Metabolic oxidation of the pyrrole ring: structure and origin of some urinary metabolites of the anti-hypertensive pyrrolylpyridazinamine, mopidralazine.: III: Studies with the ¹³C-labelled drug

References

• Assandri A., Barone D., Ferrari P., Perazzi A., Ripamonti A., Tuan G., Zerilli L. F. Metabolic fate of Premazepam, a new anti-anxiety drug, in the rat and the dog. Drug Metabolism and Disposition 1985a; 12: 257–263
   Google Scholar
• Assandri A., Bellasio E., Bernareggi A., Cristina T., Perazzi A., Odasso G. Pharmacokinetics of a new antihypertensive pyrrolyl pyridazinamine (MDL-899) in the rat and the dog. Arzneimittel Forschung (Drug Research) 1985b; 35: 508–513
   Google Scholar
• Assandri A., Perazzi A., Baldoli E., Ferrari P., Ripamonti A., Bellasio E., Tuan G., Zerilli L. F., Tarzia G. Metabolic pathways of the anti-hypertensive agent, N-(2,5-dimethyl-1H-pyrrol-1-yl)-6-(4-morpholinyl)-3-pyridazinamine hydrochloride. I. Studies in the rat. Xenobiotica 1985c; 15: 1069–1087
   Web of Science ®Google Scholar
• Assandri A., Perazzi A., Tarzia G., Ciabatti R., Ferrari P., Ripamonti A., Tuan G., Zerilli L. F. Metabolic pathways of the anti-hypertensive agent, N-(2,5-dimethyl-1H-pyrrol-1-yl)-6-(4-morpholinyl)-3-pyridazinamine hydrochlorid. II. Studies in the dog. Xenobiotica 1985d; 15: 1089–1102
   Web of Science ®Google Scholar
• Baldoli E., Bianchi G., Corsico N., Di Francesco F. G. Pharmacological studies of N-(2,5-dimethyl-1H-pyrrol-1-yl)-6-(4-morpholinyl)-3-pyridazinamine hydrochloride (MDL-899), a new long-acting antihypertensive vasodilator. Arzneimittel Forschung (Drug Research) 1985; 35: 818–826
   PubMed Web of Science ®Google Scholar
• Beedham C. Molybdenum hydroxylase as drug metabolizing enzymes. Drug Metabolism Reviews 1985; 16: 119–56
   PubMed Web of Science ®Google Scholar
• Bellasio E., Carpi C., Maffii G., Testa E. 3-Hydrazino-6-amino-pyridazines, British Patent Specification. 1,157,642, 1969, complete specification published 9 July
   Google Scholar
• Bellasio E., Ripamonti A., Parravicini F., Baldoli E. Sintesi di idrazino piridazine dotate di attività ipotensiva. Nota II. Il Farmaco Edizione Scientifica 1972; 27: 591–600
   Google Scholar
• Bellasio E., Campi A., Di Mola N., Baldoli E. Antihypertensives. N-1H-pyrrol-1-yl-3-pyridazinamines. Journal of Medicinal Chemistry 1984; 27: 1077–1083
   Google Scholar
• Di Mola N., Bellasio E., Ferrari P., Zerilli L. F. Synthesis of N-(2,5-[2-13C]dimethyl-1H-pyrrol-1-yl)-6-(4-morpholinyl)-3-pyridazinamine hydrochloride. Journal of Labelled Compounds and Radiopharmaceuticals 1985; 22: 1299–308
   Google Scholar
• Egger H., Bartlett F., Yuan H. P., Karliner J. Metabolism of pirprofen in man, monkey, rat and mouse. Drug Metabolism and Disposition 1982; 10: 529–536
   Google Scholar
• Frydman R. B., Tomaso M. L., Frydman B. Pyrrolooxygenases: isolation, properties and products formed. Biochimica et Biophysica Acta 1972; 284: 63–79
   PubMed Web of Science ®Google Scholar
• Germain G., Main P., Woolfson M. M. Application of phase relations to complex structures III. Optimum use of phase relations. Acta Crystallographica 1971; A27: 368–376
