Details of the Drug

General Information of Drug (ID: DMYEAB1)

• Drug Name: PIPERINE
• Synonyms: piperine; 94-62-2; 1-Piperoylpiperidine; Piperin; Bioperine; Piperoylpiperidine; (E,E)-1-piperoylpiperidine; N-[(E,E)-Piperoyl]piperidine; Piperidine, 1-piperoyl-, (E,E)-; UNII-U71XL721QK; FEMA No. 2909; CCRIS 5572; Piperine (aliphatic); 1-Piperoylpiperidine, (E,E)-; 7780-20-3; C17H19NO3; EINECS 202-348-0; NSC 21727; 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoyl]piperidine; N-(E,E)-piperoyl-piperidine; CHEMBL43185; U71XL721QK; CHEBI:28821; MXXWOMGUGJBKIW-YPCIICBESA-N; NSC21727; piperidine, 1-[(2E,4E)-5-(1,3-benzodioxol-5-yl)

Indication

Disease Entry	ICD 11	Status	REF
Vitiligo	ED63.0	Phase 1/2	[1], [2]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 285.34
  Topological Polar Surface Area (xlogp); 3.5
  Rotatable Bond Count (rotbonds); 3
  Hydrogen Bond Donor Count (hbonddonor); 0
  Hydrogen Bond Acceptor Count (hbondacc); 3
• Chemical Identifiers:
  Formula: C17H19NO3
  IUPAC Name: (2E,4E)-5-(1,3-benzodioxol-5-yl)-1-piperidin-1-ylpenta-2,4-dien-1-one
  Canonical SMILES: C1CCN(CC1)C(=O)/C=C/C=C/C2=CC3=C(C=C2)OCO3
  InChI: InChI=1S/C17H19NO3/c19-17(18-10-4-1-5-11-18)7-3-2-6-14-8-9-15-16(12-14)21-13-20-15/h2-3,6-9,12H,1,4-5,10-11,13H2/b6-2+,7-3+
  InChIKey: MXXWOMGUGJBKIW-YPCIICBESA-N
• Cross-matching ID:
  PubChem CID: 638024
  ChEBI ID: CHEBI:28821
  CAS Number: 94-62-2
  DrugBank ID: DB12582
  TTD ID: D0H7PW

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Monoamine oxidase type A (MAO-A)	TT3WG5C	AOFA_HUMAN	Inhibitor	[3]
Monoamine oxidase type B (MAO-B)	TTGP7BY	AOFB_HUMAN	Inhibitor	[3]

Molecular Expression Atlas of This Drug

• The Studied Disease: Vitiligo
• ICD Disease Classification: ED63.0

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Monoamine oxidase type B (MAO-B)	DTT	MAOB	2.65E-02	1.12E-02	0.07
Monoamine oxidase type A (MAO-A)	DTT	MAOA	8.14E-01	0.05	0.1

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: 2489).
• [2] ClinicalTrials.gov (NCT01383694) Effect Of Piperine In Patients With Oropharyngeal Dysphagia. U.S. National Institutes of Health.
• [3] Proposed structural basis of interaction of piperine and related compounds with monoamine oxidases. Bioorg Med Chem Lett. 2010 Jan 15;20(2):537-40.
• [4] Emerging drugs for Parkinson's disease. Expert Opin Emerg Drugs. 2006 Sep;11(3):403-17.
• [5] Limitation of adipose tissue enlargement in rats chronically treated with semicarbazide-sensitive amine oxidase and monoamine oxidase inhibitors. Pharmacol Res. 2008 Jun;57(6):426-34.
• [6] Tranylcypromine: new perspectives on an "old" drug. Eur Arch Psychiatry Clin Neurosci. 2006 Aug;256(5):268-73.
• [7] 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: 2490).
• [8] 2017 FDA drug approvals.Nat Rev Drug Discov. 2018 Feb;17(2):81-85.
• [9] Glyceraldehyde-3-phosphate dehydrogenase-monoamine oxidase B-mediated cell death-induced by ethanol is prevented by rasagiline and 1-R-aminoindan. Neurotox Res. 2009 Aug;16(2):148-59.
• [10] Novel monoamine oxidase inhibitors, 3-(2-aminoethoxy)-1,2-benzisoxazole derivatives, and their differential reversibility. Jpn J Pharmacol. 2002 Feb;88(2):174-82.
• [11] Dose-dependent activation of distinct hypertrophic pathways by serotonin in cardiac cells. Am J Physiol Heart Circ Physiol. 2009 Aug;297(2):H821-8.
• [12] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
• [13] Multiple mechanisms of action: the pharmacological profile of budipine. J Neural Transm Suppl. 1999;56:83-105.
• [14] Efficacy of citalopram and moclobemide in patients with social phobia: some preliminary findings. Hum Psychopharmacol. 2002 Dec;17(8):401-5.
• [15] Tramadol and another atypical opioid meperidine have exaggerated serotonin syndrome behavioural effects, but decreased analgesic effects, in genetically deficient serotonin transporter (SERT) mice. Int J Neuropsychopharmacol. 2009 Mar 11:1-11.
• [16] Further investigation into the mechanism of tachykinin NK(2) receptor-triggered serotonin release from guinea-pig proximal colon. J Pharmacol Sci. 2009 May;110(1):122-6.
• [17] MAOIs in the contemporary treatment of depression. Neuropsychopharmacology. 1995 May;12(3):185-219.
• [18] Binding of beta-carbolines at imidazoline I2 receptors: a structure-affinity investigation. Bioorg Med Chem Lett. 2004 Feb 23;14(4):999-1002.
• [19] Inhibition of rat brain monoamine oxidase activities by psoralen and isopsoralen: implications for the treatment of affective disorders. Pharmacol Toxicol. 2001 Feb;88(2):75-80.
• [20] Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
• [21] Ladostigil: a novel multimodal neuroprotective drug with cholinesterase and brain-selective monoamine oxidase inhibitory activities for Alzheimer's disease treatment. Curr Drug Targets. 2012 Apr;13(4):483-94.
• [22] Reversible inhibitors of monoamine oxidase-A (RIMAs): robust, reversible inhibition of human brain MAO-A by CX157. Neuropsychopharmacology. 2010 Feb;35(3):623-31.
• [23] Phase I clinical trial with desoxypeganine, a new cholinesterase and selective MAO-A inhibitor: tolerance and pharmacokinetics study of escalating single oral doses. Methods Find Exp Clin Pharmacol. 2008 Mar;30(2):141-7.