General Information of Drug (ID: DMABMPQ)

Drug Name
4-methylhistamine Drug Info
Synonyms
4-Methylhistamine; 5-Methylhistamine; 36507-31-0; 5(4)-Methylhistamine; 1H-Imidazole-4-ethanamine, 5-methyl-; 2-(5-methyl-1H-imidazol-4-yl)ethanamine; UNII-54ST71P9EE; 1H-Imidazo-4-ethanamine, 5-methyl-; 54ST71P9EE; CHEBI:74760; IMIDAZOLE, 4-(2-AMINOETHYL)-5-METHYL-; 2-(5-Methyl-4-imidazolyl)ethylamine; 2-(4-METHYL-1H-IMIDAZOL-5-YL)ETHANAMINE; p-methylhistamine; Methylhistamine-4; 5-(2-Aminoethyl)-4-methylimidazole; AC1L1XS2; SCHEMBL606803; CHEMBL275443; GTPL1269; SCHEMBL11452941; BDBM22880; UGYXPZQILZRKJJ-UHFFFAOYSA-N
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Cross-matching ID
PubChem CID
37463
ChEBI ID
CHEBI:74760
CAS Number
CAS 36507-31-0
TTD Drug ID
DMABMPQ

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Clinical Trial Drug(s)
Discontinued Drug(s)
Investigative Drug(s)
Approved Drug(s)
Drug(s) Targeting Histamine H4 receptor (H4R)
Drug Name Drug ID Indication ICD 11 Highest Status REF
PF-3893787 DMC2FAL Atopic dermatitis EA80 Phase 2 [5]
JNJ-38518168 DM9UMIO Plaque psoriasis EA90.0 Phase 2 [6]
UR-63325 DME6X27 Allergic rhinitis CA08.0 Phase 2 [7]
Thioperamide DM8S593 Cognitive impairment 6D71 Terminated [8]
2-(2-(4-tert-Butylphenylthio)ethyl)-1H-imidazole DMZVBPG Discovery agent N.A. Investigative [9]
impromidine DMTDRPM Discovery agent N.A. Investigative [10]
burimamide DMZ2VYG Discovery agent N.A. Investigative [11]
Imetit DMMJ6NS Discovery agent N.A. Investigative [12]
[125I]iodophenpropit DMN4ABU Discovery agent N.A. Investigative [13]
(R)-alpha-methylhistamine DMKAW4P Discovery agent N.A. Investigative [14]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By Interferon gamma (IFNG)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Amphotericin B DMTAJQE Acne vulgaris ED80 Approved [15]
Nitric Oxide DM1RBYG Hypertension BA00-BA04 Approved [16]
Ribavirin DMEYLH9 Hepatitis C virus infection 1E51.1 Approved [17]
Ciprofloxacin XR DM2NLS9 Acute gonococcal cervicitis Approved [18]
Methotrexate DM2TEOL Anterior urethra cancer Approved [19]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [20]
Quercetin DM3NC4M Obesity 5B81 Approved [21]
Tretinoin DM49DUI Acne vulgaris ED80 Approved [22]
Zidovudine DM4KI7O Human immunodeficiency virus infection 1C62 Approved [23]
Rifampicin DM5DSFZ Non-insulin dependent diabetes 5A11 Approved [24]
⏷ Show the Full List of 10 Drug(s)
Drug(s) Affected By C-C motif chemokine 2 (CCL2)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Indinavir DM0T3YH Human immunodeficiency virus infection 1C62 Approved [25]
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [26]
Gefitinib DM15F0X Colon adenocarcinoma Approved [27]
Hydrogen peroxide DM1NG5W Infectious disease 1A00-CA43.1 Approved [28]
Imiquimod DM1TMA3 Alopecia areata ED70.2 Approved [29]
Methimazole DM25FL8 Hyperthyroidism 5A02 Approved [30]
TECFIDERA DM2OVDT Multiple sclerosis 8A40 Approved [31]
Methotrexate DM2TEOL Anterior urethra cancer Approved [19]
Simvastatin DM30SGU Arteriosclerosis BD40 Approved [32]
Quercetin DM3NC4M Obesity 5B81 Approved [33]
⏷ 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
Histamine H4 receptor (H4R) TTXJ178 HRH4_HUMAN Agonist [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [3]
Interferon gamma (IFNG) OTXG9JM7 IFNG_HUMAN Gene/Protein Processing [4]

