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Compound Detail

CHEMBL256907

MARAVIROC
💊 Approved Drug
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💊 Approved Drug
Cc1nnc(C(C)C)n1[C@H]1C[C@H]2CC[C@@H](C1)N2CC[C@H](NC(=O)C1CCC(F)(F)CC1)c1ccccc1

Basic Information

ChEMBL ID CHEMBL256907
Name MARAVIROC
Phase Approved
Structure Type MOL
InChI Key GSNHKUDZZFZSJB-QUMGSSFMSA-N
Therapeutic ✓ Yes

Known Names

Celsentri Maraviroc Rel-maraviroc Selzentry Uk-427,857 UK-427857
10
Targets
92
Activities
4
Assay Types
30
PK Parameters
20
Publications
6
Known Names
20
Indications
1
Mechanisms

Molecular Properties

513.7
MW (Da)
5.95
ALogP
5
HBA
1
HBD
63.0
PSA (Ų)
0.47
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2007
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning First in Class
USAN Stem -vir-

Extended Properties

Molecular Formula C29H41F2N5O
MW 513.68
Aromatic Rings 2
Heavy Atoms 37
NP-Likeness -0.85

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
C-C chemokine receptor type 5 antagonist ANTAGONIST C-C chemokine receptor type 5

Indications

HIV Infections HIV Infections Virus Diseases Acquired Immunodeficiency Syndrome Infections AIDS Dementia Complex Arthritis, Rheumatoid Cognitive Dysfunction Graft vs Host Disease Hematologic Neoplasms Hodgkin Disease Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Myelogenous, Chronic, BCR-ABL Positive Lymphoma, Follicular Lymphoma, Large B-Cell, Diffuse Myelodysplastic Syndromes Sarcoma, Kaposi Severe Acute Respiratory Syndrome Stroke Hypertriglyceridemia

ATC Classification

J05AX09
maraviroc
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
hepatotoxicity
Country: United States

