CYP2C19 metabolizes many compounds including (S)-mephenytoin, omeprazole,
imipramine diazepam, and proguanil. CYP2C19 is detected in the liver and duodenum.

Enzymatic Dehydrogenation

CYP2C19 has been shown to dehydrogenate indapamide into dehydroindapamide. The primary enzyme reponsible for this action was however CYP3A4. CYP2D6 and CYP2A6 also performed this action.[2]

Indapamide CYP2C19 Dehydroindapamide
Indapamide.png —-> Dehydroindapamide.png

CYP2C19 was able to dehydrogenate estradiol at the 17beta-hydroxy position creating estrone, an action also carried out by CYP2C9 and CYP2C8.[4]

The enzyme Estradiol 17beta-dehydrogenase can also perform this action on estradiol.

Estradiol CYP2C19 Estrone
Estradiol.png —-> Estrone.png

Enzymatic Hydroxylation

CYP2C19 converts estrone into 16alpha-hydroxyestrone.[5]

Estrone CYP2C19 16alpha-Hydroxyestrone
Estrone.png —-> 16-hydroxyestrone.png

Inhibitors and Inducers

Potent Inhibitors Strength Dosage Verified in Man
Capsaicin ? ? ?
Curcumin ? ? ?
Nootkatone ? ? ?
Resveratrol 50% Inhibition IC50=11.6 µM[7] ?
Saint John’s Wort [1] 75% inhibition High doses ?
Turmeric (contains curcumin) ? ? ?
Inhibitors (unknown potency) Strength Dosage Verified in Man
Bergamottin ? ? ?
Carvone ? ? ?
Dimethylsulfoxide (DMSO) ? ? ?
Feverfew ? ? ?
Glycyrrhizin ? ? ?
Kava ? ? ?
Licorice ? ? ?
Peppermint EO ? ? ?
Pomegranate juice ? ? ?
In Vitro Inhibitors Ineffective in Man Strength Dosage Verified in Man
White Grapefruit [3] No Inhibition 300 ml Yes
Ginkgo biloba extract [1] No Inhibition[6] 120 mg Yes
Inducers Strength Dosage Verified in Man
Aspirin [8] "significantly induced" 50 mg daily Yes
DHEA (dehydroepiandrosterone) ? ? ?
Ginkgo biloba [1] 75% Induction Low doses ?
Sage [1] 100% Induction ? ?
Saint John’s Wort [1] 134% Induction Low doses Yes
Valerian Root [1] 57% Induction ? ?
1. Trade herbal products and induction of CYP2C19 and CYP2E1 in cultured human hepatocytes;
Basic Clin Pharmacol Toxicol. 2009 Jul;105(1):58-63. doi: 10.1111/j.1742-7843.2009.00412.x. Epub 2009 Apr 3; Hellum BH, Hu Z, Nilsen OG; Department of Cancer Research and Molecular Medicine, Faculty of Medicine, Norwegian University of Science and Technology, Trondheim, Norway; PubMed PMID: 19371257 (Download Attached PDF Document)
2. Dehydrogenation of the Indoline-Containing Drug 4-Chloro-N-(2-methyl-1-indolinyl)-3-sulfamoylbenzamide (Indapamide) by CYP3A4: Correlation with in Silico Predictions
Hao Sun, Chad Moore, Patrick M. Dansette, Santosh Kumar, James R. Halpert, and Garold S. Yost; PubChem PMCID: PMC2645476
3. Formation of omeprazole sulphone but not 5-hydroxyomeprazole is inhibited by grapefruit juice
Wichittra Tassaneeyakul, Wongwiwat Tassaneeyakul, Suda Vannaprasaht, and Yasushi Yamazoe; 2000; PubChem PMCID: PMC2014902
4. Role of cytochrome P450 in estradiol metabolism in vitro.
Cheng ZN, Shu Y, Liu ZQ, Wang LS, Ou-Yang DS, Zhou HH. PubMed PMID: 11741520 (Download Attached PDF Document)
5. Role of polymorphic human cytochrome P450 enzymes in estrone oxidation.
Cribb AE, Knight MJ, Dryer D, Guernsey J, Hender K, Tesch M, Saleh TM. PubMed PMID: 16537715
6. Effects of Ginkgo biloba extracts on diazepam metabolism: a pharmacokinetic study in healthy Chinese male subjects.
Zuo XC, Zhang BK, Jia SJ, Liu SK, Zhou LY, Li J, Zhang J, Dai LL, Chen BM, Yang GP, Yuan H. PubMed PMID: 20186406
7. Liquid chromatography/tandem mass spectrometric determination of inhibition of human cytochrome P450 isozymes by resveratrol and resveratrol-3-sulfate.
Yu C, Shin YG, Kosmeder JW, Pezzuto JM, van Breemen RB. PubMed PMID: 12569440
8. Isozyme-specific induction of low-dose aspirin on cytochrome P450 in healthy subjects'
Chen XP1, Tan ZR, Huang SL, Huang Z, Ou-Yang DS, Zhou HH.; Clin Pharmacol Ther. 2003 Mar;73(3):264-71; PMID: 12621391
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