Oxymatrine

Oxymatrine

Identity: Chemical, Botanical, and Physical Characterization

Oxymatrine (also known as matrine oxide, matrine N-oxide, and matrine 1-oxide) is one of many quinolizidine alkaloid compounds extracted from the root of Sophora flavescens, a Chinese herb. It is also a quinolizidine alkaloid with the molecular formula C₁₅H₂₄N₂O₂ and a molar mass of 264.36. It has a boiling point of 497.19°C and a melting point of 197°C. Structurally, oxymatrine is the N-oxide of matrine, featuring semi-polar coordination bonds. It is very similar in structure to matrine, which has one less oxygen atom, and oxymatrine is partially metabolized to matrine in the human gut.

Oxymatrine has increased polarity compared with matrine, is more soluble in water and dissolves in chloroform, but is less soluble in ether and petroleum ether. Pure oxymatrine appears brown or deep yellow, with its color deepening upon further oxidation.

Oxymatrine is a quinolizidine alkaloid mainly derived from Sophora flavescens Aiton root (Radix Sophorae Flavescentis) and Sophora tonkinensis Gapnep. root. It can also be extracted from other plants, such as Sophora subprostrata (shandougen) and the aerial parts of Sophora alopecuroides. While Sophora flavescens is the main source, Sophora angustifolia is also a minor source of Kushen.

Sophora flavescens contains a large number of alkaloids, among which the highest content is matrine and oxymatrine, which together account for approximately 2% of the total dry weight of the roots (most of which exist in the form of oxymatrine). In the 2010 edition of the Chinese Pharmacopoeia, only the main alkaloids matrine and oxymatrine are included as standards for the evaluation of Kushen quality in the pharmaceutical market; the matrine and oxymatrine content, analyzed by HPLC in the roots of Sophora flavescens, should both be no less than 1.2%.

Other alkaloids co-occurring in the plant include sophocarpine (C₁₅H₂₂N₂O), sophoranol, sophoramine, sophoridine, allomatrine, and isomatrine.

Common Preparations and Dosage Forms

Oxymatrine is prepared in multiple pharmaceutical and supplement formats. The roots of Sophora flavescens undergo an extraction process using ethanol to obtain oxymatrine, which is then purified from the crude extract through techniques like recrystallization and chromatographic separation. In clinical and research settings, it has been administered as oral capsules, intravenous injections, and topical formulations.

Pharmacokinetic studies have determined that the absolute oral bioavailability of oxymatrine is 26.43%, and the pharmacokinetic parameters C_max, T_max, and t_1/2 are 605.5 ng/mL, 0.75 h, and 4.181 h after oral administration, indicating that oxymatrine can be absorbed quickly.

In clinical hepatitis trials, intravenous formulations have also been studied. In one published trial, 40 patients were randomised to receive either an intravenous injection of 600 mg/day oxymatrine; after 3 months of treatment, 47% of the treated cases cleared HCV. In oral studies for hepatic fibrosis, a multicentre, randomised, double-blind, placebo-controlled design was used, with patients assigned to either the oxymatrine capsule group or a placebo control group, with 72 cases in each group and a treatment course of 52 weeks.

Traditional and Historical Use

Oxymatrine is a quinolizidine alkaloid extracted from the roots of Sophora flavescens (Kushen), a leguminous plant. Kushen is an important and common traditional Chinese medicine (TCM) herb. Sophora was first described in traditional Chinese medicine texts such as the Shennong Bencao Jing (around 100 A.D.). Traditionally, it was used to clear heat, dry dampness, expel wind, and eliminate intestinal parasites, leading to its use in formulas for conditions like dysentery, jaundice, edema, dysuria, eczema, and pruritus.

Sophora flavescens was first documented in the Shen Nong's Classic of Materia Medica and widely distributed in China. During the Ming dynasty, the root of Sophora flavescens was noted in the "Compendium of Materia Medica" and was utilized in the treatment of various ailments such as itching skin, dysentery, enteritis, oliguria, and inflammation.

According to TCM theory, kushen exhibits dampness drying, heat-clearing, diuretic, and insecticidal effects. Kushen is mainly used to treat damp heat diarrhea, bloody stools, jaundice, eczema, skin itching, and abnormal urination.

Sophora flavescens has been widely used in traditional Chinese medicine, primarily in combination with other medicinal plants in formulations, to treat various conditions including fever, dysentery, hematochezia, jaundice, oliguria, vulvar swelling, asthma, eczema, inflammatory disorders, ulcers, and diseases related to skin burns.