   Web of Science ®Google Scholar
• Goldstein B. P., Ripamonti F., Rodenghi F. MDL-899: a new non-mutagenic anti-hypertensive drug. Mutation Research 1983; 113: 258
   Google Scholar
• Guengerich F. P., Mitchell M. B. Metabolic activation of model pyrroles by cytochrome P-450. Drug Metabolism and Disposition 1980; 8: 34–38
   PubMed Web of Science ®Google Scholar
• Handa R., Saha N. N. Crystal and molecular structure of morpholinobiguanide hydrochloride. Journal of Crystallography and Molecular Structure 1971; 1: 235–244
   Google Scholar
• Hirata F., Hayahishi O. Studies on indoleamine 2,3-dioxygenase. I. Superoxide anion as substrate. Journal of Biological Chemistry 1975; 250: 5960–5975
   PubMed Web of Science ®Google Scholar
• Howden C. W., Elliot H. L., Lawrie C. B., Reid J. L. Pharmacodynamic studies in normal volunteers with MDL-899, a new arteriolar vasodilator. Journal of Cardiovascular Pharmacology 1983; 5: 552–556
   PubMed Web of Science ®Google Scholar
• Jones R. A., Bean G. P. The Chemistry of Pyrroles. Academic Press, London 1977; 209–247
   Google Scholar
• Murphy P. J., Williams T. L. Biological inactivation of pyrrolnitrin. Identification and synthesis of pyrrolnitrin metabolites. Journal of Medicinal Chemistry 1972; 15: 137–139
   Google Scholar
• Ohnishi T., Hirata F., Hayaishi O. Indoleamine 2,3-dioxygenase. Potassium superoxide as substrate. Journal of Biological Chemistry 1977; 252: 4643–4647
   PubMed Web of Science ®Google Scholar
• Ottersen T. The crystal and molecular structure of pyridazine hydrochloride at – 170°C. Acta Chemica Scandinavica 1975; A29: 637–640
   Google Scholar
• Reece P. A. Hydralazine and related compounds. Chemistry, metabolism and mode of action. Medicinal Research Reviews 1981; 1: 73–96
   PubMed Web of Science ®Google Scholar
• Rio G., Lecas-Nawrocka A. Etude sur la formation de N-aminopyrroles par reaction de l'hydrazine et de cis-butènediones-1,4-Photoxydation de l'amino-1 tetraphénylpyrrole. Bulletin de la Scciété Chimique de France 1971; 1723–1727
   Google Scholar
• Shaw C. R., Butler M. A., Thenot J., Haegele K. D., Matney T. S. Genetic effects of hydralazine. Mutation Research 1979; 68: 79–84
   Google Scholar
• Sheldrick G. M. SHELX 76, A Program For Crystal Structure Determinaton. University Chemical Laboratories, Cambridge 1976
   Google Scholar
• Shimizu T., Nomiyama S., Hirata F., Hayaishi O. Indoleamine 2,3-dioxygenase. Purification and some properties. Journal of Biological Chemistry 1978; 253: 4700–4706
   PubMed Web of Science ®Google Scholar
• Stetter H., Von Praun F. Uber 1,2,4-Triketone und 1,2,4,5-Tetraketone. Chemische Berichte 1969; 102: 1643–1648
   Google Scholar
• Tosk J., Schmeltz J., Hoffman D. Hydrazines as mutagens in a histidine-requiring auxotroph of. Salmonella typhimurium. Mutation Research 1979; 66: 247–252
   PubMedGoogle Scholar
• Yamamoto S., Hayaishi D. Tryptophan pyrrolase of rabbit intestine. D- and L-tryptophan-cleaving enzyme or enzymes. Journal of Biological Chemistry 1967; 242: 5260–5266
   PubMed Web of Science ®Google Scholar