Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H23NO7 |
| Molecular Weight | 413.4205 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]3([H])N(C)CCC4=CC5=C(OCO5)C(OC)=C34
InChI
InChIKey=AKNNEGZIBPJZJG-MSOLQXFVSA-N
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
| Molecular Formula | C22H23NO7 |
| Molecular Weight | 413.4205 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.jbc.org/content/289/11/7505.full.pdf+html
https://en.wikipedia.org/wiki/Noscapine
http://www.pnas.org/content/95/4/1601.full
Curator's Comment: description was created based on several sources, including
http://www.jbc.org/content/289/11/7505.full.pdf+html
https://en.wikipedia.org/wiki/Noscapine
http://www.pnas.org/content/95/4/1601.full
Noscapine (also known as Narcotine, Nectodon, Nospen, Anarcotine and (archaic) Opiane) is a benzylisoquinoline alkaloid from plants of the poppy family, without painkilling properties. This agent is primarily used for its antitussive (cough-suppressing) effects. Noscapine is often used as an antitussive medication. A 2012 Dutch guideline, however, does not recommend its use for coughing. Noscapine can increase the effects of centrally sedating substances such as alcohol and hypnotics. Noscapine should not be taken in conjunction with warfarin as the anticoagulant effects of warfarin may be increased. Noscapine, and its synthetic derivatives called noscapinoids, are known to interact with microtubules and inhibit cancer cell proliferation. Mechanisms for its antitussive action are unknown, although animal studies have suggested central nervous system as a site of action. Furthermore, noscapine causes apoptosis in many cell types and has potent antitumor activity against solid murine lymphoid tumors (even when the drug was administered orally) and against human breast and bladder tumors implanted in nude mice. Because noscapine is water-soluble and absorbed after oral administration, its chemotherapeutic potential in human cancer merits thorough evaluation. Antifibrotic effect of noscapine based on novel mechanism, which it shows through EP2 prostaglandin E2 receptor-mediated activation of protein kinase A.
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
394 μg/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2257866 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NOSCAPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
794 μg × h/L EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2257866 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NOSCAPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2257866 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
NOSCAPINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
7% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/1972403 |
NOSCAPINE serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
4 mg 1 times / day single, oral Studied dose Dose: 4 mg, 1 times / day Route: oral Route: single Dose: 4 mg, 1 times / day Sources: |
unhealthy, 57 years n = 1 Health Status: unhealthy Condition: common cold Age Group: 57 years Sex: M Population Size: 1 Sources: |
Other AEs: Drug eruption... |
50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Co-administed with:: Warfarin(mean dose 26 mg; 1 week) Sources: |
unhealthy, mean age 71 years n = 4 Health Status: unhealthy Condition: cough Age Group: mean age 71 years Sex: F Population Size: 4 Sources: |
Other AEs: International normalized ratio increased... Other AEs: International normalized ratio increased Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Drug eruption | 4 mg 1 times / day single, oral Studied dose Dose: 4 mg, 1 times / day Route: oral Route: single Dose: 4 mg, 1 times / day Sources: |
unhealthy, 57 years n = 1 Health Status: unhealthy Condition: common cold Age Group: 57 years Sex: M Population Size: 1 Sources: |
|
| International normalized ratio increased | 50 mg 3 times / day multiple, oral Recommended Dose: 50 mg, 3 times / day Route: oral Route: multiple Dose: 50 mg, 3 times / day Co-administed with:: Warfarin(mean dose 26 mg; 1 week) Sources: |
unhealthy, mean age 71 years n = 4 Health Status: unhealthy Condition: cough Age Group: mean age 71 years Sex: F Population Size: 4 Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| strong [IC50 10.8 uM] | no (co-administration study) Comment: administered with quinine. See https://pubmed.ncbi.nlm.nih.gov/20668444/ |
|||
| strong [IC50 13.3 uM] | yes (pharmacogenomic study) Comment: noscapine reduces CYP2C9 activity to the reported level in subjects with CYP2C9*2/*3. Mean increase of losartan phenotypic index was 4.9 fold. See https://pubmed.ncbi.nlm.nih.gov/20668444/ |
|||
| yes [IC50 100 uM] | ||||
| yes [Inhibition 100 uM] | ||||
| yes [Inhibition 100 uM] | ||||
