Details of Drug Off-Target (DOT)

General Information of Drug Off-Target (DOT) (ID: OTOYO4S7)

DOT Name Cytochrome P450 2B6 (CYP2B6)
Synonyms EC 1.14.13.-; 1,4-cineole 2-exo-monooxygenase; CYPIIB6; Cytochrome P450 IIB1
Gene Name CYP2B6
UniProt ID
CP2B6_HUMAN
3D Structure
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2D Sequence (FASTA)
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3D Structure (PDB)
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PDB ID
3IBD; 3QOA; 3QU8; 3UA5; 4I91; 4RQL; 4RRT; 4ZV8; 5UAP; 5UDA; 5UEC; 5UFG; 5WBG
EC Number
1.14.13.-
Pfam ID
PF00067
Sequence
MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRGLLKSFLRFRE
KYGDVFTVHLGPRPVVMLCGVEAIREALVDKAEAFSGRGKIAMVDPFFRGYGVIFANGNR
WKVLRRFSVTTMRDFGMGKRSVEERIQEEAQCLIEELRKSKGALMDPTFLFQSITANIIC
SIVFGKRFHYQDQEFLKMLNLFYQTFSLISSVFGQLFELFSGFLKYFPGAHRQVYKNLQE
INAYIGHSVEKHRETLDPSAPKDLIDTYLLHMEKEKSNAHSEFSHQNLNLNTLSLFFAGT
ETTSTTLRYGFLLMLKYPHVAERVYREIEQVIGPHRPPELHDRAKMPYTEAVIYEIQRFS
DLLPMGVPHIVTQHTSFRGYIIPKDTEVFLILSTALHDPHYFEKPDAFNPDHFLDANGAL
KKTEAFIPFSLGKRICLGEGIARAELFLFFTTILQNFSMASPVAPEDIDLTPQECGVGKI
PPTYQIRFLPR
Function
A cytochrome P450 monooxygenase involved in the metabolism of endocannabinoids and steroids. 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 epoxidation of double bonds of arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling. Hydroxylates steroid hormones, including testosterone at C-16 and estrogens at C-2. Plays a role in the oxidative metabolism of xenobiotics, including plant lipids and drugs. Acts as a 1,4-cineole 2-exo-monooxygenase ; Allele 2B6*9: Has low affinity for anandamide and can only produce 11,12 EpETrE-EAs.
Tissue Specificity Expressed in liver, lung and heart right ventricle.
KEGG Pathway
Arachidonic acid metabolism (hsa00590 )
Retinol metabolism (hsa00830 )
Metabolism of xenobiotics by cytochrome P450 (hsa00980 )
Drug metabolism - cytochrome P450 (hsa00982 )
Metabolic pathways (hsa01100 )
Chemical carcinogenesis - receptor activation (hsa05207 )
Lipid and atherosclerosis (hsa05417 )
Reactome Pathway
Phase I - Functionalization of compounds (R-HSA-211945 )
Xenobiotics (R-HSA-211981 )
CYP2E1 reactions (R-HSA-211999 )
Fatty acids (R-HSA-211935 )
BioCyc Pathway
MetaCyc:HS09587-MONOMER

Molecular Interaction Atlas (MIA) of This DOT

Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This DOT
This DOT Affected the Biotransformations of 16 Drug(s)
Drug Name Drug ID Highest Status Interaction REF
Testosterone DM7HUNW Approved Cytochrome P450 2B6 (CYP2B6) increases the hydroxylation of Testosterone. [49]
Cyclophosphamide DM4O2Z7 Approved Cytochrome P450 2B6 (CYP2B6) increases the hydroxylation of Cyclophosphamide. [73]
Amphetamine DMSZQAK Approved Cytochrome P450 2B6 (CYP2B6) decreases the methylation of Amphetamine. [76]
Lamotrigine DM8SXYG Approved Cytochrome P450 2B6 (CYP2B6) increases the glutathionylation of Lamotrigine. [77]
Cotinine DMCEZ1B Approved Cytochrome P450 2B6 (CYP2B6) increases the chemical synthesis of Cotinine. [79]
Bupropion DM5PCS7 Approved Cytochrome P450 2B6 (CYP2B6) increases the hydrolysis of Bupropion. [80]
Domperidone DMBDPY0 Approved Cytochrome P450 2B6 (CYP2B6) increases the hydroxylation of Domperidone. [82]
Mephenytoin DM5UGDK Approved Cytochrome P450 2B6 (CYP2B6) decreases the methylation of Mephenytoin. [83]
Radafaxine DMARQE0 Discontinued in Phase 2 Cytochrome P450 2B6 (CYP2B6) increases the chemical synthesis of Radafaxine. [86]
