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(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic AcidL-dopa

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Chemistry

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Also known as: L-dopa, 59-92-7, Dopar, 3,4-dihydroxy-l-phenylalanine, 3-hydroxy-l-tyrosine, Bendopa

Molecular Formula

C₉H₁₁NO₄

Molecular Weight

197.19 g/mol

InChI Key

WTDRDQBEARUVNC-LURJTMIESA-N

FDA UNII

46627O600J

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.

Levodopa is an Aromatic Amino Acid.

1 2D Structure

CAS 59-92-7

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid

2.1.2 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

2.1.3 InChI Key

WTDRDQBEARUVNC-LURJTMIESA-N

2.1.4 Canonical SMILES

C1=CC(=C(C=C1CC(C(=O)O)N)O)O

2.1.5 Isomeric SMILES

C1=CC(=C(C=C1C[C@@H](C(=O)O)N)O)O

2.2 Other Identifiers

2.2.1 UNII

46627O600J

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3 Hydroxy L Tyrosine

2. 3-hydroxy-l-tyrosine

3. Dopaflex

4. Dopar

5. L 3,4 Dihydroxyphenylalanine

6. L Dopa

7. L-3,4-dihydroxyphenylalanine

8. L-dopa

9. Larodopa

10. Levopa

2.3.2 Depositor-Supplied Synonyms

1. L-dopa

2. 59-92-7

3. Dopar

4. 3,4-dihydroxy-l-phenylalanine

5. 3-hydroxy-l-tyrosine

6. Bendopa

7. Larodopa

8. Levopa

9. 3,4-dihydroxyphenylalanine

10. Brocadopa

11. Cidandopa

12. Insulamina

13. Maipedopa

14. Dopaidan

15. Dopalina

16. Dopasol

17. Eldopal

18. Eldopar

19. Pardopa

20. Prodopa

21. Syndopa

22. 3-(3,4-dihydroxyphenyl)-l-alanine

23. (-)-dopa

24. Dihydroxy-l-phenylalanine

25. Helfo-dopa

26. Dopaflex

27. Deadopa

28. Dopal-fher

29. Doparkine

30. Dopaston

31. Dopastral

32. Eldopatec

33. Eurodopa

34. Doparl

35. Doprin

36. Veldopa

37. L-3,4-dihydroxyphenylalanine

38. (2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoic Acid

39. Levedopa

40. Levodopum

41. L-o-hydroxytyrosine

42. L-tyrosine, 3-hydroxy-

43. Dopa

44. (-)-3-(3,4-dihydroxyphenyl)-l-alanine

45. Ledopa

46. 3,4-dihydroxyphenyl-l-alanine

47. Dopaston Se

48. Beta-(3,4-dihydroxyphenyl)-l-alanine

49. L-(o-dihydroxyphenyl)alanine

50. L-(-)-dopa

51. L-3-hydroxytyrosine

52. L-beta-(3,4-dihydroxyphenyl)alanine

53. Weldopa

54. Parda

55. L-dihydroxyphenylalanine

56. L-3-(3,4-dihydroxyphenyl)alanine

57. (s)-2-amino-3-(3,4-dihydroxyphenyl)propanoic Acid

58. Ro 4-6316

59. Beta-(3,4-dihydroxyphenyl)alanine

60. Inbrija

61. Cvt-301

62. Alanine, 3-(3,4-dihydroxyphenyl)-, L-

63. Dihydroxyphenylalanine

64. Component Of Sinemet

65. Dopar (tn)

66. Chebi:15765

67. Beta-(3,4-dihydroxyphenyl)-alpha-l-alanine

68. L-beta-(3,4-dihydroxyphenyl)-alpha-alanine

69. Alanine, 3-(3,4-dihydroxyphenyl)-, (-)-

70. L(-)-dopa

71. (-)-(3,4-dihydroxyphenyl)alanine

72. Nsc-118381

73. L-.beta.-(3,4-dihydroxyphenyl)alanine

74. Chembl1009

75. .beta.-(3,4-dihydroxyphenyl)-l-alanine

76. L-(3,4-dihydroxyphenyl)alanine

77. L-tyrosine, 3-hydroxy-, Homopolymer

78. Nsc118381

79. .beta.-(3,4-dihydroxyphenyl)alanine

80. Cas-59-92-7

81. Ncgc00016270-04

82. Biodopa

83. Cerepap

84. Laradopa

85. Sobiodopa

86. L-(3,4-dihydroxyphenyl)-.alpha.-alanine

87. 46627o600j

88. Mfcd00002598

89. V-1512

90. C9h11no4

91. Helfo Dopa

92. 65170-01-6

93. Beta-(3,4-dihydroxyphenyl)-alpha-alanine

94. Atamet

95. Levodopum [inn-latin]

96. Bdbm50130192

97. L-o-dihydroxyphenylalanine

98. L Dopa

99. L-3

100. Ccris 3766

101. Hsdb 3348

102. Wln: Qvyz1r Cq Dq

103. 3,4-dihydroxyphenylalanine (van)

