General Information of Drug (ID: DMUOQZD)

Drug Name
Arachidonic acid Drug Info
Synonyms
arachidonic acid; 506-32-1; arachidonate; (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acid; Immunocytophyte; (all-Z)-5,8,11,14-Eicosatetraenoic acid; cis-5,8,11,14-Eicosatetraenoic acid; 5,8,11,14-Eicosatetraenoic acid, (all-Z)-; 5Z,8Z,11Z,14Z-eicosatetraenoic acid; UNII-27YG812J1I; all-cis-5,8,11,14-eicosatetraenoic acid; Arachidonic Acid, 99%; CHEMBL15594; CHEBI:15843; YZXBAPSDXZZRGB-DOFZRALJSA-N; 27YG812J1I; cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid; (5Z,8Z,11Z,14Z)-5,8,11,14-Eicosatetraenoic Acid
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
444899
ChEBI ID
CHEBI:15843
CAS Number
CAS 506-32-1
TTD Drug ID
DMUOQZD
INTEDE Drug ID
DR0129

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DME
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative 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 [10]
Tamoxifen DMLB0EZ Breast cancer 2C60-2C65 Approved [11]
Estradiol DMUNTE3 Breast cancer 2C60-2C65 Approved [12]
Acetaminophen DMUIE76 Pain MG30-MG3Z Approved [13]
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [14]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [13]
Verapamil DMA7PEW Hypertension BA00-BA04 Approved [15]
Diclofenac DMPIHLS Osteoarthritis FA00-FA05 Approved [3]
Estrone DM5T6US Menopausal and postmenopausal disorder GA30 Approved [16]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [17]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Cytochrome P450 4F2 (CYP4F2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Dinoprostone DMTYOPD Medical abortion JA00.1Z Approved [18]
Fingolimod DM5JVAN Primary progressive multiple sclerosis 8A40.1 Approved [19]
Ebastine DMQRX24 Irritable bowel syndrome DD91.0 Phase 4 [20]
Pafuramidine DMFKOR9 Malaria 1F40-1F45 Phase 3 [21]
Tocopherol DMBIJZ6 Phenylketonuria 5C50.0 Phase 2 [22]
GSK618334 DMJPXZ4 Drug abuse 6C4G.1Z Phase 1 [23]
⏷ Show the Full List of 6 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Imatinib DM7RJXL Acute lymphoblastic leukaemia 2A85 Approved [24]
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [25]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [24]
Diazepam DM08E9O Epilepsy 8A60-8A68 Approved [24]
Dapsone DM4LT8A Pneumocystis pneumonia CA40.20 Approved [24]
Ifosfamide DMCT3I8 Solid tumour/cancer 2A00-2F9Z Approved [24]
Nateglinide DMLK2QH Diabetic complication 5A2Y Approved [24]
Thalidomide DM70BU5 Multiple myeloma 2A83 Approved [24]
Ketobemidone DMM3L6Z Pain MG30-MG3Z Approved [24]
Irbesartan DMTP1DC Hypertension BA00-BA04 Approved [24]
Salicyclic acid DM2F8XZ Seborrhoeic dermatitis EA81 Approved [30]
Naproxen DMZ5RGV Osteoarthritis FA00-FA05 Approved [31]
Mesalazine DMOL5IU Ulcerative colitis DD71 Approved [32]
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [33]
Bromfenac DMKB79O Postoperative inflammation 1A00-CA43.1 Approved [34]
Aminosalicylic acid DMENSL5 Inflammatory bowel disease DD72 Approved [35]
Flufenamic Acid DMC8VNH Dysmenorrhea GA34.3 Approved [36]
Piroxicam DMTK234 Pain MG30-MG3Z Approved [35]
Suprofen DMKXJZ7 Miosis LA11.62 Approved [37]
Gamma-homolinolenic acid DMSXKYG Malnutrition 5B50-5B71 Approved [38]
⏷ Show the Full List of 20 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Etoposide DMNH3PG Solid tumour/cancer 2A00-2F9Z Approved [25]
Dapsone DM4LT8A Pneumocystis pneumonia CA40.20 Approved [24]
Eicosapentaenoic acid/docosa-hexaenoic acid DMMUCG4 Hypertriglyceridemia 5C80.1 Approved [26]
Epanova DMHEAGL Hypertriglyceridemia 5C80.1 Approved [27]
Gamma-homolinolenic acid DMSXKYG Malnutrition 5B50-5B71 Approved [26]
Gamolenic acid DMQN30Z Allergy 4A80-4A85 Approved [26]
Omega-6-FA DMBWY8V Attention deficit hyperactivity disorder 6A05.Z Phase 3 [28]
Alpha-linolenic acid DMY64HE Discovery agent N.A. Investigative [26]
Eicosadienoic acid DMVJK9W Discovery agent N.A. Investigative [26]
Icosapentum DMF1CM7 Discovery agent N.A. Investigative [26]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Metabolized By Arachidonate 5-lipoxygenase (ALOX5)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Epanova DMHEAGL Hypertriglyceridemia 5C80.1 Approved [29]
Omega-6-FA DMBWY8V Attention deficit hyperactivity disorder 6A05.Z Phase 3 [28]

