizing agents. Light and air sensitive.
【Storage temp】
2-8°C
【Spectral properties】
Specific optical rotation: -13.1 deg @ 13 deg C/D (c= 5.12 in 1 N HCl); max absorption (0.001 N HCl): 220.5 nm (log e= 3.79); 280 nm (log e= 3.42)
IR: 10623 (Sadtler Research Laboratories Prism Collection)
MASS: 76457 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)
UV: 20883 (Sadtler Research Laboratories Spectral Collection)
In the presence of moisture, L-dopa is rapidly oxidized by atmospheric oxygen and darkens.
【Computed Properties】
Molecular Weight:197.18794 [g/mol]
Molecular Formula:C9H11NO4
XLogP3:-2.7
H-Bond Donor:4
H-Bond Acceptor:5
Rotatable Bond Count:3
Tautomer Count:18
Exact Mass:197.068808
MonoIsotopic Mass:197.068808
Topological Polar Surface Area:104
Heavy Atom Count:14
Formal Charge:0
Complexity:209
Isotope Atom Count:0
Defined Atom Stereocenter Count:1
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Donor Count:3
Feature 3D Anion Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:1
Effective Rotor Count:3
Conformer Sampling RMSD:0.6
CID Conformer Count:21

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R22
【Safety Statements 】
S24/25
【Safety】

Poison by ingestion. Moderately toxic by intravenous and intraperitoneal routes. Human systemic effects by ingestion: somnolence, hallucinations and distorted perceptions, toxic psychosis, motor activity changes, ataxia, dyspnea. Experimental teratogenic and reproductive effects. Questionable human carcinogen producing skin tumors. Human mutation data reported. An anticholinergic agent used as an anti-Parkinsonian drug. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:? Xi
The Risk Statements information of? D-glucose?:
41:? Risk of serious damage to eyes?
36/37/38:? Irritating to eyes, respiratory system and skin?
The Risk Statements information of? D-glucose?:
22:? Do not breathe dust?
26:? In case of contact with eyes, rinse immediately with plenty of water and seek medical advice?
36:? Wear suitable protective clothing
24/25:? Avoid contact with skin and eyes??
WGK Germany: 1
Hazard Note: Irritant/Light Sensitive

【Transport】
OTH
【Formulations/Preparations】
CAPSULES USP: 100, 250, & 500 MG; TABLETS USP: 100, 250, & 500 MG.
Levodopa is one of the main ingredients along with carbidopa in the drug Sinemet ... (tablets)
Levodopa is one of the main ingredients along with carbidopa in the drug Atamet ... (tablets)
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl levodopa, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

?Levodopa , its cas register number is 59-92-7. It also can be called 3-(3,4-Dihydroxyphenyl)-L-alanine ; L-3-(3,4-Dihydroxyphenyl)alanine ; L-DOPA ; and L-o-Hydroxytyrosine . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin:?Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Or in the eyes:?Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product:?Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
In addition, Levodopa (CAS NO.59-92-7) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products:?Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.

【Octanol/Water Partition Coefficient】
log Kow = -2.39
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Derived from several types of beans including vanilla.
Preparation from L-tyrosine: Vorbruggen, Krolikiewicz, Ber. 105, 1168 (1972); Bretschneider et al., Helv. Chim. Acta 56, 2857 (1973); from Vicia faba beans: Wysong, US 3253023 (1966 to Dow Chem.); by fermentation of L-tyrosine: Sih et al., J. Am. Chem. Soc. 91, 6204 (1969); Florent, Renaut, DE 2102793 (1971 to Rhone-Poulenc), C.A. 75, 108505f (1971). Separation from racemate: Vogler, Baumgartner, Helv. Chim. Acta 35, 1776 (1952); NL 6514950; US 3405159 (1966, 1968 both to Merck & Co.)
Production: glycine + acetic anhydride + vanillin (amide formation/carbonyl condensation/chiral catalytic hydrogenation/hydrolysis. Production: 2,4-dihydroxybenzaldehyde + hydrogen cyanide + ammonia (Strecker synthesis/racemate separation). Production: catechol + pyruvic acid + ammonia (microbial conversion)
【Usage】

Natural isomer of the immediate precursor of dopamine; product of tyrsine hydroxylase