104. Sr-01000075384

105. Einecs 200-445-2

106. Nsc 118381

107. L-3,4-dihydrophenylalanine

108. Dopastone

109. Dopicar

110. Prolopa

111. (2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoate

112. Unii-46627o600j

113. Prestwick_185

114. Levodopa (sinemet)

115. L-dopa; Levodopa

116. Madopa (salt/mix)

117. Levodopa [usan:usp:inn:ban:jan]

118. Spectrum_000454

119. 4-dihydroxyphenylalanine

120. Levodopa [hsdb]

121. Levodopa [usan]

122. Levodopa [inn]

123. Levodopa [jan]

124. Carbidopa Ep Impurity A

125. Levodopa [mi]

126. Levodopa [vandf]

127. Prestwick0_000017

128. Prestwick1_000017

129. Prestwick2_000017

130. Prestwick3_000017

131. Spectrum2_000496

132. Spectrum4_000539

133. Spectrum5_001899

134. Lopac-d-9628

135. Levodopa (jp15/usp)

136. Dsstox_cid_3209

137. Levodopa [mart.]

138. Bmse000322

139. Epitope Id:150927

140. Levodopa [usp-rs]

141. Levodopa [who-dd]

142. Levodopa [who-ip]

143. Dopa, L-

144. 3, 4-dihydroxyphenylalanine

145. Alanine,4-dihydroxyphenyl)-

146. Dsstox_rid_76926

147. Levodopa [ema Epar]

148. Dsstox_gsid_23209

149. Lopac0_000454

150. Schembl22655

151. Bspbio_000053

152. Bspbio_002354

153. Kbiogr_001177

154. Kbioss_000934

155. L-4-5-dihydroxyphenylalanine

156. Mls000028514

157. Bidd:gt0158

158. Divk1c_000452

159. Spectrum2300205

160. Levodopa (jp17/usp/inn)

161. Spbio_000391

162. Spbio_001974

163. Dhivy Component Levodopa

164. Duopa Component Levodopa

165. Levodopa [ep Impurity]

166. Levodopa [orange Book]

167. Bpbio1_000059

168. Gtpl3639

169. Levodopa [ep Monograph]

170. Rytary Component Levodopa

171. B-(3,4-dihydroxyphenyl)alanine

172. Dtxsid9023209

173. Levodopa [usp Monograph]

174. Wln: Qvyz1r Cq Dq -l

175. 3, 4-dihydroxy-l-phenylalanine

176. Bdbm60928

177. Hms501g14

178. Kbio1_000452

179. Kbio2_000934

180. Kbio2_003502

181. Kbio2_006070

182. Parcopa Component Levodopa

183. Stalevo Component Levodopa

184. Levodopum [who-ip Latin]

185. Alanine,4-dihydroxyphenyl)-, L-

186. Carbilev Component Levodopa

187. Corbilta Component Levodopa

188. Dopasnap Component Levodopa

189. Ipx203 Component Levodopa

190. L-(3, 4-dihydroxyphenyl)alanine

191. Ninds_000452

192. Hms1568c15

193. Hms1922j14

194. Hms2090o08

195. Hms2093n04

196. Hms2095c15

197. Hms2230b04

198. Hms3261k10

199. Hms3712c15

200. Levodopa Component Of Dhivy

201. Levodopa Component Of Duopa

202. Pharmakon1600-02300205

203. Zinc895199

204. H-phe{3,4-(oh)2}-oh

205. Hy-n0304

206. Ipx-203 Component Levodopa

207. Levodopa Component Of Rytary

208. Levodopa;3,4-dihydroxyphenylalanine

209. B-(3,4-dihydroxyphenyl)-l-alanine

210. Inbrija (levodopa Inhalation Powder)

211. Levodopa Component Of Parcopa

212. Levodopa Component Of Sinemet

