General Information of Drug (ID: DM0N8ZM)

Drug Name
Coumarin Drug Info
Synonyms
coumarin; 2H-Chromen-2-one; 91-64-5; 2H-1-Benzopyran-2-one; cumarin; 1,2-Benzopyrone; Rattex; Tonka bean camphor; Coumarinic anhydride; chromen-2-one; Coumarine; Benzo-alpha-pyrone; cis-o-Coumarinic acid lactone; o-Hydroxycinnamic acid lactone; o-Hydroxycinnamic lactone; 2-Oxo-1,2-benzopyran; Coumarinic lactone; Kumarin; Benzo-a-pyrone; Kumarin [Czech]; 5,6-Benzo-2-pyrone; 2H-1-Benzopyran, 2-oxo-; 5,6-Benzo-alpha-pyrone; 2H-Benzo(b)pyran-2-one; 2H-Benzo[b]pyran-2-one; Caswell No. 259C; o-Coumaric acid lactone
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
323
ChEBI ID
CHEBI:28794
CAS Number
CAS 91-64-5
TTD Drug ID
DM0N8ZM
VARIDT Drug ID
DR00864
INTEDE Drug ID
DR0386

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
Drug Status:
Approved Drug(s)
Investigative Drug(s)
Clinical Trial Drug(s)
Patented Agent(s)
Discontinued Drug(s)
Drug(s) Metabolized By Cytochrome P450 2C9 (CYP2C9)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Progesterone DMUY35B Premature labour JB00 Approved [6]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [7]
Estradiol DMUNTE3 Breast cancer 2C60-2C65 Approved [8]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [9]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [10]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [9]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [11]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [12]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [13]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [14]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 102D1 (cyp102)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Daidzein DMRFTJX Discovery agent N.A. Investigative [4]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Seborrhoeic dermatitis EA81 Approved [15]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [16]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [17]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [18]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [19]
SAR566658 DM6Q295 Solid tumour/cancer 2A00-2F9Z Phase 2 [20]
Ferulic Acid DMJC7NF Discovery agent N.A. Patented [18]
Spermine DMD4BFY N. A. N. A. Terminated [21]
ELLAGIC ACID DMX8BS5 Discovery agent N.A. Investigative [18]
CATECHIN DMY38SB Discovery agent N.A. Investigative [17]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Carbonic anhydrase I (CA-I)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Seborrhoeic dermatitis EA81 Approved [15]
Ethoxzolamide DMVO4ED Glaucoma/ocular hypertension 9C61 Approved [22]
Dichlorphenamide DMH7IDQ Chronic glaucoma 9C61.0Z Approved [22]
Methazolamide DM7J2TA Glaucoma/ocular hypertension 9C61 Approved [23]
Acetazolamide DM1AF5U Glaucoma/ocular hypertension 9C61 Approved [22]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [17]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [18]
CG-100649 DMIKMA9 Arthritis FA20 Phase 3 [24]
Phenol DM1QSM3 N. A. N. A. Phase 2/3 [17]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [19]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Seborrhoeic dermatitis EA81 Approved [15]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [25]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [17]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [18]
Phenol DM1QSM3 N. A. N. A. Phase 2/3 [17]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [19]
Ferulic Acid DMJC7NF Discovery agent N.A. Patented [18]
ELLAGIC ACID DMX8BS5 Discovery agent N.A. Investigative [18]
CATECHIN DMY38SB Discovery agent N.A. Investigative [17]
GALLICACID DM6Y3A0 Discovery agent N.A. Investigative [18]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Seborrhoeic dermatitis EA81 Approved [15]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [25]
