TMC-310911

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

Download

MOLSDFPDBSMILESInChI

Similar Structures

Structure for TMC-310911 (DB15623)

×

Close

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 rates

Build, train, & validate machine-learning models
with evidence-based and structured datasets.

See how

Build, train, & validate predictive machine-learning models with structured datasets.

See how

Contraindications & Blackbox Warnings

Avoid life-threatening adverse drug events

Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.

Learn more

Avoid life-threatening adverse drug events & improve clinical decision support.

Learn more

Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
UHIV-1 protease	inhibitor	Human 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 outcomes

With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.

Learn more

Improve decision support & research outcomes with our structured adverse effects data.

Learn more

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Integrate drug-drug interactions in your software
Adenovirus 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.
Aluminum hydroxide	Aluminum hydroxide can cause a decrease in the absorption of TMC-310911 resulting in a reduced serum concentration and potentially a decrease in efficacy.
Amiodarone	The serum concentration of Amiodarone can be increased when it is combined with TMC-310911.
Anthrax vaccine	The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with TMC-310911.
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 TMC-310911.
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 TMC-310911.

Identify potential medication risks

Easily 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

• Acids, Acyclic
• Amides
• Anti-HIV Agents
• Antiviral Agents
• Antivirals for Systemic Use
• Enzyme Inhibitors
• Experimental Unapproved Treatments for COVID-19
• Heterocyclic Compounds, Fused-Ring
• HIV Protease Inhibitors
• Protease Inhibitors
• Sulfones
• Sulfur Compounds
• Thiazoles

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

1. 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]
2. 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]
3. 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]
4. NIH AIDSinfo: TMC-310911 Pharmacology [Link]
5. 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

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

Not Available

Targets

Build, predict & validate machine-learning models

Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.

Learn more

Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.

Learn more

Details1. HIV-1 protease

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

1. 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]
2. 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]

×

Identify potential medication risks

Easily compare up to 40 drugs with our drug interaction checker.

Get severity rating, description, and management advice.

Learn more

Drug created at March 04, 2020 17:20 / Updated at June 12, 2020 16:53