Activity Summary

IC50 63 meas. best 9.7
EC50 25 meas. best 9.52
Ki 3 meas. best 9.62
Kd 1 meas. best 7.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
C-C chemokine receptor type 5
CHEMBL274
IC50 9.7 8.77 0.2 20
Unchecked
CHEMBL612545
IC50 9.7 9.7 0.2 1
C-C chemokine receptor type 5
CHEMBL274
Ki 9.62 9.62 0.2 1
C-C chemokine receptor type 5
CHEMBL3217397
Ki 9.62 9.62 0.2 2
Human immunodeficiency virus 1
CHEMBL378
EC50 9.52 8.6329 0.3 24
Human immunodeficiency virus 1
CHEMBL378
IC50 9.52 8.3963 0.3 27
C-C chemokine receptor type 5
CHEMBL274
EC50 9.0 9.0 1.0 1
C-C chemokine receptor type 5
CHEMBL3676
IC50 8.28 8.28 5.2 1
C-C chemokine receptor type 5
CHEMBL274
Kd 7.6 7.6 25.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 5.51 5.17 3100.0 2
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 5.11 4.5367 7750.0 3
Cytochrome P450 2C9
CHEMBL3397
IC50 4.84 4.84 14400.0 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
IC50 4.76 4.76 17300.0 1
Voltage-gated potassium channel, IKs; KCNQ1(Kv7.1)/KCNE1(MinK)
CHEMBL2221347
IC50 4.2 4.2 63095.7 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 583.0 ng.hr.mL-1 Canis lupus familiaris
AUC 12.4 ng.hr.mL-1 Rattus norvegicus
AUC 12.4 ng.hr.mL-1 Rattus norvegicus
AUC 2099.0 ng.hr.mL-1 Homo sapiens
AUC 1761.0 ng.hr.mL-1 Homo sapiens
AUC 1238.0 ng.hr.mL-1 Homo sapiens
AUC 12.4 ng.hr.mL-1 Rattus norvegicus
AUC 567.17 ng.hr.mL-1 Rattus norvegicus
CL 20.0 mL.min-1.g-1 Homo sapiens
CL 74.0 mL.min-1.kg-1 Rattus norvegicus
CL 9.0 mL.min-1.g-1 Canis lupus familiaris
CL 6.0 mL.min-1.g-1 Rattus norvegicus
CL 53.0 mL.min-1.kg-1 Canis lupus familiaris
CL 21.0 mL.min-1.kg-1 Canis lupus familiaris
CL 137.0 mL.min-1.kg-1 Rattus norvegicus
CL 74.0 mL.min-1.kg-1 Rattus norvegicus
CL 49.0 mL.min-1.g-1 Homo sapiens
CL 1233.33 mL.min-1.kg-1 Rattus norvegicus
CL 350.0 mL.min-1.kg-1 Canis lupus familiaris
CL 74000.0 mL.min-1.g-1 Rattus norvegicus
Cmax 10.71 nM Rattus norvegicus
Cmax 10.71 nM Rattus norvegicus
Cmax 498.36 nM Canis lupus familiaris
Cmax 10.71 nM Rattus norvegicus
F 42.0 % Canis lupus familiaris
F 6.0 % Rattus norvegicus
F 6.0 % Rattus norvegicus
F 6.0 % Rattus norvegicus
F 40.0 % Canis lupus familiaris
F 6.0 % Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
C-C chemokine receptor type 5 IC50 = 0.2 nM 9.7 Antagonist activity at human recombinant CCR5 expressed in human HeLa-P4 cells a... 19185490
C-C chemokine receptor type 5 IC50 = 0.2 nM 9.7 Antagonist activity at human recombinant CCR5 expressed in human HeLa-P4 cells a... 19171484
Unchecked IC50 = 0.2 nM 9.7 Inhibition of CXCR4-Y251A mutant (unknown origin) 28165741
C-C chemokine receptor type 5 IC50 = 0.2 nM 9.7 Inhibition of CCR5 in human TZM-bl cells infected with HIV1 Bal R5 assessed as a... 28082070
C-C chemokine receptor type 5 IC50 = 0.2 nM 9.7 Antagonist activity at CCR5 receptor expressed in HeLa-P4 cells co-expressing CD... 21128663
C-C chemokine receptor type 5 Ki = 0.24 nM 9.62 Displacement of [125I]MIP-1alpha from CCR5 receptor in rhesus monkey membrane in... 27720326
C-C chemokine receptor type 5 Ki = 0.24 nM 9.62 Radioligand Binding Assay: Afterwards, the pharmacological profile of bivalent l... -
C-C chemokine receptor type 5 Ki = 0.24 nM 9.62 Displacement of [125I]-MIP-1alpha from CCR5 in rhesus monkey Chem-1 cell membran... 23682308
Human immunodeficiency virus 1 EC50 = 0.3 nM 9.52 Antiviral activity against HIV1 US2 clade B, R5 in human PBMC assessed as p24 an... 19805567
Human immunodeficiency virus 1 IC50 = 0.3 nM 9.52 Antiviral activity against Human immunodeficiency virus 1 clade B isolate US2 in... 24090135
Human immunodeficiency virus 1 EC50 = 0.34 nM 9.47 Antiviral activity against HIV-1 Ba-L infected in human PM1 cells measured after... 36472561
C-C chemokine receptor type 5 IC50 = 0.37 nM 9.43 Antagonist activity against CCR5 receptor in human TZM-bl cells assessed as inhi... 24563723
Human immunodeficiency virus 1 EC50 = 0.4 nM 9.4 Antiviral activity against HIV1 strain I-2496 in human PBMC assessed as p24 anti... 19805567
C-C chemokine receptor type 5 IC50 = 0.43 nM 9.37 Antagonist activity against CCR5 receptor in human TZM-bl cells assessed as inhi... 24563723
C-C chemokine receptor type 5 IC50 = 0.82 nM 9.09 Antagonist activity at human CCR5 receptor expressed in HEK293 cells co-expressi... 34261320
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against HIV1 clade D (UG270) infected in human PBMCs assessed... 22712652
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against HIV1 clade A/E (ID12) infected in human PBMCs assesse... 22712652
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against HIV1 clade C (DJ259) infected in human PBMCs assessed... 22712652
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against HIV1 clade A (UG273) infected in human PBMCs assessed... 22712652
Human immunodeficiency virus 1 EC50 = 1.0 nM 9.0 Antiviral activity against HIV1 clade B (BaL) infected in human PBMCs assessed a... 22712652

Literature References

PubMed DOI Target Context # Activities
24090135 10.1021/jm401101p Human immunodeficiency virus 1 22
32097005 10.1021/acs.jmedchem.9b01840 Unchecked 20
36472561 10.1021/acs.jmedchem.2c01383 ADMET 14
30108760 10.1039/C6MD00575F Human immunodeficiency virus 1 14
32097005 10.1021/acs.jmedchem.9b01840 ADMET 13
36472561 10.1021/acs.jmedchem.2c01383 Human immunodeficiency virus 1 10
30234300 10.1021/acs.jmedchem.8b01077 Unchecked 10
30234300 10.1021/acs.jmedchem.8b01077 Rattus norvegicus 9
19805567 10.1128/aac.00827-09 Human immunodeficiency virus 1 8
21128663 10.1021/jm100978n Canis familiaris 8
22712652 10.1021/jm300477h Human immunodeficiency virus 1 8
21128663 10.1021/jm100978n Rattus norvegicus 7
30234300 10.1021/acs.jmedchem.8b01077 ADMET 7
30234300 10.1021/acs.jmedchem.8b01077 Human immunodeficiency virus 1 7
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
30234300 10.1021/acs.jmedchem.8b01077 Canis familiaris 6
18194864 10.1016/j.bmcl.2007.12.058 Human immunodeficiency virus 1 5
24563723 10.1021/ml400370w C-C chemokine receptor type 5 4
27720326 10.1016/j.bmc.2016.09.059 Human immunodeficiency virus 1 4
25087753 10.1016/j.vascn.2014.07.002 Voltage-gated inwardly rectifying potassium channel KCNH2 3

Data from ChEMBL 36 via Core Engine