SML3836

Delamanid

≥98% (HPLC), mycolic acid biosynthesis inhibitor, powder

• Synonym(s): (2R)-2,3-Dihydro-2-methyl-6-nitro-2-{4-[4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl]phenoxy]methyl]-imidazo[2,1-b]oxazole, (R)-2-Methyl-6-nitro-2-{4-[4-(4-trifluoromethoxyphenoxy)piperidin-1-yl]phenoxymethyl}-2,3-dihydroimidazo[2,1-b]oxazole, Deltyba, OPC 67683, OPC-67683, OPC67683
• Empirical Formula (Hill Notation): C₂₅H₂₅F₃N₄O₆
• CAS Number: 681492-22-8
• Molecular Weight: 534.48
• UNSPSC Code: 51111800
• NACRES: NA.21
• MDL number: MFCD18251539
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Product Name: Delamanid, ≥98% (HPLC)
• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D -8 to -12°, c = 0.5 in chloroform-d
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: -10 to -25°C
• SMILES string: FC(F)(F)Oc1ccc(cc1)OC2CCN(CC2)c3ccc(cc3)OC[C@@]4(Oc5[n](cc(n5)[N+](=O)[O-])C4)C
• InChI: 1S/C25H25F3N4O6/c1-24(15-31-14-22(32(33)34)29-23(31)38-24)16-35-18-4-2-17(3-5-18)30-12-10-20(11-13-30)36-19-6-8-21(9-7-19)37-25(26,27)28/h2-9,14,20H,10-13,15-16H2,1H3/t24-/m1/s1
• InChI key: XDAOLTSRNUSPPH-XMMPIXPASA-N

Description

Biochem/physiol Actions

Delamanid (OPC-67683) is an orally active mycolic acid biosynthesis inhibitor that is effective against both drug-susceptible and drug-resistant strains of M. tuberculosis H37Rv in vitro (MIC = 6 ng/mL) and exhibits significant in vivo efficacy with ~15-fold higher potency than rifampicin (RFP) in mice infected with M. tuberculosis Kurono (fold of lung CFU reduction post 28 days = 41.5 with 5 mg RFP/kg or 0.313 mg delamanid/kg daily orally dosage, 11,000-fold reduction with 0.625 mg delamanid/kg daily orally dosage).

Orally active mycolic acid biosynthesis inhibitor that is effective against drug-resistant strains of M. tuberculosis and is superior to rifampicin in vivo.

Safety Information

• pictograms: GHS08
• signalword: Warning
• hcodes: H361d
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 2
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable