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

LM-94 Drug Info

Bilcolic; Bilicante; Hymecromone; Cantabilin; Cantabiline; Cholestil; Cholonerton; Coumarin 4; Crodimon; Cumarote-C; Eurogale; Himecromona; Hymecromon; Hymecromonum; Imecromone; Imecromone [DCIT]; Medilla; Mendiaxon; Omega 127; Pilot 447; Resocyanine; beta-Methylumbelliferone; 2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-; 4-MU; 4-Methyl-7-hydroxycoumarin; 4-Methylumbelliferon; 4-methylumbelliferone; 7-HYDROXY-4-METHYLCOUMARIN; 7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyran; 7-Hydroxy-4-methyl-2H-chromen-2-one; 90-33-5; LM 94; NSC 19026; NSC 9408

Cross-matching ID

PubChem CID

5280567

ChEBI ID

CHEBI:17224

CAS Number

CAS 90-33-5

TTD Drug ID

DMW3QGJ

INTEDE Drug ID

DR0841

General Information of Drug (ID: DMW3QGJ)

Molecule-Related Drug Atlas

Molecule Type:

DME

DOT

Drug Status:

Approved Drug(s)

Clinical Trial Drug(s)

Investigative Drug(s)

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Drug(s) Metabolized By UDP-glucuronosyltransferase 1A1 (UGT1A1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Tamoxifen	DMLB0EZ	Breast cancer	2C60-2C65	Approved	[10]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[11]
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[12]
Etoposide	DMNH3PG	Acute myelogenous leukaemia	2A41	Approved	[13]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[14]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[15]
Mycophenolate mofetil	DMPQAGE	Hepatosplenic T-cell lymphoma		Approved	[16]
Metronidazole	DMTIVEN	Abscess		Approved	[17]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[18]
Ethanol	DMDRQZU	Chronic pain	MG30	Approved	[19]
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Drug(s) Metabolized By UDP-glucuronosyltransferase 1A9 (UGT1A9)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[20]
Diclofenac	DMPIHLS	Chronic renal failure	GB61.Z	Approved	[21]
Sorafenib	DMS8IFC	Adenocarcinoma	2D40	Approved	[22]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[23]
Mycophenolate mofetil	DMPQAGE	Hepatosplenic T-cell lymphoma		Approved	[24]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[23]
Ibuprofen	DM8VCBE	Dysmenorrhea	GA34.3	Approved	[23]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[25]
Nateglinide	DMLK2QH	Diabetic complication	5A2Y	Approved	[23]
Haloperidol	DM96SE0	Delirium		Approved	[23]
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Drug(s) Metabolized By UDP-glucuronosyltransferase 1A4 (UGT1A4)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Lorlatinib	DMICDLV	Non-small-cell lung cancer	2C25.Y	Approved	[26]
Lamotrigine	DM8SXYG	Bipolar disorder	6A60	Approved	[27]
Rilpivirine	DMJ0QOW	Human immunodeficiency virus infection	1C62	Approved	[28]
Calcitriol	DM8ZVJ7	Congenital alopecia	LC30	Approved	[29]
Bevirimat	DML2D8Q	Human immunodeficiency virus infection	1C62	Phase 2	[30]
UDP-glucuronic acid	DMW16X2	Discovery agent	N.A.	Investigative	[3]
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Drug(s) Metabolized By UDP-glucuronosyltransferase 1A6 (UGT1A6)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[31]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[32]