| yes [Inhibition 100 uM] | ||||
| yes [Inhibition 100 uM] | no (co-administration study) Comment: administered with caffeine. See https://pubmed.ncbi.nlm.nih.gov/20668444/ |
|||
| yes | yes (co-administration study) Comment: Mean increase of omeprazole phenotypic index was 3.6 fold. |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The significance of putative urinary markers of illicit heroin use after consumption of poppy seed products. | 2006 Aug |
|
| Synthesis of microtubule-interfering halogenated noscapine analogs that perturb mitosis in cancer cells followed by cell death. | 2006 Aug 14 |
|
| Synthesis and biological evaluation of a cyclic ether fluorinated noscapine analog. | 2006 Dec 15 |
|
| Anxiolytic effect of noscapine in mice. | 2006 Jul-Aug |
|
| Coated wire potentiometric detection for capillary electrophoresis studied using organic amines, drugs, and biogenic amines. | 2006 Jun 1 |
|
| Quantitative analysis of morphine and noscapine using corona discharge ion mobility spectrometry with ammonia reagent gas. | 2006 Jun 15 |
|
| Interaction of papaverine with the enalapril-induced cough in guinea pig. | 2006 Mar |
|
| Noscapine and diltiazem augment taxol and radiation-induced S-phase arrest and clonogenic death of C6 glioma in vitro. | 2006 May |
|
| Synthesis and in vitro cytotoxicity of haloderivatives of noscapine. | 2006 Oct 1 |
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| Treatment of hormone-refractory breast cancer: apoptosis and regression of human tumors implanted in mice. | 2006 Sep |
|
| p53 and p21 determine the sensitivity of noscapine-induced apoptosis in colon cancer cells. | 2007 Apr 15 |
|
| A simple and rapid flow-injection chemiluminescence method for the determination of noscapine with Ru(phen)3(2+)-Ce(IV) system. | 2007 Aug |
|
| Optimum conditions for detecting hepatic micronuclei caused by numerical chromosome aberration inducers in mice. | 2007 Aug 15 |
|
| Differentiation of opium and poppy straw using capillary electrophoresis and pattern recognition techniques. | 2007 Dec 12 |
|
| Validation of meconin as a marker for illicit opiate use. | 2007 Mar |
|
| Separation and determination of five major opium alkaloids with mixed mode of hydrophilic/cation-exchange monolith by pressurized capillary electrochromatography. | 2007 Nov |
|
| Apoptotic pathway induced by noscapine in human myelogenous leukemic cells. | 2007 Nov |
|
| Preclinical pharmacokinetics and bioavailability of noscapine, a tubulin-binding anticancer agent. | 2007 Nov |
|
| Simultaneous voltammetric determination of morphine and noscapine by adsorptive differential pulse stripping method and least-squares support vector machines. | 2007 Nov 30 |
|
| Fatal poisoning by alcohol and heroin. | 2007 Sep |
|
| Role of CAP350 in centriolar tubule stability and centriole assembly. | 2008 |
|
| Persistence of DNA threads in human anaphase cells suggests late completion of sister chromatid decatenation. | 2008 Apr |
|
| Applicability of ultra-performance liquid chromatography-tandem mass spectrometry for heroin profiling. | 2008 Apr 25 |
|
| Effect of noscapine and vincristine combination on demyelination and cell proliferation in vitro. | 2008 Aug |
|
| Antiangiogenic effects of noscapine enhance radioresponse for GL261 tumors. | 2008 Aug 1 |
|
| Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. | 2008 Dec |
|
| Antitumor activity of noscapine in human non-small cell lung cancer xenograft model. | 2008 Dec |
|
| Noscapine may increase the effect of warfarin. | 2008 Feb |
|
| Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures. | 2008 Jan 22 |
|
| Noscapine induces apoptosis in human glioma cells by an apoptosis-inducing factor-dependent pathway. | 2008 Jul |
|
| Warfarin-noscapine interaction: a series of four case reports. | 2008 Mar |
|
| Noscapine inhibits human prostate cancer progression and metastasis in a mouse model. | 2008 Nov-Dec |
|
| Adulterant profile of illicit street heroin and reduction of its precipitated physical dependence withdrawal syndrome by extracts of St John's wort (Hypericum perforatum). | 2009 Apr |
|
| 9-bromonoscapine-induced mitotic arrest of cigarette smoke condensate-transformed breast epithelial cells. | 2009 Apr 15 |
|
| Simultaneous determination of codeine and noscapine by flow-injection chemiluminescence method using N-PLS regression. | 2009 Feb 20 |
|
| The anti-cancer activity of noscapine: a review. | 2009 Jan |
|
| [Noscapine and warfarin--a potentially dangerous interaction]. | 2009 Mar 12 |
|
| Capillary zone electrophoresis with diode-array detection for analysis of local anaesthetics and opium alkaloids in urine samples. | 2009 Mar 15 |
|
| Tubulin-interactive natural products as anticancer agents. | 2009 Mar 27 |