The dried root of the shrub Sophora flavescens Aiton is an important herbal medicine in China, Japan, Korea, India, and in some of Europe. In traditional preparations, the root was typically decocted in water or combined with other herbs in multi-ingredient formulas. In traditional remedies, preparations containing oxymatrine were administered to address a variety of conditions, including hepatitis, dysentery, and skin diseases such as eczema. Historical use extended to cooling the blood, reducing swelling, and as a supportive remedy for respiratory and gastrointestinal complaints.

Key Constituents and Active Compounds

More than 200 chemical compounds have been identified in Kushen, with oxymatrine being one of the most important components. Quinolizidine alkaloids and flavonoids are considered to be the main active components of Sophora flavescens. The principal alkaloids include oxymatrine, matrine, sophocarpine, sophoridine, and several minor related compounds.

The plant contains active components such as matrine, oxymatrine, sophoridine, flavonoids, alkylxanthones, quinones, triterpene glycosides, fatty acids, and essential oils. Of these, oxymatrine is the dominant form of the matrine-type alkaloids found in the root.

Established Mechanisms of Action

Anti-Inflammatory Signaling

Oxymatrine, extracted from the root of Sophora flavescens Aiton (Fabaceae), has been shown to inhibit TLR4 levels in LPS-stimulated cells and the translocation of p65 to the cell nucleus, thereby reducing the release of IL-1β and alleviating the inflammatory response.

Studies have found that oxymatrine exerts anti-inflammatory effects by regulating the release of inflammatory mediators such as TNF-α from inflammatory cells and inhibiting the TLR4/NF-κB signaling pathway.

Antiviral Mechanisms

In studies of influenza A virus (IAV), oxymatrine demonstrated excellent anti-IAV activity on eight IAV strains in vitro. It could significantly decrease the promoter activity of TLR3, TLR4, TLR7, MyD88, and TRAF6 genes, inhibit IAV-induced activations of Akt, ERK1/2, p38 MAPK, and NF-κB pathways, and suppress the expressions of inflammatory cytokines and MMP-2/-9.

In conclusion from that work, oxymatrine possesses anti-IAV and anti-inflammatory activities, with the mechanism of action linked to its ability to inhibit IAV-induced activations of TLR4, p38 MAPK, and NF-κB pathways.

Anti-Fibrotic Pathways

Oxymatrine treatment inhibits cardiac fibroblast proliferation and the cardiac fibroblast-to-myofibroblast transition induced by TGF-β1, at least in part through inhibition of ERK1/2 and p38 MAPK signaling.

Abundant experimental evidence indicates that oxymatrine may exert a protective effect on the cardiovascular system, with studies designed to explore its role against myocardial fibrosis induced by acute myocardial infarction and its modulation of transforming growth factor beta-1 (TGF-β1)-Smads signaling pathways.

Neuroprotective Mechanisms

Oxymatrine is an alkaloid extracted from Sophora flavescens which has broad anti-inflammatory, antitumor and immunosuppressant actions. It has been investigated for whether it exerts anti-inflammatory effects by inhibiting microglial activation; western blot and ELISA analyses showed that oxymatrine decreased the expression and release of HSP60 by LPS-activated BV2 cells, and the expression of heat shock factor 1, the transcription factor of HSP60, was also suppressed by oxymatrine.

Antitumor Mechanisms

Oxymatrine is cytotoxic toward cancer cells via regulation of multiple carcinogenic signaling pathways, such as Akt, epidermal growth factor receptor, and the NF-κB cascade.

The mechanisms of protective effects of oxymatrine are mainly related to its anti-inflammatory, anti-oxidative stress, anti- or pro-apoptotic, anti-fibrotic, metabolism-regulation, and anti-nociceptive functions, and a variety of signal pathways, cells, and molecules are influenced by oxymatrine, through which comprehensive therapeutic effects can be achieved.

Clinical pharmacology research has identified numerous novel molecular mechanisms of oxymatrine, such as JAK/STAT, Nrf2/HO-1, PI3K/AKT, TGF-β1/Smad, and Notch pathways, providing new evidence supporting therapeutic potential against cardiovascular diseases.

Scientific Evidence by Area of Use

Liver Disease and Hepatic Fibrosis

Overview: Pharmacological studies have demonstrated that oxymatrine exhibits anti-hepatitis B virus (HBV) and antifibrosis effects. An increasing number of clinical controlled studies have found that oxymatrine combined with conventional therapy could improve the curative effect and reduce adverse events incidence in treating hepatitis B cirrhosis.

