General Information of Drug (ID: DM340FH)

Drug Name
cinnamic acid Drug Info
Synonyms
CINNAMIC ACID; TRANS-CINNAMIC ACID; 140-10-3; 621-82-9; (E)-Cinnamic acid; trans-3-Phenylacrylic acid; 3-Phenylacrylic acid; Phenylacrylic acid; Zimtsaeure; (2E)-3-phenylprop-2-enoic acid; 3-phenylprop-2-enoic acid; E-Cinnamic Acid; 3-Phenylpropenoic acid; (E)-3-phenylprop-2-enoic acid; trans-beta-Carboxystyrene; Benzenepropenoic acid; trans-Cinnamate; (E)-3-Phenyl-2-propenoic acid; (E)-cinnamate; Benzeneacrylic acid; trans-3-Phenyl-2-propenoic acid; Cinnamylic acid; Cinnamic acid, (E)-; t-Cinnamic acid; (2E)-3-Phenyl-2-propenoic
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
444539
ChEBI ID
CHEMBL35697
CAS Number
CAS 140-10-3
TTD Drug ID
DM340FH
INTEDE Drug ID
DR2499

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Investigative Drug(s)
Approved Drug(s)
Clinical Trial Drug(s)
Discontinued Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
(R)-5-diphosphomevalonate DMOESL1 Discovery agent N.A. Investigative [8]
isoferulic acid DMN23KT Discovery agent N.A. Investigative [3]
3-hydroxy-3-methyl-6-phosphohexanoic acid DM3YO72 Discovery agent N.A. Investigative [9]
Drug Name Drug ID Indication ICD 11 Highest Status REF
Vitamin B3 DMQVRZH Chronic renal failure GB61.Z Approved [10]
ARI-3037MO DM9LNXS Cardiovascular disease BA00-BE2Z Phase 2 [11]
SCH-900271 DMBJY1Z Ischemic stroke 8B11.5Z Phase 2 [12]
GSK-256073 DMMAIY2 Hyperlipidaemia 5C80 Phase 2 [13]
MK-1903 DMVJB09 Arteriosclerosis BD40 Phase 2 [14]
MK-0354 DMWFTRJ N. A. N. A. Phase 2 [15]
NIA-114 DM3ADQW Plaque psoriasis EA90.0 Clinical trial [16]
INCB19602 DMRHZBD Type-2 diabetes 5A11 Discontinued in Phase 2 [17]
5-Benzyl-1H-pyrazole-3-carboxylic acid DMJVGUZ Discovery agent N.A. Investigative [18]
Sazetidine-A DM68JI5 Major depressive disorder 6A70.3 Investigative [12]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Tretinoin DM49DUI Acne vulgaris ED80 Approved [19]
Leflunomide DMR8ONJ Arthritis FA20 Approved [20]
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [21]
Folic Acid DMEMBJC Colorectal carcinoma Approved [22]
Cisplatin DMRHGI9 Adenocarcinoma 2D40 Approved [23]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [24]
Urethane DM7NSI0 N. A. N. A. Phase 4 [25]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [26]
Milchsaure DM462BT Pruritus EC90 Investigative [27]
[3H]cAMP DMZRQU7 Discovery agent N.A. Investigative [28]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Troglitazone DM3VFPD Diabetic complication 5A2Y Approved [4]
Topiramate DM82Z30 Alcohol dependence 6C40.2 Approved [29]
Lamotrigine DM8SXYG Bipolar disorder 6A60 Approved [29]
Lindane DMB8CNL Infestations of lice and scabies 1G00.Z Approved [30]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [31]
Metyrapone DMI7FVQ Cushing disease 5A70 Approved [32]
Rosiglitazone DMILWZR Chronic kidney disease GB61 Approved [4]
Niclosamide DMJAGXQ Cestodes infection 1F70-1F76 Approved [33]
Pioglitazone DMKJ485 Amyotrophic lateral sclerosis 8B60.0 Approved [34]
Levetiracetam DMTGDN8 Epilepsy 8A60-8A68 Approved [31]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Cytochrome P450 2C19 (CYP2C19)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Cannabidiol DM0659E Dravet syndrome 8A61.11 Approved [35]
Thioridazine DM35M8J Schizophrenia 6A20 Approved [36]
