UC-781
Identification
- Generic Name
- UC-781
- DrugBank Accession Number
- DB05871
- Background
UC-781 is a thiocarboxanilide non-nucleoside reverse transcriptase inhibitor (NNRTI). It is a topical microbicide targeted against the AIDS virus.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 335.848
Monoisotopic: 335.074677222 - Chemical Formula
- C17H18ClNO2S
- Synonyms
- Not Available
- External IDs
- NSC-675186
- UC-781
- UC781
Pharmacology
- Indication
Investigated for use/treatment in HIV infection.
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- Pharmacodynamics
Not Available
- Mechanism of action
UC-781 is an HIV non-nucleoside reverse transcriptase inhibitor (NNRTI) that has shown in vitro to be very active specifically against HIV-1. UC-781 exhibits synergy with the NRTI zidovudine in vitro.[12] The combination of UC-781 and another candidate microbicide, cellulose acetate 1,2-benzenedicarboxylate, resulted in effective synergy for inhibition of HIV-1 in vitro and in peripheral blood mononuclear cells
Target Actions Organism UGag-Pol polyprotein Not Available - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAdenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with UC-781. Anthrax vaccine The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with UC-781. Bacillus calmette-guerin substrain connaught live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with UC-781. Bacillus calmette-guerin substrain russian BCG-I live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with UC-781. Bacillus calmette-guerin substrain tice live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with UC-781. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with UC-781. Human adenovirus e serotype 4 strain cl-68578 antigen The therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with UC-781. Rubella virus vaccine The therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with UC-781. Typhoid Vaccine Live The therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with UC-781. Varicella zoster vaccine (live/attenuated) The therapeutic efficacy of Varicella zoster vaccine (live/attenuated) can be decreased when used in combination with UC-781. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenol ethers
- Sub Class
- Not Available
- Direct Parent
- Phenol ethers
- Alternative Parents
- Phenoxy compounds / Chlorobenzenes / Alkyl aryl ethers / Aryl chlorides / Thioamides / Heteroaromatic compounds / Furans / Thiocarboxylic acid amides / Oxacyclic compounds / Thiocarbonyl compounds show 4 more
- Substituents
- Alkyl aryl ether / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Ether / Furan / Halobenzene / Heteroaromatic compound / Hydrocarbon derivative show 16 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- L7K247H29H
- CAS number
- 178870-32-1
- InChI Key
- YZHIXLCGPOTQNB-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H18ClNO2S/c1-11(2)6-8-21-16-10-13(4-5-15(16)18)19-17(22)14-7-9-20-12(14)3/h4-7,9-10H,8H2,1-3H3,(H,19,22)
- IUPAC Name
- N-{4-chloro-3-[(3-methylbut-2-en-1-yl)oxy]phenyl}-2-methylfuran-3-carbothioamide
- SMILES
- CC(C)=CCOC1=C(Cl)C=CC(NC(=S)C2=C(C)OC=C2)=C1
References
- General References
- Patton DL, Sweeney YT, Balkus JE, Rohan LC, Moncla BJ, Parniak MA, Hillier SL: Preclinical safety assessments of UC781 anti-human immunodeficiency virus topical microbicide formulations. Antimicrob Agents Chemother. 2007 May;51(5):1608-15. Epub 2007 Mar 12. [Article]
- Hossain MM, Parniak MA: In vitro microbicidal activity of the nonnucleoside reverse transcriptase inhibitor (NNRTI) UC781 against NNRTI-resistant human immunodeficiency virus type 1. J Virol. 2006 May;80(9):4440-6. [Article]
- External Links
- PubChem Compound
- 3000926
- PubChem Substance
- 175427049
- ChemSpider
- 2272425
- BindingDB
- 50105629
- ChEMBL
- CHEMBL54893
- ZINC
- ZINC000006069063
- PDBe Ligand
- UC1
- PDB Entries
- 1jlg / 1rt4 / 1s1t / 1s1w
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Prevention Human Immunodeficiency Virus (HIV) Infections 4 1 Withdrawn Prevention Human Immunodeficiency Virus (HIV) Infections 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0123 mg/mL ALOGPS logP 4.07 ALOGPS logP 5.1 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 10.85 Chemaxon pKa (Strongest Basic) -2.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 34.4 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 97.63 m3·mol-1 Chemaxon Polarizability 35.48 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9944 Blood Brain Barrier + 0.868 Caco-2 permeable + 0.5624 P-glycoprotein substrate Non-substrate 0.7838 P-glycoprotein inhibitor I Inhibitor 0.7317 P-glycoprotein inhibitor II Non-inhibitor 0.7672 Renal organic cation transporter Non-inhibitor 0.7839 CYP450 2C9 substrate Non-substrate 0.7202 CYP450 2D6 substrate Non-substrate 0.7351 CYP450 3A4 substrate Substrate 0.5916 CYP450 1A2 substrate Inhibitor 0.8428 CYP450 2C9 inhibitor Inhibitor 0.7788 CYP450 2D6 inhibitor Non-inhibitor 0.7976 CYP450 2C19 inhibitor Inhibitor 0.8637 CYP450 3A4 inhibitor Inhibitor 0.6668 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.97 Ames test Non AMES toxic 0.5371 Carcinogenicity Non-carcinogens 0.7322 Biodegradation Not ready biodegradable 0.9941 Rat acute toxicity 2.5074 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7043 hERG inhibition (predictor II) Non-inhibitor 0.7358
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

- Kind
- Protein
- Organism
- Not Available
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Gag-Pol polyprotein: Mediates, with Gag polyrotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spher...
- Gene Name
- gag-pol
- Uniprot ID
- P03366
- Uniprot Name
- Gag-Pol polyprotein
- Molecular Weight
- 163287.51 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at November 18, 2007 18:28 / Updated at August 13, 2021 04:44