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Temad Noscapine

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Chemistry

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Also known as: 128-62-1, Narcotine, Tusscapine, Methoxyhydrastine, Terbenol, Capval

Molecular Formula

C₂₂H₂₃NO₇

Molecular Weight

413.4 g/mol

InChI Key

AKNNEGZIBPJZJG-MSOLQXFVSA-N

FDA UNII

A4C6WE7BZN

A naturally occurring opium alkaloid that is a centrally acting antitussive agent.

1 2D Structure

Noscapine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one

2.1.2 InChI

InChI=1S/C22H23NO7/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18/h5-6,9,17-18H,7-8,10H2,1-4H3/t17-,18+/m1/s1

2.1.3 InChI Key

AKNNEGZIBPJZJG-MSOLQXFVSA-N

2.1.4 Canonical SMILES

CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3

2.1.5 Isomeric SMILES

CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3

2.2 Other Identifiers

2.2.1 UNII

A4C6WE7BZN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Capval

2. Capval Tropfen

3. Embonate, Noscapine Hydrogen

4. Hydrochloride, Noscapine

5. Hydrogen Embonate, Noscapine

6. Librochin Prikkelhoest

7. Narcotine

8. Noscapect

9. Noscapine Hydrochloride

10. Noscapine Hydrogen Embonate

11. Prikkelhoest, Librochin

12. Tropfen, Capval

13. Tuscalman

2.3.2 Depositor-Supplied Synonyms

1. 128-62-1

2. Narcotine

3. Tusscapine

4. Methoxyhydrastine

5. Terbenol

6. Capval

7. Coscopin

8. Narcompren

9. Narcosine

10. Noscapin

11. Vadebex

12. (-)-narcotine

13. Narcotin

14. Narkotin

15. Noscapalin

16. Opianine

17. Opianin

18. Narcotussin

19. Longatin

20. Nectadon

21. Nicolane

22. Nipaxon

23. Lyobex

24. Opian

25. Alpha-narcotine

26. O-methylnarcotoline

27. Coscotabs

28. Noscapinum

29. Key-tusscapine

30. Longactin

31. Noscapal

32. Noscapina

33. Hederix (free Base)

34. (-)-alpha-narcotine

35. L-alpha-narcotine

36. Gnoscopine

37. Narcotinum

38. Noscopine

39. (-)-.alpha.-narcotine

40. Nsc 5366

41. Nsc-5366

42. .alpha.-narcotine

43. Dl-narcotine

44. (+/-)-noscapine

45. L-.alpha.-narcotine

46. A4c6we7bzn

47. 8v32u4aoqu

48. Alpha-gnoscopine

49. (3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3h)-one

50. (s)-6,7-dimethoxy-3-((r)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3h)-one

51. Chebi:73237

52. Nsc5366

53. (3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3h-2-benzofuran-1-one

54. Dsstox_cid_3385

55. Dsstox_rid_77007

56. Dsstox_gsid_23385

57. 1(3h)-isobenzofuranone, 6,7-dimethoxy-3-((5r)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (3s)-rel-

58. 1(3h)-isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)-isoquinolin-5-yl), (s-(r*,s*))-

59. 1(3h)-isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (r*,s*)-

60. 6035-40-1

61. Narcotine Alkaloid

62. Noskapin

63. .alpha.-gnoscopine

64. Noscapine Dl-form

65. L-alpha-noscapine

66. 8-methoxyhydrastin

67. Coscopin (van)

68. (3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-2h,5h,6h,7h,8h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-1,3-dihydro-2-benzofuran-1-one

69. Smr000059119

70. (+-)-noscapine

71. (-)-.alpha.-norcotine

72. (-)-alpha-norcotine

73. (+-)-alpha-narcotine

74. 1(3h)-isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (s-(r*,s*))-

75. 1(3h)-isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [s-(r*,s*)]-

76. Noscapinum [inn-latin]

77. Noscapina [inn-spanish]

78. Unii-a4c6we7bzn

79. Unii-8v32u4aoqu

80. Ccris 9304

81. Nsc-96350

82. Hsdb 3372

83. Noscapine [usp:inn:ban:jan]

84. .beta.-narcotine

85. Noscapine (tn)

86. (-)-noscapine

87. Ncgc00016388-01

88. [s-(r*,s*)]-6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-1(3h)-isobenzofuranone

