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UC-781

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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
3D
Similar Structures
Weight
Average: 335.848
Monoisotopic: 335.074677222
Chemical Formula
C17H18ClNO2S
Synonyms
Not Available
External IDs
  • NSC-675186
  • UC-781
  • UC781
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Pharmacology

Indication

Investigated for use/treatment in HIV infection.

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Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
AGag-Pol polyprotein
inhibitor
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
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with UC-781.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with UC-781.
Bacillus calmette-guerin substrain connaught live antigenThe 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 antigenThe 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 antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with UC-781.
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
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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
  1. 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]
  2. 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]
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

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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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1CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections4somestatusstop reasonjust information to hide
1WithdrawnPreventionHuman Immunodeficiency Virus (HIV) Infections1somestatusstop reasonjust information to hide

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
PropertyValueSource
Water Solubility0.0123 mg/mLALOGPS
logP4.07ALOGPS
logP5.1Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)10.85Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area34.4 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity97.63 m3·mol-1Chemaxon
Polarizability35.48 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.868
Caco-2 permeable+0.5624
P-glycoprotein substrateNon-substrate0.7838
P-glycoprotein inhibitor IInhibitor0.7317
P-glycoprotein inhibitor IINon-inhibitor0.7672
Renal organic cation transporterNon-inhibitor0.7839
CYP450 2C9 substrateNon-substrate0.7202
CYP450 2D6 substrateNon-substrate0.7351
CYP450 3A4 substrateSubstrate0.5916
CYP450 1A2 substrateInhibitor0.8428
CYP450 2C9 inhibitorInhibitor0.7788
CYP450 2D6 inhibitorNon-inhibitor0.7976
CYP450 2C19 inhibitorInhibitor0.8637
CYP450 3A4 inhibitorInhibitor0.6668
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.97
Ames testNon AMES toxic0.5371
CarcinogenicityNon-carcinogens0.7322
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.5074 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7043
hERG inhibition (predictor II)Non-inhibitor0.7358
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-014i-6291000000-a694af04a3323eb12b82
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-5359000000-84cff0f997d4dc11c3f6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0091000000-a3d30791c2438acdb31a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-053r-6690000000-69a5a7b9930629ffe173
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gws-1095000000-6abc689d6c655a1a2eba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0910000000-97641d38a025da2a2b11
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gyx-4793000000-fa12ad4f1ac50fc51e94
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-178.20537
predicted
DeepCCS 1.0 (2019)
[M+H]+180.56337
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.65652
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Gag-Pol polyprotein
Kind
Protein
Organism
Not Available
Pharmacological action
Yes
Actions
Inhibitor
General Function
Gag-Pol polyprotein Mediates, with Gag polyprotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spherical particles, recruiting the viral Env proteins, and packaging the genomic RNA via direct interactions with the RNA packaging sequence (Psi). Gag-Pol polyprotein may regulate its own translation, by the binding genomic RNA in the 5'-UTR. At low concentration, the polyprotein would promote translation, whereas at high concentration, the polyprotein would encapsidate genomic RNA and then shut off translation.
Specific Function
aspartic-type endopeptidase activity
Gene Name
gag-pol
Uniprot ID
P03366
Uniprot Name
Gag-Pol polyprotein
Molecular Weight
163287.51 Da
References
  1. 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]
  2. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at November 18, 2007 18:28 / Updated at August 26, 2024 19:22