Nimesulide DMR1NMD Terminated Cytochrome P450 2B6 (CYP2B6) increases the glutathionylation of Nimesulide. [87]
HELENALIN DMMCI4H Terminated Cytochrome P450 2B6 (CYP2B6) increases the oxidation of HELENALIN. [88]
Chlorphrifos oxon DMGBT68 Investigative Cytochrome P450 2B6 (CYP2B6) increases the chemical synthesis of Chlorphrifos oxon. [92]
Aloe-emodin DMPTY8S Investigative Cytochrome P450 2B6 (CYP2B6) increases the chemical synthesis of Aloe-emodin. [94]
ACMC-1AKLT DMRQ70X Investigative Cytochrome P450 2B6 (CYP2B6) increases the chemical synthesis of ACMC-1AKLT. [95]
NSC-26745 DMNX245 Investigative Cytochrome P450 2B6 (CYP2B6) increases the oxidation of NSC-26745. [96]
Dimemorfan DM2Q3CL Investigative Cytochrome P450 2B6 (CYP2B6) increases the oxidation of Dimemorfan. [97]
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⏷ Show the Full List of 16 Drug(s)
This DOT Affected the Regulation of Drug Effects of 13 Drug(s)
Drug Name Drug ID Highest Status Interaction REF
Ethinyl estradiol DMODJ40 Approved Cytochrome P450 2B6 (CYP2B6) affects the metabolism of Ethinyl estradiol. [72]
Amodiaquine DME4RA8 Approved Cytochrome P450 2B6 (CYP2B6) increases the metabolism of Amodiaquine. [75]
Dronedarone DMA8FS5 Approved Cytochrome P450 2B6 (CYP2B6) increases the metabolism of Dronedarone. [78]
Primaquine DMWQ16I Approved Cytochrome P450 2B6 (CYP2B6) increases the metabolism of Primaquine. [81]
Afimoxifene DMFORDT Phase 2 Cytochrome P450 2B6 (CYP2B6) increases the metabolism of Afimoxifene. [85]
(Z)-endoxifen DMGDOS2 Phase 2 Cytochrome P450 2B6 (CYP2B6) increases the metabolism of (Z)-endoxifen. [85]
Piclamilast DMYL7VR Phase 2 Cytochrome P450 2B6 (CYP2B6) increases the metabolism of Piclamilast. [44]
geraniol DMS3CBD Investigative Cytochrome P450 2B6 (CYP2B6) increases the metabolism of geraniol. [89]
Arachidonic acid DMUOQZD Investigative Cytochrome P450 2B6 (CYP2B6) increases the metabolism of Arachidonic acid. [90]
1,4-Naphthoquinone DMTCMH7 Investigative Cytochrome P450 2B6 (CYP2B6) increases the abundance of 1,4-Naphthoquinone. [93]
TEPA (possesses cytotoxic activity) DMROS5K Investigative Cytochrome P450 2B6 (CYP2B6) affects the export of TEPA (possesses cytotoxic activity). [98]
Imipramine oxide DMZKABS Investigative Cytochrome P450 2B6 (CYP2B6) increases the abundance of Imipramine oxide. [99]
Benzyloxyresorufin DM26SR7 Investigative Cytochrome P450 2B6 (CYP2B6) increases the metabolism of Benzyloxyresorufin. [44]
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⏷ Show the Full List of 13 Drug(s)
This DOT Affected the Drug Response of 4 Drug(s)
Drug Name Drug ID Highest Status Interaction REF
Ifosfamide DMCT3I8 Approved Cytochrome P450 2B6 (CYP2B6) increases the response to substance of Ifosfamide. [74]
Chlorpromazine DMBGZI3 Phase 3 Trial Cytochrome P450 2B6 (CYP2B6) decreases the response to substance of Chlorpromazine. [84]
Amiodarone DMUTEX3 Phase 2/3 Trial Cytochrome P450 2B6 (CYP2B6) decreases the response to substance of Amiodarone. [84]
BRN-3548355 DM4KXT0 Investigative Cytochrome P450 2B6 (CYP2B6) increases the activity of BRN-3548355. [91]
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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 2B6 (CYP2B6). [1]
Benzo(a)pyrene DMN7J43 Phase 1 Benzo(a)pyrene increases the methylation of Cytochrome P450 2B6 (CYP2B6). [47]
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97 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 2B6 (CYP2B6). [2]
