Compounds > ancriviroc
Page last updated: 2024-12-11

ancriviroc

Description

Ancriviroc: CCR5 receptor antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5479787
CHEMBL ID336672
CHEBI ID177442
SCHEMBL ID2939135
MeSH IDM0403945

Synonyms (14)

Synonym
CHEBI:177442
[4-[4-[(e)-c-(4-bromophenyl)-n-ethoxycarbonimidoyl]piperidin-1-yl]-4-methylpiperidin-1-yl]-(2,4-dimethyl-1-oxidopyridin-1-ium-3-yl)methanone
3-[(4-{4-[(1z)-(4-bromophenyl)(ethoxyimino)methyl]piperidin-1-yl}-4-methylpiperidin-1-yl)carbonyl]-2,4-dimethylpyridin-1-ium-1-olate
gtpl802
[3h]sch-351125
[3h]sch 351125
gtpl804
[3h]ancriviroc
ancriviroc
L000937
chembl336672 ,
schering c
SCHEMBL2939135
Q27074462

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Compound 1, which has good oral bioavailability in rats, dogs, and monkeys, is proposed as a potential therapeutic agent for the treatment of HIV-1 and has entered human clinical trials."( Discovery of 4-[(Z)-(4-bromophenyl)- (ethoxyimino)methyl]-1'-[(2,4-dimethyl-3- pyridinyl)carbonyl]-4'-methyl-1,4'- bipiperidine N-oxide (SCH 351125): an orally bioavailable human CCR5 antagonist for the treatment of HIV infection.
Baroudy, BM; Clader, JW; Cox, K; Endres, M; Greenlee, WJ; Palani, A; Shapiro, S; Strizki, J, 2001)		0.31
"We previously reported the discovery of 4-[(Z)-(4-bromophenyl)(ethoxyimino)methyl]-1'-[(2,4-dimethyl-3-pyridinyl)carbonyl]-4'-methyl-1,4'-bipiperidine N-oxide 1 (SCH 351125) as an orally bioavailable human CCR5 antagonist for the treatment of HIV-1 infection."( Synthesis, SAR, and biological evaluation of oximino-piperidino-piperidine amides. 1. Orally bioavailable CCR5 receptor antagonists with potent anti-HIV activity.
Bara, T; Baroudy, BM; Clader, JW; Cox, K; Greenlee, WJ; Josien, H; Palani, A; Shapiro, S; Strizki, JM, 2002)		0.31
" A series of potent and orally bioavailable CCR5 antagonists containing symmetrical 2,6-dimethyl isonicotinamides and 2, 6-dimethyl pyrimidines amides were generated with enhanced affinity for the CCR5 receptor."( Oximino-piperidino-piperidine-based CCR5 antagonists. Part 2: synthesis, SAR and biological evaluation of symmetrical heteroaryl carboxamides.
Baroudy, BM; Clader, JW; Cox, K; Greenlee, WJ; McCombie, S; Palani, A; Shapiro, S; Strizki, J; Vice, S, 2003)		0.32
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
pyridinemonocarboxylic acidA monocarboxylic acid in which the carboxy group is attached to a pyridine (or substituted pyridine) ring.
aromatic carboxylic acidAny carboxylic acid in which the carboxy group is directly bonded to an aromatic ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
C-C chemokine receptor type 5Homo sapiens (human)IC50 (µMol)0.04000.00020.25679.0000AID589841
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
MAPK cascadeC-C chemokine receptor type 5Homo sapiens (human)
dendritic cell chemotaxisC-C chemokine receptor type 5Homo sapiens (human)
calcium ion transportC-C chemokine receptor type 5Homo sapiens (human)
chemotaxisC-C chemokine receptor type 5Homo sapiens (human)
cellular defense responseC-C chemokine receptor type 5Homo sapiens (human)
cell surface receptor signaling pathwayC-C chemokine receptor type 5Homo sapiens (human)
G protein-coupled receptor signaling pathwayC-C chemokine receptor type 5Homo sapiens (human)
cell-cell signalingC-C chemokine receptor type 5Homo sapiens (human)
release of sequestered calcium ion into cytosol by sarcoplasmic reticulumC-C chemokine receptor type 5Homo sapiens (human)
calcium-mediated signalingC-C chemokine receptor type 5Homo sapiens (human)
signalingC-C chemokine receptor type 5Homo sapiens (human)
symbiont entry into host cellC-C chemokine receptor type 5Homo sapiens (human)
chemokine-mediated signaling pathwayC-C chemokine receptor type 5Homo sapiens (human)
response to cholesterolC-C chemokine receptor type 5Homo sapiens (human)
cellular response to lipopolysaccharideC-C chemokine receptor type 5Homo sapiens (human)
negative regulation of macrophage apoptotic processC-C chemokine receptor type 5Homo sapiens (human)
inflammatory responseC-C chemokine receptor type 5Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationC-C chemokine receptor type 5Homo sapiens (human)
immune responseC-C chemokine receptor type 5Homo sapiens (human)
