This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
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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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Common cold Combination Product in combination with: Phenylephrine (DB00388), Acetaminophen (DB00316), Chlorpheniramine (DB01114) ••• ••• ••••••• Treatment of Coughing •••••••••••• ••••••••• ••••••••••• •••••• Used in combination for symptomatic treatment of Respiratory diseases Combination Product in combination with: Guaifenesin (DB00874) •••••••••••• ••••• ••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The serum concentration of Abemaciclib can be increased when it is combined with Noscapine. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Noscapine. Acalabrutinib The serum concentration of Acalabrutinib can be increased when it is 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. - Food Interactions
- 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 BODREX COUGH & COLD NC Noscapine (15 mg) + Acetaminophen (500 mg) + Phenylephrine hydrochloride (10 mg) Tablet Tempo Scan Pacific Tbk 2018-10-25 2026-10-21 Indonesia 
COLDEKS KAPSUL, 20 ADET Noscapine (10 mg) + Acetaminophen (325 mg) + Chlorpheniramine maleate (1 mg) + Phenylephrine hydrochloride (5 mg) Capsule Oral Deva Holding A.S. 1989-12-05 2018-11-06 Turkey 
FLUCODIN Noscapine (10 mg) + Acetaminophen (500 mg) + Chlorpheniramine maleate (2 mg) + Guaifenesin (50 mg) + Phenylpropanolamine hydrochloride (15 mg) Tablet, film coated Oral Coronet Crown 2018-09-26 2025-07-05 Indonesia NASMINE N.F. JARABE Noscapine hydrochloride (50 mg) + Loratadine (100 mg) + Terbutaline sulfate (30 mg) Syrup Oral ARBOFARMA S.A.S. 2009-10-06 2021-10-01 Colombia 
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 
Categories
- ATC Codes
- R05DA07 — Noscapine
- Drug Categories
- Alkaloids
- Antitussive Agents
- Central Nervous System 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
- PDBe Ligand
- 08N
- Wikipedia
- Noscapine
- PDB Entries
- 7n4z / 7uqn
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data1 Terminated Treatment Refractory Multiple Myeloma 1 somestatus stop reason just information to hide 1, 2 Terminated Treatment Chronic Lymphocytic Leukemia / Non-Hodgkin's Lymphoma (NHL) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet 10 mg Solution Oral 25 mg/mL Suspension Oral 25 mg/5g Tablet, coated Oral 25 mg/1 Capsule Oral Tablet, film coated Oral 2 mg Capsule 25 MG Capsule 50 MG Solution / drops; suspension / drops 10 MG/ML Syrup Oral Lozenge Oral 60 mg Tablet Oral Tablet - 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) 13.07 Chemaxon pKa (Strongest Basic) 7.14 Chemaxon Physiological Charge 1 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 42.17 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 211.9973751 predictedDarkChem Lite v0.1.0 [M-H]- 212.0983751 predictedDarkChem Lite v0.1.0 [M-H]- 212.4029751 predictedDarkChem Lite v0.1.0 [M-H]- 183.56111 predictedDeepCCS 1.0 (2019) [M+H]+ 211.7144751 predictedDarkChem Lite v0.1.0 [M+H]+ 211.6423751 predictedDarkChem Lite v0.1.0 [M+H]+ 212.7309751 predictedDarkChem Lite v0.1.0 [M+H]+ 185.95668 predictedDeepCCS 1.0 (2019) [M+Na]+ 211.4187751 predictedDarkChem Lite v0.1.0 [M+Na]+ 212.2683751 predictedDarkChem Lite v0.1.0 [M+Na]+ 211.7066751 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.86922 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 membrane. Involved in the regulation of different receptors it plays a role in BDNF signaling and EGF signaling. Also regulates ion channels like the potassium channel and could modulate neurotransmitter release. Plays a role in calcium signaling through modulation together with ANK2 of the ITP3R-dependent calcium efflux at the endoplasmic reticulum. Plays a role in several other cell functions including proliferation, survival and death. Originally identified for its ability to bind various psychoactive drugs it is involved in learning processes, memory and mood alteration (PubMed:16472803, PubMed:9341151). Necessary for proper mitochondrial axonal transport in motor neurons, in particular the retrograde movement of mitochondria. Plays a role in protecting cells against oxidative stress-induced cell death via its interaction with RNF112 (By similarity)
- Specific Function
- G protein-coupled opioid receptor activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (R)-limonene 6-monooxygenase activity
- 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
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- 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