Details of the Drug-Related molecule(s) Interaction Atlas

Hydroxybenzo(a)pyrene Drug Info

3-Hydroxybenzo(a)pyrene; Benzo(a)pyrene, 3-hydroxy-; Benzo[def]chrysen-3-ol; Benzo[pqr]tetraphen-3-ol; SCHEMBL145489; benzo[a]pyren-3-ol; 13345-21-6; 3-Hydroxy Benzopyrene; 3-Hydroxy benzo[a]pyrene; 3-Hydroxy-3,4-benzo[a]pyrene; 3-Hydroxybenzo[a]pyrene; 3-hydroxybenz[a]pyrene; 4-06-00-05133 (Beilstein Handbook Reference); 672ICH1Q4L; 8-Hydroxy-3,4-benzpyrene; BENZO(a)PYREN-3-OL; AC1L19Z3; BIDD:ER0040; BP-3-Hydroxy; BRN 2333868; CCRIS 1071; CHEBI:34337; CHEMBL8020; CTK0H7534; DTXSID7038319; UNII-672ICH1Q4L

Cross-matching ID

PubChem CID

25890

ChEBI ID

CHEBI:34337

CAS Number

CAS 13345-21-6

TTD Drug ID

DM9H5EN

INTEDE Drug ID

DR1965

General Information of Drug (ID: DM9H5EN)

Molecule-Related Drug Atlas

Molecule Type:

DME

DOT

Drug Status:

Approved Drug(s)

Investigative Drug(s)

Clinical Trial Drug(s)

Download the Complete Related Drug List

Drug(s) Metabolized By UDP-glucuronosyltransferase 2B15 (UGT2B15)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[4]
Ezetimibe	DM7A8TW	Atherosclerosis	BD40	Approved	[5]
Lorazepam	DM84ZXF	Absence epilepsy		Approved	[6]
Hydroxybenzo[a]pyrene	DMFSKYE	N. A.	N. A.	Investigative	[1]
BRN-1980310	DMOTU4P	N. A.	N. A.	Investigative	[1]
------------------------------------------------------------------------------------

Drug(s) Metabolized By UDP-glucuronosyltransferase 2B17 (UGT2B17)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Vorinostat	DMWMPD4	Adult acute monocytic leukemia		Approved	[7]
Darolutamide	DMV7YFT	Prostate cancer	2C82.0	Approved	[8]
Denopamine	DM8C3GN	Cardiac disease	BA00-BE2Z	Approved	[9]
MK-7246	DMLQOF1	Respiratory disease	CB40	Phase 1	[10]
Hydroxybenzo[a]pyrene	DMFSKYE	N. A.	N. A.	Investigative	[1]
BRN-1980310	DMOTU4P	N. A.	N. A.	Investigative	[1]
------------------------------------------------------------------------------------


⏷ Show the Full List of 6 Drug(s)