cell chemotaxisC-C chemokine receptor type 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
virus receptor activityC-C chemokine receptor type 5Homo sapiens (human)
actin bindingC-C chemokine receptor type 5Homo sapiens (human)
phosphatidylinositol phospholipase C activityC-C chemokine receptor type 5Homo sapiens (human)
chemokine receptor activityC-C chemokine receptor type 5Homo sapiens (human)
protein bindingC-C chemokine receptor type 5Homo sapiens (human)
coreceptor activityC-C chemokine receptor type 5Homo sapiens (human)
C-C chemokine receptor activityC-C chemokine receptor type 5Homo sapiens (human)
C-C chemokine bindingC-C chemokine receptor type 5Homo sapiens (human)
identical protein bindingC-C chemokine receptor type 5Homo sapiens (human)
chemokine (C-C motif) ligand 5 bindingC-C chemokine receptor type 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
cell surfaceC-C chemokine receptor type 5Homo sapiens (human)
endosomeC-C chemokine receptor type 5Homo sapiens (human)
plasma membraneC-C chemokine receptor type 5Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 5Homo sapiens (human)
cell surfaceC-C chemokine receptor type 5Homo sapiens (human)
external side of plasma membraneC-C chemokine receptor type 5Homo sapiens (human)
cytoplasmC-C chemokine receptor type 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1346815Human CCR5 (Chemokine receptors)2006The Journal of biological chemistry, May-05, Volume: 281, Issue:18
Structural and molecular interactions of CCR5 inhibitors with CCR5.
AID1346815Human CCR5 (Chemokine receptors)2001Journal of medicinal chemistry, Oct-11, Volume: 44, Issue:21
Discovery of 4-[(Z)-(4-bromophenyl)- (ethoxyimino)methyl]-1'-[(2,4-dimethyl-3- pyridinyl)carbonyl]-4'-methyl-1,4'- bipiperidine N-oxide (SCH 351125): an orally bioavailable human CCR5 antagonist for the treatment of HIV infection.
AID1346815Human CCR5 (Chemokine receptors)2005Antimicrobial agents and chemotherapy, Dec, Volume: 49, Issue:12
Discovery and characterization of vicriviroc (SCH 417690), a CCR5 antagonist with potent activity against human immunodeficiency virus type 1.
AID589850Volume of distribution at steady state in rat at 10 umol/kg, iv2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Design and synthesis of pyridin-2-yloxymethylpiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.
AID589848Clearance in rat at 10 umol/kg, iv2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Design and synthesis of pyridin-2-yloxymethylpiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.
AID589846AUC (0 to infinity) in rat2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Design and synthesis of pyridin-2-yloxymethylpiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.
AID589854Oral bioavailability in rat at 100 umol/kg2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Design and synthesis of pyridin-2-yloxymethylpiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.
AID589844Cmax in rat2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Design and synthesis of pyridin-2-yloxymethylpiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.
AID589842Antiviral activity against Human immunodeficiency virus 1 BAL infected in human PBMC assessed as inhibition of viral replication by p24 antigen specific ELISA2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Design and synthesis of pyridin-2-yloxymethylpiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.
AID589852Half life in rat at 10 umol/kg, iv2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Design and synthesis of pyridin-2-yloxymethylpiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.
AID589841Displacement of [128I]-RANTES from CCR5 expressed in HEK293F cells2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Design and synthesis of pyridin-2-yloxymethylpiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.
AID589843Cytotoxicity against human PBMC2011Bioorganic & medicinal chemistry letters, Apr-15, Volume: 21, Issue:8
Design and synthesis of pyridin-2-yloxymethylpiperidin-1-ylbutyl amide CCR5 antagonists that are potent inhibitors of M-tropic (R5) HIV-1 replication.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (30)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's27 (90.00)29.6817
2010's3 (10.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.74