213. Levodopa Component Of Stalevo

214. Tox21_110338

215. Tox21_500454

216. Ccg-39571

217. L-3-(3,4-dihydroxy-phenyl)alanine

218. L-3-(3,4-dihydroxyphenyl)-alanine

219. Nsc759573

220. Pdsp1_001541

221. Pdsp2_001525

222. S1726

223. Alanine, 3-(3,4-dihydroxyphenyl)-

224. Alanine,4-dihydroxyphenyl)-, (-)-

225. Levodopa Component Of Carbilev

226. Levodopa Component Of Corbilta

227. Levodopa Component Of Dopasnap

228. Akos010396267

229. B-(3,4-dihydroxyphenyl)-a-l-alanine

230. L-b-(3,4-dihydroxyphenyl)-a-alanine

231. .beta.-(3, 4-dihydroxyphenyl)alanine

232. Ac-8432

233. Am82124

234. Cs-1945

235. Db01235

236. Lp00454

237. Nsc-759573

238. Sdccgmls-0066924.p001

239. Sdccgsbi-0050439.p004

240. Idi1_000452

241. Ncgc00015384-01

242. Ncgc00016270-01

243. Ncgc00016270-06

244. Ncgc00016270-07

245. Ncgc00016270-09

246. Ncgc00016270-10

247. Ncgc00016270-22

248. Ncgc00093869-04

249. Ncgc00261139-01

250. As-13287

251. Bp-12850

252. Smr000058312

253. Sbi-0050439.p003

254. L-(3, 4-dihydroxyphenyl)-.alpha.-alanine

255. D0600

256. D9628

257. Eu-0100454

258. N1648

259. 59l927

260. Alanine, 3-(3, 4-dihydroxyphenyl)-, (-)-

261. C00355

262. D 9628

263. D00059

264. D70595

265. 3,4-dihydroxy-l-phenylalanine, >=98% (tlc)

266. Ab00052418-06

267. Ab00052418-07

268. Ab00052418_08

269. Ab00052418_09

270. A832543

271. Q300989

272. Q-201294

273. Sr-01000075384-1

274. Sr-01000075384-4

275. Sr-01000075384-6

276. Sr-01000075384-7

277. (s)-2-amino-3-(3,4-dihydroxy-phenyl)-propionic Acid

278. F0347-4695

279. Levodopa, British Pharmacopoeia (bp) Reference Standard

280. Levodopa, European Pharmacopoeia (ep) Reference Standard

281. Z1762772338

282. (2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoic Acidl-dopa

283. 1e83f927-c221-46aa-b90a-81b33c5f3868

284. 3,4-dihydroxy-l-phenylalanine, Vetec(tm) Reagent Grade, 98%

285. Levodopa Component Of Levodopa/carbidopa/entacapone Orion

286. Levodopa, United States Pharmacopeia (usp) Reference Standard

287. Levodopa/carbidopa/entacapone Orion Component Levodopa

288. 3,4-dihydroxy-l-phenylalanine, Certified Reference Material, Tracecert(r)

289. Levodopa, Pharmaceutical Secondary Standard; Certified Reference Material

290. 122769-74-8

291. L-methyldopa ; (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic Acid; 3-(3,4-dihydroxyphenyl)-?-methyl-l-alanine; 3-hydroxy-a-methyl-l-tyrosine

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₉H₁₁NO₄
Molecular Weight	197.19 g/mol
XLogP3	-2.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	197.06880783 g/mol
Monoisotopic Mass	197.06880783 g/mol
Topological Polar Surface Area	104 Å²
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

