CYP3A4 Inhibitory Activity of New Bisalkaloids, Dipiperamides D and E, and Cognates from White Pepper

Tsukamoto, Sachiko; Tomise, Kyoko; Miyakawa, Keiko; Cheon, Bae; Abe, Takeyuki; Hamada, Toshiyuki; Harada, Hiroshi; Ohta, Tomihisa

doi:10.1016/s0968-0896(02)00130-x

Cited by 64 publications

(49 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Another report demonstrated that alkaloids isolated from white pepper exhibited remarkable inhibition of CYP3A4-mediated nifedipine oxidation with IC 50 values of 0.18-0.79 mM, whereas the main alkaloid piperine showed a moderate inhibition with an IC 50 ϭ12 mM. 8) In this study, piperine at 10 mM revealed 66% and 2.2% of inhibition on CYP3A4-mediated TST and CYP2C9-mediated DIC hydroxylation, respectively (data not shown). These findings suggest that inhibitory effects of alkaloids and piperine derived from black/white pepper on CYP3A4 activity are stronger than those on CYP2C9 activity.…”

Section: Resultssupporting

confidence: 46%

Effects of Mace and Nutmeg on Human Cytochrome P450 3A4 and 2C9 Activity

Kimura

Ito

Hatano

2010

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

Section: Resultssupporting

confidence: 46%

Effects of Mace and Nutmeg on Human Cytochrome P450 3A4 and 2C9 Activity

Kimura

Ito

Hatano

2010

Biological & Pharmaceutical Bulletin

View full text Add to dashboard Cite

“…If the present study could be extrapolated to humans, a modification of the dosage regimen of DA-8159 seems to be required in patients who are concurrently taking foods [32,33] or drugs that can induce or inhibit CYP3A1/2. More studies are required in humans to prove the above hypothesis.…”

Section: Discussionmentioning

confidence: 99%

Effects of enzyme inducers and inhibitors on the pharmacokinetics of intravenous DA‐8159, a new erectogenic, in rats

Kim¹,

Shim²,

Lee³

et al. 2005

Biopharm & Drug Disp

View full text Add to dashboard Cite

In order to find what types of hepatic microsomal cytochrome P450 (CYP) isozymes are involved in the metabolism of DA-8159 and in the formation of DA-8164 in rats, enzyme inducers, such as dexamethasone, phenobarbital, 3-methylcholanthrene and isoniazid, and enzyme inhibitors, such as troleandomycin and quinine, were pretreated in rats. After a 1 min intravenous administration of DA-8159 at a dose of 30 mg/kg to rats pretreated with dexamethasone (a main inducer of CYP3A1/2 in rats), the total areas under the plasma concentration-time curve from time zero to time infinity (AUC) values of DA-8159 (283 versus 349 microg min/ml) and DA-8164 (98.0 versus 79.8 microg min/ml) were significantly smaller and greater, respectively, than those in control rats. However, the AUC values of DA-8159 were not significantly different after pretreatment with phenobarbital, isoniazid and 3-methylcholanthrene (main inducers of CYP2B1/2, 2E1 and 1A1/2, respectively, in rats). In rats pretreated with troleandomycin (a main inhibitor of CYP3A1/2 in rats), the AUC values of DA-8159 (435 versus 370 microg min/ml) and DA-8164 (34.8 versus 76.5 microg min/ml) were significantly greater and smaller, respectively. However, in rats pretreated with quinine (a main inhibitor of CYP2D1 in rats), the AUC of DA-8159 was comparable to that in control rats. The above data indicate that DA-8159 was metabolized and DA-8164 was formed mainly via CYP3A1/2 in rats.

show abstract

“…Herein, we report as imple and powerful catalytic method for styrene dimerization using hypervalent iodine reagents.It is especially notable in that it allows the rapid formation of unsymmetrical tetrasubstituted cyclobutanes,a nd we are not aware of any examples of this motif being prepared by such an oxidative pathway.T he products are formed with high diastereoselectivity (all trans)b yareliable head to head coupling process.M oreover,w ea lso illustrate the power of this methodology with ashort synthesis of the tetrasubstituted natural product [11] nigramide R. [12] Our work began by screening hypervalent iodine reagents for the dimerization of 1a to form 2a (Table 1). Initially,w e found that aw ide range of standard solvents were not compatible with the reaction at all and only starting material was recovered.…”

mentioning

confidence: 99%

Catalytic Hypervalent Iodine Promoters Lead to Styrene Dimerization and the Formation of Tri‐ and Tetrasubstituted Cyclobutanes

2016

View full text Add to dashboard Cite

Reported herein is that the use of catalytic quantities of hypervalent iodine reagents (phenyliodine diacetate or Dess-Martin periodinane) allows the rapid and stereoselective formation of cyclobutanes under very mild reaction conditions. The presence of a fluorinated solvent is essential for the success of these reactions which form unsymmetrical tri- and tetrasubstituted cyclobutanes through a heterodimerization process involving two different alkenes.

show abstract

CYP3A4 Inhibitory Activity of New Bisalkaloids, Dipiperamides D and E, and Cognates from White Pepper

Cited by 64 publications

References 14 publications

Effects of Mace and Nutmeg on Human Cytochrome P450 3A4 and 2C9 Activity

Effects of Mace and Nutmeg on Human Cytochrome P450 3A4 and 2C9 Activity

Effects of enzyme inducers and inhibitors on the pharmacokinetics of intravenous DA‐8159, a new erectogenic, in rats

Catalytic Hypervalent Iodine Promoters Lead to Styrene Dimerization and the Formation of Tri‐ and Tetrasubstituted Cyclobutanes

Contact Info

Product

Resources

About