Natural Product (NP) Details

General Information of the NP (ID: NP7094)
Name
Noscapine
Synonyms
noscapine; 128-62-1; NARCOTINE; Tusscapine; Terbenol; Capval; Coscopin; Narcompren; Narcosine; Noscapin; Vadebex; Methoxyhydrastine; Narcotin; Narkotin; Noscapalin; Opianine; Opianin; Narcotussin; Longatin; Nectadon; Nicolane; Nipaxon; Lyobex; Opian; (-)-Narcotine; alpha-Narcotine; O-Methylnarcotoline; Coscotabs; Key-tusscapine; Longactin; Noscapal; Noscapina; Noscapinum; Hederix (free base); (-)-alpha-narcotine; L-alpha-Narcotine; Noscopine; UNII-8V32U4AOQU; NSC 5366; NSC-5366; .alpha.-Narcotine; Gnoscopine; L-.alpha.-Narcotine; 8V32U4AOQU; dl-Narcotine; alpha-Gnoscopine; (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; (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; CHEBI:73237; NSC5366; (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; DSSTox_CID_3385; DSSTox_RID_77007; DSSTox_GSID_23385; Q60998699; Narcotine alkaloid; Noskapin; Noscapine dl-form; L-alpha-Noscapine; 8-Methoxyhydrastin; Coscopin (VAN); (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; (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; 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*))-; SMR000059119; (+-)-Noscapine; (-)-.alpha.-Norcotine; (-)-alpha-Norcotine; (+-)-alpha-Narcotine; 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*))-; 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*)]-; 6035-40-1; Noscapinum [INN-Latin]; Noscapina [INN-Spanish]; CCRIS 9304; HSDB 3372; Noscapine [USP:INN:BAN:JAN]; .beta.-Narcotine; Noscapine (TN); (-)-noscapine; NCGC00016388-01; [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; CAS-128-62-1; Narcotine (8CI); Prestwick_959; (-)-a-Narcotine; EINECS 204-899-2; NSC 96350; 1-.alpha.-Narcotine; BRN 0099933; Tocris-1697; Narcotine, (+-)-; Prestwick0_000563; Prestwick1_000563; Prestwick2_000563; Prestwick3_000563; (-)-.alpha.-Narcotine; CBMicro_048259; SCHEMBL4559; (S,R)-Noscapine, 97%; Lopac0_000840; BSPBio_000346; 4-27-00-06838 (Beilstein Handbook Reference); MLS000069475; MLS001060855; ARONIS24067; SPBio_002565; Noscapine (JP15/USP/INN); Noscapine (JP17/USP/INN); BPBio1_000382; CHEMBL364713; DTXSID4023385; GTPL10212; HMS1569B08; HMS2096B08; HMS2269P05; 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)-; 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*))- #; Phthalide, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-; Tox21_110413; BBL012344; BDBM50424716; MFCD00069316; NSC121869; STK054401; ZINC19418974; Noscapine 1.0 mg/ml in Acetonitrile; AKOS000278036; Tox21_110413_1; CCG-204096; CS-5115; DB06174; MCULE-5334942206; NSC-121869; SDCCGSBI-0048054.P004; (-)-3-(2-Methyl-6,7-methylendioxy-8-methoxy-1-isochinolyl)-6,7-dimethoxyphthalid; NCGC00023230-02; NCGC00023230-04; NCGC00023230-05; NCGC00023230-07; NCGC00023230-08; NCGC00023230-10; NCGC00023230-14; 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-; 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*)-; 5-(6,7-Dimethoxyphthalidyl)-5,6,7,8-tetrahydro-4-methoxy-8-methyl-1,3-dioxolo(4,5-g)isoquinoline; AC-20272; AC-33191; HY-13716; L-alpha-2-Methyl-8-methoxy-6,7-methylenedioxy-1-(6,7-dimethoxy-3-phthalidyl)-1,2,3,4-tetrahydroisoquinaline; NCI60_004322; VS-03291; BIM-0048054.P001; H2069; C09592; D01036; A805851; SR-01000075529-6; W-201012; BRD-K89237706-001-03-8; Noscapine, European Pharmacopoeia (EP) Reference Standard; UNII-A4C6WE7BZN component AKNNEGZIBPJZJG-MSOLQXFVSA-N; Noscapine, United States Pharmacopeia (USP) Reference Standard; WLN: T C566 DO FO KN EH & & TJ HO1 K1 J-DT56 BVO DHJ HO1 IO1; (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; 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*)-(+-)-; 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*)]-; Phthalide,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-
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Species Origin Papaver somniferum ...     Click to Show/Hide
Papaver somniferum
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Ranunculales
Family: Papaveraceae
Genus: Papaver
Species: Papaver somniferum
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Phase 1/2 [1]
Structure
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2D MOL