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: 1269).
2 Compared pharmacology of human histamine H3 and H4 receptors: structure-activity relationships of histamine derivatives. Br J Pharmacol. 2006 Apr;147(7):744-54.
3 Histamine downregulates monocyte CCL2 production through the histamine H4 receptor. J Allergy Clin Immunol. 2007 Aug;120(2):300-7. doi: 10.1016/j.jaci.2007.03.024. Epub 2007 May 15.
4 Histamine H4 receptor agonists have more activities than H4 agonism in antigen-specific human T-cell responses. Immunology. 2007 Jun;121(2):266-75. doi: 10.1111/j.1365-2567.2007.02574.x. Epub 2007 Mar 7.
5 Challenges of drug discovery in novel target space. The discovery and evaluation of PF-3893787: a novel histamine H4 receptor antagonist. Bioorg Med Chem Lett. 2011 Nov 1;21(21):6596-602.
6 The histamine H4 receptor: from orphan to the clinic. Front Pharmacol. 2015; 6: 65.
7 Azines as histamine H4 receptor antagonists. Front Biosci (Schol Ed). 2012 Jan 1;4:967-87.
8 Role of histamine in short- and long-term effects of methamphetamine on the developing mouse brain. J Neurochem. 2008 Nov;107(4):976-86.
9 Synthesis and structure-activity relationships of N-aryl-piperidine derivatives as potent (partial) agonists for human histamine H3 receptor. Bioorg Med Chem. 2010 Jul 15;18(14):5441-8.
10 Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: identification of 4-methylhistamine as the first pote... J Pharmacol Exp Ther. 2005 Sep;314(3):1310-21.
11 Comparison of human, mouse, rat, and guinea pig histamine H4 receptors reveals substantial pharmacological species variation. J Pharmacol Exp Ther. 2001 Oct;299(1):121-30.
12 Histamine excites neonatal rat sympathetic preganglionic neurons in vitro via activation of H1 receptors. J Neurophysiol. 2006 Apr;95(4):2492-500.
13 Discovery of novel human histamine H4 receptor ligands by large-scale structure-based virtual screening. J Med Chem. 2008 Jun 12;51(11):3145-53.
14 Cloning and pharmacological characterization of a fourth histamine receptor (H(4)) expressed in bone marrow. Mol Pharmacol. 2001 Mar;59(3):420-6.
15 Differential expression of microRNAs and their predicted targets in renal cells exposed to amphotericin B and its complex with copper (II) ions. Toxicol Mech Methods. 2017 Sep;27(7):537-543. doi: 10.1080/15376516.2017.1333554. Epub 2017 Jun 8.
16 Regulatory role of nitric oxide on monocyte-derived dendritic cell functions. J Interferon Cytokine Res. 2003 Aug;23(8):423-31. doi: 10.1089/107999003322277838.
17 Direct evidence for immunomodulatory properties of ribavirin on T-cell reactivity to hepatitis C virus. Antiviral Res. 2007 Jul;75(1):36-42. doi: 10.1016/j.antiviral.2006.11.008. Epub 2006 Dec 13.
18 Differential effects of three antibiotics on T helper cell cytokine expression. J Antimicrob Chemother. 2005 Sep;56(3):502-6. doi: 10.1093/jac/dki251. Epub 2005 Jul 8.
19 The contribution of methotrexate exposure and host factors on transcriptional variance in human liver. Toxicol Sci. 2007 Jun;97(2):582-94.
20 Simvastatin inhibits IL-17 secretion by targeting multiple IL-17-regulatory cytokines and by inhibiting the expression of IL-17 transcription factor RORC in CD4+ lymphocytes. J Immunol. 2008 May 15;180(10):6988-96. doi: 10.4049/jimmunol.180.10.6988.
21 The flavonoid, quercetin, differentially regulates Th-1 (IFNgamma) and Th-2 (IL4) cytokine gene expression by normal peripheral blood mononuclear cells. Biochim Biophys Acta. 2002 Dec 16;1593(1):29-36. doi: 10.1016/s0167-4889(02)00328-2.
22 [Effects of vitamin A on the differentiation, maturation and functions of dendritic cells from cord blood]. Zhonghua Er Ke Za Zhi. 2004 May;42(5):340-3.
23 Effect of zidovudine therapy in patients with HIV infection on endogenous interferon plasma levels and the hepatic cytochrome P450 enzyme system. Chemotherapy. 1998 May-Jun;44(3):174-80. doi: 10.1159/000007112.
24 Detection of Drug-Responsive T-Lymphocytes in a Case of Fatal Antituberculosis Drug-Related Liver Injury. Chem Res Toxicol. 2016 Nov 21;29(11):1793-1795. doi: 10.1021/acs.chemrestox.6b00393. Epub 2016 Nov 9.
25 Some HIV antiretrovirals increase oxidative stress and alter chemokine, cytokine or adiponectin production in human adipocytes and macrophages. Antivir Ther. 2007;12(4):489-500.
26 Arsenite and cadmium promote the development of mammary tumors. Carcinogenesis. 2020 Jul 14;41(7):1005-1014. doi: 10.1093/carcin/bgz176.
27 Crosstalk between alveolar macrophages and alveolar epithelial cells/fibroblasts contributes to the pulmonary toxicity of gefitinib. Toxicol Lett. 2021 Mar 1;338:1-9. doi: 10.1016/j.toxlet.2020.11.011. Epub 2020 Nov 25.
28 Oxidative Stress Alters miRNA and Gene Expression Profiles in Villous First Trimester Trophoblasts. Biomed Res Int. 2015;2015:257090. doi: 10.1155/2015/257090. Epub 2015 Aug 3.
29 Cannabidiol selectively modulates interleukin (IL)-1 and IL-6 production in toll-like receptor activated human peripheral blood monocytes. Toxicology. 2021 Dec;464:153016. doi: 10.1016/j.tox.2021.153016. Epub 2021 Nov 2.
30 Monitoring of deiodinase deficiency based on transcriptomic responses in SH-SY5Y cells. Arch Toxicol. 2013 Jun;87(6):1103-13. doi: 10.1007/s00204-013-1018-4. Epub 2013 Feb 10.
31 Dimethyl Fumarate Inhibits the Nuclear Factor B Pathway in Breast Cancer Cells by Covalent Modification of p65 Protein. J Biol Chem. 2016 Feb 12;291(7):3639-47. doi: 10.1074/jbc.M115.679704. Epub 2015 Dec 18.
32 Simvastatin reduces expression of cytokines interleukin-6, interleukin-8, and monocyte chemoattractant protein-1 in circulating monocytes from hypercholesterolemic patients. Arterioscler Thromb Vasc Biol. 2002 Jul 1;22(7):1194-9. doi: 10.1161/01.atv.0000022694.16328.cc.
33 Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFB and AhR and EGFR-ERK pathway. Toxicol Appl Pharmacol. 2011 Sep 1;255(2):138-49.