NAV

Noscapine

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

Identification

Summary

Noscapine is a non-sedating isoquinoline alkaloid used primarily for its antitussive properties.

Generic Name
Noscapine
DrugBank Accession Number
DB06174
Background

Not Available

Type
Small Molecule
Groups
Approved, Investigational
Structure
3D
Similar Structures
Weight
Average: 413.4205
Monoisotopic: 413.147452095
Chemical Formula
C22H23NO7
Synonyms
  • (−)-narcotine
  • (−)-α-narcotine
  • alpha-Narcotine
  • Noscapina
  • Noscapine
  • Noscapinum
External IDs
  • CB3304
  • NSC-5366

Pharmacology

Indication

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

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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Noscapine.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Noscapine.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Noscapine.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Noscapine.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Noscapine.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Noscapine.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Noscapine.
AlectinibThe metabolism of Alectinib can be decreased when combined with Noscapine.
AlfuzosinThe metabolism of Alfuzosin can be decreased when combined with Noscapine.
AlosetronThe metabolism of Alosetron can be decreased when combined with Noscapine.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Noscapine hydrochlorideTTN62ITH9I912-60-7MFLVZFXCSKVCSH-URBRKQAFSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
COLDEKS KAPSUL, 20 ADETNoscapine (10 mg) + Acetaminophen (325 mg) + Chlorpheniramine maleate (1 mg) + Phenylephrine hydrochloride (5 mg)CapsuleOralDeva Holding A.S.2020-08-142018-11-06Turkey flag
NEW TONIN TROCHE LNoscapine (60 mg) + Glycyrrhiza glabra (125 mg) + Prunus armeniaca seed (60 mg)LozengeOralSATO PHARMACEUTICAL (SINGAPORE) PTE LTD1990-05-21Not applicable
TONIN COUGH SYRUP SNoscapine hydrochloride (60 mg/30ml) + Guaifenesin (300 mg/30ml)SyrupOralSATO PHARMACEUTICAL (SINGAPORE) PTE LTD1998-07-03Not applicable
Tuscalman - HustensirupNoscapine hydrochloride (0.15 g) + Guaifenesin (1 g)SyrupOralLaboratorio Farmaceutico S.I.T. S.R.L.1970-02-09Not applicableAustria flag

Categories

ATC Codes
R05DA07 — Noscapine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Acetal / Alkyl aryl ether / Amine / Amino acid or derivatives / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzodioxole
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tertiary amino compound, benzylisoquinoline alkaloid, cyclic acetal, isobenzofuranone (CHEBI:73237) / Isoquinoline alkaloids (C09592)
Affected organisms
Not Available

Chemical Identifiers

UNII
8V32U4AOQU
CAS number
128-62-1
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

References

General References
  1. Mahmoudian M, Rahimi-Moghaddam P: The anti-cancer activity of noscapine: a review. Recent Pat Anticancer Drug Discov. 2009 Jan;4(1):92-7. doi: 10.2174/157489209787002524. [Article]
Human Metabolome Database
HMDB0033439
KEGG Compound
C09592
ChemSpider
242139
BindingDB
50424716
RxNav
7533
ChEBI
73237
ChEMBL
CHEMBL364713
ZINC
ZINC000019418974
PDBe Ligand
08N
Wikipedia
Noscapine
PDB Entries
7n4z

Clinical Trials

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

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral25 mg/mL
SuspensionOral25 mg/5g
Tablet, coatedOral25 mg/1
CapsuleOral
Capsule
Solution / drops; suspension / drops
SyrupOral
LozengeOral60 mg
TabletOral
Tablet
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)13.07Chemaxon
pKa (Strongest Basic)7.14Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area75.69 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity107.08 m3·mol-1Chemaxon
Polarizability42.17 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

Targets

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Details1. Sigma non-opioid intracellular receptor 1
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. [Article]

Enzymes

Details1. Cytochrome P450 2C9
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. [Article]
  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. [Article]
Details2. Cytochrome P450 3A4
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. [Article]

Drug created at March 19, 2008 16:15 / Updated at June 16, 2021 12:31