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SML3836

Sigma-Aldrich

Delamanid

≥98% (HPLC)

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

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About This Item

Empirical Formula (Hill Notation):
C25H25F3N4O6
CAS Number:
681492-22-8
Molecular Weight:
534.48
MDL number:
MFCD18251539
UNSPSC Code:
51111800
UNSPSC Code:
12352200
NACRES:
NA.21

Quality Level

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

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).

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Delamanid Kills Dormant Mycobacteria In Vitro and in a Guinea Pig Model of Tuberculosis
Antimicrobial Agents and Chemotherapy, 61(6), e02402-e02416 (2017)
Hirofumi Sasaki et al.
Journal of medicinal chemistry, 49(26), 7854-7860 (2006-12-22)
In an effort to develop potent new antituberculosis agents that would be effective against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis, we prepared a novel series of optically active 6-nitro-2,3-dihydroimidazo[2,1-b]oxazoles substituted at the 2-position with various phenoxymethyl groups and
Makoto Matsumoto et al.
PLoS medicine, 3(11), e466-e466 (2006-11-30)
Tuberculosis (TB) is still a leading cause of death worldwide. Almost a third of the world's population is infected with TB bacilli, and each year approximately 8 million people develop active TB and 2 million die as a result. Today's

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