Details of Drug Off-Target (DOT)

General Information of Drug Off-Target (DOT) (ID: OTFMJYYE)

DOT Name	Cytochrome P450 2C19 (CYP2C19)
Synonyms	EC 1.14.14.1; (R)-limonene 6-monooxygenase; EC 1.14.14.53; (S)-limonene 6-monooxygenase; EC 1.14.14.51; (S)-limonene 7-monooxygenase; EC 1.14.14.52; CYPIIC17; CYPIIC19; Cytochrome P450-11A; Cytochrome P450-254C; Fenbendazole monooxygenase (4'-hydroxylating); EC 1.14.14.75; Mephenytoin 4-hydroxylase
Gene Name	CYP2C19
UniProt ID	CP2CJ_HUMAN
3D Structure	Download 2D Sequence (FASTA) Download 3D Structure (PDB) Download
PDB ID	4GQS
EC Number	1.14.14.1; 1.14.14.51; 1.14.14.52; 1.14.14.53; 1.14.14.75
Pfam ID	PF00067
Sequence	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE TTSTTLRYALLLLLKHPEVTAKVQEEIERVIGRNRSPCMQDRGHMPYTDAVVHEVQRYID LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP PFYQLCFIPV
Function	A cytochrome P450 monooxygenase involved in the metabolism of polyunsaturated fatty acids (PUFA). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates PUFA specifically at the omega-1 position. Catalyzes the epoxidation of double bonds of PUFA. Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol. Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine. Hydroxylates fenbendazole at the 4' position.
KEGG Pathway	Arachidonic acid metabolism (hsa00590 ) Linoleic acid metabolism (hsa00591 ) Drug metabolism - cytochrome P450 (hsa00982 ) Metabolic pathways (hsa01100 ) Serotonergic sy.pse (hsa04726 ) Chemical carcinogenesis - D. adducts (hsa05204 )
Reactome Pathway	CYP2E1 reactions (R-HSA-211999 ) Synthesis of epoxy (EET) and dihydroxyeicosatrienoic acids (DHET) (R-HSA-2142670 ) Synthesis of (16-20)-hydroxyeicosatetraenoic acids (HETE) (R-HSA-2142816 ) Aspirin ADME (R-HSA-9749641 ) Xenobiotics (R-HSA-211981 )
BioCyc Pathway	MetaCyc:HS09293-MONOMER

Molecular Interaction Atlas (MIA) of This DOT

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This DOT

This DOT Affected the Biotransformations of 24 Drug(s)

Drug Name	Drug ID	Highest Status	Interaction	REF
Estradiol	DMUNTE3	Approved	Cytochrome P450 2C19 (CYP2C19) increases the chemical synthesis of Estradiol.	[46]
Progesterone	DMUY35B	Approved	Cytochrome P450 2C19 (CYP2C19) increases the hydroxylation of Progesterone.	[47]
Diclofenac	DMPIHLS	Approved	Cytochrome P450 2C19 (CYP2C19) increases the hydroxylation of Diclofenac.	[49]
Ethinyl estradiol	DMODJ40	Approved	Cytochrome P450 2C19 (CYP2C19) increases the hydroxylation of Ethinyl estradiol.	[51]
Thalidomide	DM70BU5	Approved	Cytochrome P450 2C19 (CYP2C19) increases the hydroxylation of Thalidomide.	[53]
Phenytoin	DMNOKBV	Approved	Cytochrome P450 2C19 (CYP2C19) decreases the hydroxylation of Phenytoin.	[54]
Sertraline	DM0FB1J	Approved	Cytochrome P450 2C19 (CYP2C19) decreases the methylation of Sertraline.	[55]
Melatonin	DMKWFBT	Approved	Cytochrome P450 2C19 (CYP2C19) decreases the methylation of Melatonin.	[56]
Propranolol	DM79NTF	Approved	Cytochrome P450 2C19 (CYP2C19) increases the oxidation of Propranolol.	[58]
Mefenamic acid	DMK7HFI	Approved	Cytochrome P450 2C19 (CYP2C19) increases the hydroxylation of Mefenamic acid.	[60]
Citalopram	DM2G9AE	Approved	Cytochrome P450 2C19 (CYP2C19) decreases the methylation of Citalopram.	[62]
Pomalidomide	DMTGBAX	Approved	Cytochrome P450 2C19 (CYP2C19) increases the oxidation of Pomalidomide.	[63]
Amphetamine	DMSZQAK	Approved	Cytochrome P450 2C19 (CYP2C19) decreases the methylation of Amphetamine.	[64]
Bromfenac	DMKB79O	Approved	Cytochrome P450 2C19 (CYP2C19) increases the hydroxylation of Bromfenac.	[67]
Tolbutamide	DM02AWV	Approved	Cytochrome P450 2C19 (CYP2C19) increases the hydroxylation of Tolbutamide.	[68]
Almogran	DM7I64Z	Approved	Cytochrome P450 2C19 (CYP2C19) decreases the methylation of Almogran.	[69]
Adinazolam	DMBHO9Y	Approved	Cytochrome P450 2C19 (CYP2C19) decreases the methylation of Adinazolam.	[73]
N-DESMETHYLCLOZAPINE	DMVIRN3	Phase 2	Cytochrome P450 2C19 (CYP2C19) increases the chemical synthesis of N-DESMETHYLCLOZAPINE.	[76]
EMODIN	DMAEDQG	Terminated	Cytochrome P450 2C19 (CYP2C19) increases the oxidation of EMODIN.	[78]
Nimesulide	DMR1NMD	Terminated	Cytochrome P450 2C19 (CYP2C19) increases the glutathionylation of Nimesulide.	[79]
Mononitrophenol	DM4QO9G	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the hydroxylation of Mononitrophenol.	[17]
ACMC-1AKLT	DMRQ70X	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the chemical synthesis of ACMC-1AKLT.	[85]
Dimemorfan	DM2Q3CL	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the oxidation of Dimemorfan.	[86]
Bufuralol	DMJSC07	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the hydroxylation of Bufuralol.	[87]
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⏷ Show the Full List of 24 Drug(s)

