Pharmacokinetics and excretion of cryptotanshinone after intravenous injection in pigs

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1 Asian Journal of Drug Metabolism and Pharmacokinetics Paper ID Copyright by Hong Kong Medical Publisher Received April 5, 2005 ISSN ; 5(3): Accepted June 21, 2005 Pharmacokinetics and excretion of cryptotanshinone after intravenous injection in pigs Yin Cui a, Ming Xue *,a,b, Yong-Jiang Luo a, Bin Zhang a, and Zhong-Tian Zhou a a Lanzhou Institute of Animal & Pharmaceuticals, Chinese Academy of Agricultural Sciences, Lanzhou , China; b Department of Pharmacology, Capital University of Medical Sciences, Beijing , China Abstract Key words Aim To investigate the pharmacokinetics and excretion of cryptotanshinone in pigs which had the obvious antibacterial and anti-inflammatory activity. Methods The plasma concentration of cryptotanshinone was determined by high performance liquid chromatography with dibenyl as a internal standard at absorption wavelength of 254 nm. A mixture of methanol and water (85:15) was used as the mobile phase with a flow rate of 1 ml min -1, The concentration time profile of cryptotanshinone was found to be best fitted to a first order absorption two compartment open model after iv a single dose (10 mg kg -1 ) in pigs. Results The main pharmacokinetic parameters of cryptotanshinone were as follows: t 1/2α 2.36 h, t 1/2β min, AUC mg min L -1, V L mg -1,V B L kg -1.The excretion of cryptotanshinone in porcine urine in hour was very few after i.v. a administration of cryptotanshinone. Conclusion The results provide important information for the clinical use of cryptotanshinone and for developing the novel antibacterial drug. Cryptotanshinone; pharmacokinetics; excretion; high-performance liquid chromatography Introduction Cryptotanshinone (CT) is the mainly active component isolated from the rhizome of Salvia miltiorrhiza Bunge and S. przewalskii Maxim (Labiatae) which has been used widely in China to treat coronary heart diseases, particularly angina pectoris and myocardi infarction. [1] Cryptotanshinone is a diterpene quinone pigment and its structure has been identified [2-4]. Diterpenoid tanshinones have attracted particular attention of medicinal chemists and clinicians because many of them exhibit significant antibacterial and antidermatophytic, [5] antioxidant, [6,7] antineoplastic [8] and antiinflammatory [5,9] activitis. It is found that tanshinons are effective in the treatment of the animal mastitis, endometritis, wound infection and metabolism in order in veterinary practice. [10] *Correspondence to Professor Ming Xue (Xue M). Department of Pharmacology, Capital University of Medical Sciences. Youanmen, Beijing , People s Republic of China, Phn: ; Fax: ; xuemd@163.net In this paper, we reported a simple reversed-phase HPLC method employing asingle-step liquid-liquid extraction and UV detection for the rapid quantitative determinatin of cryptotanshinone in porcine plasma and urine. And the pharmacokinetics and excretion of cryptotanshinone in pigs were also investigated. The results can provide important information for the clinical use of cryptotanshinone and for developing the novel antibacterial drug. Materials and methods Drug and reagents Cryptotanshinone was obtained by our laboratory, which isolated and puried from the roots of Salvia miltiorrhiza Bunge or Salvia przewalskii Maxim and identified as pure compound from the melting point, IR, UV, NMR [2,3,11] and compared with the standard compound purchased from the National Institute for the Control of Pharmaceutical and 231

