Details of the Drug

General Information of Drug (ID: DMCT2YF)

• Drug Name: Emetine
• Synonyms: Emetine hydrochloride; EMETINE; 14198-59-5; MLS000028478; SMR000058444; NSC-33669; NSC33669; Emetine monohydrochloride; Opera_ID_1460; Cephaeline methyl ether HCl; AC1O7FP4; SCHEMBL636599; CHEMBL513000; DTXSID80424947; MolPort-004-964-890; Cephaeline methyl ether hydrochloride; NSC752340; AKOS024374935; NSC-752340; ST51014995; Emetan,7',10,11-tetramethoxy-, dihydrochloride; Q-100155; 10-[((1R)-6,7-dimethoxy(1,2,3,4-tetrahydroisoquinolyl))methyl](10S,11aS,9R)-9- ethyl-2,3-dimethoxy-5,6,7,11a-tetrahydropiperidino[2,1-a]isoquinolin

Indication

Disease Entry	ICD 11	Status	REF
Hepatitis virus infection	1E50-1E51	Approved	[1]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 480.6
  Logarithm of the Partition Coefficient (xlogp); 4.7
  Rotatable Bond Count (rotbonds); 7
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 6
• Chemical Identifiers:
  Formula: C29H40N2O4
  IUPAC Name: (2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine
  Canonical SMILES: CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC
  InChI: InChI=1S/C29H40N2O4/c1-6-18-17-31-10-8-20-14-27(33-3)29(35-5)16-23(20)25(31)12-21(18)11-24-22-15-28(34-4)26(32-2)13-19(22)7-9-30-24/h13-16,18,21,24-25,30H,6-12,17H2,1-5H3/t18-,21-,24+,25-/m0/s1
  InChIKey: AUVVAXYIELKVAI-CKBKHPSWSA-N
• Cross-matching ID:
  PubChem CID: 10219
  ChEBI ID: CHEBI:4781
  CAS Number: 483-18-1
  DrugBank ID: DB13393
  TTD ID: D07DJQ
  VARIDT ID: DR00554
  INTEDE ID: DR0571

Molecular Interaction Atlas of This Drug

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[2]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4)	DE4LYSA	CP3A4_HUMAN	Substrate	[3]
Cytochrome P450 2D6 (CYP2D6)	DECB0K3	CP2D6_HUMAN	Substrate	[3]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
72 kDa type IV collagenase (MMP2)	OT5NIWA2	MMP2_HUMAN	Gene/Protein Processing	[4]
C-C motif chemokine 2 (CCL2)	OTAD2HEL	CCL2_HUMAN	Gene/Protein Processing	[5]
C-C motif chemokine 3 (CCL3)	OTW2H3ND	CCL3_HUMAN	Gene/Protein Processing	[5]
C-C motif chemokine 4 (CCL4)	OT6B8P25	CCL4_HUMAN	Gene/Protein Processing	[5]
C-C motif chemokine 5 (CCL5)	OTSCA5CK	CCL5_HUMAN	Gene/Protein Processing	[5]
Interleukin-6 receptor subunit alpha (IL6R)	OTCQL07Z	IL6RA_HUMAN	Gene/Protein Processing	[5]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[5]
Matrix metalloproteinase-9 (MMP9)	OTB2QDAV	MMP9_HUMAN	Gene/Protein Processing	[4]
Microtubule-associated protein tau (MAPT)	OTMTP2Z7	TAU_HUMAN	Gene/Protein Processing	[6]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[4]

References

• [1] Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
• [2] Potential role of drug transporters in the pathogenesis of medically intractable epilepsy. Epilepsia. 2005 Feb;46(2):224-35.
• [3] Metabolism of ipecac alkaloids cephaeline and emetine by human hepatic microsomal cytochrome P450s, and their inhibitory effects on P450 enzyme activities. Biol Pharm Bull. 2001 Jun;24(6):678-82.
• [4] Emetine inhibits migration and invasion of human non-small-cell lung cancer cells via regulation of ERK and p38 signaling pathways. Chem Biol Interact. 2015 Dec 5;242:25-33. doi: 10.1016/j.cbi.2015.08.014. Epub 2015 Aug 30.
• [5] Cell-based and cytokine-directed chemical screen to identify potential anti-multiple myeloma agents. Leuk Res. 2010 Jul;34(7):917-24. doi: 10.1016/j.leukres.2009.12.002. Epub 2010 Feb 8.
• [6] Pharmacologic reductions of total tau levels; implications for the role of microtubule dynamics in regulating tau expression. Mol Neurodegener. 2006 Jul 26;1:6. doi: 10.1186/1750-1326-1-6.