Formation and cleavage of C–C bonds by enzymatic oxidation–reduction reactions

FP Guengerich, FK Yoshimoto - Chemical Reviews, 2018 - ACS Publications
Many oxidation–reduction (redox) enzymes, particularly oxygenases, have roles in reactions
that make and break C–C bonds. The list includes cytochrome P450 and other heme-based …

[PDF][PDF] Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates.

PRO De Montellano, KL Kunze - Journal of Biological Chemistry, 1980 - researchgate.net
The following acetylenic substrates have been shown to mediate NADPH-dependent loss of
cytochrome P-450 on incubation with hepatic microsomes from phenobarbital-pretreated …

Acetylenes: cytochrome P450 oxidation and mechanism-based enzyme inactivation

PR Ortiz de Montellano - Drug metabolism reviews, 2019 - Taylor & Francis
The oxidation of carbon–carbon triple bonds by cytochrome P450 produces ketene
metabolites that are hydrolyzed to acetic acid derivatives or are trapped by nucleophiles. In …

Insight into the effect of wastewater-derived dissolved organic matter composition on norgestrel degradation in activated sludge: Coupled bacterial community and …

Q Yu, X Hu, F Zhao, C Zhu, L Guan, H Ren, J Geng - Water Research, 2022 - Elsevier
Dissolved organic matter (DOM) mediates the microbial transformation of micropollutants,
including norgestrel (NGT) in natural waters. However, little is known of the effect of complex …

Terminal half-lives in plasma and bioavailability of norethisterone, levonorgestrel, cyproterone acetate and gestodene in rats, beagles and rhesus monkeys

B Düsterberg, M Hümpel, U Speck - Contraception, 1981 - Elsevier
Norethisterone, levonorgestrel, cyproterone acetate and gestodene have been used for a
long time in oral contraception and other indications, or are in the process of development …

Identification of 17-α-ethynylestradiol-modified active site peptides and glutathione conjugates formed during metabolism and inactivation of P450s 2B1 and 2B6

UM Kent, H Lin, DE Mills, KA Regal… - Chemical research in …, 2006 - ACS Publications
The oral contraceptive 17-α-ethynylestradiol (17EE) is a mechanism-based inactivator of
cytochrome P450s (P450s) 2B1 and 2B6. Inactivation of P450s 2B1 and 2B6 in the …

Shift of the acetylenic hydrogen during chemical and enzymatic oxidation of the biphenylacetylene triple bond

PRO De Montellano, KL Kunze - Archives of biochemistry and biophysics, 1981 - Elsevier
Abstract Oxidation of 1-[13 C] biphenylacetylene by either meta-chloroperbenzoic acid or by
liver microsomes from phenobarbital-pretreated rats yields (after esterification) methyl 2 …

Cytochrome P-450-dependent oxidation of the 17 alpha-ethynyl group of synthetic steroids. D-homoannulation or enzyme inactivation.

SE Schmid, WY Au, DE Hill, FF Kadlubar… - Drug metabolism and …, 1983 - ASPET
Metabolism of the 17 alpha-ethynyl group of the synthetic estrogen, 17 alpha-
ethynylestradiol, by hepatic microsomes from female rhesus monkeys was studied …

Ethynyl cleavage of 17 alpha-ethynylestradiol in the rhesus monkey.

LA Raitano, W Slikker, DE Hill, HE Hadd… - Drug Metabolism and …, 1981 - ASPET
17 alpha-Ethynylestradiol (EE2)[20, 21-14C] and [9, 11-3H] were administered by
intragastric intubation to three adult female rhesus monkeys. Quantification of the tritium …

The role of pharmacokinetics in preclinical safety studies of synthetic sex steroids

M Humpel, B Dusterberg, S Beier, J Schuppler… - Contraceptive Steroids …, 1986 - Springer
THE ROLE OF PHARMACOKINETICS IN PRECLINICAL SAFETY STUDIES OF SYNTHETIC SEX
STEROIDS Michael Humpel, B. Dusterberg, S. Beier, J. Page 1 THE ROLE OF …