Drug(s) Affected By Aldo-keto reductase family 1 member B10 (AKR1B10)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[11]
Clavulanate	DM2FGRT	Bacteremia	1A73	Approved	[12]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[13]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[14]
Rifampicin	DM5DSFZ	Non-insulin dependent diabetes	5A11	Approved	[15]
Isoniazid	DM5JVS3	Latent tuberculosis infection		Approved	[16]
Hydroquinone	DM6AVR4	Melasma	ED60.1	Approved	[17]
Reserpine	DM6VM38	Hypertension	BA00-BA04	Approved	[18]
Ciclosporin	DMAZJFX	Graft-versus-host disease	4B24	Approved	[19]
Disulfiram	DMCL2OK	Alcohol dependence	6C40.2	Approved	[20]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Affected By Amphiregulin (AREG)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[21]
Fulvestrant	DM0YZC6	Breast cancer	2C60-2C65	Approved	[22]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[23]
Methotrexate	DM2TEOL	Anterior urethra cancer		Approved	[24]
Deoxycholic acid	DM3GYAL	Subcutaneous fat disorder	EF02	Approved	[25]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[26]
Estrone	DM5T6US	Acne vulgaris	ED80	Approved	[27]
Chlorpromazine	DMBGZI3	Acute intermittent hepatic porphyria	5C58.11	Approved	[28]
Marinol	DM70IK5	Anorexia nervosa cachexia	6B80	Approved	[29]
Calcitriol	DM8ZVJ7	Congenital alopecia	LC30	Approved	[30]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Affected By Glutamate--cysteine ligase regulatory subunit (GCLM)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[31]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[32]
Clavulanate	DM2FGRT	Bacteremia	1A73	Approved	[12]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[33]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[34]
Isotretinoin	DM4QTBN	Acne vulgaris	ED80	Approved	[35]
Acetic Acid, Glacial	DM4SJ5Y	infection in the ear canal	AA0Y	Approved	[36]
Isoniazid	DM5JVS3	Latent tuberculosis infection		Approved	[37]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[38]
Hydroquinone	DM6AVR4	Melasma	ED60.1	Approved	[39]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Affected By Abnormal spindle-like microcephaly-associated protein (ASPM)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Methotrexate	DM2TEOL	Anterior urethra cancer		Approved	[40]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[13]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[41]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[34]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[42]
Liothyronine	DM6IR3P	Congenital hypothyroidism		Approved	[43]
Testosterone	DM7HUNW	Hot flushes	GA30	Approved	[44]
Riboflavin	DM8YMWE	Acne vulgaris	ED80	Approved	[45]
Calcitriol	DM8ZVJ7	Congenital alopecia	LC30	Approved	[44]
Leflunomide	DMR8ONJ	Arthritis	FA20	Approved	[46]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Drug(s) Affected By Sulfiredoxin-1 (SRXN1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[31]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[47]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[41]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[48]
Isoniazid	DM5JVS3	Latent tuberculosis infection		Approved	[16]
Ethacrynic acid	DM60QMR	Edema	MG29	Approved	[49]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[50]
Ibuprofen	DM8VCBE	Dysmenorrhea	GA34.3	Approved	[51]
Leflunomide	DMR8ONJ	Arthritis	FA20	Approved	[46]
Clodronate	DM9Y6X7	Hypercalcaemia	5B91.0	Approved	[51]
------------------------------------------------------------------------------------


⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Download the Complete Interaction Atlas for Visualization in Cytoscape

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
UDP-glucuronosyltransferase 2B15 (UGT2B15)	DENZ6B1	UDB15_HUMAN	Substrate	[1]
UDP-glucuronosyltransferase 2B17 (UGT2B17)	DEAZDL8	UDB17_HUMAN	Substrate	[1]

------------------------------------------------------------------------------------

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Abnormal spindle-like microcephaly-associated protein (ASPM)	OTKXQMNA	ASPM_HUMAN	Gene/Protein Processing	[2]
Aldo-keto reductase family 1 member B10 (AKR1B10)	OTOA4HTH	AK1BA_HUMAN	Gene/Protein Processing	[2]
Amphiregulin (AREG)	OTJFOR67	AREG_HUMAN	Gene/Protein Processing	[2]
Glutamate--cysteine ligase regulatory subunit (GCLM)	OT6CP234	GSH0_HUMAN	Gene/Protein Processing	[2]
Sulfiredoxin-1 (SRXN1)	OTYDBO4L	SRXN1_HUMAN	Gene/Protein Processing	[2]
UDP-glucuronosyltransferase 2A1	OTL98JZE	UD2A1_HUMAN	Biotransformations	[3]

------------------------------------------------------------------------------------

