Tìm theo
L-DOPA
Các tên gọi khác (17 ) :
  • (-)-3-(3,4-Dihydroxyphenyl)-L-alanine
  • (-)-Dopa
  • (−)-3-(3,4-dihydroxyphenyl)-L-alanine
  • (−)-dopa
  • 3-Hydroxy-L-tyrosine
  • 3,4-Dihydroxy-L-phenylalanine
  • 3,4-DIHYDROXYPHENYLALANINE
  • beta-(3,4-Dihydroxyphenyl)-L-alanine
  • beta-(3,4-Dihydroxyphenyl)alanine
  • Dihydroxy-L-phenylalanine
  • Dopar
  • L-3,4-dihydroxyphenylalanine
  • L-beta-(3,4-Dihydroxyphenyl)alanine
  • L-DOPA
  • Levodopa
  • Levodopum
  • β-(3,4-dihydroxyphenyl)alanine
dopamine agents, antiparkinson agents, antidyskinetics
Thuốc Gốc
Small Molecule
CAS: 59-92-7
ATC: N04BA01, N04BA04
ĐG : Actavis Group , http://www.actavis.com
CTHH: C9H11NO4
PTK: 197.1879
The naturally occurring form of dihydroxyphenylalanine and the immediate precursor of dopamine. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. It is used for the treatment of parkinsonian disorders and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C9H11NO4
Phân tử khối
197.1879
Monoisotopic mass
197.068807845
InChI
InChI=1S/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
InChI Key
InChIKey=WTDRDQBEARUVNC-LURJTMIESA-N
IUPAC Name
(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
Traditional IUPAC Name
levodopa
SMILES
N[C@@H](CC1=CC(O)=C(O)C=C1)C(O)=O
Độ tan chảy
284-285
Độ hòa tan
5000 mg/L (at 20 °C)
logP
-2.39
logS
-1.6
pKa (strongest acidic)
1.65
pKa (Strongest Basic)
9.06
PSA
103.78 Å2
Refractivity
49.08 m3·mol-1
Polarizability
18.91 Å3
Rotatable Bond Count
3
H Bond Acceptor Count
5
H Bond Donor Count
4
Physiological Charge
0
Number of Rings
1
Bioavailability
1
Rule of Five
true
pKa
2.32 (at 25 °C)
Dược Lực Học : Levodopa (L-dopa) is used to replace dopamine lost in Parkinson's disease because dopamine itself cannot cross the blood-brain barrier where its precursor can. However, L-DOPA is converted to dopamine in the periphery as well as in the CNS, so it is administered with a peripheral DDC (dopamine decarboxylase) inhibitor such as carbidopa, without which 90% is metabolised in the gut wall, and with a COMT inhibitor if possible; this prevents about a 5% loss. The form given therapeutically is therefore a prodrug which avoids decarboxylation in the stomach and periphery, can cross the blood-brain barrier, and once in the brain is converted to the neurotransmitter dopamine by the enzyme aromatic-L-amino-acid decarboxylase.
Cơ Chế Tác Dụng : The naturally occurring form of dihydroxyphenylalanine and the immediate precursor of dopamine. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to dopamine. It is used for the treatment of parkinsonian disorders and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system. [PubChem] Striatal dopamine levels in symptomatic Parkinson's disease are decreased by 60 to 80%, striatal dopaminergic neurotransmission may be enhanced by exogenous supplementation of dopamine through administration of dopamine's precursor, levodopa. A small percentage of each levodopa dose crosses the blood-brain barrier and is decarboxylated to dopamine. This newly formed dopamine then is available to stimulate dopaminergic receptors, thus compensating for the depleted supply of endogenous dopamine.
Dược Động Học :
▧ Absorption :
Levodopa is rapidly absorbed from the proximal small intestine by the large neutral amino acid (LNAA) transport carrier system.
▧ Protein binding :
High
▧ Metabolism :
95% of an administered oral dose of levodopa is pre-systemically decarboxylated to dopamine by the L-aromatic amino acid decarboxylase (AAAD) enzyme in the stomach, lumen of the intestine, kidney, and liver. Levodopa also may be methoxylated by the hepatic catechol-O-methyltransferase (COMT) enzyme system to 3-O-methyldopa (3-OMD), which cannot be converted to central dopamine.
▧ Half Life :
50 to 90 minutes
Độc Tính : Oral, mouse: LD50 = 2363 mg/kg; Oral, rabbit: LD50 = 609 mg/kg; Oral, rat: LD50 = 1780 mg/kg.
Chỉ Định : For the treatment of idiopathic Parkinson's disease (Paralysis Agitans), postencephalitic parkinsonism, symptomatic parkinsonism which may follow injury to the nervous system by carbon monoxide intoxication, and manganese intoxication.
Tương Tác Thuốc :
  • Fosphenytoin The hydantoin decreases the effect of levodopa
  • Iron Dextran Iron decreases the absorption of dopa derivatives
  • Isocarboxazid Possible hypertensive crisis
  • Methyldopa Methyldopa increases the effect and toxicity of levodopa
  • Metoclopramide Levodopa decreases the effect of metoclopramide
  • Paliperidone The atypical antipsychotic agent, paliperidone, may decrease the therapeutic effect of the anti-Parkinson's agent, levodopa. This interaction may be due to the dopamine antagonist properties of paliperidone. Consider an alternate antipsychotic in those with Parkinson's disease or consider using clozapine or quetiapine if an atypical antipsychotic is necessary.
  • Phenelzine Possible hypertensive crisis
  • Phenytoin The hydantoin decreases the effect of levodopa
  • Tetrabenazine Tetrabenazine may cause Parkinsonian symptoms and neutralize the effect of Levodopa.
  • Thiothixene Thiothixene may antaonize the effects of the anti-Parkinsonian agent, Levodopa. Consider alternate therapy or monitor for decreased effects of both agents.
  • Tranylcypromine Levodopa may increase the adverse effects of Tranylcypromine. Risk of severe hypertension. Concomitant therapy should be avoided or monitored closely for adverse effects of Tranylcypromine.
  • Ziprasidone The atypical antipsychotic, ziprasidone, may antagonize the effect of the dopamine agonist, levodopa. Consider alternate therapy or monitor for worsening of movement disorder.
  • Zuclopenthixol Antagonism may occur between zuclopenthixol, a dopamine D2 receptor antagonist, and levodopa, a dopamine agonist. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of both agents if concurrent therapy is initiated, discontinued or dose(s) changed.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
  • Biệt dược thương mại : Levodopa powder
    Giá bán buôn : USD >7.31
    Đơn vị tính : g
  • Biệt dược thương mại : L-dopa powder
    Giá bán buôn : USD >15.19
    Đơn vị tính : g
Nhà Sản Xuất
  • Công ty : GlaxoSmithKline
    Sản phẩm biệt dược : Bidopal
  • Công ty :
    Sản phẩm biệt dược : Dopar
  • Sản phẩm biệt dược : Doparl
  • Công ty : Daiichi Sankyo
    Sản phẩm biệt dược : Dopasol
  • Công ty : Ohara Yakuhin
    Sản phẩm biệt dược : Dopaston
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01235
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=6047
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508120
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C00355
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00059
ChemSpider
http://www.chemspider.com/Chemical-Structure.5824.html
PharmGKB
http://www.pharmgkb.org/drug/PA450213
Wikipedia
http://en.wikipedia.org/wiki/Levodopa
RxList
http://www.rxlist.com/cgi/generic3/stalevo.htm
Drugs.com
http://www.drugs.com/mtm/levodopa.html
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