RUTECARPINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H13N3O
Molecular Weight	287.3153
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1N2CCC3=C(NC4=C3C=CC=C4)C2=NC5=C1C=CC=C5

InChI

InChIKey=ACVGWSKVRYFWRP-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C18H13N3O
Molecular Weight	287.3153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.itmonline.org/articles/evodia/evodia.htm
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/20336017 https://www.ncbi.nlm.nih.gov/pubmed/21423291

Rutaecarpine is an indolopyridoquinazolinone alkaloid isolated from Evodia rutaecarpa and related herbs, first isolated by Asahina and Kashiwaki. Among the active components of evodia are quinolone and indoloquinazoline alkaloids, such as evodiamine and rutaecarpine. A significant portion of the analgesic effects of evodia is attributed to these alkaloids. Rutaecarpine has also been shown to have anti-inflammatory action that is related to inhibition of COX-2, as well as other mechanisms. Evodia rutaecarpa ('Wu-Chu-Yu') remains the most popular and multi-purpose herb traditionally used in China for treatment of headache, abdominal pain, postpartum hemorrhage, dysentery and amenorrhea. Rutaecarpine is one of the main active component isolated from 'Wu-Chu-Yu'. Rutaecarpine has been shown to have cardiovascular biological effects such as inotropic and chronotropic, vasorelaxant, anti-platelet aggregation and anti-inflammatory effects. Furthermore, rutaecarpine has the potential for use as an anti-atherosclerosis agent with a novel mechanism. Rutaecarpine prevents hypoxia-reoxygenation-induced myocardial cell apoptosis via inhibition of NADPH oxidases. Also was shown, that rutaecarpine could be effective in preventing the growth of a variety of cancer cells, including downregulating the estrogen receptor of breast cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10669112	Inhibitor 8504
PI3K-Akt signaling pathway 25 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26972495	Modulator 846
AMPK signaling pathway 7 Target ID: map04152 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26972495	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
Cardiovascular diseases 72 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20336017	Preventing	Approved 8583	Unknown Approved Use Unknown
Heart failure 106 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21423291	Preventing	Approved 8583	Unknown Approved Use Unknown
Hyperlipidemia 82 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26972495	Preventing	Approved 8583	Unknown Approved Use Unknown
Cancer 609 Sources: http://www.biolreprod.org/content/83/Suppl_1/134	Preventing	Approved 8583	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	Other AEs: Palpitation, Trembling... Other AEs: Palpitation (5%) Trembling (5%) Dizziness (15%) Nervousness (5%) Headache (10%) Dullness (10%) Insomnia (10%) Vomiting (5%) Anorexia (5%) Constipation (20%) Dysuria (5%) Dry mouth (5%) Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/

AEs

AE	Significance	Dose	Population
Dullness	10%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Headache	10%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Insomnia	10%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Dizziness	15%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Constipation	20%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Anorexia	5%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Dry mouth	5%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Dysuria	5%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Nervousness	5%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Palpitation	5%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Trembling	5%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/
Vomiting	5%	0.66 mg 3 times / day multiple, oral Highest studied dose Dose: 0.66 mg, 3 times / day Route: oral Route: multiple Dose: 0.66 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/20633465/

