General Information of Drug (ID: DMFI7A8)

Drug Name
6-Benzyloxy-9H-purin-2-ylamine Drug Info
Synonyms
6-O-Benzylguanine; 19916-73-5; 6-(Benzyloxy)-7H-purin-2-amine; 2-amino-6-benzyloxypurine; 6-(benzyloxy)-9H-purin-2-amine; 2-Amino-6-(benzyloxy)purine; O(6)-Bgua; 6-(Benzyloxy)guanine; 6-Benzyloxyguanine; 6-Benzyloxy guanine; 6-(Phenylmethoxy)-1H-purin-2-amine; 2-Amino-6-(phenylmethoxy)-9H-purine; O6-BG; UNII-01KC87F8FE; 1H-Purin-2-amine, 6-(phenylmethoxy)-; 6-BENZYLGUANINE; Purine, 2-amino-6-(benzyloxy)-; NSC 637037; CHEMBL407874; 01KC87F8FE; 6-benzyloxy-7H-purin-2-amine
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
4578
CAS Number
CAS 19916-73-5
TTD Drug ID
DMFI7A8
INTEDE Drug ID
DR0022

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
DOT
Drug Status:
Clinical Trial Drug(s)
Investigative Drug(s)
Approved Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
O6-Benzylguanine alkylade DM3L2GT Sarcoma 2A60-2C35 Phase 3 [6]
S-Methylcysteine DMAMRKS Discovery agent N.A. Investigative [7]
6-Benzyloxy-5-nitroso-pyrimidine-2,4-diamine DMUFSE2 Discovery agent N.A. Investigative [1]
6-Benzyloxy-5-nitro-pyrimidine-2,4-diamine DMK8XIO Discovery agent N.A. Investigative [1]
Benzylcysteine DMTCYHM Discovery agent N.A. Investigative [7]
6-Allyloxy-9H-purin-2-ylamine DMI2XUQ Discovery agent N.A. Investigative [8]
⏷ Show the Full List of 6 Drug(s)
Drug(s) Metabolized By Cytochrome P450 3A4 (CYP3A4)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Doxorubicin DMVP5YE Acute myelogenous leukaemia 2A41 Approved [9]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [10]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [11]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [12]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [13]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [14]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [15]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [16]
Prasterone DM67VKL Chronic obstructive pulmonary disease CA22 Approved [10]
Verapamil DMA7PEW Angina pectoris BA40 Approved [17]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 1A2 (CYP1A2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fluorouracil DMUM7HZ Adenocarcinoma 2D40 Approved [18]
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [19]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [20]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [21]
Acetaminophen DMUIE76 Allergic rhinitis CA08.0 Approved [22]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [23]
Etoposide DMNH3PG Acute myelogenous leukaemia 2A41 Approved [15]
Oxaliplatin DMQNWRD Adenocarcinoma 2D40 Approved [24]
Verapamil DMA7PEW Angina pectoris BA40 Approved [25]
Diclofenac DMPIHLS Chronic renal failure GB61.Z Approved [26]
Zolmitriptan DM1IB4Q Migraine 8A80 Approved [27]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [27]
Etoricoxib DM6A4NW Rheumatoid arthritis FA20 Approved [27]
Capsaicin DMGMF6V Back pain ME84.Z Approved [28]
Hesperetin DMKER83 High blood cholesterol level 5C80.00 Approved [29]
Stiripentol DMMSDOY Dravet syndrome 8A61.11 Approved [30]
Nifedipine DMSVOZT Angina pectoris BA40 Approved [31]
Zileuton DMVRIC2 Allergic asthma CA23.0 Approved [32]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [33]
Clonidine DM6RZ9Q Attention deficit hyperactivity disorder 6A05.Z Approved [34]
⏷ Show the Full List of 20 Drug(s)
Drug(s) Affected By Aldehyde oxidase (AOX1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Methotrexate DM2TEOL Anterior urethra cancer Approved [35]
Quercetin DM3NC4M Obesity 5B81 Approved [36]
Rofecoxib DM3P5DA Osteoarthritis FA00-FA05 Approved [37]
Methylprednisolone DM4BDON Acute adrenal insufficiency Approved [38]
Nefazodone DM4ZS8M Major depressive disorder 6A70.3 Approved [39]
Panobinostat DM58WKG Chronic graft versus host disease Approved [40]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [41]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [42]
Dasatinib DMJV2EK Blast phase chronic myelogenous leukemia, BCR-ABL1 positive Approved [43]
