| Source: | Veratrum californicim (plant extract) |
| Synonyms | 11-deoxojervine |
| Description: | Cyclopamine is a natural steroidal jerveratrum alkaloide. Cyclopamine is named after its ability to cause cyclopia(holoprosencephaly) in unborn sheep. |
| CAS number: | 4449-51-8 |
| Merck index: | not listed |
| Molecular weight: | 411.62 |
| Structure: | 
 |
| Molecular Formula: | C27H41NO2 |
| Canonical SMILES: |
|
Solubility
information: | Insoluble in water. Freely soluble in Chloroform, Dichloromethane.
Fairly soluble in benzene, warm (50ºC-60ºC) ethanol (20 mg/mL ), DMSO (4 mg/ml) and DMF (10 mg/mL). May recrystallize from ethanolic solution in cold. |
| Specifications | |
| Appearance: | White crystalline solid. |
| Purity: | Pure by TLC |
| λmax: | |
| Melting point | 225°C-230°C |
| Solubility | |
| Storage | -18°C. |
| Applications | Cyclopamine inhibits the hedgehog signaling pathway (Hh) by influencing the balance between the active and inactive forms of the Smoothened protein. Cyclopamine is currently being investigated as a treatment agent in basal cell carcinoma, medulloblastoma, and rhabdomyosarcoma, tumors connected to excessive Hh activity , glioblastoma, and as a treatment agent for multiple myeloma. |
| Warnings | Known teratogen. Causes damage to embryos. Women who are or may be pregnant should avoid any contact with Cyclopamine. |
| Classification | Veratrum
Alkaloid
Hh inhibitor |
| Related products | |
| | For Research use only. Not for Human or Drug use
GMP/API grade available on request
 Extracted
from plants; not produced from or contains any ingredients from animal origin.
No genetically modified organisms are used. |
| Publications | |
| | Zhang X, Harrington N, Moraes RC, Wu MF, Hilsenbeck SG, Lewis MT.
Cyclopamine inhibition of human breast cancer cell growth independent of Smoothened (Smo).
Breast Cancer Res Treat. 2008 Jun 19. |
| | Lipinski RJ, Hutson PR, Hannam PW, Nydza RJ, Washington IM, Moore RW, Girdaukas GG, Peterson RE, Bushman W.
ose- and route-dependent teratogenicity, toxicity, and pharmacokinetic profiles of the hedgehog signaling antagonist cyclopamine in the mouse.
Toxicol Sci. 2008 Jul;104(1):189-97 |
| | Parga JA, Rodriguez-Pallares J, Blanco V, Guerra MJ, Labandeira-Garcia JL.
Different effects of anti-sonic hedgehog antibodies and the hedgehog pathway inhibitor cyclopamine on generation of dopaminergic neurons from neurospheres of mesencephalic precursors.
Dev Dyn. 2008 Apr;237(4):909-17 |
| | Bar EE, Stearns D.
New developments in medulloblastoma treatment: the potential of a cyclopamine-lovastatin combination.
Expert Opin Investig Drugs. 2008 Feb;17(2):185-95 |
| | Chen JK, Taipale J, Cooper MK, Beachy PA.
Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened.
Genes Dev. 2002 Nov 1;16(21):2743-8 |
| | The discovery of Cyclopamine
CANCER RESEARCH 28, 2323-2326, November 1968
Effects of Teratogenic Agents in Range Plants
Wayne Binns, Lynn F. James, Richard F. Keeler, and Lew Dell Balls |
| | THERAPEUTIC USE OF AN INHIBITOR OF A HEDGEHOG SIGNALLING PATHWAY
European Patent EP1183040
Use of an inhibitor of a Hedgehog signalling pathway, or an inhibitor of a pathway which is a target of the Hedgehog signalling pathway in the preparation of a medicament for treatment of epithelial cell hyperplasia, fibrosis of tissue, inflammation, cancer or an immune disorder. Also a transgenic animal or cell line capable of expressing a component or an inhibitor of a hedgehog signalling pathway or a target pathway of the hedgehog signalling pathway. |
| |
