MARAVIROC

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Trade Names:
Synonyms:
Status: Approved (2007)
Entry Type: Small molecule
Molecule Category: Parent
ATC: J05AX09
UNII: MD6P741W8A

Structure
InChI Key GSNHKUDZZFZSJB-QYOOZWMWSA-N
Smile Cc1nnc(C(C)C)n1[C@H]1C[C@@H]2CC[C@H](C1)N2CC[C@H](NC(=O)C1CCC(F)(F)CC1)c1ccccc1
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C29H41F2N5O
Molecular Weight 513.68
AlogP 5.95
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 63.05
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 37.0

Pharmacology

Action Mechanism of Action Reference
ANTAGONIST C-C chemokine receptor type 5 antagonist DailyMed
Primary Target
CCR5
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Slow voltage-gated potassium channel accessory protein family
- 63096 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 39811-79433 - - 0-0
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CC chemokine receptor
- 0-25 25 0 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- 17300 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
HIV Infections 4 D015658 ClinicalTrials
Virus Diseases 4 D014777 ClinicalTrials
Acquired Immunodeficiency Syndrome 3 D000163 ClinicalTrials
Infections 3 D007239 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Hodgkin Disease 2 D006689 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 2 D015464 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 2 D016403 ClinicalTrials
Stroke 2 D020521 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Hematologic Neoplasms 2 D019337 ClinicalTrials
Sarcoma, Kaposi 2 D012514 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
AIDS Dementia Complex 2 D015526 ClinicalTrials
Arthritis, Rheumatoid 2 D001172 ClinicalTrials
Cognitive Dysfunction 2 D060825 ClinicalTrials
Hypertriglyceridemia 1 D015228 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Infections and infestations Upper respiratory tract infection 23.0
Infections and infestations Upper respiratory tract infection 20.0
Respiratory, thoracic and mediastinal disorders Cough 14.0
Investigations Body temperature increased 13.0
Infections and infestations Upper respiratory tract infection
Infections and infestations Upper respiratory tract infection 13.0
Respiratory, thoracic and mediastinal disorders Cough 12.7
Investigations Body temperature increased 12.0
Infections and infestations Upper respiratory tract infection
Skin and subcutaneous tissue disorders Dermatitis 11.0
Skin and subcutaneous tissue disorders Rash 11.0
Skin and subcutaneous tissue disorders Dermatitis 9.6
Skin and subcutaneous tissue disorders Rash 9.6
Investigations Body temperature increased
Investigations Body temperature increased 9.0
Cardiac disorders Dizziness 9.0
Cardiac disorders Dizziness postural 9.0
Gastrointestinal disorders Abdominal pain 8.2
Cardiac disorders Dizziness 8.2
Cardiac disorders Dizziness postural 8.2
Gastrointestinal disorders Gastrointestinal pain 8.2
Investigations Body temperature increased
Metabolism and nutrition disorders Appetite disorder 8.0
Cardiac disorders Dizziness
Cardiac disorders Dizziness postural
Infections and infestations Herpes virus infection 8.0
Gastrointestinal disorders Abdominal pain
Cardiac disorders Dizziness
Cardiac disorders Dizziness postural
Gastrointestinal disorders Gastrointestinal pain
Metabolism and nutrition disorders Appetite disorder 7.3
Metabolism and nutrition disorders Appetite disorder
Infections and infestations Bronchitis 7.0
Infections and infestations Sinusitis 7.0
Infections and infestations Herpes virus infection 6.8
Infections and infestations Sinusitis 6.3
Metabolism and nutrition disorders Appetite disorder
Gastrointestinal disorders Constipation 6.0
Infections and infestations Bronchitis 5.9
Gastrointestinal disorders Constipation 5.4
Infections and infestations Bronchitis
Infections and infestations Bronchitis 5.0
Respiratory, thoracic and mediastinal disorders Cough
Respiratory, thoracic and mediastinal disorders Cough 5.0
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 5.0