Temozolomide DMKECZD Adenocarcinoma 2D40 Approved [44]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Angiotensinogen (AGT)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [45]
Progesterone DMUY35B Amenorrhea GA20.0 Approved [46]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [47]
Reboxetine DM26PRD Depression 6A70-6A7Z Approved [48]
Spironolactone DM2AQ5N Chronic heart failure BD1Z Approved [49]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [50]
Rhucin DM3ADGP Erectile dysfunction HA01.1 Approved [51]
Quercetin DM3NC4M Obesity 5B81 Approved [36]
Lisinopril DMUOK4C Chronic heart failure BD1Z Approved [52]
Irbesartan DMTP1DC Diabetic kidney disease GB61.Z Approved [53]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 1A1 (CYP1A1)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amodiaquine DME4RA8 Malaria 1F40-1F45 Approved [54]
Riluzole DMECBWN Amyotrophic lateral sclerosis 8B60.0 Approved [55]
Flutamide DMK0O7U Prostate cancer 2C82.0 Approved [56]
Menadione DMSJDTY Vitamin K deficiency 5B59 Approved [57]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [58]
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [59]
Ethacrynic acid DM60QMR Edema MG29 Approved [60]
Marinol DM70IK5 Anorexia nervosa cachexia 6B80 Approved [61]
Ethinyl Estradiol DMODJ40 Acne vulgaris ED80 Approved [62]
Clofibrate DMPC1J7 Dysbetalipoproteinemia 5C80.2 Approved [63]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
O-6-methylguanine-DNA-alkyltransferase (MGMT) TTJ8DV7 MGMT_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [2]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aldehyde oxidase (AOX1) OT2FZP6H AOXA_HUMAN Regulation of Drug Effects [3]
Angiotensinogen (AGT) OTBZLYR3 ANGT_HUMAN Drug Response [4]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Regulation of Drug Effects [5]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [5]

References

1 Inhibition of human O6-alkylguanine-DNA alkyltransferase and potentiation of the cytotoxicity of chloroethylnitrosourea by 4(6)-(benzyloxy)-2,6(4)-... J Med Chem. 1998 Feb 12;41(4):503-8.
2 Human liver oxidative metabolism of O6-benzylguanine. Biochem Pharmacol. 1995 Oct 26;50(9):1385-9.
3 In vitro-in vivo correlation for intrinsic clearance for drugs metabolized by human aldehyde oxidase. Drug Metab Dispos. 2010 Aug;38(8):1322-7. doi: 10.1124/dmd.110.033555. Epub 2010 May 5.
4 Effect of O6-benzylguanine on alkylating agent-induced toxicity and mutagenicity. In Chinese hamster ovary cells expressing wild-type and mutant O6-alkylguanine-DNA alkyltransferases. Cancer Res. 2000 Oct 1;60(19):5464-9.
5 Role of cytochrome P450 isoenzymes in metabolism of O(6)-benzylguanine: implications for dacarbazine activation. Clin Cancer Res. 2001 Dec;7(12):4239-44.
6 Phase II trial of temozolomide plus o6-benzylguanine in adults with recurrent, temozolomide-resistant malignant glioma. J Clin Oncol. 2009 Mar 10;27(8):1262-7.
7 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
8 Resistance-modifying agents. 8. Inhibition of O(6)-alkylguanine-DNA alkyltransferase by O(6)-alkenyl-, O(6)-cycloalkenyl-, and O(6)-(2-oxoalkyl)gua... J Med Chem. 2000 Nov 2;43(22):4071-83.
9 Expression levels and activation of a PXR variant are directly related to drug resistance in osteosarcoma cell lines. Cancer. 2007 Mar 1;109(5):957-65.
10 Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47.
11 Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther. 2004 Sep;310(3):1062-75.
12 Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9.
13 Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
14 Potent mechanism-based inhibition of CYP3A4 by imatinib explains its liability to interact with CYP3A4 substrates. Br J Pharmacol. 2012 Apr;165(8):2787-98.
15 Effects of morin on the pharmacokinetics of etoposide in rats. Biopharm Drug Dispos. 2007 Apr;28(3):151-6.
16 The metabolism of zidovudine by human liver microsomes in vitro: formation of 3'-amino-3'-deoxythymidine. Biochem Pharmacol. 1994 Jul 19;48(2):267-76.
