Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H23NO7.ClH.H2O |
| Molecular Weight | 467.897 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]3([H])N(C)CCC4=CC5=C(OCO5)C(OC)=C34
InChI
InChIKey=ZYGSNVAGWKWKKI-WCRQIBMVSA-N
InChI=1S/C22H23NO7.ClH.H2O/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;1H;1H2/t17-,18+;;/m1../s1
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 |
|---|---|---|
| Peripheral T-cell lymphoma with aberrant expression of CD79a and CD20: a diagnostic pitfall. | 2001 Feb |
|
| Paclitaxel-resistant human ovarian cancer cells undergo c-Jun NH2-terminal kinase-mediated apoptosis in response to noscapine. | 2002 Oct 18 |
|
| Interaction of noscapine with the bradykinin mediation of the cough response. | 2003 |
|
| Brominated derivatives of noscapine are potent microtubule-interfering agents that perturb mitosis and inhibit cell proliferation. | 2003 Apr |
|
| Liquid chromatographic-atmospheric pressure chemical ionization mass spectrometric analysis of opiates and metabolites in rat urine after inhalation of opium. | 2003 Jun 5 |
|
| Application of capillary zone electrophoresis in the separation and determination of the principal gum opium alkaloids. | 2003 May |
|
| Noscapine hydrochloride-induced numerical aberrations in cultured human lymphocytes: a comparison of FISH detection methods and multiple end-points. | 2003 May |
|
| Discovery of S-phase arresting agents derived from noscapine. | 2005 Apr 21 |
|
| Principal opium alkaloids as possible biochemical markers for the source identification of Indian opium. | 2005 Aug |
|
| Noscapine suppresses angiotensin converting enzyme inhibitors-induced cough. | 2005 Aug |
|
| Validation of techniques to detect illicit heroin use in patients prescribed pharmaceutical heroin for the management of opioid dependence. | 2005 Dec |
|
| Identification of novel and improved antimitotic agents derived from noscapine. | 2005 Nov 17 |
|
| Synthesis of microtubule-interfering halogenated noscapine analogs that perturb mitosis in cancer cells followed by cell death. | 2006 Aug 14 |
|
| Evaluation of the HER2/neu-derived peptide GP2 for use in a peptide-based breast cancer vaccine trial. | 2006 Jun 1 |
|
| Noscapine inhibits hypoxia-mediated HIF-1alpha expression andangiogenesis in vitro: a novel function for an old drug. | 2006 May |
|
| Optimum conditions for detecting hepatic micronuclei caused by numerical chromosome aberration inducers in mice. | 2007 Aug 15 |
|
| Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures. | 2008 Jan 22 |
|
| EM011 activates a survivin-dependent apoptotic program in human non-small cell lung cancer cells. | 2009 Oct 30 |
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
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D02172
Created by
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219533-73-0
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C5YRF6QY5K
Created by
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20845981
Created by
admin on Sat Dec 16 18:28:12 GMT 2023 , Edited by admin on Sat Dec 16 18:28:12 GMT 2023
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