Mycophenolate mofetil	DMPQAGE	Hepatosplenic T-cell lymphoma		Approved	[16]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[33]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[34]
Aspirin	DM672AH	Acute coronary syndrome	BA41	Approved	[35]
Naproxen	DMZ5RGV	Bursitis		Approved	[36]
Deferiprone	DMS2M7O	Beta thalassemia	3A50.2	Approved	[37]
ANDROSTERONE	DMITJAK	N. A.	N. A.	Phase 3	[38]
BCP-13498	DM2BO9W	N. A.	N. A.	Phase 2	[39]
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Drug(s) Affected By Cellular tumor antigen p53 (TP53)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Cisplatin	DMRHGI9	Adenocarcinoma	2D40	Approved	[40]
Methotrexate	DM2TEOL	Anterior urethra cancer		Approved	[41]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[42]
Arsenic trioxide	DM61TA4	Acute lymphoblastic leukaemia	2A85	Approved	[43]
Cidofovir	DMA13GD	Cytomegalovirus infection	1D82	Approved	[44]
Paclitaxel	DMLB81S	Breast carcinoma		Approved	[45]
Floxuridine	DM04LR2	Colorectal cancer	2B91.Z	Approved	[46]
Cannabidiol	DM0659E	Dravet syndrome	8A61.11	Approved	[47]
Mechlorethamine	DM0CVXA	Chronic myelogenous leukaemia	2A20.0	Approved	[48]
Fulvestrant	DM0YZC6	Breast cancer	2C60-2C65	Approved	[49]
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Drug(s) Affected By Sulfotransferase 1A1 (SULT1A1)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Acetaminophen	DMUIE76	Allergic rhinitis	CA08.0	Approved	[50]
Liothyronine	DM6IR3P	Congenital hypothyroidism		Approved	[51]
Minoxidil	DMA2Z4F	Alopecia	ED70	Approved	[7]
Benzyl alcohol	DMBVYDI	Head and body lice	1G00.0	Approved	[52]
Estradiol	DMUNTE3	Acne vulgaris	ED80	Approved	[7]
Meclofenamic acid	DM05FXR	Ankylosing spondylitis	FA92.0	Approved	[53]
Hydrogen peroxide	DM1NG5W	Infectious disease	1A00-CA43.1	Approved	[54]
Methotrexate	DM2TEOL	Anterior urethra cancer		Approved	[55]
Quercetin	DM3NC4M	Obesity	5B81	Approved	[56]
Tretinoin	DM49DUI	Acne vulgaris	ED80	Approved	[57]
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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 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[1]
UDP-glucuronosyltransferase 1A9 (UGT1A9)	DE85D2P	UD19_HUMAN	Substrate	[2]
UDP-glucuronosyltransferase 1A6 (UGT1A6)	DESD26P	UD16_HUMAN	Substrate	[3]
UDP-glucuronosyltransferase 1A4 (UGT1A4)	DELOY3P	UD14_HUMAN	Substrate	[3]
UDP-glucuronosyltransferase 2B11 (UGT2B11)	DE7TIN4	UDB11_HUMAN	Substrate	[4]
UDP-glucuronosyltransferase 1A5 (UGT1A5)	DEPF954	UD15_HUMAN	Substrate	[5]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[6]
Sulfotransferase 1A1 (SULT1A1)	OT0K7JIE	ST1A1_HUMAN	Biotransformations	[7]
UDP-glucuronosyltransferase 1-6	OTGTQ2C9	UD16_HUMAN	Gene/Protein Processing	[8]
UDP-glucuronosyltransferase 1A1	OTH1C8OJ	UD11_HUMAN	Gene/Protein Processing	[8]
UDP-glucuronosyltransferase 1A10	OTOTZVEY	UD110_HUMAN	Gene/Protein Processing	[8]
UDP-glucuronosyltransferase 1A3	OTUEOER3	UD13_HUMAN	Gene/Protein Processing	[8]
UDP-glucuronosyltransferase 1A7	OTY4JJ32	UD17_HUMAN	Gene/Protein Processing	[8]
UDP-glucuronosyltransferase 1A8	OTTMABBG	UD18_HUMAN	Gene/Protein Processing	[8]
UDP-glucuronosyltransferase 1A9	OTPCHAFX	UD19_HUMAN	Gene/Protein Processing	[8]
UDP-glucuronosyltransferase 2A1	OTL98JZE	UD2A1_HUMAN	Biotransformations	[9]

