Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H41NO2 |
| Molecular Weight | 411.6199 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1[C@@H]2NC[C@@H](C)C[C@H]2O[C@]13CC[C@H]4[C@@H]5CC=C6C[C@@H](O)CC[C@]6(C)[C@H]5CC4=C3C
InChI
InChIKey=QASFUMOKHFSJGL-LAFRSMQTSA-N
InChI=1S/C27H41NO2/c1-15-11-24-25(28-14-15)17(3)27(30-24)10-8-20-21-6-5-18-12-19(29)7-9-26(18,4)23(21)13-22(20)16(27)2/h5,15,17,19-21,23-25,28-29H,6-14H2,1-4H3/t15-,17+,19-,20-,21-,23-,24+,25-,26-,27-/m0/s1
| Molecular Formula | C27H41NO2 |
| Molecular Weight | 411.6199 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 10 / 10 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://editor40canoe.jimdo.com/2015/02/04/hncc-cell-strains-p53-impartial-and-dependent-induction-of-apoptosis-have-been-advised-roscovitine-can-activate-p53-by-way-of-suppression-of/
Curator's Comment: description was created based on several sources, including
http://editor40canoe.jimdo.com/2015/02/04/hncc-cell-strains-p53-impartial-and-dependent-induction-of-apoptosis-have-been-advised-roscovitine-can-activate-p53-by-way-of-suppression-of/
Cyclopamine is an inhibitor of hedgehog (Hh) signaling, likely via direct inhibition of Smoothened, the accessory protein to the putative Hh receptor Patched. Cyclopamine is a teratogen isolated from the corn lily that causes usually fatal birth defects. It can prevent the fetal brain from dividing into two lobes (holoprosencephaly) and cause the development of a single eye. Cyclopamine can also be used to induce differentiation of human embryonic stem cells (hESCs) into hormone-expressing endocrine cells. In the very first at any time human affected person with metastatic pancreatic most cancers who was administered intravenous cyclopamine on a compassionate, experimental basis in Germany, cyclopamine had to be discontinued because of emergence of neurologic toxicities and hematologic toxicities. That may possibly severely impede or even prevent scientific trials with this promising therapeutic technique.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| COUP-TFII is essential for radial and anteroposterior patterning of the stomach. | 2005-05 |
|
| Sonic hedgehog regulates proliferation of the retinal ciliary marginal zone in posthatch chicks. | 2005-05 |
|
| Hedgehog signaling in normal urothelial cells and in urothelial carcinoma cell lines. | 2005-05 |
|
| Regulation and function of the sonic hedgehog signal transduction pathway in isolated gastric parietal cells. | 2005-04-22 |
|
| Sonic hedgehog has a dual effect on the growth of retinal ganglion axons depending on its concentration. | 2005-03-30 |
|
| Sonic hedgehog guides commissural axons along the longitudinal axis of the spinal cord. | 2005-03 |
|
| Hedgehog signaling is required for adult blood stem cell formation in zebrafish embryos. | 2005-03 |
|
| Basal cell nevus syndrome. | 2005-03 |
|
| Sonic hedgehog is produced by follicular dendritic cells and protects germinal center B cells from apoptosis. | 2005-02-01 |
|
| In vivo inhibition of endogenous brain tumors through systemic interference of Hedgehog signaling in mice. | 2005-02 |
|
| Craniofacial anomalies of the cultured mouse embryo induced by inhibition of sonic hedgehog signaling: an animal model of holoprosencephaly. | 2005-01 |
|
| Sonic hedgehog controls stem cell behavior in the postnatal and adult brain. | 2005-01 |
|
| The Hedgehog signaling pathway as a target for anticancer drug discovery. | 2005 |
|
| Activity-dependent internalization of smoothened mediated by beta-arrestin 2 and GRK2. | 2004-12-24 |
|
| Sonic hedgehog exerts distinct, stage-specific effects on tongue and taste papilla development. | 2004-12-15 |
|
| Spatial and temporal regulation of ventral spinal cord precursor specification by Hedgehog signaling. | 2004-12 |
|
| Retinoic-acid-concentration-dependent acquisition of neural cell identity during in vitro differentiation of mouse embryonic stem cells. | 2004-11-01 |
|
| Inhibition of smoothened signaling prevents ultraviolet B-induced basal cell carcinomas through regulation of Fas expression and apoptosis. | 2004-10-15 |
|
| Activation of the hedgehog pathway in advanced prostate cancer. | 2004-10-13 |
|
| Hedgehog signalling in prostate regeneration, neoplasia and metastasis. | 2004-10-07 |
|
| Evidence for a molecular mechanism of teratogenicity of SB-236057, a 5-HT1B receptor inverse agonist that alters axial formation. | 2004-10 |
|
| Androgen dependent development of a modified anal fin, gonopodium, as a model to understand the mechanism of secondary sexual character expression in vertebrates. | 2004-09-24 |
|
| Hedgehog signalling in foregut malignancy. | 2004-09-15 |
|