Key Human Trial: A randomized, double-blind, placebo-controlled, multicenter clinical study was conducted to evaluate the efficacy and safety of oxymatrine capsules in the treatment of hepatic fibrosis in patients with chronic viral hepatitis, enrolling 144 patients divided into an oxymatrine capsule group and a placebo group, with a treatment course of 52 weeks. All patients had liver biopsy before treatment; part of them had a second biopsy at the end of therapy. Clinical symptoms, liver function tests, and serum markers of hepatic fibrosis were assessed, and ultrasound evaluation was performed before, during, and at the end of therapy. There was an obvious difference between the two groups both in improvement of histopathology and in improvement of noninvasive indexes such as clinical manifestations and serum markers of hepatic fibrosis; associated indexes of liver function and imaging detection indicated that oxymatrine was an effective drug for anti-hepatic fibrosis.

Hepatitis C: Clinical trials have looked at the effect of oxymatrine in chronic HCV patients. In one trial, 40 patients were randomised to receive intravenous injection of 600 mg/day oxymatrine; after 3 months of treatment, 47% of the treated cases cleared HCV. No serious adverse events were reported, and the treated group had a significantly higher ALT normalisation rate relative to the control group in the first 2 months, though this significant difference was not maintained at the end of the third month.

Evidence Strength: Human clinical evidence for oxymatrine in hepatic fibrosis and chronic viral hepatitis is modest but exists at the level of randomized controlled trials. Limitations include relatively small trial sizes and the fact that the bulk of the strongest evidence originates from Chinese research groups. A bibliometric analysis of 22 years of oxymatrine research found that in total 267 studies were included, most of which were original research, and the number of annual studies slowly increased with some fluctuations. A full systematic review protocol has been registered but the field awaits large, multicenter, international trials.

Cardiovascular System

Overview: The cardioprotective effects of oxymatrine involve multiple aspects, primarily including antioxidative stress, anti-inflammatory actions, anti-atherosclerosis, restoration of vascular function, and inhibition of cardiac remodeling and failure.

Oxymatrine has a variety of effects in vitro and in animal models, including protection against apoptosis, tumor and fibrotic tissue development, and inflammation. Furthermore, oxymatrine has been shown to decrease cardiac ischemia (decreased blood perfusion), myocardial injury, arrhythmias (irregular heartbeats), and improve heart failure by increasing cardiac function.

Previous studies have demonstrated that oxymatrine exhibits diuretic, immune-modulatory, antiviral and anticancer effects, and there is growing evidence that it may also regulate extracellular matrix remodeling (ECMR) in a variety of organs, tissues and cells, including the liver, kidney, and lung.

Evidence Strength: Most cardiovascular evidence is from animal models and in vitro studies. Direct human clinical trial data specifically for cardiac indications remain limited. The mechanistic evidence from preclinical studies is robust, but translation to human outcomes requires further clinical investigation.

Antiviral Activity

During the pandemic of severe acute respiratory syndrome (SARS) in 2001, the Chinese bureau of science and technology announced that composite Sophora japonica injection (mainly containing oxymatrine) had distinct effects in the treatment of SARS, demonstrating the anti-inflammatory properties of oxymatrine in treating systemic inflammatory responses.

It has been reported that oxymatrine has anti-oxidative, anti-inflammation, anti-virus, hepatoprotective, and immunosuppression activities, and is currently employed to treat viral hepatitis, traumatic brain injury, acute pancreatitis, sepsis, and acute lung injury (ALI) in the clinic.

As a drug with various pharmacological effects, oxymatrine has been applied to the treatment of hepatitis B and liver fibrosis, in addition to preventing chronic kidney disease development into renal interstitial fibrosis in patients, with low rates of adverse reaction.

Evidence Strength: Antiviral activity has been demonstrated in multiple in vitro and animal systems. Human clinical data for viral hepatitis is emerging, as discussed above. For most other viral indications, evidence remains preclinical.

Oncology / Anticancer Activity

Overview: Kushen, the dried roots of Sophora flavescens Aiton, has a long history of use in traditional Chinese medicine to treat inflammatory diseases and cancer. Kushen alkaloids (KS-As) and kushen flavonoids (KS-Fs) are well-characterized components in kushen, and KS-As containing oxymatrine, matrine, and total alkaloids have been developed in China as anticancer drugs.

Oxymatrine has been found to have antiproliferative and antitumor effects and is therefore considered an attractive therapy for breast cancer. Oxymatrine reduces the viability, migration, and invasion of MDA-MB-231, 4T1, and MCF-7 breast cancer cells.

