Cyclopamine (Synonyms: 11-Deoxojervine)

Name: Cyclopamine
Brand: MedChemExpress
SKU: HY-17024
Rating: 5.0 (47 reviews)

Cat. No.: HY-17024 Purity: 99.97%: FAQs
Data Sheet SDS COA Handling Instructions

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Cyclopamine is a Hedgehog (Hh) pathway antagonist with an IC₅₀ of 46 nM in the Hh cell assay. Cyclopamine is also a selective Smo inhibitor.

For research use only. We do not sell to patients.

Cyclopamine Chemical Structure

CAS No. : 4449-51-8

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10 mM * 1 mL in DMSO ready for reconstitution	In-stock	Estimated Time of Arrival: December 31
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10 mM * 1 mL in DMSO	In-stock	Estimated Time of Arrival: December 31
Solid
5 mg	In-stock	Estimated Time of Arrival: December 31
10 mg	In-stock	Estimated Time of Arrival: December 31
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Based on 47 publication(s) in Google Scholar

Other Forms of Cyclopamine:

Cyclopamine (Standard) Get quote

41 Publications Citing Use of MCE Cyclopamine

: Cyclopamine purchased from MedChemExpress. Usage Cited in: Cell Death Dis. 2019 Sep 12;10(9):681. [Abstract]; Endometrial stromal cells are stimulated with 10 ng/mL TGFβ1 for 48 h. Then these cells are treated with 10 μM Cyc for 24 h and/or cocultured with 10 ng/mL VEGF165 for another 12 or 24 h. The protein levels of collagen 1, α-SMA and smad7 are examined.

: Cyclopamine purchased from MedChemExpress. Usage Cited in: Cell Death Dis. 2019 Sep 12;10(9):681. [Abstract]; Endometrial stromal cells are stimulated with 10 ng/mL TGFβ1 for 48 h. Then these cells are treated with 10 μM Cyc for 24 h and/or cocultured with 10 ng/mL VEGF165 for another 12 or 24 h. The protein levels of collagen 1, α-SMA and smad7 are examined.

: Cyclopamine purchased from MedChemExpress. Usage Cited in: Front Pharmacol. 2018 Jun 26;9:674. [Abstract]; Cyclopamine and GANT61 decrease the level of Gli1 as evidenced by western blot.

: Cyclopamine purchased from MedChemExpress. Usage Cited in: Int J Nanomedicine. 2017 Apr 20;12:3267-3280. [Abstract]; The Smo inhibitor Cyclopamine suppresses the activity of Hedgehog–Gli1 signaling. The gene expression and protein production of Smo in MG63 osteoblasts after 7 days of incubation on the different titanium surfaces.

: Cyclopamine purchased from MedChemExpress. Usage Cited in: Life Sci. 2017 Dec 15;191:82-89. [Abstract]; ORS cells are exposed to 3% oxygen for 48 h in presence or absence of Shh pathway inhibitor cyclopamine (5 μM) or GANT61 (10 μM). Immunofluorescence assay using anti-PCNA antibody is performed to detect the proliferative ORS cells (red). Cell nuclei are counterstained with DAPI (blue).

: Cyclopamine purchased from MedChemExpress. Usage Cited in: Neurochem Res. 2016 Apr;41(4):687-95. [Abstract]; Western blot and RT-qPCR assays of BDNF protein and gene expressions in primary cortical neurons in different experimental conditions. Immunoblotting bands of BDNF protein.

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Description

Cyclopamine is a Hedgehog (Hh) pathway antagonist with an IC₅₀ of 46 nM in the Hh cell assay. Cyclopamine is also a selective Smo inhibitor.