| The upregulated expression of sonic hedgehog in motor neurons after rat facial nerve axotomy. | 2004-09-08 |
|
| Hedgehog and Fgf signaling pathways regulate the development of tphR-expressing serotonergic raphe neurons in zebrafish embryos. | 2004-09-05 |
|
| Purmorphamine induces osteogenesis by activation of the hedgehog signaling pathway. | 2004-09 |
|
| Sonic Hedgehog functions by localizing the region of proliferation in early developing feather buds. | 2004-08-01 |
|
| Temporal perturbations in sonic hedgehog signaling elicit the spectrum of holoprosencephaly phenotypes. | 2004-08 |
|
| Signaling dynamics of feather tract formation from the chick somatopleure. | 2004-08 |
|
| Hedgehog signalling in colorectal tumour cells: induction of apoptosis with cyclopamine treatment. | 2004-07-20 |
|
| Indian hedgehog signaling pathway: expression and regulation in pancreatic cancer. | 2004-07-10 |
|
| Hedgehog signaling and cell cycle control in differentiating erythroid progenitors. | 2004-07-01 |
|
| Induction of the differentiation and apoptosis of tumor cells in vivo with efficiency and selectivity. | 2004-06-16 |
|
| Biomedical applications of poisonous plant research. | 2004-06-02 |
|
| Sonic hedgehog signaling regulates Gli3 processing, mesenchymal proliferation, and differentiation during mouse lung organogenesis. | 2004-06-01 |
|
| Transforming growth factor (TGF)beta, fibroblast growth factor (FGF) and retinoid signalling pathways promote pancreatic exocrine gene expression in mouse embryonic stem cells. | 2004-05-01 |
|
| Shh-dependent differentiation of intestinal tissue from embryonic pancreas by activin A. | 2004-04-15 |
|
| Sonic hedgehog signaling plays an essential role during embryonic salivary gland epithelial branching morphogenesis. | 2004-04 |
|
| Roles for Hedgehog signaling in androgen production and prostate ductal morphogenesis. | 2004-03-15 |
|
| Cooperation between sonic hedgehog and fibroblast growth factor/MAPK signalling pathways in neocortical precursors. | 2004-03 |
|
| Hedgehog--Gli signaling in brain tumors: stem cells and paradevelopmental programs in cancer. | 2004-02-20 |
|
| A role of activated Sonic hedgehog signaling for the cellular proliferation of oral squamous cell carcinoma cell line. | 2004-02-06 |
|
| Targeting Sonic Hedgehog: a new way to mow down pancreatic cancer? | 2004-02 |
|
| Molecular neuro-oncology and development of targeted therapeutic strategies for brain tumors. Part 2: PI3K/Akt/PTEN, mTOR, SHH/PTCH and angiogenesis. | 2004-02 |
|
| Rapid clearance of psoriatic skin lesions induced by topical cyclopamine. A preliminary proof of concept study. | 2004 |
|
| Cyclopamine, hedgehog and psoriasis. | 2004 |
|
| Sonic hedgehog regulates prostatic growth and epithelial differentiation. | 2003-12-15 |
|
| Hedgehog stimulates only osteoblastic differentiation of undifferentiated KS483 cells. | 2003-12 |
|
| FGF-dependent generation of oligodendrocytes by a hedgehog-independent pathway. | 2003-12 |
|
| [Cutaneous epithelial tumors. Molecular biology and pathogenesis-based therapy]. | 2003-12 |
Sample Use Guides
In Vitro Use Guide
Curator's Comment: MCF-7 cell proliferation was inhibited by cyclopamine in a dose- and time-dependent manner, and the optimal inhibiting concentration was ten µmol/L and the optimal action time at 48 hours. With the time prolongation of cyclopamine action, the cells in G0/G1 phase were significantly increased, but the cells in S phase were significantly decreased (compared with blank control group, allp < 0.05). With the time prolongation of cyclopamine action, apoptosis rate of MCF-7 cells was also significantly increased (compared with blank control group, allp < 0.05). The level of cyclin D1 of MCF-7 cells was decreased, but cyclin p21 was increased (compared with blank control group, all p < 0.05).
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:10:09 GMT 2025
by
admin
on
Mon Mar 31 19:10:09 GMT 2025
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| Record UNII |
ZH658AJ192
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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NCI_THESAURUS |
C843
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734950
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DTXSID6043709
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m4003
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442972
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4449-51-8
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C63945
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C000541
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CYCLOPAMINE
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ZH658AJ192
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