17 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
18 Roles of cytochromes P450 1A2, 2A6, and 2C8 in 5-fluorouracil formation from tegafur, an anticancer prodrug, in human liver microsomes. Drug Metab Dispos. 2000 Dec;28(12):1457-63.
19 Effects of polyunsaturated fatty acids on prostaglandin synthesis and cyclooxygenase-mediated DNA adduct formation by heterocyclic aromatic amines in human adenocarcinoma colon cells. Mol Carcinog. 2004 Jul;40(3):180-8.
20 Endoxifen and other metabolites of tamoxifen inhibit human hydroxysteroid sulfotransferase 2A1 (hSULT2A1). Drug Metab Dispos. 2014 Nov;42(11):1843-50.
21 Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65.
22 PharmGKB summary: pathways of acetaminophen metabolism at the therapeutic versus toxic doses. Pharmacogenet Genomics. 2015 Aug;25(8):416-26.
23 The effect of apigenin on pharmacokinetics of imatinib and its metabolite N-desmethyl imatinib in rats. Biomed Res Int. 2013;2013:789184.
24 The influence of metabolic gene polymorphisms on urinary 1-hydroxypyrene concentrations in Chinese coke oven workers. Sci Total Environ. 2007 Aug 1;381(1-3):38-46.
25 Identification of P450 enzymes involved in metabolism of verapamil in humans. Naunyn Schmiedebergs Arch Pharmacol. 1993 Sep;348(3):332-7.
26 Metabolism and metabolic inhibition of xanthotoxol in human liver microsomes. Evid Based Complement Alternat Med. 2016;2016:5416509.
27 In vitro inhibition of CYP1A2 by model inhibitors, anti-inflammatory analgesics and female sex steroids: predictability of in vivo interactions. Basic Clin Pharmacol Toxicol. 2008 Aug;103(2):157-65.
28 Effects of capsaicin and dihydrocapsaicin on human and rat liver microsomal CYP450 enzyme activities in vitro and in vivo. J Asian Nat Prod Res. 2012;14(4):382-95.
29 Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects. Toxicol Lett. 2018 Sep 15;294:27-36.
30 Stiripentol. Expert Opin Investig Drugs. 2005 Jul;14(7):905-11.
31 Inhibition of human cytochrome P450 enzymes by 1,4-dihydropyridine calcium antagonists: prediction of in vivo drug-drug interactions. Eur J Clin Pharmacol. 2000 Feb-Mar;55(11-12):843-52.
32 Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. Drug Metab Dispos. 2003 Nov;31(11):1352-60.
33 Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15.
34 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
35 Global molecular effects of tocilizumab therapy in rheumatoid arthritis synovium. Arthritis Rheumatol. 2014 Jan;66(1):15-23.
36 Comparison of phenotypic and transcriptomic effects of false-positive genotoxins, true genotoxins and non-genotoxins using HepG2 cells. Mutagenesis. 2011 Sep;26(5):593-604.
37 Rofecoxib modulates multiple gene expression pathways in a clinical model of acute inflammatory pain. Pain. 2007 Mar;128(1-2):136-47.
38 Antirheumatic drug response signatures in human chondrocytes: potential molecular targets to stimulate cartilage regeneration. Arthritis Res Ther. 2009;11(1):R15.
39 Robustness testing and optimization of an adverse outcome pathway on cholestatic liver injury. Arch Toxicol. 2020 Apr;94(4):1151-1172. doi: 10.1007/s00204-020-02691-9. Epub 2020 Mar 10.
40 A transcriptome-based classifier to identify developmental toxicants by stem cell testing: design, validation and optimization for histone deacetylase inhibitors. Arch Toxicol. 2015 Sep;89(9):1599-618.
41 Comparison of HepG2 and HepaRG by whole-genome gene expression analysis for the purpose of chemical hazard identification. Toxicol Sci. 2010 May;115(1):66-79.
42 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
43 Dasatinib reverses cancer-associated fibroblasts (CAFs) from primary lung carcinomas to a phenotype comparable to that of normal fibroblasts. Mol Cancer. 2010 Jun 27;9:168.
44 Temozolomide induces activation of Wnt/-catenin signaling in glioma cells via PI3K/Akt pathway: implications in glioma therapy. Cell Biol Toxicol. 2020 Jun;36(3):273-278. doi: 10.1007/s10565-019-09502-7. Epub 2019 Nov 22.