2 Biological Products (Beijing, China).The chemical structure of Cryptotanshinone are shown in Fig 1. The internal standard, Dibenyl, was obtained from Shanghai Reagent Company (Shanghai, China). Stock standard solutions of cryptotanshinone and dibenyl (0.5 and 1mg ml 1, respectively) were prepared in methanol. Methanol was of HPLC grade (Shandong Chemical Reagent Co, Jinan, China). All chemicals and solvents were of the highest grade commercially available. Distilled water, prepared from demineralized water, was used throughout the investigation. Pooled drug-free porcine plasma and urine were obtained from healthy pigs in clinic, stored at -20 and allowed to thaw at ambient temperature prior to use. Fig 1. Chemical structure of cryptotansinone Animals Chinese hybrid pigs (n=6,weighing 30 5 kg, clinic healthy ) were purchased from Department of Experimental animals of Gansu and housed under isolated and optimally hygienic conditions. The pigs had free access to food and drinking water and were fasted for 12 h before a single intravenous dose. Instruments HPLC analysis was performed using a Waters 510 pump (Waters, Milford, USA), an automatic sample injection system (Waters, Milford, USA), and an Model 486 absorbance detector (Applied Bio-systems, Millipore Co, MA, USA). The detector wave length was set at 254 nm. Data acquisition and manipulation performed on a Model 680 laboratory automation system (AST Research Inco, Irrine, CA, USA). Quantification was based on linear regression analysis of peak-area ratios of cryptotanshinone to the internal standard versus cryptotanshinone concentration. Separation was accomplished on a Nova-Pak C 18 (4µm; mm i.d.) column (Waters, Milford, MA, USA).The column temperature was maintained at 35.The mobile phase was methanol-water (85:15, v/v), and was deaerated by sonication prior to use. The flow rate was set at 1.0 ml min 1. Sample preparations Stock standard solution of cryptotanshinone, and dibenzyl were prepared in methanol. Further dilution steps were made in either porcine plasma or urine. Working standard solutions were prepared by adding appropriate volume of cryptotanshinone solution. Quality control samples were also prepared in the same way, using a separately weighed stock solution. The final concentration of cryptotanshinone in plasma standards were 0.025, 0.050, 0.075, 0.10, 0.25, 0.50, 1.00, and 2.50µg ml -1.The final concentration of cryptotanshinone of in urine standards were 0.40, 0.80, 1.60, 3.20, 6.40,12.80µg ml -1. Quality controls of approximately 0.80, 3.00 and 12.50µg ml -1 were also prepared. After aliquoting, both plasma and urine controls were stored at -20 until analysis. Sample collection and preparation The assay was evaluated in pigs receiving a vein dose of cryptotanshinone (10 mg kg -1 ). Blood samples (approximately 3 ml) were collected into heparinized tubes just prior to administration and at 2, 5, 10, 15, 30, 45, 60, 90, 120, 240, 360,and 720 min post-dose and were later centrifuged at 3000g for 10 minutes in order to harvest plasma. Urine samples were collected pre-dose and at 0-8,8-12,12-24, and 24-48h periods post-dose. To an aliquot of porcine plasma (1.0 ml) or urine (2.0 ml) was added 4µL of the internal standard stock solution. After the addition of ethyl acetate (2.0 ml), each sample was vortex mixed for 30 s and centrifuged at 3000g for 10 min. The upper organic portion were separated and removed. Each sample was extracted three times and collected together. After evaporated to dryness at 40 under a gentle stream of nitrogen. The residue was dissolved in 100µL of mobile phase and vortex mixed. A10µL aliquot of solution was injected into the HPLC system for analysis. Precision and accuracy Precision and accuracy were assayed by performing replicate analyses of quality control samples against calibration standards. The precision and accuracy of the method were calculated as the relative standard deviation (RSD) and the percentage 232

