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

General Information of Drug (ID: DMW3QGJ)

Drug Name

LM-94 Drug Info

Synonyms

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

Indication

Disease Entry	ICD 11	Status	REF
Primary sclerosing cholangitis	DB96.2	Phase 1/2	[1]

Cross-matching ID

PubChem CID: 5280567
ChEBI ID: CHEBI:17224
CAS Number: CAS 90-33-5
TTD Drug ID: DMW3QGJ
INTEDE Drug ID: DR0841

Molecule-Related Drug Atlas

Molecule Type:

DME

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	[7]
Estradiol	DMUNTE3	Breast cancer	2C60-2C65	Approved	[8]
Acetaminophen	DMUIE76	Pain	MG30-MG3Z	Approved	[9]
Etoposide	DMNH3PG	Solid tumour/cancer	2A00-2F9Z	Approved	[10]
Zidovudine	DM4KI7O	Human immunodeficiency virus infection	1C62	Approved	[11]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[12]
Mycophenolate mofetil	DMPQAGE	Organ transplant rejection	NE84	Approved	[13]
Metronidazole	DMTIVEN	Amoebiasis	1A36	Approved	[14]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[15]
Ethanol	DMDRQZU	Chronic pain	MG30	Approved	[16]
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Drug(s) Metabolized By UDP-glucuronosyltransferase 1A9 (UGT1A9)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Acetaminophen	DMUIE76	Pain	MG30-MG3Z	Approved	[17]
Diclofenac	DMPIHLS	Osteoarthritis	FA00-FA05	Approved	[18]
Sorafenib	DMS8IFC	Hepatocellular carcinoma	2C12.02	Approved	[19]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[20]
Mycophenolate mofetil	DMPQAGE	Organ transplant rejection	NE84	Approved	[21]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[20]
Ibuprofen	DM8VCBE	Pain	MG30-MG3Z	Approved	[20]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[22]
Nateglinide	DMLK2QH	Diabetic complication	5A2Y	Approved	[20]
Haloperidol	DM96SE0	Schizophrenia	6A20	Approved	[20]
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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	[23]
Lamotrigine	DM8SXYG	Bipolar disorder	6A60	Approved	[24]
Rilpivirine	DMJ0QOW	Human immunodeficiency virus infection	1C62	Approved	[25]
Calcitriol	DM8ZVJ7	Congenital alopecia	LC30	Approved	[26]
Bevirimat	DML2D8Q	Human immunodeficiency virus infection	1C62	Phase 2	[27]
UDP-glucuronic acid	DMW16X2	Discovery agent	N.A.	Investigative	[4]
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Drug(s) Metabolized By UDP-glucuronosyltransferase 1A6 (UGT1A6)

Drug Name	Drug ID	Indication	ICD 11	Highest Status	REF
Acetaminophen	DMUIE76	Pain	MG30-MG3Z	Approved	[28]
Valproate	DMCFE9I	Epilepsy	8A60-8A68	Approved	[29]
Mycophenolate mofetil	DMPQAGE	Organ transplant rejection	NE84	Approved	[13]
Propofol	DMB4OLE	Anaesthesia	9A78.6	Approved	[30]
Troglitazone	DM3VFPD	Diabetic complication	5A2Y	Approved	[31]
Aspirin	DM672AH	Myocardial infarction	BA41-BA43	Approved	[32]
Naproxen	DMZ5RGV	Osteoarthritis	FA00-FA05	Approved	[33]
Deferiprone	DMS2M7O	Thalassemia	3A50	Approved	[34]
Androsterone	DMITJAK	N. A.	N. A.	Phase 3	[35]
BCP-13498	DM2BO9W	Anaesthesia	9A78.6	Phase 2	[36]
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Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
UDP-glucuronosyltransferase 1A1 (UGT1A1)	DEYGVN4	UD11_HUMAN	Substrate	[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9)	DE85D2P	UD19_HUMAN	Substrate	[3]
UDP-glucuronosyltransferase 1A6 (UGT1A6)	DESD26P	UD16_HUMAN	Substrate	[4]
UDP-glucuronosyltransferase 1A4 (UGT1A4)	DELOY3P	UD14_HUMAN	Substrate	[4]
UDP-glucuronosyltransferase 2B11 (UGT2B11)	DE7TIN4	UDB11_HUMAN	Substrate	[5]
UDP-glucuronosyltransferase 1A5 (UGT1A5)	DEPF954	UD15_HUMAN	Substrate	[6]

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References

1	ClinicalTrials.gov (NCT02780752) A Study of Oral Hymecromone to Treat Adults With Primary Sclerosing Cholangitis.
2	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.
3	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.
4	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.
5	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.
6	A common polymorphic variant of UGT1A5 displays increased activity due to optimized cofactor binding. FEBS Lett. 2018 Jun;592(11):1837-1846.
7	Functional significance of UDP-glucuronosyltransferase variants in the metabolism of active tamoxifen metabolites. Cancer Res. 2009 Mar 1;69(5):1892-900.
8	Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8.
9	Effect of UDP-glucuronosyltransferase (UGT) 1A polymorphism (rs8330 and rs10929303) on glucuronidation status of acetaminophen. Dose Response. 2017 Sep 11;15(3):1559325817723731.
10	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.
11	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.
12	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.
13	Characterization of rat intestinal microsomal UDP-glucuronosyltransferase activity toward mycophenolic acid. Drug Metab Dispos. 2006 Sep;34(9):1632-9.
14	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.
15	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.
16	Identification and preliminary characterization of UDP-glucuronosyltransferases catalyzing formation of ethyl glucuronide. Anal Bioanal Chem. 2014 Apr;406(9-10):2325-32.
17	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.
18	Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos. 2005 Jul;33(7):1027-35.
19	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.
20	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.
21	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.
22	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.
23	FDA label of Lorlatinib. The 2020 official website of the U.S. Food and Drug Administration.
24	Studies on induction of lamotrigine metabolism in transgenic UGT1 mice. Xenobiotica. 2009 Nov;39(11):826-35.
25	Human biotransformation of the nonnucleoside reverse transcriptase inhibitor rilpivirine and a cross-species metabolism comparison. Antimicrob Agents Chemother. 2013 Oct;57(10):5067-79.
26	Identification of human UDP-glucuronosyltransferases catalyzing hepatic 1alpha,25-dihydroxyvitamin D3 conjugation. Biochem Pharmacol. 2008 Mar 1;75(5):1240-50.
27	Bevirimat: a novel maturation inhibitor for the treatment of HIV-1 infection. Antivir Chem Chemother. 2008;19(3):107-13.
28	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.
29	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.
30	Pharmacokinetics of propofol and extrahepatic UGT1A6 gene expression in anhepatic rats. Pharmacology. 2009;84(4):219-26.
31	Troglitazone glucuronidation in human liver and intestine microsomes: high catalytic activity of UGT1A8 and UGT1A10. Drug Metab Dispos. 2002 Dec;30(12):1462-9.
32	Polymorphisms of Aspirin-Metabolizing Enzymes CYP2C9, NAT2 and UGT1A6 in Aspirin-Intolerant Urticaria. Allergy Asthma Immunol Res. 2011 Oct;3(4):273-6.
33	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.
34	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.
35	Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.
36	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.