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
Structure for Noscapine (DB06174)
- 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 Therapies
- Contraindications & Blackbox Warnings
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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.
Target Actions Organism USigma non-opioid intracellular receptor 1 Not Available Humans - 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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The metabolism of Abemaciclib can be decreased when combined with Noscapine. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Noscapine. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Noscapine. Acetohexamide The metabolism of Acetohexamide can be decreased when combined with Noscapine. Acetylsalicylic acid The metabolism of Acetylsalicylic acid can be decreased when combined with Noscapine. Albendazole The metabolism of Albendazole can be decreased when combined with Noscapine. Alectinib The metabolism of Alectinib can be decreased when combined with Noscapine. Alfuzosin The metabolism of Alfuzosin can be decreased when combined with Noscapine. Alosetron The metabolism of Alosetron can be decreased when combined with Noscapine. Alpelisib The metabolism of Alpelisib can be decreased when combined with Noscapine. 
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- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Noscapine hydrochloride TTN62ITH9I 912-60-7 MFLVZFXCSKVCSH-URBRKQAFSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image COLDEKS KAPSUL, 20 ADET Noscapine (10 mg) + Acetaminophen (325 mg) + Chlorpheniramine maleate (1 mg) + Phenylephrine hydrochloride (5 mg) Capsule Oral Deva Holding A.S. 2020-08-14 2018-11-06 Turkey 
NEW TONIN TROCHE L Noscapine (60 mg) + Glycyrrhiza glabra (125 mg) + Prunus armeniaca seed (60 mg) Lozenge Oral SATO PHARMACEUTICAL (SINGAPORE) PTE LTD 1990-05-21 Not applicable Singapore TONIN COUGH SYRUP S Noscapine hydrochloride (60 mg/30ml) + Guaifenesin (300 mg/30ml) Syrup Oral SATO PHARMACEUTICAL (SINGAPORE) PTE LTD 1998-03-07 Not applicable Singapore
Categories
- ATC Codes
- R05DA07 — Noscapine
- Drug Categories
- Alkaloids
- Antitussive Agents
- Cough and Cold Preparations
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Heterocyclic Compounds, Fused-Ring
- Isoquinolines
- Opiate Alkaloids
- Opium Alkaloids and Derivatives
- Respiratory System Agents
- 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
- 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]
- External Links
- Human Metabolome Database
- HMDB0033439
- KEGG Compound
- C09592
- ChemSpider
- 242139
- BindingDB
- 50424716
- 7533
- ChEBI
- 73237
- ChEMBL
- CHEMBL364713
- ZINC
- ZINC000019418974
- Wikipedia
- Noscapine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Terminated Treatment Refractory Multiple Myeloma 1 1, 2 Terminated Treatment Chronic Lymphocytic Leukemia (CLL) / Non-Hodgkin's Lymphoma (NHL) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Oral 25 mg/mL Suspension Oral 25 mg/5g Tablet, coated Oral 25 mg/1 Capsule Oral Capsule Solution / drops; suspension / drops Syrup Oral Syrup Oral 100 mg Lozenge Oral 60 mg Tablet Oral Tablet Syrup Oral 300 mg/30ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.181 mg/mL ALOGPS logP 2 ALOGPS logP 2.58 ChemAxon logS -3.4 ALOGPS pKa (Strongest Acidic) 14.59 ChemAxon pKa (Strongest Basic) 6.44 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 75.69 Å2 ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 107.08 m3·mol-1 ChemAxon Polarizability 42.19 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- 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
- 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
- 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
- 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]
- 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]
- 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
- 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