PubMed

Title	Date	PubMed
A HAMP promoter bioassay system for identifying chemical compounds that modulate hepcidin expression.	2015-05	25633564
Zanthoxylum capense constituents with antimycobacterial activity against Mycobacterium tuberculosis in vitro and ex vivo within human macrophages.	2013-03-07	23337743
Optimization of extraction of evodiamine and rutaecarpine from fruit of Evodia rutaecarpa using modified supercritical CO(2).	2010-12-10	21067761
Reversal of isoprenaline-induced cardiac remodeling by rutaecarpine via stimulation of calcitonin gene-related peptide production.	2010-10	20962894
Investigation on fragmentation pathways of rutaecarpine and its two derivatives using electrospray ionization ion-trap time-of-flight tandem mass spectrometry.	2010-09	20814986
Anti-proliferative effects of evodiamine on human thyroid cancer cell line ARO.	2010-08-15	20503248
Regulation of dioxin receptor function by different beta-carboline alkaloids.	2010-08	20449727
A new quinolone and other constituents from the fruits of Tetradium ruticarpum: effects on neutrophil pro-inflammatory responses.	2010-07	20658672
Accelerated senescence of endothelial progenitor cells in hypertension is related to the reduction of calcitonin gene-related peptide.	2010-05	20375903
Synthesis and evaluation of novel rutaecarpine derivatives and related alkaloids derivatives as selective acetylcholinesterase inhibitors.	2010-04	20079560
Pharmacological effects of rutaecarpine as a cardiovascular protective agent.	2010-03-15	20336017
Synthesis and biological properties of benzo-annulated rutaecarpines.	2010	20930379
Up-regulation of CYP1A1 by rutaecarpine is dependent on aryl hydrocarbon receptor and calcium.	2009-12-21	19853001
Rutecarpine ameliorates bodyweight gain through the inhibition of orexigenic neuropeptides NPY and AgRP in mice.	2009-11-20	19732749
[Determination of evodiamine and rutaecarpine of compound Wuzhuyu cataplasm in plasma by SPE-HPLC: application to its pharmacokinetics].	2009-11	20209967
[Assay of evodin, evodiamine and rutaecarpine in Fructus Evodiae by QAMS].	2009-11	20209915
Effects of evodiamine and rutaecarpine on the secretion of corticosterone by zona fasciculata-reticularis cells in male rats.	2009-10-01	19639602
A flexible synthesis of 2,3-disubstituted indoles from aminobenzyl phosphonium salts. A direct synthesis of rutaecarpine.	2009-08-07	19527008
Calcitonin gene-related peptide mediates the cardioprotective effects of rutaecarpine against ischaemia-reperfusion injury in spontaneously hypertensive rats.	2009-07	19076981
Isolation of secondary metabolites from Hortia oreadica (Rutaceae) leaves through high-speed counter-current chromatography.	2009-05-08	19249788
Evodiamine and rutaecarpine inhibit migration by LIGHT via suppression of NADPH oxidase activation.	2009-05-01	19241441
[Study on vitro release and transdermal behaviors of Yulian cataplasm].	2009-04	19639777
Synthesis and vasodilator effects of rutaecarpine analogues which might be involved transient receptor potential vanilloid subfamily, member 1 (TRPV1).	2009-03-15	19254847
Involvement of prolylcarboxypeptidase in the effect of rutaecarpine on the regression of mesenteric artery hypertrophy in renovascular hypertensive rats.	2009-03	19018804
The permeability and the efflux of alkaloids of the Evodiae fructus in the Caco-2 model.	2009-01	18683848
Quality evaluation of Evodia rutaecarpa (Juss.) Benth by high performance liquid chromatography with photodiode-array detection.	2008-12-01	18930617
Solid dispersion of rutaecarpine improved its antihypertensive effect in spontaneously hypertensive rats.	2008-12	19016276
Rutaecarpine inhibits hypoxia/reoxygenation-induced apoptosis in rat hippocampal neurons.	2008-12	18809421
Reduction of asymmetric dimethylarginine in the protective effects of rutaecarpine on gastric mucosal injury.	2008-10	18841172
Calcitonin gene-related peptide-mediated antihypertensive and anti-platelet effects by rutaecarpine in spontaneously hypertensive rats.	2008-10	18625276
Induction of NAD(P)H: quinone reductase by rutaecarpine isolated from the fruits of Evodia rutaecarpa in the murine hepatic Hepa-1c1c7 cell line.	2008-09	18729042
One-pot synthesis of simple alkaloids: 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine.	2008-04	18379119
Rutaecarpine induces chloride secretion across rat isolated distal colon.	2008-04	18187619
Progress in the studies on rutaecarpine.	2008-02-06	18305418
Molecular authentication and quality control using a high performance liquid chromatography technique of Fructus Evodiae.	2008-02	18239294
The effects of rutaecarpine on the pharmacokinetics of acetaminophen in rats.	2007-12	18254252
Calcitonin gene-related Peptide-mediated depressor effect and inhibiting vascular hypertrophy of rutaecarpine in renovascular hypertensive rats.	2007-12	18091582
[Methodological studies on equivalent relationship between granule for clinical prescription and clinical decoction of fructus evodiae].	2007-06	17802873
Short communication: in vivo evaluation of microemulsion system for oral and parenteral delivery of rutaecarpine to rats.	2007-05	17520444
Anti-inflammatory effects and mechanisms of the ethanol extract of Evodia rutaecarpa and its bioactive components on neutrophils and microglial cells.	2007-01-26	17109845
Radical reactions with 3H-quinazolin-4-ones: synthesis of deoxyvasicinone, mackinazolinone, luotonin A, rutaecarpine and tryptanthrin.	2007-01-07	17164913
In vitro and in vivo antiallergic effect of the fructus of Evodia rutaecarpa and its constituents.	2007-01	17202687
Chemical and biological comparisons on Evodia with two related species of different locations and conditions.	2006-11-24	16824714
Elimination of rutaecarpine and its metabolites in rat feces and urine measured by liquid chromatography.	2006-11	16799925
Determination of evodiamine and rutecarpine in human serum by liquid chromatography-tandem mass spectrometry.	2006-07	16724219
Oxidative metabolism of the alkaloid rutaecarpine by human cytochrome P450.	2006-05	16501007
Anti-inflammatory principles from the fruits of Evodia rutaecarpa and their cellular action mechanisms.	2006-04	16681034
Anti-inflammatory activity in skin by biomimetic of Evodia rutaecarpa extract from traditional Chinese medicine.	2006-04	16423507
Development and validation of HPLC methods for the analysis of phenethylamine and indoloquinazoline alkaloids in Evodia species.	2006-03	16605082
Characterization of the Phase II metabolites of rutaecarpine in rat by liquid chromatography-electrospray ionization-tandem mass spectrometry.	2005-12	16418066