3 deviation of observed concentration from theoretical concentration, respectively. Recovery The extraction efficiency (recovery) was determined by calculating the ratio of the amount of extracted compound from drug-free plasma or urine spiked with known amounts of cryptotanshinone (quality control plasma and urine samples) to the amount of compound added at the same concentrations to water just prior to HPLC injection. Date expresure and Pharmacokinetic analysis MCPKP pharmacokinetic program [12] was used to describe the compartment-model of the plasma concentration-time curve by compartmental analysis and calculate the main pharmacokinetic parameters. Results and discussion Precision and accuracy Typical chromatograms of blank porcine plasma and urine, plasma from a subject containing 0.82µg ml -1 of cryptotanshinone and urine from a subject containing 8.28µg ml -1 of cryptotanshinone are shown in Fig.2. The retention time of cryptotanshinone and dibenzyl were 3.95 and 5.10 min, respectively. Precision and accuracy were assessed in both plasma and urine by performing replicate analysis of spiked samples against calibration standards. The procedure was repeated on the same day and for different days on the same spiked standards at concentrations in range of the standard series. Assay linearity was demonstrated in both plasma and urine, as shown by regression analysis of calibration curves. the method was shown to be linear for cryptotanshinone in the range µg ml -1 in plasma and µg ml -1 in urine. And the regression equation were Y=0.3068X , ( =0.9994, plasma) and Y=0.7727X , ( =0.9998, urine). When the ratio of signal and noise (S/N) was 3, the minimum detection concentration of cryptotanshinone was 16 ng ml -1. When the concentration of cryptotanshinone samples was 0.1, 0.5, and 2.5 µg ml -1 (plasma) and 0.80, 3.0,12.50 µg ml -1 (urine), the inter-day RSD of the various concentrations was less 3% and the intra-day RSD was less 6%, respectively in the samples. Recovery Up on analysis of quality control samples (triplicate) at concentrations of 0.05, 0.5 and 2.50µg ml -1 (plasma), and 0.80, 3.0,12.50µg ml -1 (urine), the overall recoveries were 88 95% ( %, plasma) and 86 98% ( %, urine),respectively. Fig.2 Representative chromatograms of (a) blank porcine plasma, (b) a plasma sample from a subject containing 0.81 µg ml -1 of cryptotanshinone, (c) blank urine and (d) a urine sample containing 8.28µg ml -1 of cryptotanshinone.1: cryptotanshinone; 2:dibenzy 233

4 Pharmacokinetics After the data of the plasma drug concentration time was treated by the program of MCPKP, the concentration time curves of cryptotanshinone in pigs were all best fitted to two-compartment open model after i.v. a single dose (10 mg kg -1 ). See Fig 3 and table Time (min) Cumulative excretion( g) Time (hour) (A) (B) Fig 3. Pharmacokinetic profile of cryptotanshinone in plasma (A) and urine (B) following administration of a single intravenous dose (10mg kg -1 ) to a pig Table 1. Pharmacokinetic parameters describing disposition cryptotanshinone in pigs after iv of a single dose (10mg kg -1 ) (n=6) Parameter Unit Mean ± SD A µg ml ± 2.11 B µg ml ± α min ± 0.25 β min ± t 1/2α min 2.36 ±1.62 t 1/2β min ± K 12 min ±0.22 K 21 min ±0.023 K el min ±0.048 V l L kg ±1.670 V B L kg ±22.17 Cl B L kg -1 min ±0.28 AUC mg L -1 min ±12.74 fc 0.12 ±0.086 Above the pharmacokinetic parameters of cryptotanshinone, it indicated that the distribution of cryptotanshinone in pigs was very fast (t 1/2α 2.36 min) and widespread, because the ratio of the distribution volume (V 1 /V B ) between in central compartment and in total body compartment was small. The elimination half-life was short (t 1/2β 64.8min), it showed that the elimination of cryptotanshinone in pigs was fairly fast. Cryptotanshinone plasma levels in pigs dropped below the detection limit up to approximate 4 h after a intravenous single dose administration of 10 mg kg 1. Excretion of urine The urine samples were collected from the definite time after i.v. a single dose (10 mg kg -1 ) and the urine