Colorectal Cancer: Oxymatrine can significantly inhibit cancer cell migration and invasion in vitro. The production of ATP, pyruvate, and lactate is suppressed in colorectal cancer (CRC) cells under treatment of oxymatrine, as well as glucose consumption, while extracellular acidification rates were evidently attenuated. Oxymatrine treatment triggered CRC cell mitophagy to inhibit CRC cell growth, migration, invasion, and metastasis in vitro and in vivo.

Hepatocellular Carcinoma: Research has confirmed that Kushen plus transcatheter arterial chemoembolization (TACE) is more superior to TACE alone for unresectable hepatocellular carcinoma (UHCC) patients.

Pancreatic and Other Cancers: Oxymatrine has anti-proliferative and anti-angiogenic properties, inhibiting the growth of pancreatic cancer cells and the expression of angiogenesis-associated factors VEGF and NF-κB.

Combination with Chemotherapy: Oxymatrine in combination with doxorubicin (DOX) presented an outstanding synergistic antitumor effect in CRC models. Cardiovascular side effects including tachycardia, hypotension, arrhythmias, and sequentially induced heart toxicity are frequently observed clinically with DOX, and combination with natural products which possess low toxicity characteristics has become a promising strategy to alleviate DOX cardiotoxicity.

Cancer Pain: A systematic review found positive evidence of Kushen for bone cancer pain. Kushen appeared to be able to improve total pain relief and quality of life, and seems to have beneficial effects on reduction of side effects in patients with bone cancer pain compared with radiotherapy or bisphosphonates.

Evidence Strength: The majority of anticancer evidence for oxymatrine is from in vitro cell studies and animal xenograft models. Clinical evidence is limited to small, mostly Chinese-origin trials and observational reports on Kushen preparations rather than on isolated oxymatrine. Robust phase II/III randomized controlled trials in Western oncology settings are lacking. This body of evidence should currently be considered preliminary.

Inflammatory and Immune Conditions

Research suggests that oxymatrine has a wide spectrum of pharmacological effects, including anti-inflammatory, antibacterial, immune regulation, and anti-oxidation. It has been reported that oxymatrine could alleviate ulcerative colitis (UC) through depressing the release of inflammatory factors.

Laboratory research has shown that oxymatrine prevents synovial inflammation and migration via blocking NF-κB activation in rheumatoid fibroblast-like synoviocytes. These findings are from in vitro models; clinical trials in rheumatoid arthritis have not yet been reported in the peer-reviewed literature at scale.

Evidence Strength: Evidence for anti-inflammatory applications in conditions like ulcerative colitis and rheumatoid arthritis is largely preclinical. No large randomized controlled trials were identified in the accessible literature for these specific indications.

Liver Protection (Hepatoprotection)

In animal studies, oxymatrine inhibited arsenic trioxide-induced hepatic pathological damage, liver ROS levels, and MDA levels in a dose-dependent manner. It also preserved antioxidant enzymes SOD, GPX, and CAT activity and attenuated the retention of arsenic in liver tissues, improving the expression of Nrf2 and HO-1. These results suggested that oxymatrine protected against oxidative damage by activating the Nrf2/HO-1 signaling pathway.

Evidence Strength: Hepatoprotective effects in specific toxic insult models are well-characterized in animals. Human clinical evidence for hepatoprotection beyond the hepatitis/fibrosis context is not established.

Body Systems and Health Areas Associated with Oxymatrine

• Hepatic System: Anti-fibrotic effects, hepatitis B and C virus suppression, liver function improvement, hepatoprotection against oxidative injury.
• Cardiovascular System: Effects demonstrated include protecting against myocardial ischemia-reperfusion injury, preventing ventricular arrhythmias, attenuating pulmonary fibrosis, and inhibiting platelet aggregation.
• Immune System: Immunomodulatory and immunosuppressant activity, regulation of T-cell responses and cytokine release.
• Gastrointestinal System: Used traditionally and in preclinical research for dysentery, colitis, and enteritis.
• Oncology: Preclinical antiproliferative, pro-apoptotic, and anti-metastatic activity across multiple cancer types.
• Nervous System: Neuroprotective effects via inhibition of microglial activation; analgesic effects studied in animal pain models.
• Dermatology: Traditional use for eczema, pruritus, and skin inflammation; topical preparations studied.
• Renal System: Oxymatrine has been applied to preventing chronic kidney disease development into renal interstitial fibrosis in patients.
• Metabolic: Preclinical evidence includes reducing serum lipids and protecting pancreatic beta-cell function.