This DOT Affected the Drug Response of 10 Drug(s)

Drug Name	Drug ID	Highest Status	Interaction	REF
Troglitazone	DM3VFPD	Approved	Cytochrome P450 2C19 (CYP2C19) increases the response to substance of Troglitazone.	[48]
Ifosfamide	DMCT3I8	Approved	Cytochrome P450 2C19 (CYP2C19) increases the response to substance of Ifosfamide.	[52]
Warfarin	DMJYCVW	Approved	Cytochrome P450 2C19 (CYP2C19) affects the response to substance of Warfarin.	[57]
Flutamide	DMK0O7U	Approved	Cytochrome P450 2C19 (CYP2C19) increases the response to substance of Flutamide.	[59]
Amitriptyline	DMK7F9S	Approved	Cytochrome P450 2C19 (CYP2C19) increases the Haemorrhage ADR of Amitriptyline.	[71]
Clobazam	DMW1OQ0	Approved	Cytochrome P450 2C19 (CYP2C19) increases the Metabolic disorder ADR of Clobazam.	[72]
Amiodarone	DMUTEX3	Phase 2/3 Trial	Cytochrome P450 2C19 (CYP2C19) decreases the response to substance of Amiodarone.	[74]
Clopidogrel	DMOL54H	Phase 2 Trial	Cytochrome P450 2C19 (CYP2C19) increases the Cardiovascular disorders ADR of Clopidogrel.	[77]
gingerol	DMNXYSM	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the response to substance of gingerol.	[81]
Tetramethylbutylphenol	DMW9CH2	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the response to substance of Tetramethylbutylphenol.	[82]
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⏷ Show the Full List of 10 Drug(s)

This DOT Affected the Regulation of Drug Effects of 11 Drug(s)

Drug Name	Drug ID	Highest Status	Interaction	REF
Permethrin	DMZ0Q1G	Approved	Cytochrome P450 2C19 (CYP2C19) increases the metabolism of Permethrin.	[50]
Clomipramine	DMINRKW	Approved	Cytochrome P450 2C19 (CYP2C19) decreases the metabolism of Clomipramine.	[61]
Dronedarone	DMA8FS5	Approved	Cytochrome P450 2C19 (CYP2C19) increases the metabolism of Dronedarone.	[65]
Imiquimod	DM1TMA3	Approved	Cytochrome P450 2C19 (CYP2C19) increases the metabolism of Imiquimod.	[66]
Fluconazole	DMOWZ6B	Approved	Cytochrome P450 2C19 (CYP2C19) increases the metabolism of Fluconazole.	[70]
Afimoxifene	DMFORDT	Phase 2	Cytochrome P450 2C19 (CYP2C19) increases the metabolism of Afimoxifene.	[75]
2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE	DMNQL17	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the metabolism of 2-AMINO-1-METHYL-6-PHENYLIMIDAZO[4,5-B]PYRIDINE.	[80]
1,4-Naphthoquinone	DMTCMH7	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the abundance of 1,4-Naphthoquinone.	[83]
Ellipticine	DMHPYSM	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the metabolism of Ellipticine.	[84]
Imipramine oxide	DMZKABS	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the abundance of Imipramine oxide.	[88]
2-(1H-indol-3-yl)-N,N-dimethylethanamine	DMR9Q4Y	Investigative	Cytochrome P450 2C19 (CYP2C19) increases the metabolism of 2-(1H-indol-3-yl)-N,N-dimethylethanamine.	[88]
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⏷ Show the Full List of 11 Drug(s)