Nervous system disorders Dysaesthesia 5.0
Nervous system disorders Paraesthesia 5.0
Infections and infestations Pneumonia
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 5.0
Respiratory, thoracic and mediastinal disorders Cough
Skin and subcutaneous tissue disorders Dermatitis
Infections and infestations Pneumonia
Skin and subcutaneous tissue disorders Rash
Nervous system disorders Dysaesthesia 4.7
Nervous system disorders Paraesthesia 4.7
Infections and infestations Bronchitis
Nervous system disorders Altered state of consciousness 4.0
Psychiatric disorders Anxiety 4.0
Psychiatric disorders Depression 4.0
General disorders and administration site conditions Discomfort 4.0
Dysthymic disorder 4.0
Infections and infestations Folliculitis 4.0
Infections and infestations Herpes virus infection
Infections and infestations Herpes virus infection 4.0
General disorders and administration site conditions Inflammation 4.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 4.0
Nervous system disorders Neuropathy peripheral 4.0
General disorders and administration site conditions Pain 4.0
Skin and subcutaneous tissue disorders Pruritus 4.0
Respiratory, thoracic and mediastinal disorders Respiration abnormal 4.0
Respiratory, thoracic and mediastinal disorders Respiratory disorder 4.0
Nervous system disorders Altered state of consciousness 3.8
Infections and infestations Herpes virus infection
Skin and subcutaneous tissue disorders Pruritus 3.8
Psychiatric disorders Depression 3.5
General disorders and administration site conditions Discomfort 3.5
Dysthymic disorder 3.5
General disorders and administration site conditions Inflammation 3.5
Respiratory, thoracic and mediastinal disorders Nasal congestion 3.5
General disorders and administration site conditions Pain 3.5
Infections and infestations Folliculitis 3.3
Respiratory, thoracic and mediastinal disorders Respiration abnormal 3.3
Respiratory, thoracic and mediastinal disorders Respiratory disorder 3.3
Infections and infestations Sinusitis
Skin and subcutaneous tissue disorders Dermatitis 3.1
Skin and subcutaneous tissue disorders Eczema 3.1
Nervous system disorders Neuropathy peripheral 3.1
Nervous system disorders Altered state of consciousness
Psychiatric disorders Anxiety
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Benign neoplasm of skin 3.0
Gastrointestinal disorders Constipation
Gastrointestinal disorders Constipation 3.0
Psychiatric disorders Depression
Psychiatric disorders Depression 3.0
General disorders and administration site conditions Discomfort
General disorders and administration site conditions Discomfort 3.0
Nervous system disorders Dysaesthesia
Nervous system disorders Dysaesthesia 3.0
Dysthymic disorder
Dysthymic disorder 3.0
General disorders and administration site conditions Inflammation
General disorders and administration site conditions Inflammation 3.0
Metabolism and nutrition disorders Lipodystrophy acquired 3.0
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 3.0
Musculoskeletal and connective tissue disorders Myalgia 3.0
Respiratory, thoracic and mediastinal disorders Nasal congestion
Respiratory, thoracic and mediastinal disorders Nasal congestion 3.0
Nervous system disorders Neuropathy peripheral
Nervous system disorders Neuropathy peripheral 3.0
General disorders and administration site conditions Pain
General disorders and administration site conditions Pain 3.0
Nervous system disorders Paraesthesia
Nervous system disorders Paraesthesia 3.0
Infections and infestations Sinusitis
Infections and infestations Sinusitis 3.0
Nervous system disorders Altered state of consciousness
Gastrointestinal disorders Constipation
Psychiatric disorders Depression
General disorders and administration site conditions Discomfort
Nervous system disorders Dysaesthesia
Dysthymic disorder
Nervous system disorders Neuropathy peripheral
General disorders and administration site conditions Pain
Nervous system disorders Paraesthesia
Metabolism and nutrition disorders Lipodystrophy acquired 2.8
