Cyclopamine
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MedKoo CAT#: 401235

CAS#: 4449-51-8

Description: Cyclopamine, also known as 11-deoxojervine, 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. Cyclopamine was named for one-eyed lambs which were born to sheep which grazed on wild corn lily at a farm in Idaho.


Chemical Structure

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Cyclopamine
CAS# 4449-51-8

Theoretical Analysis

MedKoo Cat#: 401235
Name: Cyclopamine
CAS#: 4449-51-8
Chemical Formula: C27H41NO2
Exact Mass: 411.31373
Molecular Weight: 411.62
Elemental Analysis: C, 78.78; H, 10.04; N, 3.40; O, 7.77

Price and Availability

Size Price Availability Quantity
50.0mg USD 450.0 2 Weeks
100.0mg USD 650.0 2 Weeks
500.0mg USD 1450.0 2 Weeks
1.0g USD 2650.0 2 Weeks
2.0g USD 3950.0 2 Weeks
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Synonym: HSDB-3505; HSDB 3505; HSDB-3505; Cyclopamine; 11-Deoxojervine.

IUPAC/Chemical Name: (2'R,3S,3'R,3a'S,6aS,6bS,6'S,7a'R,11aS,11bR)-3',6',10,11b-tetramethyl-1,2,3,3a',4,4',5',6,6a,6b,6',7,7',7a',8,11,11a,11b-octadecahydro-3'H-spiro[benzo[a]fluorene-9,2'-furo[3,2-b]pyridin]-3-ol

InChi Key: QASFUMOKHFSJGL-LAFRSMQTSA-N

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

SMILES Code: O[C@@H]1CC2=CC[C@]3([H])[C@]([C@@]2(C)CC1)([H])CC4=C(C)[C@@]5(O[C@@]6([H])[C@@]([C@H]5C)([H])NC[C@@H](C)C6)CC[C@@]34[H]

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 411.62 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Gould A, Missailidis S. Targeting the hedgehog pathway: the development of cyclopamine and the development of anti-cancer drugs targeting the hedgehog pathway. Mini Rev Med Chem. 2011 Mar;11(3):200-13. Review. PubMed PMID: 21222574.

2: Heretsch P, Tzagkaroulaki L, Giannis A. Cyclopamine and hedgehog signaling: chemistry, biology, medical perspectives. Angew Chem Int Ed Engl. 2010 May 3;49(20):3418-27. Review. PubMed PMID: 20429080.

3: 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. Review. PubMed PMID: 18230052.

4: Meth MJ, Weinberg JM. Cyclopamine: inhibiting hedgehog in the treatment of psoriasis. Cutis. 2006 Sep;78(3):185-8. Review. PubMed PMID: 17036662.

5: Miller SJ, Yu TC. Cyclopamine as a potential therapeutic agent for treatment of tumors related to hedgehog pathway mutations. Dermatol Surg. 2002 Feb;28(2):187. Review. PubMed PMID: 11860435.

6: Gaffield W, Incardona JP, Kapur RP, Roelink H. A looking glass perspective: thalidomide and cyclopamine. Cell Mol Biol (Noisy-le-grand). 1999 Jul;45(5):579-88. Review. PubMed PMID: 10512190.
  



Additional Information

Cyclopamine is currently being investigated as a treatment agent in basal cell carcinoma, medulloblastoma, and rhabdomyosarcoma, tumors that result from excessive Hh activity, glioblastoma, and as a treatment agent for multiple myeloma. Studies suggest that cyclopamine acts as a primary inhibitor of the so-called "hedgehog" signal-transduction 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. Many anticancer drugs are paradoxically carcinogenic in healthy individuals. The cyclopamine derivative IPI-926 is in clinical trials for the treatment of various types of cancer.  [source: http://en.wikipedia.org/wiki/Cyclopamine).