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References

1	In vitro inhibitory effects of non-steroidal anti-inflammatory drugs on 4-methylumbelliferone glucuronidation in recombinant human UDP-glucuronosyltransferase 1A9--potent inhibition by niflumic acid. Biopharm Drug Dispos. 2006 Jan;27(1):1-6.
2	The "albumin effect" and drug glucuronidation: bovine serum albumin and fatty acid-free human serum albumin enhance the glucuronidation of UDP-glucuronosyltransferase (UGT) 1A9 substrates but not UGT1A1 and UGT1A6 activities. Drug Metab Dispos. 2008 Jun;36(6):1056-62.
3	Identification of aspartic acid and histidine residues mediating the reaction mechanism and the substrate specificity of the human UDP-glucuronosyltransferases 1A. J Biol Chem. 2007 Dec 14;282(50):36514-24.
4	cDNA cloning and expression of two new members of the human liver UDP-glucuronosyltransferase 2B subfamily. Biochem Biophys Res Commun. 1993 Jul 15;194(1):496-503.
5	A common polymorphic variant of UGT1A5 displays increased activity due to optimized cofactor binding. FEBS Lett. 2018 Jun;592(11):1837-1846.
6	Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation. Arch Toxicol. 2022 Jul;96(7):1975-1987. doi: 10.1007/s00204-022-03291-5. Epub 2022 Apr 18.
7	Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. Drug Metab Dispos. 2001 Mar;29(3):274-81.
8	Assessment of the inhibition potential of Licochalcone A against human UDP-glucuronosyltransferases. Food Chem Toxicol. 2016 Apr;90:112-22.
9	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.
10	Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
11	Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
12	Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
13	UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics. Drug Metab Dispos. 2007 Mar;35(3):371-80.
14	Interindividual variability in pharmacokinetics of generic nucleoside reverse transcriptase inhibitors in TB/HIV-coinfected Ghanaian patients: UGT2B7*1c is associated with faster zidovudine clearance and glucuronidation. J Clin Pharmacol. 2009 Sep;49(9):1079-90.
15	Effect of aging on glucuronidation of valproic acid in human liver microsomes and the role of UDP-glucuronosyltransferase UGT1A4, UGT1A8, and UGT1A10. Drug Metab Dispos. 2009 Jan;37(1):229-36.
16	Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
17	Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8.
18	Substrate-dependent modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1) by propofol in recombinant human UGT1A1 and human liver microsomes. Basic Clin Pharmacol Toxicol. 2007 Sep;101(3):211-4.
19	Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
20	Polymorphic expression of UGT1A9 is associated with variable acetaminophen glucuronidation in neonates: a population pharmacokinetic and pharmacogenetic study. Clin Pharmacokinet. 2018 Oct;57(10):1325-1336.
21	Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35.
22	Pharmacokinetic interaction involving sorafenib and the calcium-channel blocker felodipine in a patient with hepatocellular carcinoma. Invest New Drugs. 2011 Dec;29(6):1511-4.
23	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.
24	The evolution of population pharmacokinetic models to describe the enterohepatic recycling of mycophenolic acid in solid organ transplantation and autoimmune disease. Clin Pharmacokinet. 2011 Jan;50(1):1-24.
25	The UDP-glucuronosyltransferase 1A9 enzyme is a peroxisome proliferator-activated receptor alpha and gamma target gene. J Biol Chem. 2003 Apr 18;278(16):13975-83.
26	FDA label of Lorlatinib. The 2020 official website of the U.S. Food and Drug Administration.
27	Studies on induction of lamotrigine metabolism in transgenic UGT1 mice. Xenobiotica. 2009 Nov;39(11):826-35.
28	Human biotransformation of the nonnucleoside reverse transcriptase inhibitor rilpivirine and a cross-species metabolism comparison. Antimicrob Agents Chemother. 2013 Oct;57(10):5067-79.
29	Identification of human UDP-glucuronosyltransferases catalyzing hepatic 1alpha,25-dihydroxyvitamin D3 conjugation. Biochem Pharmacol. 2008 Mar 1;75(5):1240-50.
30	Bevirimat: a novel maturation inhibitor for the treatment of HIV-1 infection. Antivir Chem Chemother. 2008;19(3):107-13.
