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Purity: ≥98%
Indirubin (also known as NSC-105327; Couroupitine B) is a potent and selective inhibitor of CDK (cyclin-dependent kinases) and GSK-3β (glycogen synthase kinase-3) with potential antitumor activity. It blocks CDK and GSK-3β with IC50 values of approximately 5 M and 0.6 M, respectively. The main component of the traditional Chinese herbal medicine Danggui Longhui Wan, indurarubin, is a naturally occurring substance.
| Targets |
GSK-3β (IC50 = 0.6 μM ); CDK2/CyclinA (IC50 = 2.2 μM); CDK5/p35 (IC50 = 5.5 μM); CDK1/CyclinB (IC50 = 10 μM); CDK4/CyclinD1 (IC50 = 12 μM)
|
|---|---|
| ln Vitro |
Indirubin (Couroupitine B) significantly reduces Td-EC angiogenesis, invasion, migration, and angiogenesis[1].
|
| ln Vivo |
In a dose-dependent manner, indorubin (Couroupitine B) (12.5 mg/kg, 25 mg/kg; intraperitoneal injected; once a day for 14 days) may lessen the pathological alterations[3].
|
| Cell Assay |
Indirubin exerted its inhibitory effects not only on interferon-γ production by human myelomonocytic HBL-38 cells but also on interferon-γ and interleukin-σ production by murine splenocytes with no influence on the proliferation of either cells.
|
| Animal Protocol |
Male mice (C57BL/6)
12.5 mg/kg, 25 mg/kg Indirubin (12.5 mg/kg, 25 mg/kg; intraperitoneal injected; once a day for 14 days) |
| References |
|
| Additional Infomation |
Indirubin is under investigation in clinical trial NCT01735864 (Dosage Determination Trial for Indigo Naturalis Extract in Oil Ointment).
Indirubin has been reported in Calanthe discolor, Couroupita guianensis, and Isatis tinctoria with data available. |
| Molecular Formula |
C16H10N2O2
|
|---|---|
| Molecular Weight |
262.2628
|
| Exact Mass |
262.074
|
| Elemental Analysis |
C, 73.27; H, 3.84; N, 10.68; O, 12.20
|
| CAS # |
479-41-4
|
| Related CAS # |
Indirubin-3'-monoxime;160807-49-8
|
| PubChem CID |
10177
|
| Appearance |
Red solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
496.6±45.0 °C at 760 mmHg
|
| Melting Point |
350 °C
|
| Flash Point |
207.0±28.9 °C
|
| Vapour Pressure |
0.0±1.3 mmHg at 25°C
|
| Index of Refraction |
1.709
|
| LogP |
2.48
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
1
|
| Heavy Atom Count |
20
|
| Complexity |
448
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O([H])C1=C(C2C(C3=C([H])C([H])=C([H])C([H])=C3N=2)=O)C2=C([H])C([H])=C([H])C([H])=C2N1[H]
|
| InChi Key |
CRDNMYFJWFXOCH-YPKPFQOOSA-N
|
| InChi Code |
InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,17H,(H,18,20)/b14-13-
|
| Chemical Name |
3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one
|
| Synonyms |
NSC 105327; Couroupitine B; C.I. 73200; Indigo red; Indigopurpurin; NSC-105327; NSC 105327; NSC105327
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: ~53 mg/mL (~202.1 mM)
Water: <1 mg/mL Ethanol: <1 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 1 mg/mL (3.81 mM) (saturation unknown) in 10% DMSO + 40% PEG300 +5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 10.0 mg/mL clear DMSO stock solution to 400 μL of PEG300 and mix evenly; then add 50 μL of Tween-80 + to the above solution and mix evenly; then add 450 μL of normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.8130 mL | 19.0650 mL | 38.1301 mL | |
| 5 mM | 0.7626 mL | 3.8130 mL | 7.6260 mL | |
| 10 mM | 0.3813 mL | 1.9065 mL | 3.8130 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
| NCT Number | Recruitment | interventions | Conditions | Sponsor/Collaborators | Start Date | Phases |
| NCT01735864 | Completed | Drug: Indirubin 10 μg/g Drug: Indirubin 50 μg/g |
Psoriasis Vulgaris | Chang Gung Memorial Hospital | November 2012 | |
| NCT02088281 | Completed | Drug: Indigo naturalis extract in oil ointment |
Psoriasis Vulgaris | Chang Gung Memorial Hospital | November 2012 | Phase 2 |
| NCT03614221 | Completed | Drug: Protopic ointment 0.1% Drug: Lindioil ointment |
Atopic Dermatitis | Chang Gung Memorial Hospital | June 3, 2019 | Phase 2 |
| NCT02669888 | Completed | Drug: Indigo naturalis ointment Drug: Placebo |
Atopic Dermatitis | Chang Gung Memorial Hospital | October 2015 | Phase 2 |
| NCT02200978 | Completed | Drug: ATO Drug: 6MP |
Childhood Acute Promyelocytic Leukemia |
South China Children's Leukemia Group |
September 2011 | Phase 4 |
J Biol Chem. 2001 Jan 5;276(1):251-60. |
Indirubin inhibits TNF-induced expression of NF-κB-dependent antiapoptotic, proliferative, and metastatic proteins. |
Indirubin enhances TNF-induced cytotoxicity. |
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