IC₅₀ & Target

Human Endogenous Metabolite

Cellular Effect

Cell Line	Type	Value	Description	References
A549	IC₅₀	49 μM Compound: 1	Anticancer activity against human A549 cells by MTS assay Anticancer activity against human A549 cells by MTS assay	[PMID: 18221872]
C3H 10T1/2	EC₅₀	0.17 μM Compound: 1	Inhibition of Hedgehog pathway-dependent oxysterol-induced mouse C3 H10T1/2 cell differentiation assessed as alkaline phosphatase production after 72 hrs Inhibition of Hedgehog pathway-dependent oxysterol-induced mouse C3 H10T1/2 cell differentiation assessed as alkaline phosphatase production after 72 hrs	[PMID: 18842035]
C3H 10T1/2	IC₅₀	0.6 μM Compound: cyclopamine	Inhibition of human Shh-induced mouse C3H10T1/2 cell differentiation after 48 hrs by alkaline phosphatase reporter assay Inhibition of human Shh-induced mouse C3H10T1/2 cell differentiation after 48 hrs by alkaline phosphatase reporter assay	[PMID: 23074541]
C3H 10T1/2	IC₅₀	0.6 μM Compound: Cyclopamine	Inhibition of N-terminal SHH activated pathway in mouse C3H10T1/2 cells assessed as SAG-induced cell differentiation by alkaline phosphatase assay Inhibition of N-terminal SHH activated pathway in mouse C3H10T1/2 cells assessed as SAG-induced cell differentiation by alkaline phosphatase assay	[PMID: 21592788]
C3H 10T1/2	IC₅₀	0.62 μM Compound: Cyclopamine	Inhibition of SAG-induced differentiation of mouse mesenchymal pluripotent C3H10T1/2 cells to alkaline phosphatase positive oeseoblasts after 6 hrs Inhibition of SAG-induced differentiation of mouse mesenchymal pluripotent C3H10T1/2 cells to alkaline phosphatase positive oeseoblasts after 6 hrs	[PMID: 22268551]
CHO	IC₅₀	1200 nM Compound: cyclopamine	Antagonist activity at mouse Smo receptor expressed in CHO cells by [3H]Hh-Ag binding assay Antagonist activity at mouse Smo receptor expressed in CHO cells by [3H]Hh-Ag binding assay	[PMID: 19091559]
CHO	IC₅₀	280 nM Compound: cyclopamine	Antagonist activity at human Smo receptor expressed in CHO cells by [3H]Hh-Ag binding assay Antagonist activity at human Smo receptor expressed in CHO cells by [3H]Hh-Ag binding assay	[PMID: 19091559]
Daoy	IC₅₀	0.16 μM Compound: 2, Cyc	Inhibition of Hedgehog signaling in human DaOY cells assessed as downregulation of Gli1 mRNA expression after 48 hrs by RT-PCR analysis Inhibition of Hedgehog signaling in human DaOY cells assessed as downregulation of Gli1 mRNA expression after 48 hrs by RT-PCR analysis	[PMID: 24900716]
HEK293	IC₅₀	64 nM Compound: Cyclopamine	Displacement of BODIPY-labelled cyclopamine from human Smo receptor expressed in HEK293 cells after 2 hrs by fluorescence microscopy Displacement of BODIPY-labelled cyclopamine from human Smo receptor expressed in HEK293 cells after 2 hrs by fluorescence microscopy	[PMID: 22268551]
Medulloblastoma cell	EC₅₀	1 μM Compound: 16	Antiproliferative activity against mouse medulloblastoma cells harboring heterozygous ptch1 gene by MTT assay Antiproliferative activity against mouse medulloblastoma cells harboring heterozygous ptch1 gene by MTT assay	[PMID: 17417631]
MEF	IC₅₀	1.9 μM Compound: cyclopamine	Inhibition of Smo in mouse Ptch-deficient MEF cells assessed as inhibition of Shh-induced Gli-responsive betagalactosidase activity after 30 hrs by BetaGLo assay Inhibition of Smo in mouse Ptch-deficient MEF cells assessed as inhibition of Shh-induced Gli-responsive betagalactosidase activity after 30 hrs by BetaGLo assay	[PMID: 23074541]
Shh Light II	IC₅₀	0.3 μM Compound: Cyclopamine	Inhibition of SHH pathway in mouse Shh Light2 cells after 40 hrs by Gli-dependent luciferase reporter gene assay Inhibition of SHH pathway in mouse Shh Light2 cells after 40 hrs by Gli-dependent luciferase reporter gene assay	[PMID: 21592788]
Shh Light II	IC₅₀	0.3 μM Compound: Cyclopamine	Inhibition of Smo-mediated Hh signaling in human Shh-light2 cells by luciferase reporter gene assay Inhibition of Smo-mediated Hh signaling in human Shh-light2 cells by luciferase reporter gene assay	[PMID: 22268551]
Shh Light II	IC₅₀	1312 nM Compound: Cyclopamine	Inhibition of SHH in mouse Shh-Light2 cells after 48 hrs by Gli1 reporter gene assay in presence of SAG Inhibition of SHH in mouse Shh-Light2 cells after 48 hrs by Gli1 reporter gene assay in presence of SAG	[PMID: 19541490]
Shh Light II	IC₅₀	484 nM Compound: Cyc	Antagonist activity at Smo in mouse Shh-Light 2 cells assessed as inhibition of Shh-induced Gli1-reporter activity after 2 days by dual-luciferase reporter gene method Antagonist activity at Smo in mouse Shh-Light 2 cells assessed as inhibition of Shh-induced Gli1-reporter activity after 2 days by dual-luciferase reporter gene method	[PMID: 23063522]
Shh Light II	EC₅₀	500 nM Compound: 3	Inhibition of SHH in mouse Shh Light2 cells by GLI-responsive firefly luciferase reporter gene assay Inhibition of SHH in mouse Shh Light2 cells by GLI-responsive firefly luciferase reporter gene assay	[PMID: 19309080]
TM3	IC₅₀	46 nM Compound: cyclopamine	Inhibition of Hedgehog signaling pathway in mouse TM3 cells bearing pTA-8xGli-Luc reporter construct assessed as transcriptional modulation of Gli after 48 hrs by luciferase assay Inhibition of Hedgehog signaling pathway in mouse TM3 cells bearing pTA-8xGli-Luc reporter construct assessed as transcriptional modulation of Gli after 48 hrs by luciferase assay	[PMID: 19091559]
U-87MG ATCC	IC₅₀	22.5 μM Compound: Cyc	Antiproliferative activity against human U87MG cells after 72 hrs by MTS assay Antiproliferative activity against human U87MG cells after 72 hrs by MTS assay	[PMID: 22226657]

