Delamanid (OPC-67683)
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MedKoo CAT#: 319510

CAS#: 681492-22-8

Description: Delamanid, also known as OPC-67683, is a drug for the treatment of multi-drug-resistant tuberculosis. It works by blocking the synthesis of mycolic acids in Mycobacterium tuberculosis, the organism which causes tuberculosis, thus destabilising its cell wall. The drug is approved in the EU. Delamanid inhibits the synthesis of mycolic acids, crucial component of the cell wall of the Mycobacterium tuberculosis complex. Delamanid is insoluble in water and its activity was proven in several in vitro and in vivo studies. Its bactericidal activity was demonstrated in individuals with drug-susceptible and drug-resistant tuberculosis (MDR- and XDR-TB).

Chemical Structure

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Delamanid (OPC-67683)
CAS# 681492-22-8
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319510
Name: Delamanid (OPC-67683)
CAS#: 681492-22-8
Chemical Formula: C25H25F3N4O6
Exact Mass: 534.17
Molecular Weight: 534.492
Elemental Analysis: C, 56.18; H, 4.71; F, 10.66; N, 10.48; O, 17.96

Price and Availability

Size Price Availability Quantity
10mg USD 110 Ready to ship
25mg USD 220 Ready to ship
50mg USD 385 Ready to ship
100mg USD 650 Ready to ship
200mg USD 1150 Ready to ship
500mg USD 2450 Ready to ship
1g USD 4250 Ready to ship
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Synonym: OPC-67683; OPC 67683; OPC67683; Delamanid; trade name Deltyba

IUPAC/Chemical Name: (2R)-2-Methyl-6-nitro-2-[(4-{4-[4-(trifluoromethoxy)phenoxy]-1-piperidinyl}phenoxy)methyl]-2,3-dihydroimidazo[2,1-b][1,3]oxazole

InChi Key: XDAOLTSRNUSPPH-XMMPIXPASA-N

InChi Code: 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

SMILES Code: FC(F)(F)OC1=CC=C(OC2CCN(C3=CC=C(OC[C@@]4(C)CN5C(O4)=NC([N+]([O-])=O)=C5)C=C3)CC2)C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Delamanid, a newer mycobacterial cell wall synthesis inhibitor, inhibits the synthesisi of mucolic acids.
In vitro activity: A study was conducted to confirm the post-antibiotic effect of OPC-67683 on intracellular M. tuberculosis in THP-1 cells, and the results were compared with RFP, INH, and PA-824. OPC-67683 was shown to be highly active against intracellular M. tuberculosis H37Rv after 4-h pulsed exposures in a dose-dependent manner. The data are shown in Figure 3. The intracellular activity of OPC-67683 at a concentration of 0.1 μg/ml was similar to that of RFP of 3 μg/ml, but was superior to INH and PA-824, which both showed poor activity during the 4-h pulsed exposure. These results indicated that even with limited contact with the bacteria within the cells, OPC-67683 might be able to effectively kill the intracellular mycobacteria. Reference: PLoS Med. 2006 Nov; 3(11): e466. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1664607/
In vivo activity: Regimen D (DLM (Delamanid) alone at 100 mg/kg) eradicated lung CFU over time (2.04 log10 CFU at 4 weeks, 0 log10 CFU at 8 weeks), equivalent to the results with the LVX-ETO-PZA-AMK (LEtZA) regimen and the standard RIF-INH-PZA (RHZ) regimen (Fig. 2 and Table 2). Replacing INH with 100 mg/kg DLM in the RHZ regimen or adding 100 mg/kg DLM to the LEtZA regimen significantly accelerated eradication of bacilli, as lungs from guinea pigs treated with the DLM-RIF-PZA (DRZ) or DLM-LVX-ETO-PZA-AMK (DLEtZA) regimen resulted in no viable bacteria being detected at 4 weeks. These results indicate that DLM plays an important role in the eradication of M. tuberculosis in guinea pig lungs. Reference: Antimicrob Agents Chemother. 2017 Jun; 61(6): e02402-16. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5444171/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 56.7 106.03
DMF 25.0 46.77
Ethanol 2.0 3.68

