Noscapine

Targets (1)Enzymes (2)

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

Description

Not Available

Type

Small Molecule

Groups

Approved, Investigational

Structure

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.

Associated Conditions

Associated Therapies

Airway secretion clearance therapy

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.

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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Toxicity

Not Available

Affected organisms

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
Unlock Additional Data
Abemaciclib	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.

Additional Data Available

Extended Description

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Severity

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A severity rating for each drug interaction, from minor to major.

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Evidence Level

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Action

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Food Interactions

Not Available

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Noscapine hydrochloride	TTN62ITH9I	912-60-7	MFLVZFXCSKVCSH-URBRKQAFSA-N

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][[email protected]@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[[email protected]]1([H])N(C)CCC2=CC3=C(OCO3)C(OC)=C12

References

General References

Not Available

External Links

Human Metabolome Database: HMDB0033439
KEGG Compound: C09592
ChemSpider: 242139
BindingDB: 50424716
RxNav: 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 Leukaemia (CLL) / Non-Hodgkin's Lymphoma (NHL)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Capsule		25 mg
Solution	Oral	25 mg/mL
Suspension	Oral	25 mg/5g
Tablet, coated	Oral	25 mg/1
Capsule	Oral	325 mg
Capsule
Solution / drops; suspension / drops
Syrup	Oral	100 mg
Syrup	Oral	0.025 g
Tablet	Oral	10 mg
Syrup	Oral	0.7 g
Syrup	Oral	0.35 g
Syrup	Oral	1 g

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

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
MS/MS Spectrum - DI-ESI-qTof , Positive	LC-MS/MS	Not Available
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-00di-0092000000-b90243e40af9870ee7a7
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-00di-0091000000-a54e072ef1d92f81334d
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-00di-0091000000-fce496b34ef93b8f503f
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0ab9-0040900000-47e532749f5b8ffb3ccc
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-00di-0002900000-254fac469b3a08249319
MS/MS Spectrum - , positive	LC-MS/MS	splash10-00di-0494000000-cb9d8aed31ebc22f9c22

Targets

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

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

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

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]
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]

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

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]