In Vitro

Treatment with small molecule Hh inhibitors such as HhAntag and the natural product Cyclopamine, both binding to Smo, induces tumor remission in a genetic mouse model of medulloblastoma^[1]. Cyclopamine is a Hedgehog (Hh) pathway antagonist. Cyclopamine suppresses cell growth. Cyclopamine (3 μM) suppression of Hh pathway activity and growth in digestive tract tumour cell lines correlates with expression of PTCHmRNA^[2]. Cyclopamine is a steroidal alkaloid that inhibits Hh signalling through direct interaction with Smo^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Cyclopamine causes durable regression of xenograft tumors. Tumors in Cyclopamine-treated animals, regress completely by 12 days^[2]. Cyclopamine (1.2 mg) treatment blocks tumour formation of human pancreatic adenocarcinoma cells after transplantation into nude mice^[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Molecular Weight

411.62

Formula

C₂₇H₄₁NO₂

CAS No.

4449-51-8

Appearance

Solid

Color

White to off-white

SMILES

CC1=C2[C@@]([C@@]3([H])[C@]([C@@]4(C(C[C@@H](O)CC4)=CC3)C)([H])C2)([H])CC[C@@]15[C@@H]([C@@]6([H])[C@](C[C@H](C)CN6)([H])O5)C

Structure Classification

Steroids

Initial Source

Endogenous metabolite

Shipping

Room temperature in continental US; may vary elsewhere.