Preparing Stock Solutions

The following data is based on the product molecular weight 534.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Sasabe H, Shimokawa Y, Shibata M, Hashizume K, Hamasako Y, Ohzone Y, Kashiyama E, Umehara K. Antitubercular Agent Delamanid and Metabolites as Substrates and Inhibitors of ABC and Solute Carrier Transporters. Antimicrob Agents Chemother. 2016 May 23;60(6):3497-508. doi: 10.1128/AAC.03049-15. Erratum in: Antimicrob Agents Chemother. 2016 Jul;60(7):4431. PMID: 27021329; PMCID: PMC4879383. 2. Matsumoto M, Hashizume H, Tomishige T, Kawasaki M, Tsubouchi H, Sasaki H, Shimokawa Y, Komatsu M. OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice. PLoS Med. 2006 Nov;3(11):e466. doi: 10.1371/journal.pmed.0030466. PMID: 17132069; PMCID: PMC1664607. 3. Chen X, Hashizume H, Tomishige T, Nakamura I, Matsuba M, Fujiwara M, Kitamoto R, Hanaki E, Ohba Y, Matsumoto M. Delamanid Kills Dormant Mycobacteria In Vitro and in a Guinea Pig Model of Tuberculosis. Antimicrob Agents Chemother. 2017 May 24;61(6):e02402-16. doi: 10.1128/AAC.02402-16. PMID: 28373190; PMCID: PMC5444171. 4. Patterson S, Wyllie S, Norval S, Stojanovski L, Simeons FR, Auer JL, Osuna-Cabello M, Read KD, Fairlamb AH. The anti-tubercular drug delamanid as a potential oral treatment for visceral leishmaniasis. Elife. 2016 May 24;5:e09744. doi: 10.7554/eLife.09744. PMID: 27215734; PMCID: PMC4878867.
In vitro protocol: 1. Sasabe H, Shimokawa Y, Shibata M, Hashizume K, Hamasako Y, Ohzone Y, Kashiyama E, Umehara K. Antitubercular Agent Delamanid and Metabolites as Substrates and Inhibitors of ABC and Solute Carrier Transporters. Antimicrob Agents Chemother. 2016 May 23;60(6):3497-508. doi: 10.1128/AAC.03049-15. Erratum in: Antimicrob Agents Chemother. 2016 Jul;60(7):4431. PMID: 27021329; PMCID: PMC4879383. 2. Matsumoto M, Hashizume H, Tomishige T, Kawasaki M, Tsubouchi H, Sasaki H, Shimokawa Y, Komatsu M. OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice. PLoS Med. 2006 Nov;3(11):e466. doi: 10.1371/journal.pmed.0030466. PMID: 17132069; PMCID: PMC1664607.
In vivo protocol: 1. Chen X, Hashizume H, Tomishige T, Nakamura I, Matsuba M, Fujiwara M, Kitamoto R, Hanaki E, Ohba Y, Matsumoto M. Delamanid Kills Dormant Mycobacteria In Vitro and in a Guinea Pig Model of Tuberculosis. Antimicrob Agents Chemother. 2017 May 24;61(6):e02402-16. doi: 10.1128/AAC.02402-16. PMID: 28373190; PMCID: PMC5444171. 2. Patterson S, Wyllie S, Norval S, Stojanovski L, Simeons FR, Auer JL, Osuna-Cabello M, Read KD, Fairlamb AH. The anti-tubercular drug delamanid as a potential oral treatment for visceral leishmaniasis. Elife. 2016 May 24;5:e09744. doi: 10.7554/eLife.09744. PMID: 27215734; PMCID: PMC4878867.

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1: Rustomjee R, Zumla A. Delamanid expanded access novel treatment of drug resistant tuberculosis. Infect Drug Resist. 2015 Oct 29;8:359-366. eCollection 2015. Review. PubMed PMID: 26604805; PubMed Central PMCID: PMC4631416.

2: Brigden G, Hewison C, Varaine F. New developments in the treatment of drug-resistant tuberculosis: clinical utility of bedaquiline and delamanid. Infect Drug Resist. 2015 Oct 30;8:367-378. eCollection 2015. Review. PubMed PMID: 26586956; PubMed Central PMCID: PMC4634826.

3: Bloemberg GV, Keller PM, Stuckia D, Trauner A, Borrell S, Latshang T, Coscolla M, Rothe T, Hömke R, Ritter C, Feldmann J, Schulthess B, Gagneux S, Böttger EC. Acquired Resistance to Bedaquiline and Delamanid in Therapy for Tuberculosis. N Engl J Med. 2015 Nov 12;373(20):1986-8. doi: 10.1056/NEJMc1505196. PubMed PMID: 26559594.

4: Furin J, Harausz E, Zimetbaum P, Cox H. In reply. QTc prolongation and delamanid: access and safety. Int J Tuberc Lung Dis. 2015 Oct;19(10):1262-3. doi: 10.5588/ijtld.15.0541-2. PubMed PMID: 26459548.

5: Gupta R, Geiter LJ, Hafkin J, Wells CD. Delamanid and QT prolongation in the treatment of multidrug-resistant tuberculosis. Int J Tuberc Lung Dis. 2015 Oct;19(10):1261-2. doi: 10.5588/ijtld.15.0541. PubMed PMID: 26459547.

6: Meng M, Smith B, Johnston B, Carter S, Brisson J, Roth SE. Simultaneous quantitation of delamanid (OPC-67683) and its eight metabolites in human plasma using UHPLC-MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:78-91. doi: 10.1016/j.jchromb.2015.07.058. Epub 2015 Aug 6. PubMed PMID: 26319300.

7: Esposito S, Bianchini S, Blasi F. Bedaquiline and delamanid in tuberculosis. Expert Opin Pharmacother. 2015 Oct;16(15):2319-30. doi: 10.1517/14656566.2015.1080240. Epub 2015 Aug 19. PubMed PMID: 26293803.

8: Gupta R, Geiter LJ, Wells CD, Gao M, Cirule A, Xiao H. Delamanid for Extensively Drug-Resistant Tuberculosis. N Engl J Med. 2015 Jul 16;373(3):291-2. doi: 10.1056/NEJMc1415332. PubMed PMID: 26176402.