Dorzolamide DMA17D0 Open-angle glaucoma 9C61 Approved [26]
Chlorothiazide DMLHESP Congestive heart failure BD10 Approved [27]
Ethoxzolamide DMVO4ED Glaucoma/ocular hypertension 9C61 Approved [28]
Dichlorphenamide DMH7IDQ Chronic glaucoma 9C61.0Z Approved [28]
Cyclothiazide DMJ4AWC Congestive heart failure BD10 Approved [29]
Ethinamate DMK57GB Insomnia 7A00-7A0Z Approved [30]
Benzthiazide DMQWZ0H High blood pressure BA00 Approved [31]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [17]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [32]
Trientine DMD2WPG Inborn error of metabolism 5C50-5C59 Approved [21]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [17]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [18]
Phenol DM1QSM3 N. A. N. A. Phase 2/3 [17]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [19]
Ferulic Acid DMJC7NF Discovery agent N.A. Patented [18]
Spermine DMD4BFY N. A. N. A. Terminated [21]
ELLAGIC ACID DMX8BS5 Discovery agent N.A. Investigative [18]
CATECHIN DMY38SB Discovery agent N.A. Investigative [17]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Targeting Carbonic anhydrase (CA)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Seborrhoeic dermatitis EA81 Approved [33]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [16]
Quinethazone DMWCOSR Hypertension BA00-BA04 Approved [34]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [17]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [18]
Phentermine+topiramate DMVEHM4 Obesity 5B81 Phase 3 [35]
Phenol DM1QSM3 N. A. N. A. Phase 2/3 [17]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [19]
SULFAMIDE DMMAS3K N. A. N. A. Phase 1 [36]
Ferulic Acid DMJC7NF Discovery agent N.A. Patented [18]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Salicyclic acid DM2F8XZ Seborrhoeic dermatitis EA81 Approved [15]
Sulfamylon DMIO1K0 Bacterial infection 1A00-1C4Z Approved [37]
Brinzolamide DMBAPFG Open-angle glaucoma 9C61 Approved [22]
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [17]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [18]
Phenol DM1QSM3 N. A. N. A. Phase 2/3 [17]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [19]
Sodium pyruvate DMST6A3 Asthma CA23 Phase 1/2 [38]
SULFAMIDE DMMAS3K N. A. N. A. Phase 1 [36]
Ferulic Acid DMJC7NF Discovery agent N.A. Patented [18]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Curcumin DMQPH29 Solid tumour/cancer 2A00-2F9Z Phase 3 [17]
PARABEN DMEW5Z8 N. A. N. A. Phase 3 [18]
Phenol DM1QSM3 N. A. N. A. Phase 2/3 [17]
Coumate DMVKW0N Breast cancer 2C60-2C65 Phase 2 [19]
Indisulam DM9SX6Y Lymphoma 2A80-2A86 Phase 2 [39]
Girentuximab I-124 DMG3O2Z Renal cell carcinoma 2C90 Phase 2 [40]
SULFAMIDE DMMAS3K N. A. N. A. Phase 1 [41]
BAY 79-4620 DM14XQN Solid tumour/cancer 2A00-2F9Z Phase 1 [42]
90Y-cG250 DMJR6TC Solid tumour/cancer 2A00-2F9Z Phase 1 [43]
Ferulic Acid DMJC7NF Discovery agent N.A. Patented [18]
⏷ 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
Carbonic anhydrase (CA) TTUNARX NOUNIPROTAC Inhibitor [1]
Carbonic anhydrase I (CA-I) TTHQPL7 CAH1_HUMAN Inhibitor [2]
Carbonic anhydrase II (CA-II) TTANPDJ CAH2_HUMAN Inhibitor [2]
Carbonic anhydrase IV (CA-IV) TTZHA0O CAH4_HUMAN Inhibitor [1]
Carbonic anhydrase IX (CA-IX) TT2LVK8 CAH9_HUMAN Inhibitor [1]
Carbonic anhydrase VI (CA-VI) TTCFSPE CAH6_HUMAN Inhibitor [1]
Carbonic anhydrase XII (CA-XII) TTSYM0R CAH12_HUMAN Inhibitor [1]
Carbonic anhydrase XIV (CA-XIV) TTEYTKG CAH14_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [3]
Cytochrome P450 102D1 (cyp102) DEUWAV0 CPXB_BACMB Substrate [4] , [5]

References

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2 7,8-disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and X... Bioorg Med Chem Lett. 2010 Dec 15;20(24):7255-8.
