An inhibitor of hedgehog signaling
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Cyclopamine

Item No. 11321

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-octadecahydro-3',6',10,11b-tetramethyl-spiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol
CAS Number
4449-51-8
Synonyms
  • 11-Deoxojervine
  • Jervine
Molecular Formula
C27H41NO2
Formula Weight
411.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 2 mg/mlEthanol: 10 mg/mlEthanol:PBS (pH 7.2) (1:3): 0.25 mg/ml
SMILES
O[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC4=C(C)[C@]5([C@H](C)[C@@](NC[C@@H](C)C6)([H])[C@]6([H])O5)CC[C@@]34[H]
InChi Code
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
InChi Key
QASFUMOKHFSJGL-LAFRSMQTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $33

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    5 mg

    $83

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    10 mg

    $132

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    Product Description

    Cyclopamine is a natural steroidal alkaloid that inhibits signaling through the hedgehog pathway at the level of the pathway activator Smoothened.1,2 By altering gene expression in this signaling sequence, cyclopamine induces defects in morphogenesis, first observed in chicks and sheep as cyclopia.1 As a readout of action, cyclopamine inhibits hedgehog-dependent expression of Pax7 with an IC50 value of 24 nM.1 Although teratogenic during development, cyclopamine has potential applications in the treatment of cancer.3,4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Incardona, J.P., Gaffield, W., Kapur, R.P., et al. The teratogenic Veratrum alkaloid cyclopamine inhibits Sonic hedgehog signal transduction. Development 125(18), 3553-3562 (1998).

    2. Frank-Kamenetsky, M., Zhang, X.M., Bottega, S., et al. Small-molecule modulators of Hedgehog signaling: Identification and characterization of smoothened agonists and antagonists. J. Biol. 1(2), 10 (2002).

    3. Xu, F.G., Ma, Q.Y., and Wang, Z. Blockade of hedgehog signaling pathway as a therapeutic strategy for pancreatic cancer. Cancer Lett. 283(2), 119-124 (2009).

    4. Heretsch, P., Tzagkaroulaki, L., and Giannis, A. Cyclopamine and hedgehog signaling: Chemistry, biology, medical perspectives. Agnew. Chem. Int. Ed. Engl. 49(20), 3418-3427 (2010).

    5. Mahindroo, N., Punchihewa, C., and Fujii, N. Hedgehog-Gli signaling pathway inhibitors as anticancer agents. J. Med. Chem. 52(13), 3829-3845 (2009).