Pharmacokinetics

The absolute oral bioavailability of oxymatrine is 26.43%, with C_max of 605.5 ng/mL, T_max of 0.75 h, and t_1/2 of 4.181 h after oral administration, indicating rapid absorption. Oxymatrine is very similar in structure to matrine, which has one less oxygen atom, and oxymatrine is partially metabolized to matrine in the human gut. This conversion to the active metabolite matrine is considered important for the pharmacological effects observed.

Structurally, oxymatrine is the N-oxide of matrine, featuring semi-polar coordination bonds. Consequently, oxymatrine has increased polarity, is more soluble in water and dissolves in chloroform, but is less soluble in solutions like ether and petroleum ether.

Dosage Forms and Reported Dosages

Oxymatrine is prepared and studied in the following forms based on published research:

• Oral capsule: Used in the hepatic fibrosis trial, with 72 patients per group and a treatment course of 52 weeks.
• Intravenous injection: In the HCV clinical trial, an intravenous dose of 600 mg/day was used for 3 months.
• Patent dosage range: In one US patent describing therapeutic use, doses of substantially pure oxymatrine are described as between about 5 mg and about 500 mg per administration, given twice daily.

No universally established standard therapeutic dose has been defined in international pharmacopoeias. Clinical dosages described in the published literature vary by indication, route, and formulation, and are based primarily on Chinese clinical trial data.

Safety Considerations

General Tolerability

Oxymatrine is currently extensively employed to treat viral hepatitis, traumatic brain injury, acute pancreatitis, sepsis, and acute lung injury in the clinic. In the HCV trial, no serious adverse events were reported.

Hepatotoxicity Risk

Despite its use in treating liver disease, dose-dependent hepatotoxicity has been documented in laboratory models. A large dose of matrine and oxymatrine can produce liver toxicity; at equal dosage, the liver toxicity of matrine is significantly higher than that of oxymatrine, and the toxic mechanism is related to oxidative stress and apoptosis. Oxymatrine-induced liver injury has been reported.

In repeated-dose toxicity evaluations, repeated intraperitoneal administration of 100–500 mg/kg of oxymatrine daily for 2–4 weeks caused no significant damage to the heart, spleen, and kidneys in mice. These laboratory test doses were close to the fatally toxic level (LD50), which by this route of administration was reported to be 521 mg/kg, but did not adversely affect the kidney; adverse renal effects were not seen in the clinical trials.

Drug–Drug Interactions

Oxymatrine is metabolized primarily by the liver, and concomitant use with other hepatotoxic drugs could exacerbate liver damage. Drugs that induce or inhibit hepatic enzymes, particularly cytochrome P450 enzymes, may alter the metabolism of oxymatrine, thereby affecting its efficacy and safety profile. Concurrent use of oxymatrine with CYP3A4 inhibitors like ketoconazole or erythromycin could elevate oxymatrine levels in the blood, increasing the risk of toxicity. Conversely, CYP3A4 inducers such as rifampin could reduce its plasma concentration, potentially diminishing its therapeutic effects.

Neurotoxicity Concerns

An increasing number of published studies indicate that matrine has serious adverse effects, the most obvious being liver toxicity and neurotoxicity, which are major factors limiting its clinical use. As oxymatrine is partially converted to matrine in vivo, neurotoxicity concerns associated with matrine are also relevant to oxymatrine use, particularly at higher doses.

Populations of Concern

Contraindications for oxymatrine use include pregnancy and breastfeeding, as there is insufficient data to support its safety in these populations. Individuals with known hypersensitivity to alkaloids or components of the Sophora flavescens plant should also avoid its use. Caution is advised in patients with severe liver or kidney impairment, as these conditions could potentially alter the metabolism and excretion of the compound, leading to increased toxicity.

Research Status and Regulatory Classification

Other than China, 11 different countries have conducted studies on oxymatrine, with the variety in country of origin of publications representing a recently increasing trend. Oxymatrine is not currently approved by the U.S. FDA or EMA as a drug, nor does it appear in the USP or European Pharmacopoeia as a recognized monograph compound. It is sold as a dietary supplement in some markets and is used as a pharmaceutical agent in China, where it appears in the Chinese Pharmacopoeia as a quality standard constituent of Kushen. No Cochrane systematic reviews on isolated oxymatrine as a human intervention were identified in the peer-reviewed literature; most systematic review activity involves Kushen preparations broadly. Evidence across all areas must be interpreted within these regulatory and methodological limitations.

References

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