Biomedical Effects and Toxicity

【Biological Activity】
Immediate precursor of dopamine, produced by tyrosine hydroxylase. Displays antiParkinsonian activity.
【Pharmacological Action】
- Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists.
- Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.
【Therapeutic Uses】
Levodopa is indicated to alleviate symptoms and allow more normal body movements with improved muscle control in the treatment of idiopathic Parkinson's disease, postencephalitic parkinsonism, or symptomatic parkinsonism that may follow injury to the nervous system by carbon monoxide intoxication or manganese intoxication. It is also indicated in parkinsonism associated with cerebral arteriosclerosis. /Included in US product labeling/
Levodopa, the metabolic precursor of dopamine, is the single most effective agent in the treatment of Parkinson's Disease.
LEVODOPA AFFORDS ONLY SYMPTOMATIC RELIEF OF PARKINSONISM. IF DRUG IS STOPPED, ALL PREEXISTING SYMPTOMS GRADUALLY RETURN WITHIN WK OR TWO; UPON RESUMPTION OF L-DOPA THERAPY AFTER PERIOD OF WITHDRAWAL, PREVIOUS THERAPEUTIC RESPONSE IS REESTABLISHED AFTER WK OR MORE.
...L-DOPA...HAS BEEN MORE CONSISTENTLY EFFECTIVE IN TREATMENT OF CHRONIC MANGANESE POISONING THAN IN PARKINSON'S DISEASE.
EXTRAPYRAMIDAL SYMPTOMS BUT NOT DEMENTIA IN PT WITH PARKINSONISM-DEMENTIA OF GUAM...RESPOND FAVORABLY TO DRUG. ...MARKED & SUSTAINED IMPROVEMENT IN PARKINSONIAN SYMPTOMS RESULTING FROM CARBON MONOXIDE POISONING.
LEVODOPA THERAPY MAY IMPROVE MENTAL & CIRCULATORY STATUS OF PT IN HEPATIC FAILURE.
/IN CLINICAL TRIALS OF DRUG/ SOME IMPROVEMENT IN MOTOR SYMPTOMS...REPORTED IN PT WITH TORSION DYSTONIAS, ATHETOID CEREBRAL PALSY, & PROGRESSIVE SUPRANUCLEAR PALSY, BUT RESULTS HAVE NOT BEEN IMPRESSIVE.
In modern practice, levodopa is almost always admin in combination with a peripherally acting inhibitor of aromatic L-amino acid decarboxylase, such as carbidopa or benserazide. If levodopa is admin alone, the drug is largely decarboxylated by enzymes in the intestinal mucosa & other peripheral sites, so that relatively little unchanged drug reaches the cerebral circulation & probably <1% penetrates the CNS.
Treatment of neuroleptic malignant syndrome
The safety and efficacy of ropinirole hydrochloride (Requip) were compared with that of benserazide hydrochloride in combination with levodopa (Madopar) over a period of 5 yr in patients with early Parkinson's disease who were given ropinirole (n=85) or the levodopa combination (n=89) in a prospective, randomized, double blind study; if symptoms were not adequately controlled by the assigned study medication, patients could receive supplementary levodopa, administered in an open-label fashion. In the ropinirole group, 29 of the 85 patients (34%) received no levodopa supplementation. At 5 yr, the cumulative incidence of dyskinesia, regardless of levodopa supplementation, was 20% in the ropinirole group and 45% in the levodopa group. There was no significant difference between the 2 groups in the mean change in scores for activities of daily living among those who completed the study. Adverse events led to the early withdrawal from the study of 48 of 179 patients in the ropinirole group (27%) and 29 of 89 patients in the levodopa group (33%). ... /Levodopa/benserazide/ [Rascol O et al; N Engl J Med 342 : 1484-1491 (2000)]
【Biomedical Effects and Toxicity】
...DRUG...MAY APPEAR IN MILK.
AFTER IP INJECTION INTO MICE, BIOTRANSFORMATION OF 60% OF RADIOACTIVELY LABELLED DL-DOPA TAKES PLACE WITHIN 10 MIN, & PEAK DOPAMINE LEVELS ARE REACHED 20 MIN AFTER ADMIN. ...APPROX 0.1% OF DOSE WAS PRESENT IN THE BRAIN AS (14)C-L-DOPA OR (14)C-DOPAMINE. /DL-DOPA/
MORE THAN 95% OF LEVODOPA IS DECARBOXYLATED IN PERIPHERY BY WIDELY DISTRIBUTED EXTRACEREBRAL AROMATIC L-AMINO ACID DECARBOXYLASE. ...LITTLE UNCHANGED DRUG REACHES CEREBRAL CIRCULATION & PROBABLY LESS THAN 1% PENETRATES INTO CNS.
MOST IS CONVERTED TO DOPAMINE... DOPAMINE METABOLITES ARE RAPIDLY EXCRETED IN URINE, ABOUT 80% OF RADIOACTIVELY LABELED DOSE BEING RECOVERED WITHIN 24 HR. ... THESE METABOLITES /3,4-DIHYDROXYPHENYLACETIC ACID & 3-METHOXY-4-HYDROXYPHENYLACETIC ACID/, AS WELL AS SMALL AMT OF LEVODOPA & DOPAMINE, ALSO APPEAR IN CEREBROSPINAL FLUID.
AFTER ADMIN OF L-DOPA TO RATS BY MOUTH, 18 METABOLITES WERE EXCRETED IN URINE...EXCRETION OF L-DOPA WAS LESS THAN 1% OF DOSE.