concentration was detected. The excretion amount of cryptotanshinone in porcine urine within 24 h was only % of the dose and the excretion amount of within 48 h was only %. The results indicated that the excretion amount of cryptotanshinone was very few after i.v. a single dose. See Fig 3. The original reason needs to investigate further. The described detection method was successfully applied to the routine analysis of plasma and urine samples during the pharmacokinetics and drug metabolism studies. The pharmacokinetics and excretion of cryptotanshinone in animals has not been reported but the metabolism of cryptotanshinone in rats, which were identified as tanshinone A, the hydroxylation at A-ring and the combine product in rats, had been reported [13]. And there were 6 major metabolites isolated and identified as the parent compound (M 1 ) and the metabolites (M 2 M 8 ) by our laboratory and there were some metabolic differences 234

5 between pigs and rats [14]. The structure of cryptotanshinone had the ortho-quinones fragment and these compounds could happen to electron transfer reaction with the biomacromolecules in vivo and the structure of cryptotanshinone was transformed and changed complexly. The anti-bacterial test result showed that the metabolites maintained the lower antibacterial activity to staphylococcus aureus and the other G + germs, and there were some differences as compared with the parent drug [12]. It could be inferred that cryptotanshinone was the main active component of diterpenoid tanshinones for anti-stphylococcus aureus and other G + germs. The investigation provides the important data for clinical use of cryptotanshinone and tanshinones analogous compounds and for developing a novel antibacterial drug. Acknowledgements This work was supported by a grant from the National tackle key projects (No ) and National Natural Science Foundation (No. C ) of China. The authors thank Dr.Y.B.Shi and Professor W.J.Xia and Zh.Y.Hu for their technical assistance. References 1. Chen WZ, Dong YL, Wang G. Pharmacological studies of sodium tanshinone sulfone. Acta Pharm Sin 1979; 14: Fang QN, Zhang PL, Xu ZP. Studies on the antibacterial components of danshen. Acta Chem Sin 1976; 34: Qian MK, Yang BJ. Studies on the chemical components of danshen. Acta Chem Sin 1978; 36: Honds G, Keezuka Y, Tabata M. Isolation of an antidermatophytic substance from the roots of Salvia Miltriorrhiza Bunge. Chem Pharm Bull 1988; 36: Gao YG, Song YM, Yang YY, Liu WF and Tang JX. Pharmacology of tanshinones. Acta Pharm Sin 1979; 14: Jiang W, Zhao Y, Zhao BL, Wan Q and Xin WJ. Studies on the scavenging effect of tanshinone on lipid free radical of cardiae sarcoplasmic reticulum during per-oxidation. Acta Biophys Sin 1994; 10: Cao EH, Liu XQ, Li JF. Effect of natural antioxidant tanshinone A on interaction of lipid peroxidation products and DNA in liver cells. Acta Biophys Sin 1996; 12: Wu WL, Chang WL. The antineoplatic effect of Salvia Miltriorrhiza Bunge. J Med Sci 1985; 6: Gao YG, Wang LZ, Tang KS. The anti-inflammatory test of tanshinone. Chin J Integr Trad West Med 1983; 3: Xue M, Cui Y, Zhang Bin, Shi YB, et al. The metabolism and the antibacterial activity of cryptotanshinone in pigs in vive and in vitro. Chinese J Vet Sci 1999; 19(1): Xue M, Shi YB, Cui Y, Wang HQ, et al. Study on the chemical constituents from Salvia przewalskii Maxim. Nat Product Res & Develop 2000; 12(6): Xia WJ and Chen ZR. MCPKP- a microcomputer program specialized for pharmacokinetic compartment analysis. Acta Pharm Sin 1988; 9: Xie MZ, Shen ZF. The absorption, distribution, excretion and metabolism of cryptotanshinone. Acta Pharm Sin 1983; 18: Xue M, Cui Y, Wang HQ et al. Identification and Determination of phase I metabolites of cryptotanshinone in pigs. Asian J Drug Metab Pharmacokinet 2002; 2(4):

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