maraviroc   

GtoPdb Ligand ID: 806

Synonyms: Celsentri® | Selzentry® | UK 427857 | UK-427,857
maraviroc is an approved drug (EMA and FDA (2007))
Compound class: Synthetic organic
Comment: Maraviroc is a small molecule antagonist of the C-C chemokine receptor type 5 (CCR5) expressed on T cells.

The stereochemistry of maraviroc as specified by the PDB compound link varies from that specified in our structure and that of CID 3002977.The compound is represented on ChEMBL by CHEMBL1201187.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 63.05
Molecular weight 513.33
XLogP 6.82
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C(C1CCC(CC1)(F)F)NC(c1ccccc1)CCN1C2CCC1CC(C2)n1c(C)nnc1C(C)C
Isomeric SMILES O=C(C1CCC(CC1)(F)F)N[C@H](c1ccccc1)CCN1[C@@H]2CC[C@H]1CC(C2)n1c(C)nnc1C(C)C
InChI InChI=1S/C29H41F2N5O/c1-19(2)27-34-33-20(3)36(27)25-17-23-9-10-24(18-25)35(23)16-13-26(21-7-5-4-6-8-21)32-28(37)22-11-14-29(30,31)15-12-22/h4-8,19,22-26H,9-18H2,1-3H3,(H,32,37)/t23-,24+,25?,26-/m0/s1
InChI Key GSNHKUDZZFZSJB-HLMSNRGBSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (EMA and FDA (2007))
IUPAC Name
4,4-difluoro-N-[(1S)-3-[(1R,5S)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-phenylpropyl]cyclohexane-1-carboxamide
International Nonproprietary Names
INN number INN
8450 maraviroc
Synonyms
Celsentri® | Selzentry® | UK 427857 | UK-427,857
Database Links
CAS Registry No. 376348-65-1 (source: Scifinder)
DrugBank Ligand DB04835
GtoPdb PubChem SID 135650567
PubChem CID 3002977
Search Google for chemical match using the InChIKey GSNHKUDZZFZSJB-HLMSNRGBSA-N
Search Google for chemicals with the same backbone GSNHKUDZZFZSJB
Search PubMed clinical trials maraviroc
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Search UniChem for chemical match using the InChIKey GSNHKUDZZFZSJB-HLMSNRGBSA-N
Search UniChem for chemicals with the same backbone GSNHKUDZZFZSJB
SynPHARM 2313 (in complex with CCR5)
Wikipedia Maraviroc