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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H23NO7
Molecular Weight 413.4205
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NOSCAPINE

SMILES

COC1=CC=C2[C@H](OC(=O)C2=C1OC)[C@@H]3N(C)CCC4=C3C(OC)=C5OCOC5=C4

InChI

InChIKey=AKNNEGZIBPJZJG-MSOLQXFVSA-N
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

HIDE SMILES / InChI

Description

Noscapine (also known as Narcotine, Nectodon, Nospen, Anarcotine and (archaic) Opiane) is a benzylisoquinoline alkaloid from plants of the poppy family, without painkilling properties. This agent is primarily used for its antitussive (cough-suppressing) effects. Noscapine is often used as an antitussive medication. A 2012 Dutch guideline, however, does not recommend its use for coughing. Noscapine can increase the effects of centrally sedating substances such as alcohol and hypnotics. Noscapine should not be taken in conjunction with warfarin as the anticoagulant effects of warfarin may be increased. Noscapine, and its synthetic derivatives called noscapinoids, are known to interact with microtubules and inhibit cancer cell proliferation. Mechanisms for its antitussive action are unknown, although animal studies have suggested central nervous system as a site of action. Furthermore, noscapine causes apoptosis in many cell types and has potent antitumor activity against solid murine lymphoid tumors (even when the drug was administered orally) and against human breast and bladder tumors implanted in nude mice. Because noscapine is water-soluble and absorbed after oral administration, its chemotherapeutic potential in human cancer merits thorough evaluation. Antifibrotic effect of noscapine based on novel mechanism, which it shows through EP2 prostaglandin E2 receptor-mediated activation of protein kinase A.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
36.8 μg/L
50 mg single, oral
NOSCAPINE plasma
Homo sapiens
394 μg/L
200 mg single, oral
NOSCAPINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
57 μg × h/L
50 mg single, oral
NOSCAPINE plasma
Homo sapiens
794 μg × h/L
200 mg single, oral
NOSCAPINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
8.42 h
50 mg single, oral
NOSCAPINE plasma
Homo sapiens
4.5 h
200 mg single, oral
NOSCAPINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
NOSCAPINE serum
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
25 to 50 mg 8 hourly
Route of Administration: Oral
In Vitro Use Guide
Noscapine effectively inhibited the proliferation of LoVo cells in vitro (IC(50)=75 μM). This cytotoxicity was reflected by cell cycle arrest at G(2)/M and subsequent apoptosis, as indicated by increased chromatin condensation and fragmentation, the upregulation of Bax and cytochrome c (Cyt-c), the downregulation of survivin and Bcl-2, and the activation of caspase-3 and caspase-9