2 Drug(s) Affected the Post-Translational Modifications of This DOT

Drug Name	Drug ID	Highest Status	Interaction	REF
Valproate	DMCFE9I	Approved	Valproate decreases the methylation of Cytochrome P450 2C19 (CYP2C19).	[1]
Bisphenol A	DM2ZLD7	Investigative	Bisphenol A decreases the methylation of Cytochrome P450 2C19 (CYP2C19).	[35]
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72 Drug(s) Affected the Gene/Protein Processing of This DOT

Drug Name	Drug ID	Highest Status	Interaction	REF
Ciclosporin	DMAZJFX	Approved	Ciclosporin decreases the expression of Cytochrome P450 2C19 (CYP2C19).	[2]
Tretinoin	DM49DUI	Approved	Tretinoin decreases the expression of Cytochrome P450 2C19 (CYP2C19).	[3]
Acetaminophen	DMUIE76	Approved	Acetaminophen decreases the expression of Cytochrome P450 2C19 (CYP2C19).	[4]
Quercetin	DM3NC4M	Approved	Quercetin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
Calcitriol	DM8ZVJ7	Approved	Calcitriol increases the expression of Cytochrome P450 2C19 (CYP2C19).	[6]
Triclosan	DMZUR4N	Approved	Triclosan increases the expression of Cytochrome P450 2C19 (CYP2C19).	[7]
Carbamazepine	DMZOLBI	Approved	Carbamazepine increases the expression of Cytochrome P450 2C19 (CYP2C19).	[8]
Cannabidiol	DM0659E	Approved	Cannabidiol decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[9]
Amphotericin B	DMTAJQE	Approved	Amphotericin B increases the expression of Cytochrome P450 2C19 (CYP2C19).	[10]
Fenofibrate	DMFKXDY	Approved	Fenofibrate increases the expression of Cytochrome P450 2C19 (CYP2C19).	[11]
Rifampicin	DM5DSFZ	Approved	Rifampicin increases the expression of Cytochrome P450 2C19 (CYP2C19).	[12]
Capsaicin	DMGMF6V	Approved	Capsaicin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[13]
Ritonavir	DMU764S	Approved	Ritonavir increases the expression of Cytochrome P450 2C19 (CYP2C19).	[14]
Dihydroartemisinin	DMBXVMZ	Approved	Dihydroartemisinin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[15]
Eicosapentaenoic acid/docosa-hexaenoic acid	DMMUCG4	Approved	Eicosapentaenoic acid/docosa-hexaenoic acid decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[16]
Hesperetin	DMKER83	Approved	Hesperetin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
Thioridazine	DM35M8J	Approved	Thioridazine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[17]
Amodiaquine	DME4RA8	Approved	Amodiaquine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[15]
Efavirenz	DMC0GSJ	Approved	Efavirenz decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[18]
Pentamidine	DMHZJCG	Approved	Pentamidine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[15]
Zafirlukast	DMHNQOG	Approved	Zafirlukast decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[19]
Chloramphenicol	DMFXEWT	Approved	Chloramphenicol decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[20]
Miconazole	DMPMYE8	Approved	Miconazole decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[21]
Ethambutol	DMR87LC	Approved	Ethambutol decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[22]
Quinine	DMSWYF5	Approved	Quinine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[15]
Desipramine	DMT2FDC	Approved	Desipramine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[17]
Dabrafenib	DMX6OE3	Approved	Dabrafenib decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[23]
Sibutramine	DMFJTDI	Approved	Sibutramine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[24]
Artemisinin	DMOY7W3	Approved	Artemisinin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[15]
Voriconazole	DMAOL2S	Approved	Voriconazole decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[25]
MELARSOPROL	DMGUZ0W	Approved	MELARSOPROL decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[15]
Tranylcypromine	DMGB5RE	Approved	Tranylcypromine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[26]
Stiripentol	DMMSDOY	Approved	Stiripentol decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[27]
Delavirdine	DM3NF5G	Approved	Delavirdine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[18]
Diethylcarbamazine	DM1TJ8F	Approved	Diethylcarbamazine increases the activity of Cytochrome P450 2C19 (CYP2C19).	[15]