4 Drug and Medication Information

4.1 Drug Information

1 of 12
Drug Name	CARBIDOPA AND LEVODOPA
Active Ingredient	CARBIDOPA; LEVODOPA
Company	ACCORD HLTHCARE (Application Number: A202323); ACTAVIS ELIZABETH (Application Number: A074260); APOTEX INC (Application Number: A077120); APOTEX (Application Number: A076212); IMPAX LABS (Application Number: A076521); MAYNE PHARMA (Application Number: A073589); MAYNE PHARMA (Application Number: A073607); MAYNE PHARMA (Application Number: A073618); MYLAN (Application Number: A075091); MYLAN (Application Number: A078893); MYLAN (Application Number: A090324); SUN PHARM INDS (Application Number: A077828); SUN PHARM INDS (Application Number: A078536); SUN PHARMA GLOBAL (Application Number: A078690)

2 of 12
Drug Name	DUOPA
Active Ingredient	CARBIDOPA; LEVODOPA
Company	ABBVIE INC (Application Number: N203952)

3 of 12
Drug Name	RYTARY
Active Ingredient	CARBIDOPA; LEVODOPA
Company	IMPAX LABS INC (Application Number: N203312. Patents: 7094427, 8377474, 8454998, 8557283, 9089607, 9089608, 9463246, 9533046, 9901640)

4 of 12
Drug Name	SINEMET CR
Active Ingredient	CARBIDOPA; LEVODOPA
Company	MERCK SHARP DOHME (Application Number: N019856)

5 of 12
Drug Name	SINEMET
Active Ingredient	CARBIDOPA; LEVODOPA
Company	MERCK SHARP DOHME (Application Number: N017555)

6 of 12
Drug Name	CARBIDOPA, LEVODOPA AND ENTACAPONE
Active Ingredient	CARBIDOPA; ENTACAPONE; LEVODOPA
Company	SUN PHARMA GLOBAL (Application Number: A079085); WOCKHARDT LTD (Application Number: A090786); WOCKHARDT LTD (Application Number: A090833)

7 of 12
Drug Name	STALEVO 100
Active Ingredient	CARBIDOPA; ENTACAPONE; LEVODOPA
Company	ORION PHARMA (Application Number: N021485. Patents: 6500867, 6797732)

8 of 12
Drug Name	STALEVO 125
Active Ingredient	CARBIDOPA; ENTACAPONE; LEVODOPA
Company	ORION PHARMA (Application Number: N021485. Patents: 6500867, 6797732)

9 of 12
Drug Name	STALEVO 150
Active Ingredient	CARBIDOPA; ENTACAPONE; LEVODOPA
Company	ORION PHARMA (Application Number: N021485. Patents: 6500867, 6797732)

10 of 12
Drug Name	STALEVO 200
Active Ingredient	CARBIDOPA; ENTACAPONE; LEVODOPA
Company	ORION PHARMA (Application Number: N021485. Patents: 6500867, 6797732)

11 of 12
Drug Name	STALEVO 50
Active Ingredient	CARBIDOPA; ENTACAPONE; LEVODOPA
Company	ORION PHARMA (Application Number: N021485. Patents: 6500867, 6797732)

12 of 12
Drug Name	STALEVO 75
Active Ingredient	CARBIDOPA; ENTACAPONE; LEVODOPA
Company	ORION PHARMA (Application Number: N021485. Patents: 6500867, 6797732)

4.2 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/

MICROMEDEX Thomson Health Care. USPDI - Drug Information for the Health Care Professional 21 st ed. Volume 1. MICROMEDEX Thomson Health Care, Englewood, CO. 2001. Content Reviewed and Approved by the U.S. Pharmacopeial Convention, Inc., p. 1902

Levodopa, the metabolic precursor of dopamine, is the single most effective agent in the treatment of Parkinson's Disease.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 555

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.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 235

...L-DOPA...HAS BEEN MORE CONSISTENTLY EFFECTIVE IN TREATMENT OF CHRONIC MANGANESE POISONING THAN IN PARKINSON'S DISEASE.

Doull, J., C.D. Klaassen, and M. D. Amdur (eds.). Casarett and Doull's Toxicology. 2nd ed. New York: Macmillan Publishing Co., 1980., p. 450

For more Therapeutic Uses (Complete) data for LEVODOPA (17 total), please visit the HSDB record page.