89. Cas-128-62-1

90. Prestwick_959

91. (-)-a-narcotine

92. Einecs 204-899-2

93. Nsc 96350

94. 1-.alpha.-narcotine

95. Brn 0099933

96. Tocris-1697

97. Narcotine, (+-)-

98. Noscapine [inn]

99. Noscapine [jan]

100. Noscapine [mi]

101. Noscapine [hsdb]

102. Prestwick0_000563

103. Prestwick1_000563

104. Prestwick2_000563

105. Prestwick3_000563

106. Narcotinum [hpus]

107. Cbmicro_048259

108. Noscapine [mart.]

109. Noscapine [usp-rs]

110. Noscapine [who-dd]

111. Noscapine [who-ip]

112. Schembl4559

113. (s,r)-noscapine, 97%

114. Lopac0_000840

115. Bspbio_000346

116. 4-27-00-06838 (beilstein Handbook Reference)

117. Mls000069475

118. Mls001060855

119. Spbio_002565

120. Noscapine (jp15/usp/inn)

121. Noscapine (jp17/usp/inn)

122. Bpbio1_000382

123. Chembl364713

124. Noscapine Dl-form [mi]

125. Dtxsid4023385

126. Noscapine [ep Monograph]

127. Noscapine, (+/-)-

128. Gtpl10212

129. Noscapine [usp Monograph]

130. Noscapinum [who-ip Latin]

131. Dtxsid901032089

132. Hms1569b08

133. Hms2096b08

134. Hms2269p05

135. 1(3h)-isobenzofuranone, 6,7-dimethoxy-3-((5r)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (3s)-

136. 6,7-dimethoxy-3-(4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-2-benzofuran-1(3h)-one, (s-(r*,s*))- #

137. Phthalide, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-

138. (+/-)-.alpha.-narcotine

139. Tox21_110413

140. Bbl012344

141. Bdbm50424716

142. Mfcd00069316

143. Nsc121869

144. Stk054401

145. Zinc19418974

146. Noscapine 1.0 Mg/ml In Acetonitrile

147. Akos000278036

148. Tox21_110413_1

149. Ccg-204096

150. Cs-5115

151. Db06174

152. Nsc-121869

153. Sdccgsbi-0048054.p004

154. (-)-3-(2-methyl-6,7-methylendioxy-8-methoxy-1-isochinolyl)-6,7-dimethoxyphthalid

155. Ncgc00023230-02

156. Ncgc00023230-04

157. Ncgc00023230-05

158. Ncgc00023230-07

159. Ncgc00023230-08

160. Ncgc00023230-10

161. Ncgc00023230-14

162. (3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-5,6,7,8-tetrahydro-2h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-2-benzofuran-1(3h)-one

163. (3s)-6,7-dimethoxy-3-[(5r)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3h)-isobenzofuranone

164. 5-(6,7-dimethoxyphthalidyl)-5,6,7,8-tetrahydro-4-methoxy-8-methyl-1,3-dioxolo(4,5-g)isoquinoline

165. Ac-20272

166. Ac-33191

167. Hy-13716

168. L-alpha-2-methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinaline

169. Nci60_004322

170. Vs-03291

171. Bim-0048054.p001

172. C09592

173. D01036

174. Sr-01000075529-6

175. W-201012

176. Brd-k89237706-001-03-8

177. Q60998699

178. Noscapine, European Pharmacopoeia (ep) Reference Standard

179. Noscapine, United States Pharmacopeia (usp) Reference Standard

180. Wln: T C566 Do Fo Kn Eh & & Tj Ho1 K1 J-dt56 Bvo Dhj Ho1 Io1

181. (3s)-3-[(5r)-6-methyl-4-(methyloxy)-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,7-bis(methyloxy)-2-benzofuran-1(3h)-one

182. (3s)-6,7-dimethoxy-3-[(5r)-4-methoxy-6-methyl-7,8-dihydro-5h-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3h-isobenzofuran-1-one

183. 08n

184. 1(3h)-isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (r*,s*)-(+-)-

185. 1(3h)-isobenzofuranone,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, [s-(r*,s*)]-