Voriconazole DMAOL2S Aspergillosis 1F20 Approved [37]
Chloramphenicol DMFXEWT Bacterial infection 1A00-1C4Z Approved [38]
Capsaicin DMGMF6V Back pain ME84.Z Approved [39]
Pentamidine DMHZJCG African trypanosomiasis 1F51 Approved [40]
Stiripentol DMMSDOY Dravet syndrome 8A61.11 Approved [41]
Quinine DMSWYF5 Malaria 1F40-1F45 Approved [40]
Desipramine DMT2FDC Attention deficit hyperactivity disorder 6A05.Z Approved [36]
Amitriptyline DMK7F9S Depression 6A70-6A7Z Approved [42]
⏷ 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
Nicotinic acid receptor (HCAR2) TTWNV8U HCAR2_HUMAN Agonist [2]
Phosphomevalonate kinase (PMVK) TTXMI0C PMVK_HUMAN Inhibitor [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2 (HSD3B2) OT02MSKN 3BHS2_HUMAN Gene/Protein Processing [4]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [4]
Hydroxycarboxylic acid receptor 2 (HCAR2) OTZM930L HCAR2_HUMAN Protein Interaction/Cellular Processes [5]
Tyrosinase OTX54MAA TYRO_HUMAN Biotransformations [6]
UDP-glucuronosyltransferase 1A10 OTOTZVEY UD110_HUMAN Biotransformations [7]
UDP-glucuronosyltransferase 1A3 OTUEOER3 UD13_HUMAN Biotransformations [7]
UDP-glucuronosyltransferase 1A7 OTY4JJ32 UD17_HUMAN Biotransformations [7]
UDP-glucuronosyltransferase 1A8 OTTMABBG UD18_HUMAN Biotransformations [7]

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: 3203).
2 Phenolic acids suppress adipocyte lipolysis via activation of the nicotinic acid receptor GPR109A (HM74a/PUMA-G). J Lipid Res. 2009 May;50(5):908-14.
3 Inhibition of rat liver mevalonate pyrophosphate decarboxylase and mevalonate phosphate kinase by phenyl and phenolic compounds. Biochem J. 1979 Jul 1;181(1):143-51.
4 Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity. J Mol Endocrinol. 2004 Apr;32(2):425-36.
5 Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A). Bioorg Med Chem Lett. 2011 May 1;21(9):2736-9. doi: 10.1016/j.bmcl.2010.11.091. Epub 2010 Nov 25.
6 Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines. Chem Biol Interact. 2010 Oct 6;188(1):1-14. doi: 10.1016/j.cbi.2010.05.018. Epub 2010 Jun 4.
7 Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. J Biol Chem. 2004 Jul 2;279(27):28320-9. doi: 10.1074/jbc.M401396200. Epub 2004 Apr 26.
8 Functional evaluation of conserved basic residues in human phosphomevalonate kinase. Biochemistry. 2007 Oct 23;46(42):11780-8.
9 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: 641).
10 Hakozaki T, Minwalla L, Zhuang J, Chhoa M, Matsubara A, Miyamoto K, Greatens A, Hillebrand GG, Bissett DL, Boissy RE: The effect of niacinamide on reducing cutaneous pigmentation and suppression of melanosome transfer. Br J Dermatol. 2002 Jul;147(1):20-31.
11 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
12 Discovery of SCH 900271, a Potent Nicotinic Acid Receptor Agonist for the Treatment of Dyslipidemia. ACS Med Chem Lett. 2011 Nov 24;3(1):63-8.
13 GSK256073, a selective agonist of G-protein coupled receptor 109A (GPR109A) reduces serum glucose in subjects with type 2 diabetes mellitus. Diabetes Obes Metab. 2013 Nov;15(11):1013-21.
14 Niacin lipid efficacy is independent of both the niacin receptor GPR109A and free fatty acid suppression. Sci Transl Med. 2012 Aug 22;4(148):148ra115.
15 GPR109a agonists. Part 2: pyrazole-acids as agonists of the human orphan G-protein coupled receptor GPR109a. Bioorg Med Chem Lett. 2010 Aug 1;20(15):4472-4.
