4136 Cyclopamine Cyclopamine is a naturally occurring chemical that belongs to the group of steroidal jerveratrum alkaloids. It is a teratogen isolated from the corn lily (Veratrum californicum) 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 (cyclopia). It does so by inhibiting the hedgehog signaling pathway (Hh). Cyclopamine is useful in studying the role of Hh in normal development, and as a potential treatment for certain cancers in which Hh is overexpressed. 4449-51-8 442972 C27H41NO2 White powder. Cyclopamine 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 (cyclopia). It does so by inhibiting the hedgehog pathway (Hh). Cyclopamine inhibits the Hh by influencing the balance between the active and inactive forms of the smoothened protein. Cyclopamine is useful in studying the role of Hh in normal development, and as a potential treatment for certain cancers in which Hh is overexpressed. Cyclopamine acts as a primary inhibitor of the hedgehog signaling pathway in cells. This pathway named for the ligand for the signal protein, is used by cells to help them react to external chemical signals. The pathway carries out important functions in embryonic development and when it goes awry, deformities can occur. However, errant activation of the pathway can also trigger cancer in adult humans, leading to basal cell carcinoma, medulloblastoma, rhabdomyosarcoma, and prostate, pancreatic and breast cancers. A way of controlling the pathway using cyclopamine could turn this problem on its head and provide a way to treat cancer. (Wikipedia) Cyclopamine inhibits the Hh pathway by binding to and preventing the activation of Smoothened (Smo), preventing downstream target gene regulation. (A15437) No indication of carcinogenicity to humans (not listed by IARC). It is a teratogen isolated from the corn lily (Veratrum californicum) that causes usually fatal birth defects. Cyclopamine is useful in studying the role of Hh in normal development, and as a potential treatment for certain cancers in which Hh is overexpressed. 2014-08-29T05:04:23Z 2026-04-05T16:31:19Z C10798 true [H][C@@]12C[C@]([H])(C)CN[C@@]1([H])[C@@]([H])(C)[C@@]1(CC[C@]3([H])C(C[C@@]4([H])[C@@]3([H])CC=C3C[C@@]([H])(O)CC[C@]43C)=C1C)O2 C27H41NO2 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 QASFUMOKHFSJGL-LAFRSMQTSA-N 411.6199 411.313729561 Exogenous Solid CHEMBL254129 391275 CHEM003042 NS00076917 41.489999999999995 122.16909999999999 50.90505200549306 0 3 2 18.2042894053165 10.034026772534146 1 6 4.27 -5.04 3.80e-03 g/l