3 Pharmacogenomics of CYP2C9: functional and clinical considerations. J Pers Med. 2017 Dec 28;8(1).
4 The metagenome of Caracolus marginella gut microbiome using culture independent approaches and shotgun sequencing. Data Brief. 2017 Nov 22;16:501-505.
5 Cloning, expression and characterization of CYP102D1, a self-sufficient P450 monooxygenase from Streptomyces avermitilis. FEBS J. 2012 May;279(9):1650-62.
6 Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
7 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
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10 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
11 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
12 New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
13 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
14 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
15 Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8.
16 Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. J Med Chem. 2009 Feb 12;52(3):646-54.
17 Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3.
18 Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-2164.
19 Carbonic anhydrase inhibitors. Interaction of the antitumor sulfamate EMD 486019 with twelve mammalian carbonic anhydrase isoforms: Kinetic and X-r... Bioorg Med Chem Lett. 2008 Aug 1;18(15):4282-6.
20 An Antibody-Drug Conjugate Targeting MUC1-Associated Carbohydrate CA6 Shows Promising Antitumor Activities. Mol Cancer Ther. 2020 Aug;19(8):1660-1669.
21 Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. J Med Chem. 2010 Aug 12;53(15):5511-22.
22 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
23 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 2597).
24 Understanding the Dual Inhibition of COX-2 and Carbonic Anhydrase-II by Celecoxib and CG100649 Using Density Functional Theory Calculations and other Molecular Modelling Approaches. Protein Pept Lett. 2015;22(10):903-12.
25 Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases. J Med Chem. 2010 Apr 8;53(7):2913-26.
26 Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15;17(14):5054-8.
27 Localization of diuretic effects along the loop of Henle: an in vivo microperfusion study in rats. Clin Sci (Lond). 2000 Apr;98(4):481-8.
28 The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
29 Selective effect of thiazides on the human osteoblast-like cell line MG-63. Kidney Int. 1996 Nov;50(5):1476-82.
30 Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50.
31 Nature of the inhibition of carbonic anhydrase by acetazolamide and benzthiazide. J Pharmacol Exp Ther. 1961 Mar;131:271-4.
32 Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides. Bioorg Med Chem Lett. 2005 Sep 1;15(17):3828-33.
33 Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. Bioorg Med Chem Lett. 2008 Jun 15;18(12):3593-6.
34 Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for th... Bioorg Med Chem Lett. 2008 Apr 15;18(8):2567-73.
35 Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
36 Carbonic anhydrase inhibitors: crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mamm... Bioorg Med Chem Lett. 2010 Jun 15;20(12):3601-5.
37 Carbonic anhydrase inhibitors. Inhibition of the membrane-bound human and bovine isozymes IV with sulfonamides. Bioorg Med Chem Lett. 2005 Feb 15;15(4):1149-54.
38 Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with carboxylates. Bioorg Med Chem Lett. 2005 Feb 1;15(3):573-8.
39 Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumor-assoc... Bioorg Med Chem Lett. 2004 Jan 5;14(1):217-23.
40 Potential role of (124)I-girentuximab in the presurgical diagnosis of clear-cell renal cell cancer. Biologics. 2012;6:395-407.
41 Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, IV, V, and IX with anions isosteric and isoelectronic with sulfate, nitrate, and carbo... Bioorg Med Chem Lett. 2005 Feb 1;15(3):567-71.
42 Therapeutic mechanism and efficacy of the antibody-drug conjugate BAY 79-4620 targeting human carbonic anhydrase 9. Mol Cancer Ther. 2012 Feb;11(2):340-9.
43 Application of monoclonal antibody G250 recognizing carbonic anhydrase IX in renal cell carcinoma. Int J Mol Sci. 2013 May 29;14(6):11402-23.