Storage

Powder	-20°C	3 years
	4°C	2 years
In solvent	-80°C	6 months
	-20°C	1 month

Solvent & Solubility

In Vitro:

Ethanol : 20 mg/mL (48.59 mM; Need ultrasonic)

DMSO : 10 mg/mL (24.29 mM; ultrasonic and warming and heat to 80°C; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	2.4294 mL	12.1471 mL	24.2943 mL
5 mM	0.4859 mL	2.4294 mL	4.8589 mL
10 mM	0.2429 mL	1.2147 mL	2.4294 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.

Molarity Calculator
Dilution Calculator

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Concentration _(start) × Volume _(start) = Concentration _(final) × Volume _(final)

This equation is commonly abbreviated as: C₁V₁ = C₂V₂

Concentration _(start)

Volume _(start)

Concentration _(final)

Volume _(final)

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% EtOH 90% Corn Oil
Solubility: ≥ 1.67 mg/mL (4.06 mM); Clear solution

This protocol yields a clear solution of ≥ 1.67 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL EtOH stock solution (16.7 mg/mL) to 900 μL Corn oil, and mix evenly.
Protocol 2

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 1 mg/mL (2.43 mM); Clear solution

This protocol yields a clear solution of ≥ 1 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (10.0 mg/mL) to 900 μL Corn oil, and mix evenly.
Protocol 3

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 0.5 mg/mL (1.21 mM); Clear solution

This protocol yields a clear solution of ≥ 0.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (5.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Protocol 4

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 0.5 mg/mL (1.21 mM); Clear solution

This protocol yields a clear solution of ≥ 0.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (5.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.

In Vivo Dissolution Calculator

Please enter the basic information of animal experiments:

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mg/kg

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(per animal)

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.

Please enter your animal formula composition:

DMSO +

Tween-80 +

Saline

Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.

The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).

Calculation results:

Working solution concentration: mg/mL

Method for preparing stock solution: mg drug dissolved in μL DMSO (Stock solution concentration: mg/mL).

The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only. If necessary, please contact MedChemExpress (MCE).

Method for preparing in vivo working solution for animal experiments: Take μL DMSO stock solution, add μL . μL , mix evenly, next add μL Tween 80, mix evenly, then add μL Saline.

If the continuous dosing period exceeds half a month, please choose this protocol carefully.

Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.

Purity & Documentation

Purity: 99.97%

Select Batch:

Data Sheet (279 KB) SDS (393 KB)

COA (248 KB) HNMR (206 KB) LCMS (123 KB) Elemental Analysis Report (105 KB)

Handling Instructions (2659 KB)

References

[1]. Peukert S, et al. Identification and structure-activity relationships of ortho-biphenyl carboxamides as potent Smoothened antagonists inhibiting the Hedgehog signaling pathway. Bioorg Med Chem Lett, 2009, 19(2), 328-331. [Content Brief]

[2]. Berman DM, et al. Widespread requirement for Hedgehog ligand stimulation in growth of digestive tract tumours. Nature, 2003, 425(6960), 846-851. [Content Brief]

[3]. Thayer SP, et al. Hedgehog is an early and late mediator of pancreatic cancer tumorigenesis. Nature, 2003, 425(6960), 851-856. [Content Brief]

[4]. Ma W, et al. Reduced Smoothened level rescued Aβ-induced memory deficits and neuronal inflammation in animal models of Alzheimer's disease. J Genet Genomics. 2018 May 20;45(5):237-246. [Content Brief]

[5]. Qi Wan, et al. Overexpression of Laminin α4 Facilitates Proliferation and Migration of Fibroblasts in Knee Arthrofibrosis by Targeting Canonical Shh/Gli1 Signaling. Connect Tissue Res. 2020 May 24. [Content Brief]

