OPC-67683
- CAS No.
- 681492-22-8
- Chemical Name:
- OPC-67683
- Synonyms
- Delamanid;CS-2255;OPC-67683;Delamanid (OPC-67683);Deflazacort Impurity 13;DELAMANID;OPC67683;OPC 67683;(2R)-2-methyl-6-nitro-2-[[4-[4-[4-(trifluoromethoxy)phenoxy]...;(2R)-2-METHYL-6-NITRO-2-[[4-[4-[4-(TRIFLUOROMETHOXY)PHENOXY]PIPERIDIN-1-YL]PHENOXY]METHYL]-3H-IMIDAZO[2,1-B][1,3]OXAZOLE;(R)-2-Methyl-6-nitro-2-((4-(4-(4-(trifluoromethoxy)phenoxy)piperidin-1-yl)phenoxy)methyl)-2,3-dihydroimidazo[2,1-b]oxazole;(2R)-2,3-Dihydro-2-methyl-6-nitro-2-[[4-[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]phenoxy]methyl]imidazo[2,1-b]oxazole
- CBNumber:
- CB82512523
- Molecular Formula:
- C25H25F3N4O6
- Molecular Weight:
- 534.48
- MDL Number:
- MFCD18251539
- MOL File:
- 681492-22-8.mol
| Melting point | 195-196℃ |
|---|---|
| Boiling point | 653.7±65.0 °C(Predicted) |
| Density | 1.45 |
| storage temp. | Hygroscopic, -20°C Freezer, Under inert atmosphere |
| solubility | Chloroform (Sparingly), Ethyl Acetate (Slightly, Sonicated) |
| pka | 3.99±0.20(Predicted) |
| form | Solid |
| color | Off-White to Light Yellow |
| Stability | Hygroscopic |
| FDA UNII | 8OOT6M1PC7 |
| ATC code | J04AK06 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P321-P362+P364-P332+P313-P337+P313-P403+P233-P405-P501 | |||||||||
| NFPA 704 |
|
OPC-67683 price More Price(24)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 29697 | Delamanid | 681492-22-8 | 10mg | $57 | 2024-03-01 | Buy |
| Cayman Chemical | 29697 | Delamanid | 681492-22-8 | 250mg | $1026 | 2024-03-01 | Buy |
| Cayman Chemical | 29697 | Delamanid | 681492-22-8 | 50mg | $249 | 2024-03-01 | Buy |
| Cayman Chemical | 29697 | Delamanid | 681492-22-8 | 100mg | $467 | 2024-03-01 | Buy |
| TRC | D230660 | Delamanid | 681492-22-8 | 500mg | $1365 | 2021-12-16 | Buy |
OPC-67683 Chemical Properties,Uses,Production
Description
Marketed by Otsuka, delamanid was approved in both the European Union and Japan in 2014 as part of combination therapies for multi-drug resistant tuberculosis (TB). Because delamanid exhibited no adverse drug–drug interactions, it has found utility as a combination therapy with standard antiretroviral drugs indicated for TB. Delamanid blocks mycolic acid biosynthesis in Mycobacterium tuberculosis, which allows its cell wall to be penetrated by small molecule antivirals.
Uses
Delamanid is a novel anti-tuberculosis medication that inhibits mycolic acid synthesis and shows potent in vitro and in vivo activity against drug-resistant strains of Mycobacterium tuberculosis.
Definition
ChEBI: Delamanid is a member of piperidines.
Clinical Use
Treatment of multi-drug resistant tuberculosis
Synthesis
Piperidine 81 was concurrently prepared by first generating biaryl ether 79, which arose from a substitution reaction between pyridine N-oxide 77 and phenol 78 that proceeded in 86% yield. Next, removal of the N-oxide functionality by means of catalytic hydrogenation under mild pressure and neutral conditions afforded diaryl ether 80 in excellent yield. Reduction of the pyridine to the corresponding piperidine (81) was affected through the use of catalytic hydrogenation as well, this time under acidic conditions and elevated pressures relative to the N-oxide reduction. At this juncture, subjection of piperidine 81 to Buchwald¨C Hartwig conditions in the presence of diol subunit 82 delivered diol 83. A two-step elimination to deliver enantiopure epoxide 84 set the stage for an interesting cascade reaction to arrive at delamanid (XI) directly?a the initial alkylation of the epoxide by imidazole 85 proceeded under basic conditions with sodium acetate which then underwent an intramolecular nucleophilic substitution reaction by the liberated alcohol on the pendant imidazole chloride in the presence of sodium hydroxide. The reaction sequence proceeded in 73% yield to provide delamanid (XI) as a free base.
Drug interactions
Potentially hazardous interactions with other drugs
Analgesics: increased risk of ventricular arrhythmias
with methadone
Anti-arrhythmics: increased risk of ventricular
arrhythmias with amiodarone and disopyramide
Antibacterials: possible increased risk of ventricular
arrhythmias with clarithromycin, erythromycin
and moxifloxacin; increased risk of ventricular
arrhythmias with pentamidine; concentration
reduced by rifampicin
Antidepressants: possible increased risk of
ventricular arrhythmias with tricyclics.
Antiepileptics: avoid with carbamazepine.
Antipsychotics: increased risk of ventricular
arrhythmias with droperidol, haloperidol,
phenothiazines that prolong the QT interval and
pimozide.
Antivirals: increased risk of ventricular arrhythmias
with saquinavir
Beta-blockers: increased risk of ventricular
arrhythmias with sotalol.
Cytotoxics: increased risk of ventricular arrhythmias
with arsenic trioxide and possibly vinblastine,
vincristine, vindesine, vinflunine and vinorelbine
Domperidone: possible increased risk of ventricular
arrhythmias.
Metabolism
Delamanid is mainly metabolised in plasma by albumin and to a lesser extent by CYP3A4. The complete metabolic profile of delamanid has not yet been elucidated. The identified metabolites do not show anti-mycobacterial activity but some contribute to QT prolongation, mainly DM-6705.
OPC-67683 Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| ATK CHEMICAL COMPANY LIMITED | +undefined-21-51877795 | ivan@atkchemical.com | China | 32480 | 60 |
| Biochempartner | 0086-13720134139 | candy@biochempartner.com | CHINA | 967 | 58 |
| BOC Sciences | +1-631-485-4226 | inquiry@bocsci.com | United States | 19553 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 47465 | 58 |
| career henan chemical co | +86-0371-86658258 15093356674; | factory@coreychem.com | China | 29826 | 58 |
| Shanxi Xuanran Import and Export Trade Co., Ltd. | +8617735180244 | mike_yan@xuanranglobal.com | CHINA | 4022 | 58 |
| AFINE CHEMICALS LIMITED | 0571-85134551 | info@afinechem.com | CHINA | 15377 | 58 |
| Dayang Chem (Hangzhou) Co.,Ltd. | 571-88938639 +8617705817739 | info@dycnchem.com | CHINA | 52867 | 58 |
| Guangzhou TongYi biochemistry technology Co.,LTD | +8613073028829 | mack@tongyon.com | China | 2996 | 58 |
| InvivoChem | +1-708-310-1919 +1-13798911105 | sales@invivochem.cn | United States | 6393 | 58 |