3D MOL

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Formula
C22H23NO7
PubChem CID
275196
Canonical SMILES
CN1CCC2=CC3=C(C(=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3
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
InChIKey
AKNNEGZIBPJZJG-MSOLQXFVSA-N
CAS Number
CAS 6035-40-1
ChEBI ID
CHEBI:73237
Herb ID
HBIN037412
SymMap ID
SMIT10475
TCMSP ID
MOL009330
TTD Drug ID
D0Y8AW
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Cisplatin      Bladder cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Up-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Down-regulation Expression BIRC5  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP8  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP9  Molecule Info 
Pathway MAP
Up-regulation Expression CASP9  Molecule Info 
Pathway MAP
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Up-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
                    In-vivo Model For a xenograft model, 3*106 H460 cells were injected subcutaneously into right flank area of mice.
                    Experimental
                    Result(s)		 Nos enhanced the anticancer activity of Cis in an additive to synergistic manner by activating multiple signaling pathways including apoptosis.
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP8  Molecule Info 
Pathway MAP
Up-regulation Expression CASP9  Molecule Info 
Pathway MAP
Down-regulation Expression NFKBIA  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
MDA-MB-468 CVCL_0419 Breast adenocarcinoma Homo sapiens
                    In-vivo Model For a xenograft model, 3*106 MDA-MB-231 cells were inoculated subcutaneously into right flank of mice.
                    Experimental
                    Result(s)		 Noscapine potentiated the anticancer activity of Doxorubicin in a synergistic manner against TNBC tumors via inactivation of NF-KB and anti-angiogenic pathways while stimulating apoptosis.
          Gemcitabine      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression BCL-2  Molecule Info 
Pathway MAP
Up-regulation Expression BID  Molecule Info 
Pathway MAP
Down-regulation Expression BIRC5  Molecule Info 
Pathway MAP
Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP8  Molecule Info 
Pathway MAP
Up-regulation Expression CASP9  Molecule Info 
Pathway MAP
Down-regulation Expression CCND1  Molecule Info 
Pathway MAP
Up-regulation Expression CDKN1A  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Down-regulation Expression PARP1  Molecule Info 
Pathway MAP
Up-regulation Expression TP53  Molecule Info 
Pathway MAP
Down-regulation Expression VEGFA  Molecule Info 
Pathway MAP
                    In-vitro Model A-549 CVCL_0023 Lung adenocarcinoma Homo sapiens
NCI-H460 CVCL_0459 Lung large cell carcinoma Homo sapiens
                    In-vivo Model For a xenograft model, 3*106 human H460 cells were injected subcutaneously into the right flanks of the mice.
                    Experimental
                    Result(s)		 Nos potentiated the anticancer activity of Gem in an additive to synergistic manner against lung cancer via antiangiogenic and apoptotic pathways.
          Radiation      Breast cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Up-regulation Apoptosis
                    In-vitro Model T98G CVCL_0556 Glioblastoma Homo sapiens
GL261 CVCL_Y003 Mouse glioblastoma Mus musculus
Murine endothelial cell line 2H11 Healthy Rattus norvegicus
                    In-vivo Model For a xenograft model, 2.0 * 106 GL261 cells were injected subcutaneously in the hind limof mice.
                    Experimental
                    Result(s)		 Antiangiogenic effects of noscapine enhance radioresponse for GL261 tumors.
          Temozolomide + Bis-chloroethylnitrosourea + Cisplatin     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression PARP1  Molecule Info 
Pathway MAP
                    In-vitro Model U87/DK CVCL_3428 Glioblastoma Homo sapiens
                    In-vivo Model For a xenograft model, 4*106 U87MG cells were inoculated subcutaneously into one flank of 5-6 weeks old, female nude mice.
                    Experimental
                    Result(s)		 NOS synergistically potentiated the efficacy of FDA-approved anti-cancer drugs against human glioblastoma cells, thereby allowing them to be used at lower doses and hence minimizing their toxic side effects.
References
Reference 1 ClinicalTrials.gov (NCT00912899) A Study of Noscapine HCl (CB3304 ) in Patients With Relapsed or Refractory Multiple Myeloma. U.S. National Institutes of Health.
Reference 2 Anticancer activity of Noscapine, an opioid alkaloid in combination with Cisplatin in human non-small cell lung cancer. Lung Cancer. 2011 Mar;71(3):271-82.
Reference 3 Antitumor activity of Noscapine in combination with Doxorubicin in triple negative breast cancer. PLoS One. 2011 Mar 15;6(3):e17733.
Reference 4 Enhanced anticancer activity of gemcitabine in combination with noscapine via antiangiogenic and apoptotic pathway against non-small cell lung cancer. PLoS One. 2011;6(11):e27394.
Reference 5 Antiangiogenic effects of noscapine enhance radioresponse for GL261 tumors. Int J Radiat Oncol Biol Phys. 2008 Aug 1;71(5):1477-84.
Reference 6 Synergistic suppression of noscapine and conventional chemotherapeutics on human glioblastoma cell growth. Acta Pharmacol Sin. 2013 Jul;34(7):930-8.
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