Details of the Drug

General Information of Drug (ID: DMQAK6T)

Drug Name

Rhodamine-123

Synonyms

RH 123; Rhodamine 123; Rh-123, Huntington; Rhodamine-123 (intravenous infusion); Rhodamine-123 (intravenous infusion), Huntington Medical Research Institutes

Indication

Disease Entry	ICD 11	Status	REF
Prostate cancer	2C82.0	Discontinued in Phase 1	[1]
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Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski):
0

Molecular Weight

380.8

Logarithm of the Partition Coefficient

Not Available

Rotatable Bond Count

3

Hydrogen Bond Donor Count

3

Hydrogen Bond Acceptor Count

5

Chemical Identifiers

Formula: C21H17ClN2O3
IUPAC Name: methyl 2-(3-amino-6-iminoxanthen-9-yl)benzoate;hydrochloride
Canonical SMILES: COC(=O)C1=CC=CC=C1C2=C3C=CC(=N)C=C3OC4=C2C=CC(=C4)N.Cl
InChI: InChI=1S/C21H16N2O3.ClH/c1-25-21(24)15-5-3-2-4-14(15)20-16-8-6-12(22)10-18(16)26-19-11-13(23)7-9-17(19)20;/h2-11,22H,23H2,1H3;1H
InChIKey: MYFATKRONKHHQL-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 9929799
ChEBI ID: CHEBI:8828
CAS Number: 62669-70-9
TTD ID: D0G1RA
VARIDT ID: DR00195

Molecular Interaction Atlas of This Drug

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Multidrug resistance-associated protein 2 (ABCC2)	DTFI42L	MRP2_HUMAN	Substrate	[2]
Organic anion transporting polypeptide 1A2 (SLCO1A2)	DTE2B1D	SO1A2_HUMAN	Substrate	[3]
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[4]
P-glycoprotein 1 (ABCB1)	DTUGYRD	MDR1_HUMAN	Substrate	[5]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
ATP-dependent translocase ABCB1 (ABCB1)	OTEJROBO	MDR1_HUMAN	Regulation of Drug Effects	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction 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: 4607).
2	Characterization of rhodamine-123, calcein and 5(6)-carboxy-2',7'-dichlorofluorescein (CDCF) export via MRP2 (ABCC2) in MES-SA and A549 cells. Eur J Pharm Sci. 2011 Aug 17;43(5):359-69.
3	Characterization of rhodamine-123 as a tracer dye for use in in vitro drug transport assays. PLoS One. 2012;7(3):e33253.
4	Alectinib (CH5424802) antagonizes ABCB1- and ABCG2-mediated multidrug resistance in vitro, in vivo and ex vivo. Exp Mol Med. 2017 Mar 17;49(3):e303.
5	Modulation of drug-stimulated ATPase activity of human MDR1/P-glycoprotein by cholesterol. Biochem J. 2007 Jan 15;401(2):597-605.
6	Structure-activity relationship and mechanism of flavonoids on the inhibitory activity of P-glycoprotein (P-gp)-mediated transport of rhodamine123 and daunorubicin in P-gp overexpressed human mouth epidermal carcinoma (KB/MDR) cells. Food Chem Toxicol. 2021 Sep;155:112381. doi: 10.1016/j.fct.2021.112381. Epub 2021 Jul 1.