Details of the Drug

General Information of Drug (ID: DM1ZQ5G)

Drug Name

(S)-Xamoterol

Synonyms

UNII-ZIB581LRDV; ZIB581LRDV; (S)-Xamoterol; Xamoterol, (S)-; 69630-22-4; SCHEMBL11533496; ZINC1532365; UNII-7HE0JQL703 component DXPOSRCHIDYWHW-AWEZNQCLSA-N; 4-Morpholinecarboxamide, N-(2-(((2S)-2-hydroxy-3-(4-hydroxyphenoxy)propyl)amino)ethyl)-

Indication

Disease Entry	ICD 11	Status	REF
Heart failure	BD10-BD13	Preclinical	[1]

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

339.39

Topological Polar Surface Area (xlogp)

-0.6

Rotatable Bond Count (rotbonds)

8

Hydrogen Bond Donor Count (hbonddonor)

4

Hydrogen Bond Acceptor Count (hbondacc)

6

Chemical Identifiers

Formula: C16H25N3O5
IUPAC Name: N-[2-[[(2S)-2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino]ethyl]morpholine-4-carboxamide
Canonical SMILES: C1COCCN1C(=O)NCCNCC(COC2=CC=C(C=C2)O)O
InChI: InChI=1S/C16H25N3O5/c20-13-1-3-15(4-2-13)24-12-14(21)11-17-5-6-18-16(22)19-7-9-23-10-8-19/h1-4,14,17,20-21H,5-12H2,(H,18,22)/t14-/m0/s1
InChIKey: DXPOSRCHIDYWHW-AWEZNQCLSA-N

Cross-matching ID

PubChem CID: 12681891
CAS Number: 69630-22-4
VARIDT ID: DR01671

Molecular Interaction Atlas of This Drug

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Xamoterol, a beta 1-adrenoceptor partial agonist: review of the clinical efficacy in heart failure. Br J Clin Pharmacol. 1989;28 Suppl 1:23S-30S.
2	Identification of novel substrates and structure-activity relationship of cellular uptake mediated by human organic cation transporters 1 and 2. J Med Chem. 2013 Sep 26;56(18):7232-42.
3	Are organic cation transporters capable of transporting prostaglandins? Naunyn Schmiedebergs Arch Pharmacol. 2005 Aug;372(2):125-30.
4	Cisplatin and oxaliplatin, but not carboplatin and nedaplatin, are substrates for human organic cation transporters (SLC22A1-3 and multidrug and toxin extrusion family). J Pharmacol Exp Ther. 2006 Nov;319(2):879-86.
5	Pharmacologic markers and predictors of responses to imatinib therapy in patients with chronic myeloid leukemia. Leuk Lymphoma. 2008 Apr;49(4):639-42.
6	Organic cation transporters are determinants of oxaliplatin cytotoxicity. Cancer Res. 2006 Sep 1;66(17):8847-57.
7	Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007.
8	Implications of genetic polymorphisms in drug transporters for pharmacotherapy. Cancer Lett. 2006 Mar 8;234(1):4-33.
9	Upregulation of histone acetylation reverses organic anion transporter 2 repression and enhances 5-fluorouracil sensitivity in hepatocellular carcinoma
10	Comparison of type I and type II organic cation transport by organic cation transporters and organic anion-transporting polypeptides. J Pharmacol Exp Ther. 2001 Jul;298(1):110-5.
11	Organic cation transporters and their pharmacokinetic and pharmacodynamic consequences. Drug Metab Pharmacokinet. 2008;23(4):243-53.
12	Influx Transport of Cationic Drug at the Blood-Retinal Barrier: Impact on the Retinal Delivery of Neuroprotectants. Biol Pharm Bull. 2017;40(8):1139-1145.