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TMC-207

Overview Synthetic Methods Pharmacological Function Pharmacology Pharmacokinetics Adverse Effect Taboo
TMC-207
TMC-207 structure
CAS No.
843663-66-1
Chemical Name:
TMC-207
Synonyms
TMC-207;Sirturo;R 207910;Bedaquiline;bedaquinline;Bedaquiline D6;(αS,βR)-Bedaquiline;TMC-207(Bedaquiline);Bedaquiline (TMC-207);Bedaquiline(R 207910,TMC 207)
CBNumber:
CB12473722
Molecular Formula:
C31H29BrN2O
Formula Weight:
525.487
MOL File:
843663-66-1.mol

TMC-207 Properties

CAS DataBase Reference
843663-66-1

SAFETY

TMC-207 price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Cayman Chemical 20247 TMC207 ≥97% 843663-66-1 1mg $55 2018-11-19 Buy
Cayman Chemical 20247 TMC207 ≥97% 843663-66-1 5mg $179 2018-11-19 Buy
Cayman Chemical 20247 TMC207 ≥97% 843663-66-1 10mg $330 2018-11-19 Buy
Cayman Chemical 20247 TMC207 ≥97% 843663-66-1 25mg $756 2018-11-19 Buy

TMC-207 Chemical Properties,Uses,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

Synthetic route of Bedaquiline
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.

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.

brand name

Sirturo

TMC-207 Preparation Products And Raw materials

Raw materials

Preparation Products


TMC-207 Suppliers

Global( 93)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Lianyungang happen teng technology co., LTD
15950718863
wang666xt@163.com CHINA 305 58
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 22043 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20786 55
Hangzhou FandaChem Co.,Ltd.
0086 158 5814 5714 (Mobile; WhatsApp; Telegram)
+86-571-56059825 fandachem@gmail.com CHINA 2456 55
Biochempartner
0086-13720134139
candy@biochempartner.com CHINA 956 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 24118 58
Hebei Guanlang Biotechnology Co., Ltd.
+8619930501651
breeduan@crovellbio.com CHINA 898 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 19997 58
Hebei Chisure Biotechnology Co., Ltd.
+8613292893290
+8613292893290 Nancy@SpeedGainpharma.com CHINA 630 58
Jiaxing Novartis Chemical Co., Ltd. 18957373295
- sales@novamedicals.com China 1581 58

View Lastest Price from TMC-207 manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-20 TMC-207
843663-66-1
US $1.00 / kg 1kg 95%-99% 100kg career henan chemical co
2018-07-19 Bedaquiline / TMC-207
843663-66-1
US $10.00 / KG 10UG 99% 500kg/month Hebei Chisure Biotechnology Co., Ltd.

843663-66-1(TMC-207)Related Search:


  • (αS,βR)-6-Bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-3-quinolineethanol
  • TMC-207(Bedaquiline)
  • TMC-207
  • 6-Bromo-alpha-[2-(dimethylamino)ethyl]-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-3-quinolineethanol
  • 1-(6-Bromo-2-methoxy-quinolin-3-yl)-4-dimethylamino-2-naphthalen-1-yl-1-phenyl-butan-2-ol
  • 3-Quinolineethanol, 6-bromo-alpha-(2-(dimethylamino)ethyl)-2-methoxy-alpha-1-naphthalenyl-beta-phenyl-, (alphas,betar)-
  • R 207910
  • Bedaquiline
  • Bedaquiline(R 207910,TMC 207)
  • Bedaquiline (TMC-207)
  • (αS,βR)-Bedaquiline
  • Sirturo
  • -
  • (1R,2S)-1-(6-BroMo-2-Methoxyquinolin-3-yl)-4-(diMethylaMino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
  • bedaquinline
  • (1R,2S)-1-(6-bromo-2-methoxyquinolin-3-yl)-4-(methylamino)-2-(naphthalen-1-yl)-1-phenylbutan-2-ol
  • 3-Quinolineethanol, 6-bromo-α-[2-(dimethylamino)ethyl]-2-methoxy-α-1-naphthalenyl-β-phenyl-, (αS,βR)-
  • Bedaquiline D6
  • (1R)-(6-Bromo-2-methoxyquinolin-3-yl)-4-(dimethylamino)-2(S)-(1-naphthyl)-1-phenylbutan-2-ol
  • 843663-66-1
  • C32H31BrN2O2
  • API
  • Inhibitors
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