Details of the Drug

General Information of Drug (ID: DM9AKVR)

Drug Name
2-APB
Synonyms 2-aminoethoxydiphenyl borate; 2-aminoethoxydiphenylborane
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski):
0		 Molecular Weight 225.1
Topological Polar Surface Area Not Available
Rotatable Bond Count 5
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 2
Chemical Identifiers
Formula
C14H16BNO
IUPAC Name
2-diphenylboranyloxyethanamine
Canonical SMILES
B(C1=CC=CC=C1)(C2=CC=CC=C2)OCCN
InChI
InChI=1S/C14H16BNO/c16-11-12-17-15(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10H,11-12,16H2
InChIKey
BLZVCIGGICSWIG-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
1598
ChEBI ID
CHEBI:131184
CAS Number
524-95-8
TTD ID
D00HCI

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Long transient receptor potential channel 2 (TRPM2) TTEBMN7 TRPM2_HUMAN Blocker (channel blocker) [2]
Long transient receptor potential channel 3 (TRPM3) TTO3TD8 TRPM3_HUMAN Inhibitor (gating inhibitor) [3]
Long transient receptor potential channel 6 (TRPM6) TTV76RD TRPM6_HUMAN Activator [4]
Long transient receptor potential channel 7 (TRPM7) TTFPVZO TRPM7_HUMAN Activator [5]
Long transient receptor potential channel 8 (TRPM8) TTXDKTO TRPM8_HUMAN Blocker (channel blocker) [6]
Short transient receptor potential channel 1 (TRPC1) TTA76X0 TRPC1_HUMAN Blocker (channel blocker) [7]
Short transient receptor potential channel 2 (TRPC2) TTSJ9E7 Q3C1U7_HUMAN Blocker (channel blocker) [8]
Short transient receptor potential channel 3 (TRPC3) TTNVC34 TRPC3_HUMAN Blocker (channel blocker) [9]
Short transient receptor potential channel 4 (TRPC4) TTX0H5W TRPC4_HUMAN Blocker (channel blocker) [10]
Short transient receptor potential channel 5 (TRPC5) TT32NQ1 TRPC5_HUMAN Blocker (channel blocker) [3]
Short transient receptor potential channel 6 (TRPC6) TTRBT3W TRPC6_HUMAN Blocker (channel blocker) [11]
Short transient receptor potential channel 7 (TRPC7) TT06GRA TRPC7_HUMAN Blocker (channel blocker) [12]
Transient receptor potential cation channel V1 (TRPV1) TTMI6F5 TRPV1_HUMAN Activator [13]
Transient receptor potential cation channel V2 (TRPV2) TTBECWA TRPV2_HUMAN Activator [14]
Transient receptor potential cation channel V3 (TRPV3) TT946IA TRPV3_HUMAN Activator [15]
Transient receptor potential cation channel V6 (TRPV6) TTBK14N TRPV6_HUMAN Activator [16]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Transient receptor potential cation channel V3 (TRPV3) DTT TRPV3 7.58E-01 5.28E-03 0.05
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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: 2433).
2 Inhibition of the transient receptor potential cation channel TRPM2 by 2-aminoethoxydiphenyl borate (2-APB). Br J Pharmacol. 2008 Mar;153(6):1324-30.
3 Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect. Br J Pharmacol. 2005 Jun;145(4):405-14.
4 Functional characterization of homo- and heteromeric channel kinases TRPM6 and TRPM7. J Gen Physiol. 2006 May;127(5):525-37.
5 LTRPC7 is a Mg.ATP-regulated divalent cation channel required for cell viability. Nature. 2001 May 31;411(6837):590-5.
6 Effects of antagonists and heat on TRPM8 channel currents in dorsal root ganglion neuron activated by nociceptive cold stress and menthol. Neurochem Res. 2012 Feb;37(2):314-20.
7 TRPC1 and TRPC5 form a novel cation channel in mammalian brain. Neuron. 2001 Mar;29(3):645-55.
8 A diacylglycerol-gated cation channel in vomeronasal neuron dendrites is impaired in TRPC2 mutant mice: mechanism of pheromone transduction. Neuron. 2003 Oct 30;40(3):551-61.