Cell Assay ^[2]	Cells are cultured in triplicate in 96-well plates in assay media to which 5E1 monoclonal antibody, ShhNp and/or Cyclopamine (3 μM) are added at 0 h at concentrations indicated in the main text. Viable cell mass is determined by optical density measurements at 490 nm (OD₄₉₀) at 2 and 4 days using the CellTiter96 colorimetric assay. Relative growth is calculated as OD (day 4)-OD (day 2)/OD (day 2)^[2]. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Animal Administration ^[3]	Mice^[3] A total of 0.1 mL Hanks’ balanced salt solution and matrigel (1:1) containing 2×10⁶ cells is injected subcutaneously into CD-1 nude mice. Tumors are grown for 4 days to a minimum volume of 125 mm³; treatment is initiated simultaneously for all subjects. Mice are injected subcutaneously with vector alone (triolein:ethanol 4:1 v/v) or a Cyclopamine suspension (1.2 mg per mouse in triolein:ethanol 4:1 v/v) daily for 7 days. At the end of the treatment period, tumours are excised from mice, weighed and then fixed for 3 h at 4°C with 4% paraformaldehyde, embedded in paraffin wax and sectioned (6 µm). Apoptotic cells are identified by TUNEL using recombinant Tdt. Sections are then counterstained with eosin. Eight ×20-magnified fields from regions corresponding to the exterior, middle and interior of two control and two cyclopamine-treated tumours are chosen at random. We counted the number of TUNEL-positive nuclei manually. Haematoxylin/eosin staining is done. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
References	[1]. Peukert S, et al. Identification and structure-activity relationships of ortho-biphenyl carboxamides as potent Smoothened antagonists inhibiting the Hedgehog signaling pathway. Bioorg Med Chem Lett, 2009, 19(2), 328-331. [Content Brief] [2]. Berman DM, et al. Widespread requirement for Hedgehog ligand stimulation in growth of digestive tract tumours. Nature, 2003, 425(6960), 846-851. [Content Brief] [3]. Thayer SP, et al. Hedgehog is an early and late mediator of pancreatic cancer tumorigenesis. Nature, 2003, 425(6960), 851-856. [Content Brief] [4]. Ma W, et al. Reduced Smoothened level rescued Aβ-induced memory deficits and neuronal inflammation in animal models of Alzheimer's disease. J Genet Genomics. 2018 May 20;45(5):237-246. [Content Brief] [5]. Qi Wan, et al. Overexpression of Laminin α4 Facilitates Proliferation and Migration of Fibroblasts in Knee Arthrofibrosis by Targeting Canonical Shh/Gli1 Signaling. Connect Tissue Res. 2020 May 24. [Content Brief]

Complete Stock Solution Preparation Table

Optional Solvent	Concentration Solvent Mass	1 mg	5 mg	10 mg	25 mg

DMSO / Ethanol	1 mM	2.4294 mL	12.1471 mL	24.2943 mL	60.7356 mL
	5 mM	0.4859 mL	2.4294 mL	4.8589 mL	12.1471 mL
	10 mM	0.2429 mL	1.2147 mL	2.4294 mL	6.0736 mL
	15 mM	0.1620 mL	0.8098 mL	1.6196 mL	4.0490 mL
	20 mM	0.1215 mL	0.6074 mL	1.2147 mL	3.0368 mL
Ethanol	25 mM	0.0972 mL	0.4859 mL	0.9718 mL	2.4294 mL
	30 mM	0.0810 mL	0.4049 mL	0.8098 mL	2.0245 mL
	40 mM	0.0607 mL	0.3037 mL	0.6074 mL	1.5184 mL

Cyclopamine Related Classifications

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Do most proteins show cross-species activity?
Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

Keywords:

Cyclopamine4449-51-811-DeoxojervineHedgehogSmoEndogenous MetaboliteSmoothenedInhibitorinhibitorinhibit

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Cyclopamine (Synonyms: 11-Deoxojervine)

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Other Forms of Cyclopamine:

Cyclopamine Related Antibodies

41 Publications Citing Use of MCE Cyclopamine

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Cyclopamine Related Antibodies

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Complete Stock Solution Preparation Table

Cyclopamine Related Classifications

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