This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Noscapine
Accession Number
DB06174
Type
Small Molecule
Groups
Approved, Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • (−)-narcotine
  • (−)-α-narcotine
  • alpha-Narcotine
  • Noscapina
  • Noscapine
  • Noscapinum
External IDs
CB3304 / NSC-5366
Product Ingredients
IngredientUNIICASInChI Key
Noscapine hydrochlorideTTN62ITH9I912-60-7MFLVZFXCSKVCSH-URBRKQAFSA-N
Categories
UNII
8V32U4AOQU
CAS number
128-62-1
Weight
Average: 413.4205
Monoisotopic: 413.147452095
Chemical Formula
C22H23NO7
InChI Key
AKNNEGZIBPJZJG-MSOLQXFVSA-N
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
IUPAC Name
(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
SMILES
[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12

Pharmacology

Indication

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

Pharmacodynamics
Not Available
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.

TargetActionsOrganism
USigma non-opioid intracellular receptor 1Not AvailableHumans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Noscapine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Noscapine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Noscapine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Noscapine.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Noscapine.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Noscapine.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Noscapine.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Noscapine.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Noscapine.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Noscapine.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0033439
KEGG Compound
C09592
ChemSpider
242139
BindingDB
50424716
ChEBI
73237
ChEMBL
CHEMBL364713
Wikipedia
Noscapine
ATC Codes
R05DA07 — Noscapine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1TerminatedTreatmentRefractory Multiple Myeloma1
1, 2TerminatedTreatmentChronic Lymphocytic Leukaemia (CLL) / Non-Hodgkin's Lymphoma (NHL)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.181 mg/mLALOGPS
logP2ALOGPS
logP2.58ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)14.59ChemAxon
pKa (Strongest Basic)6.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area75.69 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.08 m3·mol-1ChemAxon
Polarizability42.19 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0092000000-b90243e40af9870ee7a7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0091000000-a54e072ef1d92f81334d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0091000000-fce496b34ef93b8f503f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0ab9-0040900000-47e532749f5b8ffb3ccc
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0002900000-254fac469b3a08249319
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-0494000000-cb9d8aed31ebc22f9c22

Taxonomy

Description
This compound belongs to the class of organic compounds known as phthalide isoquinolines. These are organic compounds with a structure characterized by an isoquinoline moiety linked to phthalide.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Phthalide isoquinolines
Sub Class
Not Available
Direct Parent
Phthalide isoquinolines
Alternative Parents
Tetrahydroisoquinolines / Phthalides / Benzofuranones / Benzodioxoles / Anisoles / Alkyl aryl ethers / Aralkylamines / Trialkylamines / Lactones / Amino acids and derivatives
show 8 more
Substituents
Phthalide isoquinoline / Isobenzofuranone / Benzofuranone / Tetrahydroisoquinoline / Phthalide / Benzodioxole / Isocoumaran / Anisole / Alkyl aryl ether / Aralkylamine
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, benzylisoquinoline alkaloid, cyclic acetal, isobenzofuranone (CHEBI:73237) / Isoquinoline alkaloids (C09592)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Opioid receptor activity
Specific Function
Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma m...
Gene Name
SIGMAR1
Uniprot ID
Q99720
Uniprot Name
Sigma non-opioid intracellular receptor 1
Molecular Weight
25127.52 Da
References
  1. Kamei J: [Possible role of sigma-receptors in the regulation of cough reflex, gastrointestinal and retinal function]. Nihon Yakurigaku Zasshi. 1999 Jul;114(1):35-41. [PubMed:10562963]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Fang ZZ, Zhang YY, Ge GB, Huo H, Liang SC, Yang L: Time-dependent inhibition (TDI) of CYP3A4 and CYP2C9 by noscapine potentially explains clinical noscapine-warfarin interaction. Br J Clin Pharmacol. 2010 Feb;69(2):193-9. doi: 10.1111/j.1365-2125.2009.03572.x. [PubMed:20233183]
  2. Rosenborg S, Stenberg M, Otto S, Ostervall J, Masquelier M, Yue QY, Bertilsson L, Eliasson E: Clinically significant CYP2C inhibition by noscapine but not by glucosamine. Clin Pharmacol Ther. 2010 Sep;88(3):343-6. doi: 10.1038/clpt.2010.107. Epub 2010 Jul 28. [PubMed:20668444]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Fang ZZ, Zhang YY, Ge GB, Huo H, Liang SC, Yang L: Time-dependent inhibition (TDI) of CYP3A4 and CYP2C9 by noscapine potentially explains clinical noscapine-warfarin interaction. Br J Clin Pharmacol. 2010 Feb;69(2):193-9. doi: 10.1111/j.1365-2125.2009.03572.x. [PubMed:20233183]

Drug created on March 19, 2008 10:15 / Updated on December 16, 2018 07:04