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    Technical details about DSSTox_CID_3385, learn more about the structure, uses, toxicity, action, side effects and more

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    DSSTox_CID_3385

    APIs // Active Pharmaceutical Ingredients

    PRICE INFORMATION

    DOSSIERs // Finished Dosage Forms

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    ANALYTICAL SOLUTION(s)

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    2D Structure
    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

    2D Structure

    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 Weight 413.4 g/mol
    Molecular Formula C22H23NO7
    XLogP32.7
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count4
    Exact Mass413.14745207 g/mol
    Monoisotopic Mass413.14745207 g/mol
    Topological Polar Surface Area75.7 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity647
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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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