9 Mechanism of inhibition of TRPC cation channels by 2-aminoethoxydiphenylborane. Mol Pharmacol. 2005 Sep;68(3):758-62.
10 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: 489).
11 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: 491).
12 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: 492).
13 2-aminoethoxydiphenyl borate is a common activator of TRPV1, TRPV2, and TRPV3. J Biol Chem. 2004 Aug 20;279(34):35741-8.
14 Pharmacological characterization and molecular determinants of the activation of transient receptor potential V2 channel orthologs by 2-aminoethoxy... Mol Pharmacol. 2007 Nov;72(5):1258-68.
15 2-aminoethoxydiphenyl borate activates and sensitizes the heat-gated ion channel TRPV3. J Neurosci. 2004 Jun 2;24(22):5177-82.
16 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: 512).
17 Clinical pipeline report, company report or official report of Boehringer Ingelheim.
18 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: 490).
19 The Na+/Ca2+ exchange inhibitor KB-R7943 potently blocks TRPC channels. Biochem Biophys Res Commun. 2007 Sep 14;361(1):230-6.
20 Bromoenol lactone inhibits voltage-gated Ca2+ and transient receptor potential canonical channels. J Pharmacol Exp Ther. 2011 Nov;339(2):329-40.
21 Identification of ML204, a novel potent antagonist that selectively modulates native TRPC4/C5 ion channels. J Biol Chem. 2011 Sep 23;286(38):33436-46.
22 (-)-Englerin is a potent and selective activator of TRPC4 and TRPC5 calcium channels. Angew Chem Int Ed Engl. 2015 Mar 16;54(12):3787-91.
23 In vivo detection of human TRPV6-rich tumors with anti-cancer peptides derived from soricidin. PLoS One. 2013;8(3):e58866.
24 Molecular and functional characterization of a novel mouse transient receptor potential protein homologue TRP7. Ca(2+)-permeable cation channel that is constitutively activated and enhanced by stimulation of G protein-coupled receptor. J Biol Chem. 1999 Sep 24;274(39):27359-70.
25 The TRPM7 channel is inactivated by PIP(2) hydrolysis. Nat Cell Biol. 2002 May;4(5):329-36.
26 Carvacrol is a novel inhibitor of Drosophila TRPL and mammalian TRPM7 channels. Cell Calcium. 2009 Mar;45(3):300-9.
27 Waixenicin A inhibits cell proliferation through magnesium-dependent block of transient receptor potential melastatin 7 (TRPM7) channels. J Biol Chem. 2011 Nov 11;286(45):39328-35.
28 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: 488).
29 Direct activation of human TRPC6 and TRPC3 channels by diacylglycerol. Nature. 1999 Jan 21;397(6716):259-63.
30 A functional link between store-operated and TRPC channels revealed by the 3,5-bis(trifluoromethyl)pyrazole derivative, BTP2. J Biol Chem. 2005 Mar 25;280(12):10997-1006.
31 Selective and direct inhibition of TRPC3 channels underlies biological activities of a pyrazole compound. Proc Natl Acad Sci U S A. 2009 Mar 31;106(13):5400-5.
32 TRPV1-mediated itch in seasonal allergic rhinitis. Allergy. 2009 May;64(5):807-10.
33 Best of the 2009 AUA Annual Meeting: Highlights from the 2009 Annual Meeting of the American Urological Association, April 25-30, 2009, Chicago, IL. Rev Urol. 2009 Spring; 11(2): 82-107.
34 Inhibition of TRPM8 channels reduces pain in the cold pressor test in humans. J Pharmacol Exp Ther. 2014 Nov;351(2):259-69.
35 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: 500).
36 5-benzyloxytryptamine as an antagonist of TRPM8. Bioorg Med Chem Lett. 2010 Dec 1;20(23):7076-9.
37 Evolution of thermal response properties in a cold-activated TRP channel. PLoS One. 2009 May 29;4(5):e5741.
38 Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. Br J Pharmacol. 2004 Feb;141(4):737-45.
