Noscapine hydrochloride

Names

[ CAS No. ]:
912-60-7

[ Name ]:
Noscapine hydrochloride

[Synonym ]:
Narcosine hydrochloride
longatinhydrochloride
EINECS 213-014-9
Terbenol hydrochloride
Capval
NOSCAPINE BASE / HCL
MFCD00082546
nectadonhydrochloride
Nectadon hydrochloride
Opian hydrochloride
Vadebex hydrochloride
lyobexhydrochloride
coscopinhydrochloride
Coscopin hydrochloride
1,3-Dioxolo[4,5-g]isoquinolinium, 5-[(1S)-1,3-dihydro-4,5-dimethoxy-3-oxo-1-isobenzofuranyl]-5,6,7,8-tetrahydro-4-methoxy-6-methyl-, chloride, (5R)- (1:1)
Narcompren hydrochloride
opianhydrochloride
capvalhydrochloride
Opianine hydrochloride
vadebexhydrochloride
(5R)-5-[(1S)-4,5-Dimethoxy-3-oxo-1,3-dihydro-2-benzofuran-1-yl]-4-methoxy-6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-6-ium chloride
Methoxyhydrastine hydrochloride
Noscapine HCl
Noscapine hydrochloride
Narcotine hydrochloride

Biological Activity

[Description]:

Noscapine hydrochloride ((S,R)-Noscapine hydrochloride) is an orally active phthalideisoquinoline alkaloid with potent antitussive. Noscapine hydrochloride exerts its antitussive effects by activating sigma opioid receptors and is a non-competitive Bradykinin inhibitor. Noscapine hydrochloride disrupts microtubule dynamics, induces mitotic arrest and apoptosis. Noscapine hydrochloride possesses anticancer, neuroprotective, anti-inflammatory activities, and can crosse the blood-brain barrier[1][2][3][4][5].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Signaling Pathways >> GPCR/G Protein >> Opioid Receptor

Research Areas >> Inflammation/Immunology

Signaling Pathways >> Neuronal Signaling >> Opioid Receptor

Research Areas >> Neurological Disease

[Target]

Sigma opioid receptors[4]Bradykinin[5]Apoptosis[1]

[In Vitro]

Noscapine (0-1000 μM; 0-96 hours; rat C6 glioma cells) treatment inhibits cell viability of rat C6 glioma in vitro in a dose- and time-dependent manner. Noscapine inhibits the viability of rat C6 glioma cells with an IC50 of 250 μM at 72 hours[1]. Noscapine exposure causes abnormal S-phase reentry, increases mitotic arrest and results in excessive DNA accumulation[1]. Cylindromatosis increases the ability of noscapine to induce mitotic arrest and apoptosis. Cylindromatosis enhances the effect of noscapine on microtubule polymerization and promotes noscapine binding to microtubules[2]. Cell Proliferation Assay[1] Cell Line: Rat C6 glioma cells Concentration: 0 μM, 0.1 μM, 1 μM, 2 μM, 10 μM, 50 μM, 100 μM, 1000 μM Incubation Time: 0 hours, 12 hours, 24 hours, 48 hours, 72 hours, 96 hours Result: Inhibited cell viability of rat C6 glioma in vitro in a dose- and time-dependent manner.

[In Vivo]

Noscapine (300 mg/kg; oral gavage; daily; for 15 days; athymic female mice) treatment reduces tumor growth in mice[1]. Animal Model: Athymic female mice (nu/nu) (8-week-old) injected with rat C6 glioma cells[1] Dosage: 300 mg/kg Administration: Oral gavage; daily; for 15 days Result: Revealed a significant reduction of tumor volume.

[References]

[1]. Jaren W Landen, et al. Noscapine Crosses the Blood-Brain Barrier and Inhibits Glioblastoma Growth. Clin Cancer Res. 2004 Aug 1;10(15):5187-201.

[2]. Yang Y, et al. CYLD Regulates Noscapine Activity in Acute Lymphoblastic Leukemia via a Microtubule-Dependent Mechanism. Theranostics. 2015 Mar 2;5(7):656-666.

[3]. Vartika Tomar, et al. Noscapine and Its Analogs as Chemotherapeutic Agent: Current Updates. Curr Top Med Chem. 2017;17(2):174-188.

[4]. Bianca Lokhorst, et al. Interaction of OTC Drug Noscapine and Acenocoumarol and Phenprocoumon. Br J Clin Pharmacol. 2019 May;85(5):1041-1043.

[5]. S A Ebrahimi, et al. Interaction of Noscapine With the Bradykinin Mediation of the Cough Response. Acta Physiol Hung. 2003;90(2):147-55.

Chemical & Physical Properties

[ Density]:
1.332g/cm3

[ Boiling Point ]:
565.3ºC at 760mmHg

[ Melting Point ]:
221-223ºC

[ Molecular Formula ]:
C₂₂H₂₄ClNO₇

[ Molecular Weight ]:
449.882

[ Flash Point ]:
295.7ºC

[ Exact Mass ]:
449.124115

[ PSA ]:
75.69000

[ LogP ]:
3.62170

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
Freely soluble in water and in ethanol (96 per cent). Aqueous solutions are slightly acid; the base may be precipitated when the solutions are allowed to stand.

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NP7225000

CHEMICAL NAME :: 1(3H)Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methy l-1,3-dioxolo (4,5-g)isoquinolin-5-yl)-, hydrochloride, (S-(R*,S*))-

CAS REGISTRY NUMBER :: 912-60-7

LAST UPDATED :: 199009

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C22-H23-N-O7.Cl-H

MOLECULAR WEIGHT :: 449.92

WISWESSER LINE NOTATION :: T C566 DO FO KN EH&&TJ HO1 K1 J- DT56 BVO DHJ HO1 IO1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 853 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 581 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 700 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 52 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea Kidney, Ureter, Bladder - urine volume increased

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 83 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Cytogenetic analysis

TEST SYSTEM :: Rodent - hamster Lung

DOSE/DURATION :: 60 mg/L

REFERENCE :: GMCRDC Gann Monograph on Cancer Research. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No. 11- 1971- Volume(issue)/page/year: 27,95,1981

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi:Irritant;

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
UN 1544

[ WGK Germany ]:
3

[ RTECS ]:
NP7225000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Precursor & DownStream

Precursor

DownStream

Articles

Formulation approaches to improving the delivery of an antiviral drug with activity against seasonal flu.

Pharm. Dev. Technol. 20(2) , 169-75, (2015)

The main objective of the present study was to develop formulations of noscapine hydrochloride hydrate with enhanced solubility and bioavailability using co-solvent- and cyclodextrin-based approaches....

Related Compounds

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