Identification
- Generic Name
- TMC-310911
- DrugBank Accession Number
- DB15623
- Background
TMC-310911 (also known as ASC-09) is a novel investigational protease inhibitor (PI) that is structurally similar to the currently available darunavir.4 It is being investigated for use in HIV-1 infections. TMC-310911 has shown marked activity against a variety of HIV-1 strains, including multi-PI-resistant strains, and may be less likely to generate resistance, making it a potentially desirable therapy for both treatment-naive and PI-experienced patients.4,3
TMC-310911 is currently being investigated, in combination with other HIV therapies and antivirals, as a potential treatment for COVID-19 caused by SARS-CoV-2.5
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for TMC-310911 (DB15623)
- Weight
- Average: 755.987
Monoisotopic: 755.338640455 - Chemical Formula
- C38H53N5O7S2
- Synonyms
- Not Available
- External IDs
- ASC-09
- TMC 310911
- TMC-310911
- TMC310911
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UHIV-1 protease inhibitorHuman Immunodeficiency Virus - 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. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 TMC-310911. Almasilate Almasilate can cause a decrease in the absorption of TMC-310911 resulting in a reduced serum concentration and potentially a decrease in efficacy. Alprazolam The serum concentration of Alprazolam can be increased when it is combined with TMC-310911. Aluminium Aluminium can cause a decrease in the absorption of TMC-310911 resulting in a reduced serum concentration and potentially a decrease in efficacy. Aluminium phosphate Aluminium phosphate can cause a decrease in the absorption of TMC-310911 resulting in a reduced serum concentration and potentially a decrease in efficacy. - Food Interactions
- Not Available
Categories
- Drug Categories
- Classification
- Not classified
- Affected organisms
- Human immunodeficiency virus 1
- SARS-CoV-2
Chemical Identifiers
- UNII
- 0151W500HP
- CAS number
- 1000287-05-7
- InChI Key
- JQUNFHFWXCXPRK-AMMMHQJVSA-N
- InChI
- InChI=1S/C38H53N5O7S2/c1-25(2)22-43(23-33(44)32(20-26-8-4-3-5-9-26)41-38(45)50-34-24-49-36-30(34)16-19-48-36)52(46,47)29-12-13-31-35(21-29)51-37(40-31)39-27-14-17-42(18-15-27)28-10-6-7-11-28/h3-5,8-9,12-13,21,25,27-28,30,32-34,36,44H,6-7,10-11,14-20,22-24H2,1-2H3,(H,39,40)(H,41,45)/t30-,32-,33+,34-,36+/m0/s1
- IUPAC Name
- (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)2-[(1-cyclopentylpiperidin-4-yl)amino]-1,3-benzothiazole-6-sulfonamido]-1-phenylbutan-2-yl]carbamate
- SMILES
- [H][C@@]12CCO[C@]1([H])OC[C@@H]2OC(=O)N[C@@H](CC1=CC=CC=C1)[C@H](O)CN(CC(C)C)S(=O)(=O)C1=CC=C2N=C(NC3CCN(CC3)C3CCCC3)SC2=C1
References
- General References
- Dierynck I, Van Marck H, Van Ginderen M, Jonckers TH, Nalam MN, Schiffer CA, Raoof A, Kraus G, Picchio G: TMC310911, a novel human immunodeficiency virus type 1 protease inhibitor, shows in vitro an improved resistance profile and higher genetic barrier to resistance compared with current protease inhibitors. Antimicrob Agents Chemother. 2011 Dec;55(12):5723-31. doi: 10.1128/AAC.00748-11. Epub 2011 Sep 6. [Article]
- Hoetelmans RM, Dierynck I, Smyej I, Meyvisch P, Jacquemyn B, Marien K, Simmen K, Verloes R: Safety and pharmacokinetics of the HIV-1 protease inhibitor TMC310911 coadministered with ritonavir in healthy participants: results from 2 phase 1 studies. J Acquir Immune Defic Syndr. 2014 Mar 1;65(3):299-305. doi: 10.1097/QAI.0000000000000011. [Article]
- Stellbrink HJ, Arasteh K, Schurmann D, Stephan C, Dierynck I, Smyej I, Hoetelmans RM, Truyers C, Meyvisch P, Jacquemyn B, Marien K, Simmen K, Verloes R: Antiviral activity, pharmacokinetics, and safety of the HIV-1 protease inhibitor TMC310911, coadministered with ritonavir, in treatment-naive HIV-1-infected patients. J Acquir Immune Defic Syndr. 2014 Mar 1;65(3):283-9. doi: 10.1097/QAI.0000000000000003. [Article]
- NIH AIDSinfo: TMC-310911 Pharmacology [Link]
- Nature Biotechnology: Coronavirus puts drug repurposing on the fast track [Link]
- External Links
- ChemSpider
- 34554561
- ZINC
- ZINC000098208561
- PDBe Ligand
- 74T
- PDB Entries
- 3r4b
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Completed Treatment Human Immunodeficiency Virus Type 1 (HIV-1) 1 1 Withdrawn Treatment Human Immunodeficiency Virus (HIV) Infections 1 Not Available Terminated Treatment Coronavirus Disease 2019 (COVID‑19) 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 0.00544 mg/mL ALOGPS logP 4.5 ALOGPS logP 5.32 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 13.46 Chemaxon pKa (Strongest Basic) 9.02 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 142.56 Å2 Chemaxon Rotatable Bond Count 14 Chemaxon Refractivity 200.24 m3·mol-1 Chemaxon Polarizability 80.09 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 252.08955 predictedDeepCCS 1.0 (2019) [M+H]+ 254.25485 predictedDeepCCS 1.0 (2019) [M+Na]+ 260.3187 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Human Immunodeficiency Virus
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Aspartic-type endopeptidase activity
- Specific Function
- Not Available
- Gene Name
- HIV-1 protease
- Uniprot ID
- O90777
- Uniprot Name
- HIV-1 protease
- Molecular Weight
- 10724.61 Da
References
- Hoetelmans RM, Dierynck I, Smyej I, Meyvisch P, Jacquemyn B, Marien K, Simmen K, Verloes R: Safety and pharmacokinetics of the HIV-1 protease inhibitor TMC310911 coadministered with ritonavir in healthy participants: results from 2 phase 1 studies. J Acquir Immune Defic Syndr. 2014 Mar 1;65(3):299-305. doi: 10.1097/QAI.0000000000000011. [Article]
- Dierynck I, Van Marck H, Van Ginderen M, Jonckers TH, Nalam MN, Schiffer CA, Raoof A, Kraus G, Picchio G: TMC310911, a novel human immunodeficiency virus type 1 protease inhibitor, shows in vitro an improved resistance profile and higher genetic barrier to resistance compared with current protease inhibitors. Antimicrob Agents Chemother. 2011 Dec;55(12):5723-31. doi: 10.1128/AAC.00748-11. Epub 2011 Sep 6. [Article]
Drug created at March 04, 2020 17:20 / Updated at June 12, 2020 16:53