Acetaminophen DMUIE76 Approved Acetaminophen decreases the expression of Cytochrome P450 2B6 (CYP2B6). [3]
Cupric Sulfate DMP0NFQ Approved Cupric Sulfate increases the expression of Cytochrome P450 2B6 (CYP2B6). [4]
Estradiol DMUNTE3 Approved Estradiol increases the expression of Cytochrome P450 2B6 (CYP2B6). [5]
Triclosan DMZUR4N Approved Triclosan increases the expression of Cytochrome P450 2B6 (CYP2B6). [6]
Carbamazepine DMZOLBI Approved Carbamazepine increases the expression of Cytochrome P450 2B6 (CYP2B6). [7]
Phenobarbital DMXZOCG Approved Phenobarbital increases the expression of Cytochrome P450 2B6 (CYP2B6). [8]
Progesterone DMUY35B Approved Progesterone increases the expression of Cytochrome P450 2B6 (CYP2B6). [9]
Dexamethasone DMMWZET Approved Dexamethasone increases the expression of Cytochrome P450 2B6 (CYP2B6). [10]
Cannabidiol DM0659E Approved Cannabidiol decreases the activity of Cytochrome P450 2B6 (CYP2B6). [11]
Troglitazone DM3VFPD Approved Troglitazone increases the expression of Cytochrome P450 2B6 (CYP2B6). [12]
Diethylstilbestrol DMN3UXQ Approved Diethylstilbestrol increases the expression of Cytochrome P450 2B6 (CYP2B6). [13]
Rosiglitazone DMILWZR Approved Rosiglitazone increases the expression of Cytochrome P450 2B6 (CYP2B6). [14]
Ethanol DMDRQZU Approved Ethanol increases the expression of Cytochrome P450 2B6 (CYP2B6). [15]
Malathion DMXZ84M Approved Malathion increases the expression of Cytochrome P450 2B6 (CYP2B6). [16]
Permethrin DMZ0Q1G Approved Permethrin increases the expression of Cytochrome P450 2B6 (CYP2B6). [17]
Simvastatin DM30SGU Approved Simvastatin increases the expression of Cytochrome P450 2B6 (CYP2B6). [18]
Rifampicin DM5DSFZ Approved Rifampicin increases the expression of Cytochrome P450 2B6 (CYP2B6). [19]
Alitretinoin DMME8LH Approved Alitretinoin increases the expression of Cytochrome P450 2B6 (CYP2B6). [20]
Clorgyline DMCEUJD Approved Clorgyline decreases the activity of Cytochrome P450 2B6 (CYP2B6). [21]
Pioglitazone DMKJ485 Approved Pioglitazone increases the expression of Cytochrome P450 2B6 (CYP2B6). [14]
Thalidomide DM70BU5 Approved Thalidomide increases the expression of Cytochrome P450 2B6 (CYP2B6). [22]
Lindane DMB8CNL Approved Lindane increases the expression of Cytochrome P450 2B6 (CYP2B6). [23]
Phenytoin DMNOKBV Approved Phenytoin increases the expression of Cytochrome P450 2B6 (CYP2B6). [24]
Sertraline DM0FB1J Approved Sertraline decreases the activity of Cytochrome P450 2B6 (CYP2B6). [25]
Ritonavir DMU764S Approved Ritonavir increases the activity of Cytochrome P450 2B6 (CYP2B6). [26]
Nefazodone DM4ZS8M Approved Nefazodone decreases the expression of Cytochrome P450 2B6 (CYP2B6). [27]
Bexarotene DMOBIKY Approved Bexarotene increases the expression of Cytochrome P450 2B6 (CYP2B6). [20]
Cholecalciferol DMGU74E Approved Cholecalciferol increases the expression of Cytochrome P450 2B6 (CYP2B6). [28]
Bosentan DMIOGBU Approved Bosentan increases the expression of Cytochrome P450 2B6 (CYP2B6). [29]
Deoxycholic acid DM3GYAL Approved Deoxycholic acid increases the expression of Cytochrome P450 2B6 (CYP2B6). [30]
Atazanavir DMSYRBX Approved Atazanavir decreases the expression of Cytochrome P450 2B6 (CYP2B6). [27]
Omeprazole DM471KJ Approved Omeprazole increases the expression of Cytochrome P450 2B6 (CYP2B6). [12]
Cimetidine DMH61ZB Approved Cimetidine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [31]
Mitotane DMU1GX0 Approved Mitotane increases the expression of Cytochrome P450 2B6 (CYP2B6). [20]