39 Pharmacological profiling of the TRPV3 channel in recombinant and native assays. Br J Pharmacol. 2014 May;171(10):2631-44.
40 Biphasic currents evoked by chemical or thermal activation of the heat-gated ion channel, TRPV3. J Biol Chem. 2005 Apr 22;280(16):15928-41.
41 Citral sensing by Transient [corrected] receptor potential channels in dorsal root ganglion neurons. PLoS One. 2008 May 7;3(5):e2082.
42 17(R)-resolvin D1 specifically inhibits transient receptor potential ion channel vanilloid 3 leading to peripheral antinociception. Br J Pharmacol. 2012 Feb;165(3):683-92.
43 Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels. Nat Neurosci. 2006 May;9(5):628-35.
44 More than cool: promiscuous relationships of menthol and other sensory compounds. Mol Cell Neurosci. 2006 Aug;32(4):335-43.
45 Monoterpenoid agonists of TRPV3. Br J Pharmacol. 2007 Jun;151(4):530-40.
46 Cannabinoid actions at TRPV channels: effects on TRPV3 and TRPV4 and their potential relevance to gastrointestinal inflammation. Acta Physiol (Oxf). 2012 Feb;204(2):255-66.
47 Activation of the melastatin-related cation channel TRPM3 by D-erythro-sphingosine [corrected]. Mol Pharmacol. 2005 Mar;67(3):798-805.
48 Cis-isomerism and other chemical requirements of steroidal agonists and partial agonists acting at TRPM3 channels. Br J Pharmacol. 2010 Sep;161(2):430-41.
49 Inhibition of TRPM2 cation channels by N-(p-amylcinnamoyl)anthranilic acid. Br J Pharmacol. 2006 Jun;148(3):264-73.
50 Nicotinic acid adenine dinucleotide phosphate and cyclic ADP-ribose regulate TRPM2 channels in T lymphocytes. FASEB J. 2006 May;20(7):962-4.
51 Metabolite of SIR2 reaction modulates TRPM2 ion channel. J Biol Chem. 2006 May 19;281(20):14057-65.
52 ADP-ribose gating of the calcium-permeable LTRPC2 channel revealed by Nudix motif homology. Nature. 2001 May 31;411(6837):595-9.
53 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: 494).
54 Simple 2,4-diacylphloroglucinols as classic transient receptor potential-6 activators--identification of a novel pharmacophore. Mol Pharmacol. 2010 Mar;77(3):368-77.
55 Lysophospholipids stimulate prostate cancer cell migration via TRPV2 channel activation. Biochim Biophys Acta. 2009 Mar;1793(3):528-39.
56 TRPV2 is activated by cannabidiol and mediates CGRP release in cultured rat dorsal root ganglion neurons. J Neurosci. 2008 Jun 11;28(24):6231-8.
57 Capsaicin receptor: TRPV1 a promiscuous TRP channel. Handb Exp Pharmacol. 2007;(179):155-71.
58 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
59 An investigation of the safety and pharmacokinetics of the novel TRPV1 antagonist XEN-D0501 in healthy subjects. Br J Clin Pharmacol. 2011 Dec;72(6):921-31.
60 Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
61 Development of PAC-14028, a novel transient receptor potential vanilloid type 1 (TRPV1) channel antagonist as a new drug for refractory skin diseases. Arch Pharm Res. 2012 Mar;35(3):393-6.
62 The discovery and development of analgesics: new mechanisms, new modalities. J Clin Invest. 2010 November 1; 120(11): 3753-3759.
63 TRPV1 Antagonists as Analgesic Agents. The Open Pain Journal, 2013, 6, (Suppl 1: M11), 108-118 .
64 Analgesic potential of TRPV1 antagonists. Biochem Pharmacol. 2009 Aug 1;78(3):211-6.
65 GRC-6211, a new oral specific TRPV1 antagonist, decreases bladder overactivity and noxious bladder input in cystitis animal models. J Urol. 2009 Jan;181(1):379-86.