4.3 Drug Warning

PT WITH CARDIAC ARRHYTHMIAS OR HISTORY OF MYOCARDIAL INFARCTION SHOULD UNDERGO INITIAL THERAPY WITH LEVODOPA ONLY IN FACILITY EQUIPPED FOR INTENSIVE CORONARY CARE. ...DIABETIC PT...SHOULD BE CAREFULLY MONITORED FOR ANY NECESSITY TO MODIFY THEIR REGIMEN. CAUTION ALSO NECESSARY IN PT WITH HISTORY OF PEPTIC ULCER, CONVULSIONS...

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 233

DISCONTINUATION OF LEVODOPA THERAPY FOR 6-24 HR PRIOR TO GENERAL ANESTHESIA IS RECOMMENDED... SAFETY OF L-DOPA DURING PREGNANCY HAS NOT BEEN ESTABLISHED, HOWEVER, INFANTS SHOULD NOT BE NURSED BY MOTHERS RECEIVING DRUG SINCE IT MAY APPEAR IN MILK. ...DRUG MAY INHIBIT LACTATION.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 233

...IS CONTRAINDICATED IN PATIENTS WITH NARROW-ANGLE GLAUCOMA, ACUTE PSYCHOSIS, OR SEVERE PSYCHONEUROSIS. IT SHOULD NOT BE ADMIN TO PT WITH UNCOMPENSATED ENDOCRINE, RENAL, HEPATIC, CARDIOVASCULAR, OR PULMONARY DISEASE. /USE/...EXTREME CAUTION IN PT WITH ASTHMA OR EMPHYSEMA WHO MAY REQUIRE SYMPATHOMIMETIC DRUGS.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 233

SINCE LEVODOPA THERAPY...ASSOC WITH INCR GROWTH OF MELANOMA, PT WITH KNOWN MELANOMAS OR PIGMENTED LESIONS SHOULD BE CAREFULLY MONITORED FOR CHANGES IN SUCH LESIONS & DRUG WITHDRAWN IF CHANGES OCCUR.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 233

For more Drug Warnings (Complete) data for LEVODOPA (49 total), please visit the HSDB record page.

4.4 Drug Indication

Levodopa on its own is formulated as an oral inhalation powder indicated for intermittent treatment of off episodes in Parkinson's patients who are already being treated with carbidopa and levodopa. Levodopa is most commonly formulated as an oral tablet with a peripheral dopa decarboxylase inhibitor indicated for treatment of Parkinson's disease, post-encephalitic parkinsonism, and symptomatic parkinsonism following carbon monoxide intoxication or manganese intoxication.

FDA Label

Inbrija is indicated for the intermittent treatment of episodic motor fluctuations (OFF episodes) in adult patients with Parkinsons disease (PD) treated with a levodopa/dopa-decarboxylase inhibitor.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Levodopa is able to cross the blood-brain barrier while dopamine is not. The addition of a peripheral dopa decarboxylase inhibitor prevents the conversion of levodopa to dopamine in the periphery so that more levodopa can reach the blood-brain barrier. Once past the blood-brain barrier, levodopa is converted to dopamine by aromatic-L-amino-acid decarboxylase.

5.2 MeSH Pharmacological Classification

Antiparkinson Agents

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. (See all compounds classified as Antiparkinson Agents.)

Dopamine Agents

Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons. (See all compounds classified as Dopamine Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

LEVODOPA

5.3.2 FDA UNII

46627O600J

5.3.3 Pharmacological Classes

Aromatic Amino Acid [EPC]; Amino Acids, Aromatic [CS]

5.4 ATC Code

N04BA01

N04BA02

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N04 - Anti-parkinson drugs

N04B - Dopaminergic agents

N04BA - Dopa and dopa derivatives

N04BA01 - Levodopa

5.5 Absorption, Distribution and Excretion

Absorption

Orally inhaled levodopa reaches a peak concentration in 0.5 hours with a bioavailability than is 70% that of the immediate release levodopa tablets with a peripheral dopa decarboxylase inhibitor like carbidopa or benserazide.

Route of Elimination

After 48 hours, 0.17% of an orally administered dose is recovered in stool, 0.28% is exhaled, and 78.4% is recovered in urine

Volume of Distribution

168L for orally inhaled levodopa.

Clearance

Intravenously administered levodopa is cleared at a rate of 14.2mL/min/kg in elderly patients and 23.4mL/min/kg in younger patients. When given carbidopa, the clearance of levodopa was 5.8mL/min/kg in elderyly patients and 9.3mL/min/kg in younger patients.