Clotrimazole DMMFCIH Approved Clotrimazole increases the activity of Cytochrome P450 2B6 (CYP2B6). [32]
Teriflunomide DMQ2FKJ Approved Teriflunomide increases the expression of Cytochrome P450 2B6 (CYP2B6). [33]
Clopidogrel DMOL54H Approved Clopidogrel increases the expression of Cytochrome P450 2B6 (CYP2B6). [20]
Amlodipine DMBDAZV Approved Amlodipine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [34]
Thiotepa DMIZKOP Approved Thiotepa decreases the activity of Cytochrome P450 2B6 (CYP2B6). [35]
Felodipine DMOSW35 Approved Felodipine increases the expression of Cytochrome P450 2B6 (CYP2B6). [36]
Paroxetine DM5PVQE Approved Paroxetine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [37]
Pazopanib DMF57DM Approved Pazopanib increases the expression of Cytochrome P450 2B6 (CYP2B6). [38]
Isradipine DMA5XGH Approved Isradipine increases the expression of Cytochrome P450 2B6 (CYP2B6). [36]
Artemisinin DMOY7W3 Approved Artemisinin increases the expression of Cytochrome P450 2B6 (CYP2B6). [39]
Sibutramine DMFJTDI Approved Sibutramine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [40]
Selegiline DM6034S Approved Selegiline decreases the activity of Cytochrome P450 2B6 (CYP2B6). [21]
Pimecrolimus DMZLGRB Approved Pimecrolimus increases the expression of Cytochrome P450 2B6 (CYP2B6). [38]
Thiabendazole DM7YCK3 Approved Thiabendazole increases the expression of Cytochrome P450 2B6 (CYP2B6). [41]
Sulfinpyrazone DMEV954 Approved Sulfinpyrazone increases the expression of Cytochrome P450 2B6 (CYP2B6). [32]
Tranylcypromine DMGB5RE Approved Tranylcypromine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [42]
Phenelzine DMHIDUE Approved Phenelzine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [21]
Yn-968D1 DMMP3Y2 Approved Yn-968D1 decreases the activity of Cytochrome P450 2B6 (CYP2B6). [43]
Orphenadrine DMW542E Approved Orphenadrine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [44]
Pargyline DMM0HR1 Approved Pargyline decreases the activity of Cytochrome P450 2B6 (CYP2B6). [21]
Moricizine DMOMBJW Approved Moricizine increases the expression of Cytochrome P450 2B6 (CYP2B6). [29]
Benidipine DMWNP6B Phase 4 Benidipine increases the expression of Cytochrome P450 2B6 (CYP2B6). [36]
Barnidipine DMJSDBE Phase 4 Barnidipine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [34]
Camptothecin DM6CHNJ Phase 3 Camptothecin decreases the expression of Cytochrome P450 2B6 (CYP2B6). [38]
Atorvastatin DMF28YC Phase 3 Trial Atorvastatin increases the expression of Cytochrome P450 2B6 (CYP2B6). [18]
BAICALEIN DM4C7E6 Phase 2 BAICALEIN increases the expression of Cytochrome P450 2B6 (CYP2B6). [45]
APC-100 DM71I53 Phase 1/2 APC-100 increases the expression of Cytochrome P450 2B6 (CYP2B6). [46]
(+)-JQ1 DM1CZSJ Phase 1 (+)-JQ1 decreases the expression of Cytochrome P450 2B6 (CYP2B6). [48]
Leflunomide DMR8ONJ Phase 1 Trial Leflunomide increases the expression of Cytochrome P450 2B6 (CYP2B6). [33]
Clemizole DM4UAPD Phase 1 Clemizole increases the expression of Cytochrome P450 2B6 (CYP2B6). [20]
BUTYLATEDHYDROXYTOLUENE DMJ56MS Phase 1 BUTYLATEDHYDROXYTOLUENE increases the expression of Cytochrome P450 2B6 (CYP2B6). [41]
PMID26560530-Compound-34 DMLGZPO Patented PMID26560530-Compound-34 increases the expression of Cytochrome P450 2B6 (CYP2B6). [49]
Ticrynafen DMLFSTR Withdrawn from market Ticrynafen decreases the activity of Cytochrome P450 2B6 (CYP2B6). [37]