31	UGT1A6 and UGT2B15 polymorphisms and acetaminophen conjugation in response to a randomized, controlled diet of select fruits and vegetables. Drug Metab Dispos. 2011 Sep;39(9):1650-7.
32	UDP glucuronosyltransferase (UGT) 1A6 pharmacogenetics: II. Functional impact of the three most common nonsynonymous UGT1A6 polymorphisms (S7A, T181A, and R184S). J Pharmacol Exp Ther. 2005 Jun;313(3):1340-6.
33	Pharmacokinetics of propofol and extrahepatic UGT1A6 gene expression in anhepatic rats. Pharmacology. 2009;84(4):219-26.
34	Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9.
35	Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6.
36	S-Naproxen and desmethylnaproxen glucuronidation by human liver microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT2B7 in the elimination of naproxen. Br J Clin Pharmacol. 2005 Oct;60(4):423-33.
37	Deferiprone glucuronidation by human tissues and recombinant UDP glucuronosyltransferase 1A6: an in vitro investigation of genetic and splice variants. Drug Metab Dispos. 2009 Feb;37(2):322-9.
38	Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.
39	Human UGT1A6 pharmacogenetics: identification of a novel SNP, characterization of allele frequencies and functional analysis of recombinant allozymes in human liver tissue and in cultured cells. Pharmacogenetics. 2004 Aug;14(8):487-99.
40	p53-R175H mutant gains new function in regulation of doxorubicin-induced apoptosis. Int J Cancer. 2005 Apr 10;114(3):331-6. doi: 10.1002/ijc.20818.
41	The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
42	Azidothymidine and cisplatin increase p14ARF expression in OVCAR-3 ovarian cancer cell line. Toxicol Appl Pharmacol. 2006 Oct 1;216(1):89-97. doi: 10.1016/j.taap.2006.04.015. Epub 2006 May 19.
43	Quantitative analysis of gene expression changes in response to genotoxic compounds. Toxicol In Vitro. 2017 Mar;39:15-28. doi: 10.1016/j.tiv.2016.11.004. Epub 2016 Nov 5.
44	Induction of apoptosis by cidofovir in human papillomavirus (HPV)-positive cells. Oncol Res. 2000;12(9-10):397-408. doi: 10.3727/096504001108747855.
45	Gallic acid potentiates the apoptotic effect of paclitaxel and carboplatin via overexpression of Bax and P53 on the MCF-7 human breast cancer cell line. J Biochem Mol Toxicol. 2021 Feb;35(2):e22638. doi: 10.1002/jbt.22638. Epub 2020 Oct 1.
46	Regulation of human dUTPase gene expression and p53-mediated transcriptional repression in response to oxaliplatin-induced DNA damage. Nucleic Acids Res. 2009 Jan;37(1):78-95. doi: 10.1093/nar/gkn910. Epub 2008 Nov 16.
47	Role of miRNA in the regulation of cannabidiol-mediated apoptosis in neuroblastoma cells. Oncotarget. 2019 Jan 1;10(1):45-59. doi: 10.18632/oncotarget.26534. eCollection 2019 Jan 1.
48	Nitrogen Mustard Alkylates and Cross-Links p53 in Human Keratinocytes. Chem Res Toxicol. 2022 Apr 18;35(4):636-650. doi: 10.1021/acs.chemrestox.1c00420. Epub 2022 Mar 21.
49	Fulvestrant induces resistance by modulating GPER and CDK6 expression: implication of methyltransferases, deacetylases and the hSWI/SNF chromatin remodelling complex. Br J Cancer. 2013 Nov 12;109(10):2751-62. doi: 10.1038/bjc.2013.583. Epub 2013 Oct 29.
50	Multiple microRNAs function as self-protective modules in acetaminophen-induced hepatotoxicity in humans. Arch Toxicol. 2018 Feb;92(2):845-858.
51	Characterization of human liver thermostable phenol sulfotransferase (SULT1A1) allozymes with 3,3',5-triiodothyronine as the substrate. J Endocrinol. 2001 Dec;171(3):525-32.
52	Sulfation of benzyl alcohol by the human cytosolic sulfotransferases (SULTs): a systematic analysis. J Appl Toxicol. 2016 Sep;36(9):1090-4.
53	Inhibition of human phenol and estrogen sulfotransferase by certain non-steroidal anti-inflammatory agents. Curr Drug Metab. 2006 Oct;7(7):745-53.
54	Minimal peroxide exposure of neuronal cells induces multifaceted adaptive responses. PLoS One. 2010 Dec 17;5(12):e14352. doi: 10.1371/journal.pone.0014352.
55	Methotrexate induction of human sulfotransferases in Hep G2 and Caco-2 cells. J Appl Toxicol. 2005 Sep-Oct;25(5):354-60.
56	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.
57	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.