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.74 (24.57)
Research Supply Index3.50 (2.92)
Research Growth Index4.24 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.74)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (6.67%)5.53%
Reviews2 (6.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other26 (86.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		2.01106-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
butyric acid
Butyric Acid: A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.. butyrate : A short-chain fatty acid anion that is the conjugate base of butyric acid, obtained by deprotonation of the carboxy group.. butyric acid : A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.		2.0110fatty acid 4:0;
straight-chain saturated fatty acid		human urinary metabolite;
Mycoplasma genitalium metabolite
dimethyl sulfoxide
Dimethyl Sulfoxide: A highly polar organic liquid, that is used widely as a chemical solvent. Because of its ability to penetrate biological membranes, it is used as a vehicle for topical application of pharmaceuticals. It is also used to protect tissue during CRYOPRESERVATION. Dimethyl sulfoxide shows a range of pharmacological activity including analgesia and anti-inflammation.. dimethyl sulfoxide : A 2-carbon sulfoxide in which the sulfur atom has two methyl substituents.		2.0110sulfoxide;
volatile organic compound		alkylating agent;
antidote;
Escherichia coli metabolite;
geroprotector;
MRI contrast agent;
non-narcotic analgesic;
polar aprotic solvent;
radical scavenger
plerixafor
plerixafor: a bicyclam derivate, highly potent & selective inhibitor of HIV-1 & HIV-2. plerixafor : An azamacrocycle consisting of two cyclam rings connected by a 1,4-phenylenebis(methylene) linker. It is a CXCR4 chemokine receptor antagonist and a hematopoietic stem cell mobilizer. It is used in combination with grulocyte-colony stimulating factor (G-CSF) to mobilize hematopoietic stem cells to the perpheral blood for collection and subsequent autologous transplantation in patients with non-Hodgkin's lymphoma and multiple myeloma.		2.0210azacycloalkane;
azamacrocycle;
benzenes;
crown amine;
secondary amino compound;
tertiary amino compound		anti-HIV agent;
antineoplastic agent;
C-X-C chemokine receptor type 4 antagonist;
immunological adjuvant
triazoles
Triazoles: Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.. triazoles : An azole in which the five-membered heterocyclic aromatic skeleton contains three N atoms and two C atoms.		2.42201,2,3-triazole
organophosphonates
hydrogenphosphite : A divalent inorganic anion resulting from the removal of a proton from two of the hydroxy groups of phosphorous acid.		2.0110divalent inorganic anion;
phosphite ion
tak 779
[no description available]		3.1350
etravirine
[no description available]		2.4120aminopyrimidine;
aromatic ether;
dinitrile;
organobromine compound		antiviral agent;
HIV-1 reverse transcriptase inhibitor
tenofovir
tenofovir (anhydrous) : A member of the class of phosphonic acids that is methylphosphonic acid in which one of the methyl hydrogens is replaced by a [(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy group. An inhibitor of HIV-1 reverse transcriptase, the bis(isopropyloxycarbonyloxymethyl) ester (disoproxil ester) prodrug is used as the fumaric acid salt in combination therapy for the treatment of HIV infection.		2.0110nucleoside analogue;
phosphonic acids		antiviral drug;
drug metabolite;
HIV-1 reverse transcriptase inhibitor
aplaviroc
aplaviroc: a spiro-diketo-piperazine; a potent noncompetitive allosteric antagonist of the CCR5 receptor with concomitantly potent antiviral effects for HIV-1; structure in first source		4.0440
maraviroc
[no description available]		2.0310tropane alkaloid
vicriviroc
vicriviroc: structure in first source		4.4420(trifluoromethyl)benzenes
bms 806
BMS 806: prevents entry of HIV into cells by binding HIV envelope protein gp120; no further info available 4/2002		2.0110
s 1360
[no description available]		2.0110
enfuvirtide
Enfuvirtide: A synthetic 36-amino acid peptide that corresponds to the heptad repeat sequence of HIV-1 gp41. It blocks HIV cell fusion and viral entry and is used with other anti-retrovirals for combination therapy of HIV INFECTIONS and AIDS.. enfuvirtide : A synthetic 36-amino acid peptide consisting of N-acetyltyrosyl, threonyl, seryl, leucyl, isoleucyl, histidyl, seryl, leucyl, isoleucyl, alpha-glutamyl, alpha-glutamyl, seryl, glutaminyl, asparaginyl, glutaminyl, glutaminyl, alpha-glutamyl, lysyl, asparaginyl, alpha-glutamyl, alpha-glutamyl, alpha-glutamyl, leucyl, leucyl, alpha-glutamyl, leucyl, alpha-aspartyl, lysyl, tryptophyl, alanyl, seryl, leucyl, tryptophyl, asparaginyl, tryptophyl, and phenylalaninamide residues joined in sequence. An HIV fusion inhibitor, it was the first of a novel class of antiretroviral drugs used in combination therapy for the treatment of HIV-1 infection. It interferes with entry of HIV into cells by binding to the gp41 sub-unit of the viral envelope glycoprotein, so inhibiting fusion of viral and cellular membranes.		4.0340
piperidines
Piperidines: A family of hexahydropyridines.		8.25282
ConditionIndicatedRelationship StrengthStudiesTrials
Rheumatoid Arthritis
[description not available]		03.4411
Arthritis, Rheumatoid
A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.		03.4411
HIV
Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.		02.9340
HIV Coinfection
[description not available]		04.980
HIV Infections
Includes the spectrum of human immunodeficiency virus infections that range from asymptomatic seropositivity, thru AIDS-related complex (ARC), to acquired immunodeficiency syndrome (AIDS).		04.980
Palmoplantaris Pustulosis
[description not available]		03.4211
Psoriasis
A common genetically determined, chronic, inflammatory skin disease characterized by rounded erythematous, dry, scaling patches. The lesions have a predilection for nails, scalp, genitalia, extensor surfaces, and the lumbosacral region. Accelerated epidermopoiesis is considered to be the fundamental pathologic feature in psoriasis.		03.4211
Acquired Immune Deficiency Syndrome
[description not available]		0210
Acquired Immunodeficiency Syndrome
An acquired defect of cellular immunity associated with infection by the human immunodeficiency virus (HIV), a CD4-positive T-lymphocyte count under 200 cells/microliter or less than 14% of total lymphocytes, and increased susceptibility to opportunistic infections and malignant neoplasms. Clinical manifestations also include emaciation (wasting) and dementia. These elements reflect criteria for AIDS as defined by the CDC in 1993.		0210
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