TMC-207
Overview Synthetic Methods Pharmacological Function Pharmacology Pharmacokinetics Adverse Effect Taboo- Product Name
- TMC-207
- CAS No.
- 843663-66-1
- Chemical Name
- TMC-207
- Synonyms
- Bedaquiline;1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol;Sirturo;6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol;3-Quinolineethanol, 6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-, (αS,βR)-;3-Quinolineethanol, 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-, (alphas,betar)-;141027;CS-751;TMC-207;R 207910
- CBNumber
- CB12473722
- Molecular Formula
- C32H31BrN2O2
- Formula Weight
- 555.5
- MOL File
- 843663-66-1.mol
TMC-207 Property
- Melting point:
- 104 °C
- Boiling point:
- 702.7±60.0 °C(Predicted)
- Density
- 1.322±0.06 g/cm3(Predicted)
- storage temp.
- Room temperature
- solubility
- Soluble in DMSO (10 mg/ml)
- pka
- 13.05±0.29(Predicted)
- form
- solid
- color
- White
- Stability:
- Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
- CAS DataBase Reference
- 843663-66-1
Safety
- HS Code
- 2933499090
- Hazardous Substances Data
- 843663-66-1(Hazardous Substances Data)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H301Toxic if swalloed
H373May cause damage to organs through prolonged or repeated exposure
H400Very toxic to aquatic life
H410Very toxic to aquatic life with long lasting effects
- Precautionary statements
-
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P273Avoid release to the environment.
P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P314Get medical advice/attention if you feel unwell.
P321Specific treatment (see … on this label).
P330Rinse mouth.
P391Collect spillage. Hazardous to the aquatic environment
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- 20247
- Product name
- TMC207
- Purity
- ≥97%
- Packaging
- 1mg
- Price
- $56
- Updated
- 2024/03/01
- Product number
- 20247
- Product name
- TMC207
- Purity
- ≥97%
- Packaging
- 5mg
- Price
- $194
- Updated
- 2024/03/01
- Product number
- 20247
- Product name
- TMC207
- Purity
- ≥97%
- Packaging
- 10mg
- Price
- $359
- Updated
- 2024/03/01
- Product number
- 20247
- Product name
- TMC207
- Purity
- ≥97%
- Packaging
- 25mg
- Price
- $817
- Updated
- 2022/04/27
- Product number
- 003131
- Product name
- Bedaquiline
- Packaging
- 10mg
- Price
- $460
- Updated
- 2021/12/16
TMC-207 Chemical Properties,Usage,Production
Overview
Bedaquiline, formally called (1R, 2S)-1-(6-Bromo-2-methoxy-3-quinolinyl)-4-(dimethylamino)-2-(1-naphthyl)-1-phenyl-2-butanol in chemistry and known as Sirturo in commercial, is a new anti-mycobacterial medicine of diarylquinolines. It impinges on the
ATP synthesis of Mycobacterium tuberculosis by inhibiting the activity of proton pump on the cell’s ATP synthetase, and thereby eliminates M. tuberculosis (TB). It’s used for adult multi-drug resistant tuberculosis (MDR-PTB).
Synthetic Methods
Fig: Synthetic route of Bedaquiline
Pharmacological Function
Bedaquinoline has the same bactericidal activity against both sensitive and resistant strains of mycobacterium tuberculosis as well as on dormant bacteria.
Pharmacology
The proton pump on the cell’s ATP synthetase, which is a crucial enzyme for M. tuberculosis (TB) to synthesize ATP, is the unique and specific locus of Bedaquinoline.
After the combination onto the oligomer and lipoprotein subunit c, Bedaquinoline can inhibit the synthesis of ATP and bring the death to the bacterium cell. Compared with those existing anti-TB medicines, it presents a novel pharmacology and no cross resistance effect was found between Bedaquinoline and other anti-TB medicines. The gene sequence of the subunit c of ATP synthetase is named as atpE, whose amino acid sequence is highly conservative. The resistance of TB to Bedaquinoline comes from its reduced combination onto subunit c of ATP synthetase due to the mutation of the 63rd or 66th on atpE.
Pharmacokinetics
Bedaquinoline is easy for oral assimilation. The bioavailability of Bedaquinoline taken with food is twice higher than when taken with an empty stomach. It reaches its blood concentration in 5 hours after taken and has a plasma protein binding rate of 99.9% as well as a plasma half-life of 173 hours. Bedaquinoline can be widely distributed in human body with a homeostasis distribution volume of 1000Ｌ. Its clearance rate is low enough and the elimination half-life is 5.5 months. Bedaquinoline is metabolize into metabolite 1~8 in the demethylation mainly through CYP3A4 and partly though CYP2C8 and CYP2C19. Metabolite 2 （M2）, the most important metabolite, which has only 1/3-1/6 the activity of Bedaquinoline, yet present a more strong cytotoxicity and is more likely to cause the drug-induced phospholipidosis. Bedaquinoline and its metabolites are mostly excreted by feces, only 1% to 4% by urine.
