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).


Price and Availability

Size
Price

10mg
USD 90
100mg
USD 450
1g
USD 1750
Size
Price

25mg
USD 150
200mg
USD 650
2g
USD 2950
Size
Price

50mg
USD 250
500mg
USD 1150
5g
Ask price

Delamanid (OPC-67683), purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 2g may be 2 months.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 319510
Name: Delamanid (OPC-67683)
CAS#: 681492-22-8
Chemical Formula: C25H25F3N4O6
Exact Mass: 534.17262
Molecular Weight: 534.49221
Elemental Analysis: C, 56.18; H, 4.71; F, 10.66; N, 10.48; O, 17.96


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


Technical Data

Appearance:
Solid powder

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

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


References

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.