16 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
17 DOI: 10.1038/scibx.2010.313
18 Pyrazole derivatives as partial agonists for the nicotinic acid receptor. J Med Chem. 2003 Aug 28;46(18):3945-51.
19 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.
20 Endoplasmic reticulum stress and MAPK signaling pathway activation underlie leflunomide-induced toxicity in HepG2 Cells. Toxicology. 2017 Dec 1;392:11-21.
21 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.
22 Folic acid supplementation dysregulates gene expression in lymphoblastoid cells--implications in nutrition. Biochem Biophys Res Commun. 2011 Sep 9;412(4):688-92. doi: 10.1016/j.bbrc.2011.08.027. Epub 2011 Aug 16.
23 Activation of AIFM2 enhances apoptosis of human lung cancer cells undergoing toxicological stress. Toxicol Lett. 2016 Sep 6;258:227-236.
24 17-Estradiol Activates HSF1 via MAPK Signaling in ER-Positive Breast Cancer Cells. Cancers (Basel). 2019 Oct 11;11(10):1533. doi: 10.3390/cancers11101533.
25 Ethyl carbamate induces cell death through its effects on multiple metabolic pathways. Chem Biol Interact. 2017 Nov 1;277:21-32.
26 Air pollution and DNA methylation alterations in lung cancer: A systematic and comparative study. Oncotarget. 2017 Jan 3;8(1):1369-1391. doi: 10.18632/oncotarget.13622.
27 Transcriptional profiling of lactic acid treated reconstructed human epidermis reveals pathways underlying stinging and itch. Toxicol In Vitro. 2019 Jun;57:164-173.
28 Modulation of HDL metabolism by the niacin receptor GPR109A in mouse hepatocytes. Biochem Pharmacol. 2010 Nov 1;80(9):1450-7. doi: 10.1016/j.bcp.2010.07.023. Epub 2010 Jul 22.
29 Effects of anticonvulsants on human p450c17 (17alpha-hydroxylase/17,20 lyase) and 3beta-hydroxysteroid dehydrogenase type 2. Epilepsia. 2005 Mar;46(3):444-8.
30 Steroidogenic gene expression in H295R cells and the human adrenal gland: adrenotoxic effects of lindane in vitro. J Appl Toxicol. 2006 Nov-Dec;26(6):484-92.
31 Differential effects of antiepileptic drugs on steroidogenesis in a human in vitro cell model. Acta Neurol Scand Suppl. 2009;(189):14-21.
32 The H295R system for evaluation of endocrine-disrupting effects. Ecotoxicol Environ Saf. 2006 Nov;65(3):293-305.
33 Mitochondrial Uncoupling Induces Epigenome Remodeling and Promotes Differentiation in Neuroblastoma. Cancer Res. 2023 Jan 18;83(2):181-194. doi: 10.1158/0008-5472.CAN-22-1029.
34 Pioglitazone inhibits androgen production in NCI-H295R cells by regulating gene expression of CYP17 and HSD3B2. Mol Pharmacol. 2007 Mar;71(3):787-98.
35 Characterization of the structural determinants required for potent mechanism-based inhibition of human cytochrome P450 1A1 by cannabidiol. Chem Biol Interact. 2014 May 25;215:62-8.
36 Inhibition of cytochrome P450 enzymes participating in p-nitrophenol hydroxylation by drugs known as CYP2E1 inhibitors. Chem Biol Interact. 2004 Apr 15;147(3):331-40.
37 The novel azole R126638 is a selective inhibitor of ergosterol synthesis in Candida albicans, Trichophyton spp., and Microsporum canis. Antimicrob Agents Chemother. 2004 Sep;48(9):3272-8.
38 Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class. Toxicol Lett. 2016 Jan 22;241:82-94.
39 Effects of capsaicin and dihydrocapsaicin on human and rat liver microsomal CYP450 enzyme activities in vitro and in vivo. J Asian Nat Prod Res. 2012;14(4):382-95.
40 Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5.
41 Stiripentol. Expert Opin Investig Drugs. 2005 Jul;14(7):905-11.
42 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.