Urinary Metabolites of 3a,4,5,6,7,7a‐Hexahydro‐3‐(1‐methyl‐5‐nitro‐1H‐imidazol‐2‐yl)‐1,2‐benzisoxazole in the Dog
W. J. A. VANDENHEUVEL
1
,
B.H. Arison
1
,
T.W. Miller
1
,
P Kulsa
1
,
P. Eskola
1
,
H Mrozik
1
,
A. K. Miller
2
,
H Skeggs
3
,
S B Zimmerman
2
,
B M Miller
2
1
Merck, Sharp and Dohme Research Laboratories, Rahway, NJ 07065.
|
2
Merck Institute for Therapeutic Research, Rahway, NJ 07065
|
3
Merck Sharp & Dohme Research Laboratories, West Point, PA 19486
|
Publication type: Journal Article
Publication date: 1979-09-01
scimago Q1
wos Q2
SJR: 0.737
CiteScore: 7.2
Impact factor: 3.8
ISSN: 00223549, 15206017
PubMed ID:
115987
Pharmaceutical Science
Abstract
The antiprotozoal drug 3a,4,5,6,7,7a-hexahydro-3-(1-methyl-5-nitro-1H-imidazol-2-yl)-1,2-benzisoxazole (I), which exhibits activity against trypanosomiasis, is also antibacterial in vivo. Since the urine from a dog dosed with I showed a broader spectrum of antibacterial activity than I itself, metabolites from this urine were isolated and partially characterized. The metabolites were mono- and dihydroxy-substituted species with the hydroxyl groups on carbons 4--7 of the hexahydrobenzisoxazole ring. These observations led to the synthesis of several such hydroxy derivatives of I, and their properties fully supported the proposed positions of metabolic hydroxylation. One synthetic compound, the 6,7-cis-dihydroxy compound, exhibited higher antibacterial activity against Salmonella schottmuelleri in mice and greater trypanocidal activity in vivo against Trypanosoma cruzi (Brazil strain) than I.
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VANDENHEUVEL W. J. A. et al. Urinary Metabolites of 3a,4,5,6,7,7a‐Hexahydro‐3‐(1‐methyl‐5‐nitro‐1H‐imidazol‐2‐yl)‐1,2‐benzisoxazole in the Dog // Journal of Pharmaceutical Sciences. 1979. Vol. 68. No. 9. pp. 1156-1158.
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VANDENHEUVEL W. J. A., Arison B., Miller T., Kulsa P., Eskola P., Mrozik H., Miller A. K., Skeggs H., Zimmerman S. B., Miller B. M. Urinary Metabolites of 3a,4,5,6,7,7a‐Hexahydro‐3‐(1‐methyl‐5‐nitro‐1H‐imidazol‐2‐yl)‐1,2‐benzisoxazole in the Dog // Journal of Pharmaceutical Sciences. 1979. Vol. 68. No. 9. pp. 1156-1158.
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TY - JOUR
DO - 10.1002/jps.2600680926
UR - https://doi.org/10.1002/jps.2600680926
TI - Urinary Metabolites of 3a,4,5,6,7,7a‐Hexahydro‐3‐(1‐methyl‐5‐nitro‐1H‐imidazol‐2‐yl)‐1,2‐benzisoxazole in the Dog
T2 - Journal of Pharmaceutical Sciences
AU - VANDENHEUVEL, W. J. A.
AU - Arison, B.H.
AU - Miller, T.W.
AU - Kulsa, P
AU - Eskola, P.
AU - Mrozik, H
AU - Miller, A. K.
AU - Skeggs, H
AU - Zimmerman, S B
AU - Miller, B M
PY - 1979
DA - 1979/09/01
PB - Elsevier
SP - 1156-1158
IS - 9
VL - 68
PMID - 115987
SN - 0022-3549
SN - 1520-6017
ER -
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@article{1979_VANDENHEUVEL,
author = {W. J. A. VANDENHEUVEL and B.H. Arison and T.W. Miller and P Kulsa and P. Eskola and H Mrozik and A. K. Miller and H Skeggs and S B Zimmerman and B M Miller},
title = {Urinary Metabolites of 3a,4,5,6,7,7a‐Hexahydro‐3‐(1‐methyl‐5‐nitro‐1H‐imidazol‐2‐yl)‐1,2‐benzisoxazole in the Dog},
journal = {Journal of Pharmaceutical Sciences},
year = {1979},
volume = {68},
publisher = {Elsevier},
month = {sep},
url = {https://doi.org/10.1002/jps.2600680926},
number = {9},
pages = {1156--1158},
doi = {10.1002/jps.2600680926}
}
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MLA
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VANDENHEUVEL, W. J. A., et al. “Urinary Metabolites of 3a,4,5,6,7,7a‐Hexahydro‐3‐(1‐methyl‐5‐nitro‐1H‐imidazol‐2‐yl)‐1,2‐benzisoxazole in the Dog.” Journal of Pharmaceutical Sciences, vol. 68, no. 9, Sep. 1979, pp. 1156-1158. https://doi.org/10.1002/jps.2600680926.