Tetracycloxides. II. Transformations at the C-4 Position

Esse, Robert C.; Lowery, John A.; Tamorria, C. Richard.; Sieger, G. M.

doi:10.1021/ja01072a057

Search citation statements

Order By: Relevance

Paper Sections

Select...

Discussion2

Citation Types

Supporting

Mentioning

Contrasting

Year Published

1965

2007

Publication Types

Select...

Book4

Article3

Relationship

Self Cite0

Independent7

Authors

Journals

Cited by 9 publications

(4 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…8) (BLACKWOOD and STE-PHENS 1965;ESSE et al 1964 a;HLAvKA and BOOTHE 1973). U nder anhydrous conditions the C6 hydroxy group of compound (51) or (52) reacts with the 4-imino group to produce compounds (53) and (54) (ESSE et al 1964a;BLACKWOOD and STEPHENS 1964;.…”

mentioning

confidence: 99%

Chemical Modification of the Tetracyclines

Rogalski¹

1985

The Tetracyclines

View full text Add to dashboard Cite

mentioning

confidence: 99%

Chemical Modification of the Tetracyclines

Rogalski¹

1985

The Tetracyclines

View full text Add to dashboard Cite

“…These epimers appear to be as well-tolerated as the parent antibiotics [Benitz and D ierm eier, 1964], but possess much less antibacterial potency. A possible, but quantitatively certainly unimpor tant metabolic route for all tetracyclines is N-demethylation which would lead almost exclusively into the C-4 epimer series [Esse et al, 1964], derivatives that might escape detection in presence of the unme tabolized compounds.…”

Section: Discussionmentioning

confidence: 99%

The Disposition of Doxycycline by Man and Dog

Wittenau¹,

Twomey²

1971

Chemotherapy

View full text Add to dashboard Cite

The disposition of doxycycline by man and dog was investigated with the aid of labeled drug. Isotope dilution methods were instrumental in the successful identification of fecal excretion products. More than 90% of dose was recovered as undegraded drug from urine and feces of both species, but some labeled doxycycline was excreted by dogs in antibacterially inactive form. Dogs appear to eliminate most of intravenously administered doxycycline by secretion into the intestinal tract, by a route different from biliary secretion. It is inferred from these results that the lack of doxycycline accumulation observed by other investigators in patients with impaired renal function is probably due to elimination of unchanged drug with feces, and not the result of extensive metabolic degradation.

show abstract

“…This is a complex degradation scheme and most likely results in more than one product (6)(7)(8). I t is this type of reaction to which Dony-Crotteux attributed the loss of antibiotic potency in the presence of riboflavin, light, and air.…”

Section: Discussionmentioning

confidence: 99%