Roxithromycin DMVMIK2 Withdrawn from market Roxithromycin decreases the activity of Cytochrome P450 2B6 (CYP2B6). [50]
Avasimibe DMFG4OM Discontinued in Phase 3 Avasimibe increases the expression of Cytochrome P450 2B6 (CYP2B6). [51]
PIRINIXIC ACID DM82Y75 Preclinical PIRINIXIC ACID increases the expression of Cytochrome P450 2B6 (CYP2B6). [52]
Bisphenol A DM2ZLD7 Investigative Bisphenol A increases the expression of Cytochrome P450 2B6 (CYP2B6). [53]
3R14S-OCHRATOXIN A DM2KEW6 Investigative 3R14S-OCHRATOXIN A decreases the expression of Cytochrome P450 2B6 (CYP2B6). [54]
Paraquat DMR8O3X Investigative Paraquat increases the expression of Cytochrome P450 2B6 (CYP2B6). [55]
Phencyclidine DMQBEYX Investigative Phencyclidine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [56]
Butanoic acid DMTAJP7 Investigative Butanoic acid increases the expression of Cytochrome P450 2B6 (CYP2B6). [57]
Chlorpyrifos DMKPUI6 Investigative Chlorpyrifos increases the expression of Cytochrome P450 2B6 (CYP2B6). [58]
Rapamycin Immunosuppressant Drug DM678IB Investigative Rapamycin Immunosuppressant Drug increases the expression of Cytochrome P450 2B6 (CYP2B6). [59]
Bilirubin DMI0V4O Investigative Bilirubin increases the expression of Cytochrome P450 2B6 (CYP2B6). [60]
U0126 DM31OGF Investigative U0126 decreases the expression of Cytochrome P450 2B6 (CYP2B6). [61]
Chrysin DM7V2LG Investigative Chrysin increases the expression of Cytochrome P450 2B6 (CYP2B6). [45]
(E)-4-(3,5-dimethoxystyryl)phenol DMYXI2V Investigative (E)-4-(3,5-dimethoxystyryl)phenol increases the expression of Cytochrome P450 2B6 (CYP2B6). [62]
Oleic acid DM54O1Z Investigative Oleic acid decreases the expression of Cytochrome P450 2B6 (CYP2B6). [63]
GW7647 DM9RD0C Investigative GW7647 increases the expression of Cytochrome P450 2B6 (CYP2B6). [64]
Farnesol DMV2X1B Investigative Farnesol increases the expression of Cytochrome P450 2B6 (CYP2B6). [63]
Galangin DM5TQ2O Investigative Galangin increases the expression of Cytochrome P450 2B6 (CYP2B6). [45]
N-nonylphenol DMH3OUX Investigative N-nonylphenol increases the expression of Cytochrome P450 2B6 (CYP2B6). [65]
Isoarnebin 4 DM0B7NO Investigative Isoarnebin 4 decreases the activity of Cytochrome P450 2B6 (CYP2B6). [66]
Hyperforin DM2L3PE Investigative Hyperforin increases the expression of Cytochrome P450 2B6 (CYP2B6). [67]
CITCO DM0N634 Investigative CITCO increases the expression of Cytochrome P450 2B6 (CYP2B6). [68]
chlordane DMMHU8G Investigative chlordane increases the expression of Cytochrome P450 2B6 (CYP2B6). [69]
(11-BETA)-11,21-DIHYDROXY-PREGN-4-ENE-3,20-DIONE DMTPQ84 Investigative (11-BETA)-11,21-DIHYDROXY-PREGN-4-ENE-3,20-DIONE increases the expression of Cytochrome P450 2B6 (CYP2B6). [15]
PK 11195 DMDOZPU Investigative PK 11195 increases the expression of Cytochrome P450 2B6 (CYP2B6). [70]
2-(5-fluoro-1H-indol-3-yl)ethanamine DMHW5FT Investigative 2-(5-fluoro-1H-indol-3-yl)ethanamine decreases the activity of Cytochrome P450 2B6 (CYP2B6). [25]
FGIN-1-27 DM4T5DY Investigative FGIN-1-27 increases the expression of Cytochrome P450 2B6 (CYP2B6). [70]
GINKGOLIDE A DMKZJ7T Investigative GINKGOLIDE A increases the expression of Cytochrome P450 2B6 (CYP2B6). [71]
5-MEO-DMT DMG0EL7 Investigative 5-MEO-DMT decreases the activity of Cytochrome P450 2B6 (CYP2B6). [25]
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⏷ Show the Full List of 97 Drug(s)

References

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