9: The Use of Delamanid in the Treatment of Multidrug-Resistant Tuberculosis: Interim Policy Guidance. Geneva: World Health Organization; 2014. PubMed PMID: 26110189.

10: Shimokawa Y, Sasahara K, Koyama N, Kitano K, Shibata M, Yoda N, Umehara K. Metabolic Mechanism of Delamanid, a New Anti-Tuberculosis Drug, in Human Plasma. Drug Metab Dispos. 2015 Aug;43(8):1277-83. doi: 10.1124/dmd.115.064550. Epub 2015 Jun 8. PubMed PMID: 26055621.

11: Sasahara K, Shimokawa Y, Hirao Y, Koyama N, Kitano K, Shibata M, Umehara K. Pharmacokinetics and Metabolism of Delamanid, a Novel Anti-Tuberculosis Drug, in Animals and Humans: Importance of Albumin Metabolism In Vivo. Drug Metab Dispos. 2015 Aug;43(8):1267-76. doi: 10.1124/dmd.115.064527. Epub 2015 Jun 8. PubMed PMID: 26055620.

12: Lewis JM, Sloan DJ. The role of delamanid in the treatment of drug-resistant tuberculosis. Ther Clin Risk Manag. 2015 May 13;11:779-91. doi: 10.2147/TCRM.S71076. eCollection 2015. Review. PubMed PMID: 25999726; PubMed Central PMCID: PMC4437614.

13: Keller PM, Hömke R, Ritter C, Valsesia G, Bloemberg GV, Böttger EC. Determination of MIC distribution and epidemiological cutoff values for bedaquiline and delamanid in Mycobacterium tuberculosis using the MGIT 960 system equipped with TB eXiST. Antimicrob Agents Chemother. 2015 Jul;59(7):4352-5. doi: 10.1128/AAC.00614-15. Epub 2015 May 4. PubMed PMID: 25941226; PubMed Central PMCID: PMC4468675.

14: Thakare R, Soni I, Dasgupta A, Chopra S. Delamanid for the treatment of pulmonary multidrug-resistant tuberculosis. Drugs Today (Barc). 2015 Feb;51(2):117-23. doi: 10.1358/dot.2015.51.2.2245645. PubMed PMID: 25756067.

15: Barry CE 3rd. Timing is everything for compassionate use of delamanid. Nat Med. 2015 Mar;21(3):211. doi: 10.1038/nm.3823. PubMed PMID: 25742452.

16: Wells CD, Gupta R, Hittel N, Geiter LJ. Long-term mortality assessment of multidrug-resistant tuberculosis patients treated with delamanid. Eur Respir J. 2015 May;45(5):1498-501. doi: 10.1183/09031936.00176314. Epub 2015 Feb 19. PubMed PMID: 25700385; PubMed Central PMCID: PMC4416109.

17: Szumowski JD, Lynch JB. Profile of delamanid for the treatment of multidrug-resistant tuberculosis. Drug Des Devel Ther. 2015 Jan 29;9:677-82. doi: 10.2147/DDDT.S60923. eCollection 2015. Review. PubMed PMID: 25678771; PubMed Central PMCID: PMC4319680.

18: Sotgiu G, Pontali E, Centis R, D'Ambrosio L, Migliori GB. Delamanid (OPC-67683) for treatment of multi-drug-resistant tuberculosis. Expert Rev Anti Infect Ther. 2015 Mar;13(3):305-15. doi: 10.1586/14787210.2015.1011127. Epub 2015 Feb 3. Review. PubMed PMID: 25645397.

19: Blair HA, Scott LJ. Delamanid: a review of its use in patients with multidrug-resistant tuberculosis. Drugs. 2015 Jan;75(1):91-100. doi: 10.1007/s40265-014-0331-4. Review. PubMed PMID: 25404020.

20: Shimokawa Y, Sasahara K, Yoda N, Mizuno K, Umehara K. Delamanid does not inhibit or induce cytochrome p450 enzymes in vitro. Biol Pharm Bull. 2014;37(11):1727-35. PubMed PMID: 25366478.


1. Reckers A, Huo S, Esmail A, Dheda K, Bacchetti P, Gandhi M, Metcalfe J, Gerona R. Development and validation of a liquid chromatography-tandem mass spectrometry method for quantifying delamanid and its metabolite in small hair samples. J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Apr 15;1169:122467. doi: 10.1016/j.jchromb.2020.122467. Epub 2020 Dec 10. PMID: 33713954; PMCID: PMC7987786.

2. Kreutzfeldt KM, Jansen RS, Hartman TE, Gouzy A, Wang R, Krieger IV, Zimmerman MD, Gengenbacher M, Sarathy JP, Xie M, Dartois V, Sacchettini JC, Rhee KY, Schnappinger D, Ehrt S. CinA mediates multidrug tolerance in Mycobacterium tuberculosis. Nat Commun. 2022 Apr 22;13(1):2203. doi: 10.1038/s41467-022-29832-1. PMID: 35459278.