Details of the Drug

General Information of Drug (ID: DM9G5XD)

Drug Name

IB-MECA

Synonyms

IB-Meca; 152918-18-8; piclidenoson; CF-101; 3-IB-Meca; N(6)-Ibamu; CF 101; Cf101; N(6)-(3-iodobenzyl)-5'-N-methylcarboxamidoadenosine; UNII-30679UMI0N; N(6)-(3-Iodobenzyl)adenosine-5'-N-methyluronamide; 1-Deoxy-1-(6-(((3-iodophenyl)methyl)amino)-9H-purin-9-yl)-N-methyl-beta-D-ribofuranuronamide; CHEMBL119709; CHEBI:73286; 30679UMI0N; RPR-113090; 3-iodobenzyl-5'-N-methylcarboxamidoadenosine; N(6)-(3-iodo-benzyl)adenosine-5'-N-methyluronamide; 3-IB-MECA

Indication

Disease Entry	ICD 11	Status	REF
Psoriasis vulgaris	EA90	Phase 3	[1]
Solid tumour/cancer	2A00-2F9Z	Phase 3	[2]
Plaque psoriasis	EA90.0	Phase 2/3	[3]
Rheumatoid arthritis	FA20	Phase 2	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

510.3

Logarithm of the Partition Coefficient (xlogp)

0.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C18H19IN6O4
IUPAC Name: (2S,3S,4R,5R)-3,4-dihydroxy-5-[6-[(3-iodophenyl)methylamino]purin-9-yl]-N-methyloxolane-2-carboxamide
Canonical SMILES: CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=CC=C4)I)O)O
InChI: InChI=1S/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1
InChIKey: HUJXGQILHAUCCV-MOROJQBDSA-N

Cross-matching ID

PubChem CID: 123683
ChEBI ID: CHEBI:73286
CAS Number: 152918-18-8
DrugBank ID: DB05511
TTD ID: D0Y6ZK

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adenosine A3 receptor (ADORA3)	TTJFY5U	AA3R_HUMAN	Agonist	[4]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Baculoviral IAP repeat-containing protein 1 (NAIP)	OTLA925F	BIRC1_HUMAN	Gene/Protein Processing	[5]
Baculoviral IAP repeat-containing protein 3 (BIRC3)	OT3E95KB	BIRC3_HUMAN	Gene/Protein Processing	[5]
Baculoviral IAP repeat-containing protein 5 (BIRC5)	OTILXZYL	BIRC5_HUMAN	Drug Response	[5]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2	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: 422).
3	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4	A role for central A3-adenosine receptors. Mediation of behavioral depressant effects. FEBS Lett. 1993 Dec 20;336(1):57-60.
5	Induction of apoptosis by the adenosine derivative IB-MECA in parental or multidrug-resistant HL-60 leukemia cells: possible relationship to the effects on inhibitor of apoptosis protein levels. Chemotherapy. 2005 Aug;51(5):272-9. doi: 10.1159/000087255. Epub 2005 Jul 26.