Details of the Drug

General Information of Drug (ID: DMDINFS)

Drug Name

Sanguinarine

Synonyms

SANGUINARINE; 2447-54-3; Pseudochelerythrine; Sanguinarin; sangvinarin; Veadent; Sanguiritrin; SANGUINARIUM; Dimethylenedioxy benzphenanthridine; UNII-AV9VK043SS; C20H14NO4; EINECS 219-503-3; Benzophenanthridine alkaloid; BRN 3915507; AV9VK043SS; CHEBI:17183; NCGC00015959-03; CAS-2447-54-3; [1,3]Benzodioxolo[5,6-c]-1,3-dioxolo[4,5-i]phenanthridinium, 13-methyl-; DSSTox_RID_80748; DSSTox_CID_25204; DSSTox_GSID_45204; 13-Methyl[1,3]benzodioxolo[5,6-C][1,3]dioxolo[4,5-I]phenanthridin-13-Ium; Sangrovit; y-Chelerythrine; SR-01000075650

Indication

Disease Entry	ICD 11	Status	REF
Dental plaque	DA08.4	Approved	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

332.3

Logarithm of the Partition Coefficient (xlogp)

4.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C20H14NO4+
IUPAC Name: 24-methyl-5,7,18,20-tetraoxa-24-azoniahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(24),2,4(8),9,11,13,15,17(21),22-nonaene
Canonical SMILES: C[N+]1=C2C(=C3C=CC4=C(C3=C1)OCO4)C=CC5=CC6=C(C=C52)OCO6
InChI: InChI=1S/C20H14NO4/c1-21-8-15-12(4-5-16-20(15)25-10-22-16)13-3-2-11-6-17-18(24-9-23-17)7-14(11)19(13)21/h2-8H,9-10H2,1H3/q+1
InChIKey: INVGWHRKADIJHF-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5154
ChEBI ID: CHEMBL417799
CAS Number: 2447-54-3
TTD ID: D0T3NB
VARIDT ID: DR00919

Drug-Molecule Activity Atlas (DMA)^NEW

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Drug Pharmacogenomic Perturbation (DPP)^NEW

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Drug ADMET Endpoint Profile (DAE)^NEW

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Sodium/potassium-transporting ATPase (SPT ATPase)	TTQ38E9	AT1A1_HUMAN ; AT1A2_HUMAN ; AT1A3_HUMAN ; AT1B1_HUMAN ; AT1B2_HUMAN ; AT1B3_HUMAN	Modulator	[2]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis facilitator Bcl-2-like protein 14 (BCL2L14)	OT87E7HW	B2L14_HUMAN	Gene/Protein Processing	[3]
BH3-interacting domain death agonist (BID)	OTOSHSHU	BID_HUMAN	Protein Interaction/Cellular Processes	[4]
Claudin-2 (CLDN2)	OTRF3D6Y	CLD2_HUMAN	Gene/Protein Processing	[5]
Claudin-3 (CLDN3)	OT71MN9S	CLD3_HUMAN	Gene/Protein Processing	[5]
Claudin-5 (CLDN5)	OTUX60YO	CLD5_HUMAN	Gene/Protein Processing	[5]
Hematopoietic prostaglandin D synthase (HPGDS)	OTU8FWHU	HPGDS_HUMAN	Gene/Protein Processing	[6]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[7]
Mitogen-activated protein kinase 3 (MAPK3)	OTCYKGKO	MK03_HUMAN	Post-Translational Modifications	[7]
Mitogen-activated protein kinase 8 (MAPK8)	OTEREYS5	MK08_HUMAN	Post-Translational Modifications	[7]
Mitogen-activated protein kinase 9 (MAPK9)	OTCEVJ9E	MK09_HUMAN	Post-Translational Modifications	[7]

Molecular Interaction Atlas (MIA)

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References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Medicinal plants in therapy. Bull World Health Organ. 1985;63(6):965-81.
3	Improved apoptotic cell death in drug-resistant non-small-cell lung cancer cells by tumor necrosis factor-related apoptosis-inducing ligand-based treatment. J Pharmacol Exp Ther. 2014 Mar;348(3):360-71. doi: 10.1124/jpet.113.210054. Epub 2013 Dec 17.
4	Sanguinarine induces apoptosis in human colorectal cancer HCT-116 cells through ROS-mediated Egr-1 activation and mitochondrial dysfunction. Toxicol Lett. 2013 Jul 4;220(2):157-66. doi: 10.1016/j.toxlet.2013.04.020. Epub 2013 May 6.
5	Anti-invasive activity of sanguinarine through modulation of tight junctions and matrix metalloproteinase activities in MDA-MB-231 human breast carcinoma cells. Chem Biol Interact. 2009 May 15;179(2-3):185-91. doi: 10.1016/j.cbi.2008.11.009. Epub 2008 Nov 21.
6	Identification of new inhibitors for human hematopoietic prostaglandin D2 synthase among FDA-approved drugs and other compounds. Chem Biol Interact. 2015 Mar 5;229:91-9. doi: 10.1016/j.cbi.2015.01.014. Epub 2015 Jan 17.
7	Sanguinarine induces apoptosis in A549 human lung cancer cells primarily via cellular glutathione depletion. Toxicol In Vitro. 2009 Mar;23(2):281-7. doi: 10.1016/j.tiv.2008.12.013. Epub 2008 Dec 24.