|
| Validation of a liquid chromatography-tandem mass spectrometric assay for the quantitative determination of hydrastine and berberine in human serum. | 2009 May 1 |
|
| [Pharmacological treatment of acute cough]. | 2009 May 14 |
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| A validated hybrid quadrupole linear ion-trap LC-MS method for the analysis of morphine and morphine glucuronides applied to opiate deaths. | 2009 May 30 |
|
| Recent patents reveal microtubules as persistent promising target for novel drug development for cancers. | 2009 Nov |
|
| Relevance of an opioid, noscapine in reducing cystogeneses in rat experimental model of polycystic ovary syndrome. | 2009 Nov |
|
| EM011 activates a survivin-dependent apoptotic program in human non-small cell lung cancer cells. | 2009 Oct 30 |
|
| General unknown screening procedure for the characterization of human drug metabolites in forensic toxicology: applications and constraints. | 2009 Sep |
|
| Simultaneous chemiluminescence determination of thebaine and noscapine using support vector machine regression. | 2010 Feb |
|
| Inclusion complexes of noscapine in beta-cyclodextrin offer better solubility and improved pharmacokinetics. | 2010 Feb |
|
| Potent anti-inflammatory activity of novel microtubule-modulating brominated noscapine analogs. | 2010 Feb 11 |
|
| Simultaneous liquid chromatography-mass spectrometry quantification of urinary opiates, cocaine, and metabolites in opiate-dependent pregnant women in methadone-maintenance treatment. | 2010 Jan-Feb |
Sample Use Guides
Noscapine effectively inhibited the proliferation of LoVo cells in vitro (IC(50)=75 μM). This cytotoxicity was reflected by cell cycle arrest at G(2)/M and subsequent apoptosis, as indicated by increased chromatin condensation and fragmentation, the upregulation of Bax and cytochrome c (Cyt-c), the downregulation of survivin and Bcl-2, and the activation of caspase-3 and caspase-9
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:08:05 GMT 2023
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admin
on
Fri Dec 15 15:08:05 GMT 2023
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| Record UNII |
8V32U4AOQU
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| Record Status |
Validated (UNII)
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
500615
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WHO-ATC |
R05DA07
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NCI_THESAURUS |
C67413
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NCI_THESAURUS |
C25974
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WHO-VATC |
QR05DA07
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| Code System | Code | Type | Description | ||
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100000083604
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3372
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73237
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NOSCAPINE
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PRIMARY | Description: Colourless crystals or a white, crystalline powder; odourless or almost odourless. Solubility: Practically insoluble in water; sparingly soluble in boiling water; slightly soluble in ethanol (~750 g/l) TS and ether R. Category: Antitussive drug. Storage: Noscapine should be kept in a well-closed container. Definition: Noscapine contains not less than 98.5% and not more than 101.0% of C22H23NO7, calculated with reference to thedried substance. | ||
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C80589
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m8077
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CHEMBL364713
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1474504
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128-62-1
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NOSCAPINE
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D009665
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1973
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275196
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SUB09383MIG
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DB06174
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5366
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204-899-2
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8V32U4AOQU
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632
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7533
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PRIMARY | RxNorm |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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RACEMATE -> ENANTIOMER |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
