Structure via PubChem · Public domain (PubChem)
vicriviroc
Sign in to saveAlso known as SCH 417690, SCH-417690, SCH-D690, SCH-DS
Vicriviroc, previously named SCH 417690 and SCH-D, is a pyrimidine CCR5 entry inhibitor of HIV-1. It was developed by the pharmaceutical company Schering-Plough. Merck decided to not pursue regulatory approval for use in treatment-experienced patients because the drug did not meet primary efficacy endpoints in late stage trials. Clinical trials continue in patients previously untreated for HIV.
Chemical data
- Formula
- C28H38F3N5O2
- Molecular weight
- 533.6 g/mol
- IUPAC name
- (4,6-dimethylpyrimidin-5-yl)-[4-[(3S)-4-[(1R)-2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl]-3-methylpiperazin-1-yl]-4-methylpiperidin-1-yl]methanone
- SMILES
- C[C@H]1CN(CCN1[C@@H](COC)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C
- InChIKey
- CNPVJJQCETWNEU-CYFREDJKSA-N
- XLogP
- 3.7
- Polar surface area
- 61.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- HIV infection, AIDS, colorectal neoplasm
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 533.29776
Show 5 more facts
- chemical formula
- C₂₈H₃₈F₃N₅O₂
- isomeric SMILES
- C[C@H]1CN(CCN1[C@@H](COC)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C
- canonical SMILES
- CC1CN(CCN1C(COC)C2=CC=C(C=C2)C(F)(F)F)C3(CCN(CC3)C(=O)C4=C(N=CN=C4C)C)C
- physically interacts with
- C-C motif chemokine receptor 5
- Commons category
- Vicriviroc
Sources (2)
via Wikidata · CC0
~10 min read
Encyclopedic overview
10 sectionsContents
- HIV-1 background
- HIV-1 entry
- Coreceptors and tropism
- CCR5-Δ32
- SCH-C and vicriviroc
- Method of action
- Clinical trials
- Concerns surrounding CCR5 antagonists
- See also
- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 470630044 | ImageFile = Vicriviroc structure.svg | ImageClass = skin-invert-image | ImageSize = 270px | IUPACName = 5-({4-[(3S)-4-{2-methoxy-1-[4-(trifluoromethyl)phenyl]ethyl}-3-methylpiperazin-1-yl]-4-methylpiperidin-1-yl}carbonyl)-4,6-dimethylpyrimidine | OtherNames = |Section1 = |Section2= |Section3= }} Vicriviroc, previously named SCH 417690 and SCH-D, is a pyrimidine CCR5 entry inhibitor of HIV-1. It was developed by the pharmaceutical company Schering-Plough. Merck decided to not pursue regulatory approval for use in treatment-experienced patients because the drug did not meet primary efficacy endpoints in late stage trials. Clinical trials continue in patients previously untreated for HIV.
==HIV-1 background==
Excerpted from Wikipedia’s “vicriviroc” article, available under the CC BY-SA 4.0 licence.