Sample Use Guides

In Vivo Use Guide

The appropriate dose of evodia depends on several factors such as the user's age, health, and several other conditions. At this time there is not enough scientific information to determine an appropriate range of doses for evodia. Keep in mind that natural products are not always necessarily safe and dosages can be important. Be sure to follow relevant directions on product labels and consult your pharmacist or physician or other healthcare professional before using. Evodia is a tree that is native to China and Korea. Evodia fruit, which has a strong bitter taste, is commonly used in Traditional Chinese Medicine. The fruit and root bark are also used as medicine in other herbal practice. Among the active components of evodia are quinolone and indoloquinazoline alkaloids, such as evodiamine and rutaecarpine.

Route of Administration: Oral

In Vitro Use Guide

Rutaecarpine was reported to inhibited monocyte migration, which indicates its potential for anti-atherosclerosis activity. There were evaluzted the effect of rutaecarpine on endothelial dysfunction, and focused on the regulation of connexin expression in endothelial cells by rutaecarpine. Endothelia damage was induced by exposing HUVEC-12 to Ox-LDL (100 mg/L) for 24h, which decreased the expression of protective proteins Cx37 and Cx40, but induced atherogenic Cx43 expression, in both mRNA and protein levels, concomitant with the impaired propidium iodide diffusion through the gap junctions. Pretreatment with rutaecarpine effectively recovered the expression of Cx37 and Cx40, but inhibited Cx43 expression, thereby improving gap junction communication and significantly prevented the endothelial dysfunction

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:02:47 GMT 2025` Edited by `admin` on `Mon Mar 31 19:02:47 GMT 2025`
Record UNII	8XZV289PRY
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RUTECARPINE

Common Name

English

NSC-258317

Preferred Name

English

8,13-DIHYDROINDOLO(2',3':3,4)PYRIDO(2,1-B)QUINAZOLIN-5(7H)-ONE

Systematic Name

English

RUTAECARPINE

Common Name

English

RUTECARPINE [MI]

Common Name

English

Classification Tree Code System Code

DSLD

1394 (Number of products:104)