Noscapine hydrochloride

Modify Date: 2024-01-03 00:16:42

Noscapine hydrochloride Structure
Noscapine hydrochloride structure
Common Name Noscapine hydrochloride
CAS Number 912-60-7 Molecular Weight 449.882
Density 1.332g/cm3 Boiling Point 565.3ºC at 760mmHg
Molecular Formula C22H24ClNO7 Melting Point 221-223ºC
MSDS Chinese USA Flash Point 295.7ºC
Symbol GHS07
GHS07
Signal Word Warning

 Use of Noscapine hydrochloride


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].

 Names

Name Noscapine hydrochloride,(3S)-6,7-Dimethoxy-3-[(5R)-5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl]-1(3H)-isobenzofuranonehydrochloride
Synonym More Synonyms

 Noscapine 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
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
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)

 Articles1

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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....

 Synonyms

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