Pharmacokinetics & pharmacodynamics of levodopa were evaluated at a high-resolution level in a heterogeneous group of 10 patients with idiopathic Parkinson's disease during their normal daily activity. A physician & a nurse spent 10 hrs with each patient from the first morning dose of levodopa during daily activities at home & at work. Plasma samples were obtained every 20 min for analysis of levodopa & 3-O-methyldopa by high-performance liquid chromatography. To assess clinical response, mobility was rated on every test occasion by patients & by investigators. Food & fluid intake & physical activity were also monitored. There was a large intra- & interindividual variability in the pharmacokinetics of levodopa regardless of the different drug combinations used. Mean plasma levodopa concn ranged between 0.45-7.07 ug/ml & peak concns between 0.95-13.75 ug/ml. In 44 of 58 dosing events, an oral dose of levodopa was related to a peak in plasma concn. Assessment of the clinical effects was more sensitive when given by patients than when given by the investigators. The fluctuations of the levodopa concn in plasma had a clear effect on the clinical parameters assessed, even during early disease stages. Variation in levodopa concn is the determining factor for motor fluctuations also in patients on clinically optimized combinations with dopamine agonists & enzyme inhibitors. [Nyholm D, et al; Clin Neuropharmacol 25 (2): 89-96 (2002)] PubMed Abstract
The effects of age on the oral and systemic availability of levodopa (I) and the relative contribution of intestinal and hepatic first pass metabolism to the overall first pass effect of I were studied by comparing the plasma I levels after intravenous injection, oral administration and intraportal injection of 20 mg/kg I to rats. The contribution of the gut to the overall first pass effect of I was greater than that of the liver in any age group of the rats. Both the overall and intestinal first pass effects of I were greatest in 11 wk old rats and relatively small in both young and aged rats. In contrast, the hepatic first pass effect did not show any significant age dependent change. Age related change in the jejunal blood flow could not explain the unique age dependence in the intestinal first pass metabolism of I. It was noted that the age dependence in the oral systemic availability of I between adult and aged rats was found to be similar to the tendency that has been reported between normal adult subjects and aged patients with Parkinson disease. [Iwamoto K et al; J Pharm Pharmacol 39 : 421-425 (1987)] PubMed Abstract
The effects of multiple dosing of levodopa on gastric emptying and levodopa absorption were studied in 8 healthy volunteers, ages 23-25 yr, who received in a randomized, 2-way crossover, double-blind manner, 3 oral doses of levodopa 125 mg suspended in 100 ml water, given at 2 h intervals on one day and 2 doses of placebo and a single oral dose of levodopa 125 mg suspension at 2 h intervals on the next day. A low incidence of multiple peak plasma concentrations of levodopa was detected after all doses of levodopa. The area under the plasma concentration-time curves (AUC) for the final dose of levodopa was lower than for the two preceding doses but not different from that of the single dose given at the same time of day, indicating that the lower AUC of the final dose of levodopa was related to the time of administration and not the result of the two preceding doses. It was concluded that multiple small doses of 125 mg of levodopa produced no cumulative effects on gastric emptying in young healthy volunteers. [Waller DG et al; Br J Clin Pharmacol 32 : 691-695 (1991)] PubMed Abstract
When admin orally, levodopa is rapidly absorbed from the small bowel by an active transport system for aromatic amino acids.
... LEVODOPA IS RAPIDLY ABSORBED FROM THE SMALL BOWEL BY ACTIVE TRANSPORT SYSTEM FOR AROMATIC AMINO ACIDS. CONCN OF THE DRUG IN PLASMA USUALLY PEAK BETWEEN 0.5 & 2 HR AFTER ORAL DOSE. THE HALF-LIFE IN PLASMA IS SHORT (1-3 HR). THE RATE & EXTENT OF ABSORPTION OF LEVODOPA IS DEPENDENT UPON THE RATE OF GASTRIC EMPTYING, THE pH OF GASTRIC JUICE, & THE LENGTH OF TIME THE DRUG IS EXPOSED TO THE DEGRADATIVE ENZYMES OF GASTRIC & INTESTINAL MUCOSA.
The clinical effects and pharmacokinetics of levodopa (I) after an oral 100 mg capsule and following an intravenous injection of 200 mg were studied in 7 patients (aged 42-66 yr) with Parkinson's disease. Plasma I concentrations were maintained within narrower limits after an IV dose as compared to conventional oral therapy. There was considerable variation in the oral absorption and elimination of I both within and between subjects. The concentration of the 3-OME dopa metabolite in plasma hardly increased during each day's therapy and in all cases levels were greater than the maximum concentrations of I, by about a factor of 10. ... [Hardie RJ et al; Br J Clin Pharmacol 22 : 429-436 (1986)] PubMed Abstract

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