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 2.8
Musculoskeletal and connective tissue disorders Myalgia 2.8
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Benign neoplasm of skin 2.6
Gastrointestinal disorders Stomatitis 2.6
General disorders and administration site conditions Ulcer 2.6
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Eczema
General disorders and administration site conditions Inflammation
Respiratory, thoracic and mediastinal disorders Nasal congestion
Gastrointestinal disorders Anogenital warts 2.1
Immune system disorders Bronchospasm 2.1
Infections and infestations Pneumonia 2.1
Gastrointestinal disorders Anogenital warts 2.0
Eye disorders Conjunctivitis 2.0
Skin and subcutaneous tissue disorders Erythema 2.0
Eye disorders Eye infection 2.0
Infections and infestations Folliculitis
Infections and infestations Folliculitis 2.0
General disorders and administration site conditions Inflammation 2.0
Infections and infestations Influenza 2.0
Ear and labyrinth disorders Otitis media 2.0
Infections and infestations Pneumonia 2.0
Skin and subcutaneous tissue disorders Pruritus
Skin and subcutaneous tissue disorders Pruritus 2.0
Respiratory, thoracic and mediastinal disorders Respiration abnormal
Respiratory, thoracic and mediastinal disorders Respiration abnormal 2.0
Respiratory, thoracic and mediastinal disorders Respiratory disorder
Respiratory, thoracic and mediastinal disorders Respiratory disorder 2.0
Infections and infestations Folliculitis
Skin and subcutaneous tissue disorders Pruritus
Respiratory, thoracic and mediastinal disorders Respiration abnormal
Respiratory, thoracic and mediastinal disorders Respiratory disorder
Infections and infestations Influenza 1.6
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Benign neoplasm of skin
Immune system disorders Bronchospasm
Gastrointestinal disorders Stomatitis
General disorders and administration site conditions Ulcer
Gastrointestinal disorders Anogenital warts
Gastrointestinal disorders Anogenital warts 1.0
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Benign neoplasm of skin
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Benign neoplasm of skin 1.0
Eye disorders Conjunctivitis
Eye disorders Conjunctivitis 1.0
Skin and subcutaneous tissue disorders Erythema
Skin and subcutaneous tissue disorders Erythema 1.0
Eye disorders Eye infection
Eye disorders Eye infection 1.0
General disorders and administration site conditions Inflammation
General disorders and administration site conditions Inflammation 1.0
Infections and infestations Influenza
Infections and infestations Influenza 0.5
Metabolism and nutrition disorders Lipodystrophy acquired
Metabolism and nutrition disorders Lipodystrophy acquired 0.5
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.5
Musculoskeletal and connective tissue disorders Myalgia
Musculoskeletal and connective tissue disorders Myalgia 0.5
Ear and labyrinth disorders Otitis media
Ear and labyrinth disorders Otitis media 0.5

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Infections and infestations
8.56
General disorders and administration site conditions
7.99
Vascular disorders
7.43
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
7.22
Nervous system disorders
6.92
Gastrointestinal disorders
6.76
Injury, poisoning and procedural complications
5.71
Metabolism and nutrition disorders
5.43
Blood and lymphatic system disorders
4.92
Cardiac disorders
4.87
Respiratory, thoracic and mediastinal disorders
4.35
Investigations
3.56
Skin and subcutaneous tissue disorders
3.48
Psychiatric disorders
3.38
Hepatobiliary disorders
2.82
Renal and urinary disorders
2.82
Pregnancy, puerperium and perinatal conditions
2.36
Surgical and medical procedures
2.25
Eye disorders
2.1
Musculoskeletal and connective tissue disorders
2.05

Cross References

Resources Reference
CAS NUMBER 376348-65-1
ChEBI 63608
ChEMBL CHEMBL1201187
DrugBank DB04835
FDA SRS MD6P741W8A
Guide to Pharmacology 806
PDB MRV
SureChEMBL SCHEMBL51991
ZINC ZINC000100003902
CONTENTS