Adverse Effect
Common adverse reactions are nausea, headache, arthralgia, loss of appetite, vomiting and rash, dizziness, elevated transaminase, increased hemodiastase, muscle pain, diarrhea and prolonged TQ interval.
Taboo
1.The allergic to this product;
2.Patients suffer serious dysfunction of heart, liver, kidney (relative contraindication);
3.Pregnant women, lactating women, children, the old and co-infected HIV sufferers (relative contraindication).
Description
In December 2012, the US FDA approved bedaquiline as part of combination therapy for the treatment of multi-drug resistant tuberculosis (MDRTB). Bedaquiline is the first drug approved for MDR-TB and is the first approval from a new class of antituberculosis agents in the past 40 years. Due to the high unmetmedical need for treating MDR-TB, the FDA granted bedaquiline accelerated approval based on Phase II results, providing patients access to the drug while additional clinical studies are carried out. Bedaquiline (also known as TMC207 and R207910) is a diarylquinoline that was discovered from a high-throughput, whole-cell screening strategy with Mycobacterium smegmatis used as a surrogate for M. tuberculosis. Bedaquiline is a single enantiomer of an initial screening hit. Bedaquiline has potent and selective activity against mycobacteria, and is active against both drug-sensitive and drug-resistant M. tuberculosis. The mechanism of action of bedaquiline is unique amongst anti-TB drugs and involves inhibition of mycobacterial ATP synthase; it is not active against human ATP synthase. Bedaquiline has in vivo activity in numerous preclinical models of TB infection, alone and in combination with other anti-TB agents, and has bactericidal activity in established TB infection models. Bedaquiline is synthesized in five steps from 3-phenylpropionic acid and para-bromoaniline. Following amide formation, treatment with POCl3 and DMF under Vilsmeier–Hack conditions gave a 2-chloroquinoline product. Treatment with sodium methoxide, followed by condensation with 3-(dimethylamino)-1-(naphthalen-1-yl)propan-1-one, and separation of isomers gave bedaquiline.
Description
TMC207 is a diarylquinoline that selectively inhibits the proton pump of the mycobacterial ATP synthase. It demonstrates potent activity against both drug-sensitive and drug-resistant M. tuberculosis and other mycobacterial species with MIC50 values of ~0.03 μg/ml.
Originator
Janssen (Belgium)
Uses
(αS,βR)-Bedaquiline is a diarylquinoline derivative that acts as a mycobacterial inhibitor. Bedaquiline shows promise as potential drug in the treatment of tuberculosis.
Uses
Labeled Bedaquiline, intended for use as an internal standard for the quantification of Bedaquiline by GC- or LC-mass spectrometry.
Definition
ChEBI: Bedaquiline is a quinoline-based antimycobacterial drug used (as its fumarate salt) for the treatment of pulmonary multi-drug resistant tuberculosis by inhibition of ATP synthase, an enzyme essential for the replication of the mycobacteria. It has a role as an antitubercular agent and an ATP synthase inhibitor. It is a member of quinolines, a member of naphthalenes, an organobromine compound, an aromatic ether, a tertiary alcohol and a tertiary amino compound. It is a conjugate base of a bedaquiline(2+).
brand name
Sirturo
References
Andries et al. (2005), A diarylquinoline drug active on the ATP synthase of Mycobacterium tuberculosis; Science, 307 223 Koul et al. (2007), Diarylquinolines target subunit c of mycobacterial ATP synthase; Nat. Chem. Biol., 3 323 Biukovic et al. (2013), Variations of subunit {varepsilon} of the Mycobacterium tuberculosis F1F0 ATP synthase and a novel model for mechanism of action of the tuberculosis drug TMC207; Antimicrob. Agents Chemother., 57 168 Sarathy et al. (2019), Re-Understanding the Mechanisms of Action of the Anti-Mycobacterial Drug Bedaquiline; Antibiotics (Basel), 8 261 Ghahremanpour et al. (2020), Identification of 14 Known Drugs as Inhibitors of the Main Protease of SARS-CoV-2; ACS Med. Chem. Lett., 11 2526
TMC-207 Preparation Products And Raw materials
Raw materials
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View Lastest Price from TMC-207 manufacturers
- Product
- Bedaquiline 843663-66-1
- Price
- US $0.00-0.00/mg
- Min. Order
- 10mg
- Purity
- 0.98
- Supply Ability
- 10g
- Release date
- 2024-05-15
- Product
- Bedaquinline 843663-66-1
- Price
- US $0.01-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%min
- Supply Ability
- 20 tons
- Release date
- 2020-05-08
- Product
- TMC-207 843663-66-1
- Price
- US $32.00-1.30/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-04-15