Comparative metabolism and kinetics of coumarin in mice and rats

Food and Chemical Toxicology

Volumn 41, Issue 2, 2003, Pages 247-258

  Born, S L ^a,d   Api, A M ^a   Ford, R A ^a,e   Lefever, F R ^b   Hawkins, D R ^c  

^a RESEARCH INSTITUTE FOR FRAGRANCE MATERIALS   (United States)

^b PROCTER AND GAMBLE COMPANY   (United States)

^c HUNTINGDON LIFE SCIENCES   (United Kingdom)

^d BRISTOL MYERS SQUIBB   (United States)

^e NONE   (United Kingdom)

Author keywords

Coumarin; Epoxidation; In vivo; Metabolism; Pharmacokinetics

Indexed keywords

2 HYDROXYPHENYLACETALDEHYDE; 2 HYDROXYPHENYLACETIC ACID; ACETALDEHYDE; ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; CARBON 14; COUMARIN; COUMARIN 3,4 EPOXIDE; COUMARIN DERIVATIVE; UMBELLIFERONE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL FOOD; ARTICLE; BIOASSAY; CONTROLLED STUDY; DIET; DRUG BLOOD LEVEL; DRUG EXPOSURE; DRUG HALF LIFE; DRUG METABOLISM; EPOXIDATION; LUNG TOXICITY; MOUSE; MOUSE STRAIN; NONHUMAN; QUANTITATIVE ANALYSIS; RADIOACTIVITY; RAT; RAT STRAIN; SPECIES DIFFERENCE; STRAIN DIFFERENCE; URINALYSIS;

ADMINISTRATION, ORAL; ANIMALS; ANTINEOPLASTIC AGENTS; AUTORADIOGRAPHY; CARCINOGENS; COUMARINS; DIET; DOSE-RESPONSE RELATIONSHIP, DRUG; HALF-LIFE; MICE; MICE, INBRED STRAINS; PHENYLACETATES; RATS; RATS, INBRED F344; SPECIES SPECIFICITY; UMBELLIFERONES;

RODENTIA;

EID: 0037290588     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0278-6915(02)00227-2     Document Type: Article

References (39)

