maraviroc   Click here for help

GtoPdb Ligand ID: 806

Synonyms: Celsentri® | Selzentry® | UK 427857 | UK-427,857
Approved drug Immunopharmacology Ligand
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.
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2D Structure
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Physico-chemical Properties
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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
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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 Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA and FDA (2007))
IUPAC Name Click here for help
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 Click here for help
INN number INN
8450 maraviroc
Synonyms Click here for help
Celsentri® | Selzentry® | UK 427857 | UK-427,857
Database Links Click here for help
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
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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