186. Phthalide,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₃NO₇
Molecular Weight	413.4 g/mol
XLogP3	2.7
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	413.14745207 g/mol
Monoisotopic Mass	413.14745207 g/mol
Topological Polar Surface Area	75.7 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	647
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 Therapeutic Uses

Antitussive Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

ANTITUSSIVE AGENT WHICH DEPRESSES MEDULLARY CENTERS & SUPPRESSES COUGH REFLEX. IT IS USED IN MGMNT OF COUGH IN BRONCHIAL ASTHMA & PULMONARY EMPHYSEMA. DRUG REDUCES FREQUENCY & INTENSITY OF COUGHING PAROXYSMS.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 805

DRUG HAS NO MORPHINE-LIKE EFFECTS & HAS NO EFFECT ON MORPHNE ABSTINENCE SYNDROME. TOLERANCE TO ANTITUSSIVE EFFECT HAS NOT BEEN OBSERVED. NOSCAPINE IS NO LONGER CONTROLLED UNDER FEDERAL NARCOTIC LAW.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 805

NOSCAPINE HAS NO ANALGESIC PROPERTIES OR DEPENDENCE LIABILITY.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 667

NOSCAPINE HAD NO ANTITUSSIVE ACTIVITY IN VOLUNTEERS.

EMPEY ET AL; COMPARISON OF THE ANTITUSSIVE EFFECTS OF CODEINE PHOSPHATE 20 MG, DEXTROMETHORPHAN 30 MG AND NOSCAPINE 30 MG USING CITRIC ACID-INDUCED COUGH IN NORMAL SUBJECTS; EUR J CLIN PHARMACOL 16(6) 393 (1979)

4.2 Drug Warning

THERAPEUTICALLY EFFECTIVE DOSES ARE ESSENTIALLY DEVOID OF UNPLEASANT SIDE EFFECTS OF CODEINE &, EXCEPT FOR OCCASIONAL NAUSEA, ITS SIDE EFFECTS ARE NEGLIGIBLE. DOSES UP TO 90 MG HAVE NO EFFECT ON RESPIRATION IN MAN.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 805

SIDE EFFECTS, PREDOMINANTLY GI, ARE SEEN IN UP TO 30% OF PT STUDIED.

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 988

Maternal Medication usually Compatible with Breast-Feeding: Noscapine: Reported Sign or Symptom in Infant or Effect on Lactation: None. /from Table 6/

Report of the American Academy of Pediatrics Committee on Drugs in Pediatrics 93 (1): 141 (1994)

4.3 Drug Indication

Investigated for use/treatment in lymphoma (non-hodgkin's), leukemia (lymphoid), cancer/tumors (unspecified), and multiple myeloma.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antitussive Agents

Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)

5.2 ATC Code

R - Respiratory system

R05 - Cough and cold preparations

R05D - Cough suppressants, excl. combinations with expectorants

R05DA - Opium alkaloids and derivatives

R05DA07 - Noscapine

5.3 Absorption, Distribution and Excretion

ITS ANTITUSSIVE POTENCY & ONSET & DURATION OF ACTION ARE APPROX EQUAL, MG FOR MG, TO THOSE OF CODEINE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 805

5.4 Metabolism/Metabolites

MECONIN WAS THE MAJOR URINARY METABOLITE OF RATS, RABBITS, & HUMANS WHO HAD RECEIVED 120, 150 MG/KG & 10 MG, RESPECTIVELY, ORALLY. IT ACCOUNTED FOR APPROX 3, 8, & 2% OF DOSE RESPECTIVELY, AFTER 24 HR. O-DEMETHYLATED METABOLITES WERE ALSO FOUND.

TSUNODA, YOSHIMURA; XENOBIOTICA 9(3) 181 (1979)

5.5 Mechanism of Action

Noscapine's antitussive effects appear to be primarily mediated by its sigma receptor agonist activity. Evidence for this mechanism is suggested by experimental evidence in rats. Pretreatment with rimcazole, a sigma specific antagonist, causes a dose-dependent reduction in antitussive activity of noscapine.

...EXCEPT FOR ITS ANTITUSSIVE EFFECT, IT HAS NO SIGNIFICANT ACTIONS ON CNS IN DOSES WITHIN THERAPEUTIC RANGE.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 279

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