...DRUG...MAY APPEAR IN MILK.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 233

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/

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 213

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.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 230

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.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 231

For more Absorption, Distribution and Excretion (Complete) data for LEVODOPA (11 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Levodopa is either converted to dopamine by aromatic-L-amino-acid decarboxylase or O-methylated to 3-O-methyldopa by catechol-O-methyltransferase. 3-O-methyldopa cannot be metabolized to dopamine. Once levodopa is converted to dopamine, it is converted to sulfated or glucuronidated metabolites, epinephrine E, or homovanillic acid through various metabolic processes. The primary metabolites are 3,4-dihydroxyphenylacetic acid (13-47%) and homovanillic acid (23-39%).

MOST IS CONVERTED TO DOPAMINE... BIOTRANSFORMATION OF DOPAMINE PROCEEDS RAPIDLY...EXCRETION PRODUCTS, 3,4-DIHYDROXYPHENYLACETIC ACID...& 3-METHOXY-4-HYDROXYPHENYLACETIC ACID... SOME BIOCHEMICAL EVIDENCE INDICATES THAT ACCELERATION OF LEVODOPA METABOLISM OCCURS DURING PROLONGED THERAPY, POSSIBLY DUE TO ENZYME INDUCTION.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 230

MORE THAN 95%...IS DECARBOXYLATED...BY...AROMATIC L-AMINO ACID DECARBOXYLASE. ... A SMALL AMT /OF L-DOPA/ IS METHYLATED TO 3-O-METHYL-DOPA... MOST IS CONVERTED TO DOPAMINE, SMALL AMT OF WHICH IN TURN ARE METABOLIZED TO NOREPINEPHRINE & EPINEPHRINE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 230

...IS ESTIMATED THAT ABOUT THREE FOURTHS OF DIETARY METHIONINE IS UTILIZED FOR METABOLISM OF LARGE THERAPEUTIC DOSES OF LEVODOPA.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 231

LEVODOPA (L-DOPA) IS FORMED IN MAMMALS FROM L-TYROSINE AS INTERMEDIARY METABOLITE IN ENZYMATIC SYNTHESIS OF CATECHOLAMINES.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 228

5.7 Biological Half-Life

2.3 hours for orally inhaled levodopa. Oral levodopa has a half life of 50 minutes but when combined with a peripheral dopa decarboxylase inhibitor, the half life is increased to 1.5 hours.

THE HALF-LIFE IN PLASMA IS SHORT (1-3 HR).

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 555

5.8 Mechanism of Action

Levodopa by various routes crosses the blood brain barrier, is decarboxylated to form dopamine. This supplemental dopamine performs the role that endogenous dopamine cannot due to a decrease of natural concentrations and stimulates dopaminergic receptors.

MOST WIDELY ACCEPTED THEORY IS THAT LEVODOPA INCR LEVEL OF DOPAMINE & THUS ACTIVATION OF DOPAMINE RECEPTORS IN EXTRA-PYRAMIDAL CENTERS IN THE BRAIN (PRIMARILY IN CAUDATE NUCLEUS & SUBSTANTIA NIGRA).

Evaluations of Drug Interactions. 2nd ed. and supplements. Washington, DC: American Pharmaceutical Assn., 1976, 1978., p. 124

The present data indicate that the major effects observed after administration of exogenous levodopa are not due to a direct action of levodopa on dopamine receptors, or to extrastriatal release of dopamine, but to conversion of levodopa to dopamine by serotonergic terminals and probably some intrastriatal cells.

PMID:11274784 Lopez A et al; Neuroscience 103(3) : 639-651 (2001)

EFFECTS OF LEVODOPA ON HUMAN & MURINE MELANOMA CELLS EXAMINED. WHEN EXPONENTIALLY GROWING CELLS WERE EXPOSED TO L-DOPA, CHARACTERISTIC INHIBITION OF THYMIDINE INCORPORATION OBSERVED.

PMID:6768447 WICK MM; CANCER RES 40 (5): 1414 (1980)

IN RATS, DOPAMINERGIC AGONISTS ALL CAUSED DECR IN SERUM PROLACTIN LEVELS.

HOROWSKI R ET AL; ARCH TOXICOL (SUPPL 2): 93 (1979)