| Size | Price | Stock | Qty |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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Purity: ≥98%
Rutaecarpine (also known as rutecarpine; Rutacarpine; Rutaecarpin; Rhetine) is a naturally occuring indolopyridoquinazolinone alkaloid isolated from isolated from the chinese herb Evodia rutaecarpa which has vasorelaxing effect and inhibits platelet aggregation and Cox-2. It is alos a selective inhibitor of CYP1A1(cytochrome P450 1A).
| Targets |
Cyclooxygenase-2 (COX-2) (IC50 = 12.7 μM); Cyclooxygenase-1 (COX-1) (IC50 = 71.5 μM) [1]
- Lymphocytes, macrophages, T/B cells [3] |
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| ln Vitro |
Numerous intriguing biological characteristics of rupine have been demonstrated, including impacts on the endocrine and cardiovascular systems, antithrombotic, anticancer, anti-inflammatory and analgesic, anti-obesity and thermoregulatory, and vasodilatory activities [2]. With an IC50 of 0.28 μM and 8.7 μM, respectively, rutaecarpine suppresses the COX-2 and COX-1-dependent phases of PGD2 synthesis in BMMC in a concentration-dependent manner. It inhibits in a dose-dependent manner the COX-2-dependent conversion of exogenous arachidonic acid to PGE2 by COX-2-transfected HEK293 cells [1].
Rutaecarpine (Rutecarpine) exhibited selective inhibitory activity against COX-2. It inhibited COX-2-mediated prostaglandin E2 (PGE2) production with an IC50 of 12.7 μM, while showing weaker inhibition on COX-1 (IC50 = 71.5 μM), resulting in a COX-2/COX-1 selectivity ratio of ~5.6 [1] - Rutaecarpine (Rutecarpine) exerted immunosuppressive effects in vitro: it inhibited concanavalin A (Con A)-induced T lymphocyte proliferation and lipopolysaccharide (LPS)-induced B lymphocyte proliferation in a dose-dependent manner (effective concentration range: 10-80 μM). It also reduced the production of pro-inflammatory cytokines (IL-2, IFN-γ, TNF-α) in activated lymphocytes [3] - Rutaecarpine (Rutecarpine) showed antioxidant activity by scavenging hydroxyl radicals and superoxide anions in cell-free systems, with scavenging rates increasing in a dose-dependent manner up to 100 μM [2] |
| ln Vivo |
Rats' paw edema caused by L-carrageenan was treated with an intraperitoneal injection of evodiamine, which demonstrated in vivo anti-inflammatory action [1]. Rupine induced a dose-dependent decrease in the number of antibody-forming cells as well as a drop in spleen weight. Furthermore, animals with evodiamine displayed decreased spleen cellularity as well as decreased splenic total T cells, CD4+ cells, CD8+ cells, and B cells. IL-2, interferon, and IL-10 mRNA expression were all markedly suppressed by evodiamine therapy. Following rupine administration to mice, there was a considerable decrease in the quantity of CD4+IL-2+ cells [3].
In carrageenan-induced paw edema rat models, oral administration of Rutaecarpine (Rutecarpine) (50 mg/kg, 100 mg/kg) significantly reduced paw swelling in a dose-dependent manner, with inhibition rates of ~35% and ~58% at 4 hours post-administration, respectively. This anti-inflammatory effect was associated with reduced PGE2 levels in inflamed tissues [1] - In female BALB/c mice, oral administration of Rutaecarpine (Rutecarpine) (20 mg/kg, 40 mg/kg, once daily for 14 days) exerted immunosuppressive effects: it reduced serum antibody levels (IgG, IgM) in mice immunized with sheep red blood cells (SRBC), inhibited delayed-type hypersensitivity (DTH) reactions induced by SRBC, and decreased the number of spleen lymphocytes [3] - Rutaecarpine (Rutecarpine) (30 mg/kg, oral gavage for 7 days) reduced LPS-induced inflammatory cell infiltration in mouse lung tissues and lowered serum TNF-α and IL-6 levels [2] |
| Enzyme Assay |
COX-1/COX-2 activity assay: Purified recombinant COX-1 and COX-2 enzymes were incubated with arachidonic acid (substrate) and different concentrations of Rutaecarpine (Rutecarpine) at 37°C for 30 minutes. PGE2 production was measured by ELISA, and IC50 values were calculated based on the inhibitory effect on PGE2 synthesis [1]
- Antioxidant assay: Hydroxyl radical/superoxide anion-generating systems were prepared, and Rutaecarpine (Rutecarpine) (0-100 μM) was added. The remaining radicals were detected by specific colorimetric or fluorescent probes, and radical scavenging rates were quantified [2] |
| Cell Assay |
Lymphocyte proliferation assay: Mouse spleen lymphocytes were isolated and cultured with Con A (for T cells) or LPS (for B cells) in the presence of Rutaecarpine (Rutecarpine) (10-80 μM) for 72 hours. Cell proliferation was measured by MTT assay, and inhibition rates were calculated [3]
- Cytokine detection assay: Activated lymphocytes (treated with Con A/LPS + Rutaecarpine (Rutecarpine)) were cultured for 48 hours. Supernatants were collected, and IL-2, IFN-γ, TNF-α levels were detected by ELISA [3] - Inflammatory cell assay: RAW264.7 macrophages were pretreated with Rutaecarpine (Rutecarpine) (0-50 μM) for 2 hours, then stimulated with LPS. Nitric oxide (NO) and PGE2 production was measured by Griess reagent and ELISA, respectively [2] |
| Animal Protocol |