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Prostaglandin G/H synthase 1 (COX-1) TT8NGED PGH1_HUMAN Inhibitor [2]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [3]
Prostaglandin G/H synthase 2 (COX-2) DE492CE PGH2_HUMAN Substrate [4]
Prostaglandin G/H synthase 1 (COX-1) DE073H6 PGH1_HUMAN Substrate [5]
Arachidonate 5-lipoxygenase (ALOX5) DE87OZS LOX5_HUMAN Substrate [6]
Arachidonate 12-lipoxygenase (ALOX12B) DEISPU8 LX12B_HUMAN Substrate [7]
Arachidonate 15-lipoxygenase (ALOX15) DEH0J8X LOX15_HUMAN Substrate [8]
Cytochrome P450 4F2 (CYP4F2) DE3GT9C CP4F2_HUMAN Substrate [9]

References

1 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. (Ligand id: 2391).
2 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
3 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.
4 PharmGKB summary: very important pharmacogene information for PTGS2. Pharmacogenet Genomics. 2011 Sep;21(9):607-13.
5 Identification and functional characterization of polymorphisms in human cyclooxygenase-1 (PTGS1). Pharmacogenet Genomics. 2007 Feb;17(2):145-60.
6 A rat air pouch model for evaluating the efficacy and selectivity of 5-lipoxygenase inhibitors. Eur J Pharmacol. 2008 Apr 14;584(1):166-74.
7 Mitochondrial uncoupling reveals a novel therapeutic opportunity for p53-defective cancers. Nat Commun. 2018 Sep 26;9(1):3931.
8 Effect of human 15-lipoxygenase-1 metabolites on vascular function in mouse mesenteric arteries and hearts. Prostaglandins Other Lipid Mediat. 2013 Oct;106:8-15.
9 Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acids. Biochim Biophys Acta. 2011 Jan;1814(1):210-22.
10 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.
11 Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
12 Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
13 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
14 Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
15 Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
16 A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
17 A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
18 Cloning and characterization of CYP4F21: a prostaglandin E2 20-hydroxylase of ram seminal vesicles. Arch Biochem Biophys. 2001 May 1;389(1):123-9.
19 CYP4F enzymes are responsible for the elimination of fingolimod (FTY720), a novel treatment of relapsing multiple sclerosis. Drug Metab Dispos. 2011 Feb;39(2):191-8.
20 cDNA cloning and expression of a novel cytochrome p450 (cyp4f12) from human small intestine. Biochem Biophys Res Commun. 2001 Feb 2;280(4):1135-41.
21 Human enteric microsomal CYP4F enzymes O-demethylate the antiparasitic prodrug pafuramidine. Drug Metab Dispos. 2007 Nov;35(11):2067-75.
22 Discovery, characterization, and significance of the cytochrome P450 omega-hydroxylase pathway of vitamin E catabolism. Ann N Y Acad Sci. 2004 Dec;1031:13-21.
23 Product information - Gilenya.
24 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.
25 Peroxidative free radical formation and O-demethylation of etoposide(VP-16) and teniposide(VM-26). Biochem Biophys Res Commun. 1986 Feb 26;135(1):215-20.
26 Divergent cyclooxygenase responses to fatty acid structure and peroxide level in fish and mammalian prostaglandin H synthases. FASEB J. 2006 Jun;20(8):1097-108.
27 Structural basis of fatty acid substrate binding to cyclooxygenase-2. J Biol Chem. 2010 Jul 16;285(29):22152-63.
28 Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426.
29 Omega-3 fatty acids and inflammatory processes. Nutrients. 2010 Mar;2(3):355-74.
30 The C50T polymorphism of the cyclooxygenase-1 gene and the risk of thrombotic events during low-dose therapy with acetyl salicylic acid. Thromb Haemost. 2008 Jul;100(1):70-5.
31 Comparative inhibitory activity of rofecoxib, meloxicam, diclofenac, ibuprofen, and naproxen on COX-2 versus COX-1 in healthy volunteers. J Clin Pharmacol. 2000 Oct;40(10):1109-20.
32 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
33 Cox-2 inhibitory effects of naturally occurring and modified fatty acids. J Nat Prod. 2001 Jun;64(6):745-9.
34 Comparison of cyclooxygenase inhibitory activity and ocular anti-inflammatory effects of ketorolac tromethamine and bromfenac sodium. Curr Med Res Opin. 2006 Jun;22(6):1133-40.
35 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
36 Ouellet M, Percival MD: Effect of inhibitor time-dependency on selectivity towards cyclooxygenase isoforms. Biochem J. 1995 Feb 15;306 ( Pt 1):247-51.
37 Differential binding mode of diverse cyclooxygenase inhibitors. J Mol Graph Model. 2002 Mar;20(5):359-71.
38 Differential metabolism of dihomo-gamma-linolenic acid and arachidonic acid by cyclo-oxygenase-1 and cyclo-oxygenase-2: implications for cellular synthesis of prostaglandin E1 and prostaglandin E2. Biochem J. 2002 Jul 15;365(Pt 2):489-96.