45 Genistein disrupts glucocorticoid receptor signaling in human uterine endometrial Ishikawa cells. Environ Health Perspect. 2015 Jan;123(1):80-7. doi: 10.1289/ehp.1408437. Epub 2014 Aug 19.
46 Steroid profiling in H295R cells to identify chemicals potentially disrupting the production of adrenal steroids. Toxicology. 2017 Apr 15;381:51-63.
47 Global gene expression analysis reveals differences in cellular responses to hydroxyl- and superoxide anion radical-induced oxidative stress in caco-2 cells. Toxicol Sci. 2010 Apr;114(2):193-203. doi: 10.1093/toxsci/kfp309. Epub 2009 Dec 31.
48 Influences of norepinephrine transporter function on the distribution of sympathetic activity in humans. Hypertension. 2006 Jul;48(1):120-6. doi: 10.1161/01.HYP.0000225424.13138.5d. Epub 2006 May 22.
49 Amiloride, spironolactone, and potassium chloride in thiazide-treated hypertensive patients. Clin Pharmacol Ther. 1980 Apr;27(4):533-43. doi: 10.1038/clpt.1980.75.
50 Simvastatin treatment in subjects at high cardiovascular risk modulates AT1R expression on circulating monocytes and T lymphocytes. J Hypertens. 2008 Jun;26(6):1147-55. doi: 10.1097/HJH.0b013e3282f97dde.
51 Inhibition of cGMP-specific phosphodiesterase type 5 reduces sodium excretion and arterial blood pressure in patients with NaCl retention and ascites. Am J Physiol Renal Physiol. 2005 May;288(5):F1044-52. doi: 10.1152/ajprenal.00142.2004. Epub 2004 Dec 21.
52 Effects of lisinopril on cardiorespiratory, neuroendocrine, and renal function in patients with asymptomatic left ventricular dysfunction. Br Heart J. 1993 Jun;69(6):512-5. doi: 10.1136/hrt.69.6.512.
53 Angiotensin II receptor blockade in normotensive subjects: A direct comparison of three AT1 receptor antagonists. Hypertension. 1999 Mar;33(3):850-5. doi: 10.1161/01.hyp.33.3.850.
54 Cytochrome P450 1A1/2 induction by antiparasitic drugs: dose-dependent increase in ethoxyresorufin O-deethylase activity and mRNA caused by quinine, primaquine and albendazole in HepG2 cells. Eur J Clin Pharmacol. 2002 Nov;58(8):537-42.
55 Association of CYP1A1 and CYP1B1 inhibition in in vitro assays with drug-induced liver injury. J Toxicol Sci. 2021;46(4):167-176. doi: 10.2131/jts.46.167.
56 Anti-androgenic effect of 6-formylindolo[3,2-b]carbazole (FICZ) in LNCaP cells is mediated by the aryl hydrocarbon-androgen receptors cross-talk. Steroids. 2020 Jan;153:108508. doi: 10.1016/j.steroids.2019.108508. Epub 2019 Oct 3.
57 Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. Arch Toxicol. 2008 Dec;82(12):909-21.
58 Effect of CYP1A1 gene polymorphisms on estrogen metabolism and bone density. J Bone Miner Res. 2005 Feb;20(2):232-9. doi: 10.1359/JBMR.041110. Epub 2004 Nov 16.
59 Increased sensitivity for troglitazone-induced cytotoxicity using a human in vitro co-culture model. Toxicol In Vitro. 2009 Oct;23(7):1387-95.
60 Isoform-specific induction of a human aldo-keto reductase by polycyclic aromatic hydrocarbons (PAHs), electrophiles, and oxidative stress: implications for the alternative pathway of PAH activation catalyzed by human dihydrodiol dehydrogenase. Cancer Res. 1999 Feb 1;59(3):607-14.
61 Gene expression changes in human small airway epithelial cells exposed to Delta9-tetrahydrocannabinol. Toxicol Lett. 2005 Aug 14;158(2):95-107.
62 The metallohormone cadmium modulates AhR-associated gene expression in the small intestine of rats similar to ethinyl-estradiol. Arch Toxicol. 2013 Apr;87(4):633-43.
63 Evidence for a new human CYP1A1 regulation pathway involving PPAR-alpha and 2 PPRE sites. Gastroenterology. 2004 Nov;127(5):1436-45.