References

1	Importance of UDP-glucuronosyltransferase 1A10 (UGT1A10) in the detoxification of polycyclic aromatic hydrocarbons: decreased glucuronidative activity of the UGT1A10139Lys isoform. Drug Metab Dispos. 2006 Jun;34(6):943-9.
2	New insights into BaP-induced toxicity: role of major metabolites in transcriptomics and contribution to hepatocarcinogenesis. Arch Toxicol. 2016 Jun;90(6):1449-58.
3	Characterization of UDP-glucuronosyltransferase 2A1 (UGT2A1) variants and their potential role in tobacco carcinogenesis. Pharmacogenet Genomics. 2011 Feb;21(2):55-65. doi: 10.1097/FPC.0b013e328341db05.
4	Characterization of niflumic acid as a selective inhibitor of human liver microsomal UDP-glucuronosyltransferase 1A9: application to the reaction phenotyping of acetaminophen glucuronidation. Drug Metab Dispos. 2011 Apr;39(4):644-52.
5	Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94.
6	Effect of the UGT2B15 genotype on the pharmacokinetics, pharmacodynamics, and drug interactions of intravenous lorazepam in healthy volunteers. Clin Pharmacol Ther. 2005 Jun;77(6):486-94.
7	Age-dependent hepatic UDP-glucuronosyltransferase gene expression and activity in children. Front Pharmacol. 2016 Nov 16;7:437.
8	Drug-drug interaction potential of darolutamide: in vitro and clinical studies. Eur J Drug Metab Pharmacokinet. 2019 Dec;44(6):747-759.
9	Regioselective glucuronidation of denopamine: marked species differences and identification of human udp-glucuronosyltransferase isoform. Drug Metab Dispos. 2005 Mar;33(3):403-12.
10	UGT2B17 genetic polymorphisms dramatically affect the pharmacokinetics of MK-7246 in healthy subjects in a first-in-human study. Clin Pharmacol Ther. 2012 Jul;92(1):96-102.
11	Time series analysis of oxidative stress response patterns in HepG2: a toxicogenomics approach. Toxicology. 2013 Apr 5;306:24-34.
12	Molecular mechanisms of hepatotoxic cholestasis by clavulanic acid: Role of NRF2 and FXR pathways. Food Chem Toxicol. 2021 Dec;158:112664. doi: 10.1016/j.fct.2021.112664. Epub 2021 Nov 9.
13	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.
14	Transcriptomic analysis of untreated and drug-treated differentiated HepaRG cells over a 2-week period. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):27-35.
15	Identification of approved drugs as potent inhibitors of pregnane X receptor activation with differential receptor interaction profiles. Arch Toxicol. 2018 Apr;92(4):1435-1451.
16	Characterization of drug-specific signaling between primary human hepatocytes and immune cells. Toxicol Sci. 2017 Jul 1;158(1):76-89.
17	Keratinocyte-derived IL-36gama plays a role in hydroquinone-induced chemical leukoderma through inhibition of melanogenesis in human epidermal melanocytes. Arch Toxicol. 2019 Aug;93(8):2307-2320.
18	Oxidative stress mechanisms do not discriminate between genotoxic and nongenotoxic liver carcinogens. Chem Res Toxicol. 2015 Aug 17;28(8):1636-46.
19	Integrative "-Omics" analysis in primary human hepatocytes unravels persistent mechanisms of cyclosporine A-induced cholestasis. Chem Res Toxicol. 2016 Dec 19;29(12):2164-2174.
20	Keratinocyte gene expression profiles discriminate sensitizing and irritating compounds. Toxicol Sci. 2010 Sep;117(1):81-9.
21	Cannabidiol enhances cytotoxicity of anti-cancer drugs in human head and neck squamous cell carcinoma. Sci Rep. 2020 Nov 26;10(1):20622. doi: 10.1038/s41598-020-77674-y.
22	Analysis of estrogen agonism and antagonism of tamoxifen, raloxifene, and ICI182780 in endometrial cancer cells: a putative role for the epidermal growth factor receptor ligand amphiregulin. J Soc Gynecol Investig. 2005 Oct;12(7):e55-67.
23	Gene expression after treatment with hydrogen peroxide, menadione, or t-butyl hydroperoxide in breast cancer cells. Cancer Res. 2002 Nov 1;62(21):6246-54.
24	Global molecular effects of tocilizumab therapy in rheumatoid arthritis synovium. Arthritis Rheumatol. 2014 Jan;66(1):15-23.
25	Ligand-dependent activation of the epidermal growth factor receptor by secondary bile acids in polarizing colon cancer cells. Surgery. 2005 Sep;138(3):415-21. doi: 10.1016/j.surg.2005.06.030.
26	Retinoid-induced epidermal hyperplasia is mediated by epidermal growth factor receptor activation via specific induction of its ligands heparin-binding EGF and amphiregulin in human skin in vivo. J Invest Dermatol. 2006 Apr;126(4):732-9. doi: 10.1038/sj.jid.5700202.