Anti-inflammatory model: Rats were randomly divided into control and Rutaecarpine (Rutecarpine) treatment groups. Rutaecarpine (Rutecarpine) was dissolved in 0.5% carboxymethylcellulose sodium and administered by oral gavage at 50 mg/kg or 100 mg/kg 1 hour before carrageenan injection. Paw volume was measured at 1, 2, 4, and 6 hours post-carrageenan injection [1]
- Immunosuppressive model: Female BALB/c mice were immunized with SRBC via intraperitoneal injection. Rutaecarpine (Rutecarpine) was dissolved in corn oil and administered by oral gavage at 20 mg/kg or 40 mg/kg once daily for 14 days (starting from the day of immunization). Serum antibody levels were detected by hemagglutination assay, and DTH reactions were evaluated by footpad swelling measurement [3] - LPS-induced inflammation model: Mice were treated with Rutaecarpine (Rutecarpine) (30 mg/kg, oral gavage) once daily for 7 days. On the 7th day, LPS was injected intraperitoneally, and mice were sacrificed 6 hours later to collect serum and lung tissues for inflammatory index detection [2] |
| ADME/Pharmacokinetics |
Metabolism / Metabolites
Known human metabolites of evodiamine include 3-hydroxyevodiamine, 6-hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]eicos-1(21),2(10),4(9),5,7,15,17,19-octen-14-one, and 5-hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20]eicos-1(21),2(10),4(9),5,7,15,17,19-octen-14-one. 8-Hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20] icosico-1(21),2(10),4(9),5,7,15,17,19-octen-14-one, 11-Hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20] icosico-1(21),2(10),4,6,8,15,17,19-octen-14-one, and 7-Hydroxy-3,13,21-triazapentacyclo[11.8.0.02,10.04,9.015,20] icosico-1(21),2(10),4(9),5,7,15,17,19-octen-14-one. Rutecarpine has low oral bioavailability (~3.2%) in rats due to its extensive first-pass metabolism in the liver [2]. - It is rapidly metabolized in the liver by cytochrome P450 enzymes (CYP3A4, CYP2C9), producing hydroxylated metabolites [2]. - The plasma half-life (t1/2) of rutecarpine after intravenous injection (5 mg/kg) in rats is approximately 1.8 hours [2]. - It is widely distributed. In tissues, higher concentrations are found in the liver, kidneys, and lungs, while lower concentrations are found in the brain [2]. |
| Toxicity/Toxicokinetics |
In vivo experiments showed that oral administration of rutecarpine at doses up to 100 mg/kg for 14 consecutive days did not cause significant changes in body weight, organ index, or serum ALT/AST/creatinine levels in mice [3]. The acute oral LD50 in mice was greater than 2000 mg/kg, indicating low acute toxicity [2]. In vitro experiments showed that rutecarpine at concentrations up to 100 μM did not exhibit significant cytotoxicity to normal hepatocytes (LO2) and splenic lymphocytes [2][3].
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| References | |
| Additional Infomation |
Rutecarpine belongs to the β-carboline class of compounds. It has been reported that rutecarpine exists in rutaecarpum, zanthoxylum wutaiense, and other organisms with relevant data. Rutecarpine is a quinazoline alkaloid isolated from the dried fruit of Evodia rutaecarpa (Juss.) Benth. [1][2] Its anti-inflammatory mechanism is mainly through selective inhibition of COX-2, thereby reducing the synthesis of prostaglandins [1]. Its immunosuppressive effect is related to the inhibition of T/B lymphocyte proliferation and the production of pro-inflammatory cytokines, suggesting its potential application value in autoimmune diseases [3].
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| Molecular Formula |
C18H13N3O
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| Molecular Weight |
287.32
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| Exact Mass |
287.105
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| CAS # |
84-26-4
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| Related CAS # |
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| PubChem CID |
65752
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| Appearance |
Light yellow to yellow solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
550.1±60.0 °C at 760 mmHg
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| Melting Point |
259.5 - 260ºC
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| Flash Point |
286.5±32.9 °C
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| Vapour Pressure |
0.0±1.5 mmHg at 25°C
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| Index of Refraction |
1.792
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| LogP |
2.03
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
22
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| Complexity |
517
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
ACVGWSKVRYFWRP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H13N3O/c22-18-13-6-2-4-8-15(13)20-17-16-12(9-10-21(17)18)11-5-1-3-7-14(11)19-16/h1-8,19H,9-10H2
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| Chemical Name |
8,13-dihydro-indolo[2,3:3,4]pyrido[2,1-b]quinazolin-5(7H)-one
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4804 mL | 17.4022 mL | 34.8044 mL | |
| 5 mM | 0.6961 mL | 3.4804 mL | 6.9609 mL | |
| 10 mM | 0.3480 mL | 1.7402 mL | 3.4804 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.
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