Benidipine	DMWNP6B	Phase 4	Benidipine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[28]
Barnidipine	DMJSDBE	Phase 4	Barnidipine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[28]
Resveratrol	DM3RWXL	Phase 3	Resveratrol decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[29]
Chlorpromazine	DMBGZI3	Phase 3 Trial	Chlorpromazine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[17]
MLN8237	DMO8PT9	Phase 3	MLN8237 affects the activity of Cytochrome P450 2C19 (CYP2C19).	[30]
Genistein	DM0JETC	Phase 2/3	Genistein decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
BAICALEIN	DM4C7E6	Phase 2	BAICALEIN decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
URSOLIC ACID	DM4SOAW	Phase 2	URSOLIC ACID decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[31]
Icaritin	DMGHQ37	Phase 2	Icaritin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
Benzo(a)pyrene	DMN7J43	Phase 1	Benzo(a)pyrene decreases the expression of Cytochrome P450 2C19 (CYP2C19).	[32]
Flavonoid derivative 1	DMCQP0B	Patented	Flavonoid derivative 1 decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
PMID27841045-Compound-156	DML4AVX	Patented	PMID27841045-Compound-156 decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
Avasimibe	DMFG4OM	Discontinued in Phase 3	Avasimibe decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[33]
Miltirone	DMZNWAV	Terminated	Miltirone decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[34]
Acetaldehyde	DMJFKG4	Investigative	Acetaldehyde decreases the expression of Cytochrome P450 2C19 (CYP2C19).	[36]
Phencyclidine	DMQBEYX	Investigative	Phencyclidine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[37]
Chlorpyrifos	DMKPUI6	Investigative	Chlorpyrifos increases the expression of Cytochrome P450 2C19 (CYP2C19).	[38]
Arachidonic acid	DMUOQZD	Investigative	Arachidonic acid decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[16]
(E)-4-(3,5-dimethoxystyryl)phenol	DMYXI2V	Investigative	(E)-4-(3,5-dimethoxystyryl)phenol decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[39]
2-tert-butylbenzene-1,4-diol	DMNXI1E	Investigative	2-tert-butylbenzene-1,4-diol increases the expression of Cytochrome P450 2C19 (CYP2C19).	[40]
Myricetin	DMTV4L0	Investigative	Myricetin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
NSC-1771	DMNXDGQ	Investigative	NSC-1771 decreases the expression of Cytochrome P450 2C19 (CYP2C19).	[41]
Linoleic acid	DMDGPY9	Investigative	Linoleic acid decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[16]
LICOAGROCHACONE A	DMWY0TN	Investigative	LICOAGROCHACONE A decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[42]
Aloe-emodin	DMPTY8S	Investigative	Aloe-emodin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[43]
Icosapentum	DMF1CM7	Investigative	Icosapentum decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[16]
RHEIN	DMS6IJ0	Investigative	RHEIN decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[43]
Alpha-linolenic acid	DMY64HE	Investigative	Alpha-linolenic acid decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[16]
Cinnamic acid	DM340FH	Investigative	Cinnamic acid decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[44]
Purpurin	DMYWRL6	Investigative	Purpurin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[43]
Fluphenazine	DMIT8LX	Investigative	Fluphenazine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[17]
Suramin	DMTOUY9	Investigative	Suramin decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[15]
DIOSMETIN	DM4KXIM	Investigative	DIOSMETIN decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[45]
NSC-94258	DM6VY3P	Investigative	NSC-94258 decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
2-(5-fluoro-1H-indol-3-yl)ethanamine	DMHW5FT	Investigative	2-(5-fluoro-1H-indol-3-yl)ethanamine decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[20]
LIQUIRTIGENIN	DM6YSG3	Investigative	LIQUIRTIGENIN decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
Maackiain	DMDHGM2	Investigative	Maackiain decreases the activity of Cytochrome P450 2C19 (CYP2C19).	[5]
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⏷ Show the Full List of 72 Drug(s)

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