27	Moving toward integrating gene expression profiling into high-throughput testing: a gene expression biomarker accurately predicts estrogen receptor alpha modulation in a microarray compendium. Toxicol Sci. 2016 May;151(1):88-103.
28	Effects of chlorpromazine with and without UV irradiation on gene expression of HepG2 cells. Mutat Res. 2005 Aug 4;575(1-2):47-60. doi: 10.1016/j.mrfmmm.2005.03.002. Epub 2005 Apr 26.
29	THC exposure of human iPSC neurons impacts genes associated with neuropsychiatric disorders. Transl Psychiatry. 2018 Apr 25;8(1):89. doi: 10.1038/s41398-018-0137-3.
30	Amphiregulin is a vitamin D3 target gene in squamous cell and breast carcinoma. Biochem Biophys Res Commun. 2001 Mar 9;281(4):1051-6. doi: 10.1006/bbrc.2001.4466.
31	Cannabidiol induces antioxidant pathways in keratinocytes by targeting BACH1. Redox Biol. 2020 Jan;28:101321. doi: 10.1016/j.redox.2019.101321. Epub 2019 Sep 5.
32	Oxidative stress modulates theophylline effects on steroid responsiveness. Biochem Biophys Res Commun. 2008 Dec 19;377(3):797-802.
33	Essential role of Nrf2 in keratinocyte protection from UVA by quercetin. Biochem Biophys Res Commun. 2009 Sep 11;387(1):109-14. doi: 10.1016/j.bbrc.2009.06.136. Epub 2009 Jul 1.
34	Transcriptional and Metabolic Dissection of ATRA-Induced Granulocytic Differentiation in NB4 Acute Promyelocytic Leukemia Cells. Cells. 2020 Nov 5;9(11):2423. doi: 10.3390/cells9112423.
35	Temporal changes in gene expression in the skin of patients treated with isotretinoin provide insight into its mechanism of action. Dermatoendocrinol. 2009 May;1(3):177-87.
36	Motexafin gadolinium and zinc induce oxidative stress responses and apoptosis in B-cell lymphoma lines. Cancer Res. 2005 Dec 15;65(24):11676-88.
37	Comparison of base-line and chemical-induced transcriptomic responses in HepaRG and RPTEC/TERT1 cells using TempO-Seq. Arch Toxicol. 2018 Aug;92(8):2517-2531.
38	Changes in gene expression profiles of multiple myeloma cells induced by arsenic trioxide (ATO): possible mechanisms to explain ATO resistance in vivo. Br J Haematol. 2005 Mar;128(5):636-44.
39	An in vitro skin sensitization assay termed EpiSensA for broad sets of chemicals including lipophilic chemicals and pre/pro-haptens. Toxicol In Vitro. 2017 Apr;40:11-25. doi: 10.1016/j.tiv.2016.12.005. Epub 2016 Dec 10.
40	Methotrexate modulates folate phenotype and inflammatory profile in EA.hy 926 cells. Eur J Pharmacol. 2014 Jun 5;732:60-7.
41	Effects of ciglitazone and troglitazone on the proliferation of human stomach cancer cells. World J Gastroenterol. 2009 Jan 21;15(3):310-20.
42	Essential role of cell cycle regulatory genes p21 and p27 expression in inhibition of breast cancer cells by arsenic trioxide. Med Oncol. 2011 Dec;28(4):1225-54.
43	Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells. Arch Toxicol. 2013 Jun;87(6):1103-13. doi: 10.1007/s00204-013-1018-4. Epub 2013 Feb 10.
44	Effects of 1alpha,25 dihydroxyvitamin D3 and testosterone on miRNA and mRNA expression in LNCaP cells. Mol Cancer. 2011 May 18;10:58.
45	Riboflavin depletion impairs cell proliferation in adult human duodenum: identification of potential effectors. Dig Dis Sci. 2011 Apr;56(4):1007-19. doi: 10.1007/s10620-010-1374-3. Epub 2010 Sep 17.
46	Endoplasmic reticulum stress and MAPK signaling pathway activation underlie leflunomide-induced toxicity in HepG2 Cells. Toxicology. 2017 Dec 1;392:11-21.
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	Phenotypic characterization of retinoic acid differentiated SH-SY5Y cells by transcriptional profiling. PLoS One. 2013 May 28;8(5):e63862.
49	Mapping the dynamics of Nrf2 antioxidant and NFB inflammatory responses by soft electrophilic chemicals in human liver cells defines the transition from adaptive to adverse responses. Toxicol In Vitro. 2022 Oct;84:105419. doi: 10.1016/j.tiv.2022.105419. Epub 2022 Jun 17.
50	Transcriptome-based functional classifiers for direct immunotoxicity. Arch Toxicol. 2014 Mar;88(3):673-89.
51	Transcriptomics hit the target: monitoring of ligand-activated and stress response pathways for chemical testing. Toxicol In Vitro. 2015 Dec 25;30(1 Pt A):7-18.