1. Born S.L., Fix A.S., Caudill D., Lehman-McKeeman L.D. Selective Clara cell injury in mouse lung following acute administration of coumarin. Toxicology and Applied Pharmacology. 151:1998;45-56.
2. Born S.L., Fix A.S., Caudill D., Lehman-McKeeman L.D. Development of tolerance to Clara cell necrosis with repeat administration of coumarin. Toxicological Sciences. 51:1999;300-309.
3. Born S.L., Lehman-McKeeman L.D. In vitro rates of coumarin 3,4-epoxidation are not predictive of species differences in hepatotoxicity. Toxicologist. 48(1-S):1999;225-226.
4. Born S.L., Hu J.K., Lehman-McKeeman L.D. o-Hydroxyphenylacetaldehyde is a hepatotoxic metabolite of coumarin. Drug Metabolism and Disposition. 28:2000;218-223.
5. Born S.L., Caudill D., Smith B.J., Lehman-McKeeman L.D. In vitro kinetics of coumarin 3,4-epoxidation. Application to species differences in toxicity and carcinogenicity Toxicological Sciences. 58:2000;23-31.
6. Born S.L., Rodriguez P.A., Eddy C.L., Lehman-McKeeman L.D. Synthesis and reactivity of coumarin 3,4-epoxide. Drug Metabolism and Disposition. 25:1997;1318-1324.
7. Born S.L., Caudill D., Fliter K.L., Purdon M.P. Identification of the cytochromes P450 that catalyze coumarin 3,4-epoxidation and 3-hydroxylation. Drug Metabolism and Disposition. 30:2002;483-487.
8. Carlton B.D., Auburn J.C., Simon G.S. Effects of coumarin following perinatal and chronic exposure in Sprague-Dawley rats and CD-1 mice. Fundamental and Applied Toxicology. 30:1996;145-151.
9. Caudill D., Smith G.B.J., Massey T.E., Born S.L. Characterization of coumarin 3,4-epoxidation in B6C3F1 mouse, F344 rat, and human lung microsomes. Toxicological Sciences. 54:2000;1743.
10. Clewell H.J., Gentry P.R., Gearhart J.M., Born S.L., Lehman-McKeeman L.D., Covington T.R. Development of a physiologically-based pharmacokinetic (PB-PK) model and human health risk assessment for coumarin. Toxicological Sciences. 54:2000;513.
11. Dexeus F.H., Logothetis C.J., Sella A., Fitz K., Amato R., Reuben J.M., Dozier N. Phase II study of coumarin and cimetidine in patients with metastatic renal cell carcinoma. Journal of Clinical Oncology. 8(2):1990;325-329.
12. Egan D., O'Kennedy R., Morgan E., Cox D., Prosser E., Thornes R.D. The pharmacology, metabolism, analysis and applications of coumarin and coumarin-related compounds. Drug Metabolism Reviews. 22(5):1990;503-529.
13. Feron V.J., Til H.P., De Vrijer F., Woutersen R.A., Cassee F.R., Van Bladeren P.J. Aldehydes. occurrence, carcinogenic potential, mechanism of action, and risk assessment Mutation Research. 259:1991;363-385.
14. Foster J.R., Green T., Smith L.L., Lewis R.W., Hext P.M., Wyatt I. Methylene chloride. An inhalation study to investigate pathological and biochemical events occurring in the lungs of mice over an exposure period of 90 days Fundamental and Applied Toxicology. 37:1992;125-130.
15. Foster J.R., Green T., Smith L.L., Tittensor S., Wyatt I. Methylene chloride. an inhalation study to investigate toxicity in the mouse lung using morphological, biochemical, and Clara cell culture techniques Fundamental and Applied Toxicology. 91:1994;221-234.
16. Furia T.E., Ballanca N. Fenaroli's Handbook of Flavor Ingredients, Vol 1. second ed. 1975;CRC Press, Boca Raton, FL.
17. Green T., Mainwaring G.W., Foster J.R. Trichloroethylene-induced mouse lung tumors. Studies of the mode of action and comparisons between species Fundamental and Applied Toxicology. 37:1997;125-130.
18. Kaighen M., Williams R.T. The metabolism of [3-14C]coumarin. Journal of Medicinal Pharmacology and Chemistry. 3:1961;25-43.
19. Kaipainen P., Koivusaari U., Lang M. Catalytic and immunological comparison of coumarin 7-hydroxylation in different species. Comparative Biochemistry and Physiology C. 81C:1985;293-296.
20. Lake B.G. Investigation into the mechanism of coumarin-induced hepatotoxicity in the rat. Archives of Toxicology. 7 (Suppl.):1984;16-29.
21. Lake B.G. Coumarin metabolism, toxicity and carcinogenicity. relevance for human risk assessment Food and Chemical Toxicology. 37:1999;423-453.
22. Lake B.G., Gray T.J.B., Evans J.G., Lewis D.F.V., Beamand J.A., Hue K.L. Studies on the mechanism of coumarin-induced toxicity in rat hepatocytes. Comparison with dihydrocoumarin and other coumarin metabolites Toxicology and Applied Pharmacology. 97:1989;311-323.
23. 14C] coumarin in the rat and marmoset (Callithrix jacchus). Toxicology Letters. 45:1989;299-306.
24. Leung A.Y., Foster S. Encyclopedia of Common Natural Ingredients used in Food, Drugs and Cosmetics. second ed. 1996;John Wiley & Sons, New York.
25. Lush I.E., Andrews K.M. Genetic variation between mice in their metabolism of coumarin and its derivatives. Genetic Research. 31:1978;177-186.
26. Marshall M.E., Mendelsohn L., Butler K., Riley L., Cantrell J., Wiseman C., Taylor R., Macdonald J.S. Treatment of metastatic renal cell carcinoma with coumarin (1,2-benzopyrone) and cimetidine. a pilot study Journal of Clinical Oncology. 5(6):1987;862-866.
27. Marshall M.E., Butler K., Cantrell J., Wiseman C., Mendelsohn L. Treatment of advanced malignant melanoma with coumarin and cimetidine. pilot study Cancer Chemotherapy and Pharmacology. 24(1):1989;65-66.
28. NTP (National Toxicology Program), 1986. Toxicology and Carcinogenic Studies of Dichloromethane in F344/N Rats and B6C3F1 Mice. Technical Report series No. 306. U.S. Department of Health and Human Services. National Institutes of Health, Public Health Service.
29. NTP (National Toxicology Program), 1990. Toxicology and Carcinogenic Studies of Trichloroethylene (without Epichlorohydrin) in F344/N Rats and B6C3F1 Mice. Technical Report series No. 243. US Department of Health and Human Services. National Institutes of Health, Public Health Service.
30. NTP (National Toxicology Program), 1992. Toxicology and Carcinogenic Studies of Naphthalene in B6C3F1 Mice. Technical Report series No. 410. US Department of Health and Human Services. National Institutes of Health, Public Health Service.
31. NTP (National Toxicology Program), 1993a. Toxicology and Carcinogenic Studies of Coumarin (CAS No. 91-64-5) in F344/N Rats and B6C3F1 Mice (Gavage Studies). Technical Report series No. 422. US Department of Health and Human Services. National Institutes of Health, Public Health Service.
32. NTP (National Toxicology Program), 1993b. Toxicology and Carcinogenesis Studies of 3,4-Dihydrocoumarin in F344/N rats and B6C3F1 Mice. Technical Report series No. 423. US Department of Health and Human Services. National Institutes of Health, Public Health Service.
33. O'Brien K.A.F., Suverkropp C., Kanekal S., Plopper C.G., Buckpitt A.R. Tolerance to multiple doses of the pulmonary toxicant naphthalene. Toxicology and Applied Pharmacology. 99:1989;487-500.
34. Odum J., Foster J.R., Green T. A mechanism for the development of Clara cell lesions in the mouse lung after exposure to trichloroethylene. Chemico-Biological Interactions. 83:1992;135-153.
35. Plopper C.G., Marisassy A.T., Hill L.H. Ultrastructure of the nonciliated bronchiolar epithelial (Clara) cell of mammalian lung: I. A comparison of rabbit, guinea pig, rat, hamster, and mouse. Experimental Lung Research. 1:1980;139-154.
36. Sharifi S., Lotterer E., Christoph Michaelis H., Bircher J. Pharmacokinetics of coumarin and its metabolites. Preliminary results in three healthy volunteers. Journal of the Irish Colleges of Physicians and Surgeons. 22:1993;29-32.
37. Shopp G.M., White J.L. Jr., Holsapple D.W., Duke S.S., Anderson A.C., Condie L.W. Jr., Hayes J.R., Borzelleca J.F. Naphthalene toxicity in CD-1 mice: General toxicology and immunotoxicology. Fundamental and Applied Toxicology. 4:1984;406-419.
38. Ullberg, S., 1954. Acta. Radiol. Suppl., 118, 22.
39. Zhuo X., Gu J., Zhang Q.Y., Spink D.C., Kaminsky L.S., Ding X. Biotransformation of coumarin by rodent and human cytochrome P450. metabolic basis of tissue-selective toxicity in olfactory mucosa of rats and mice Journal of Pharmacology and Experimental Therapeutics. 288:1999;463-471.