Delamanid

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Delamanid
File:Delamanid.svg
Systematic (IUPAC) 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
Clinical data
Trade names Deltyba
AHFS/Drugs.com International Drug Names
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Metabolism CYP3A4
Biological half-life 38 hrs
Identifiers
CAS Number 681492-22-8
ATC code J04AK06 (WHO)
PubChem CID: 6480466
ChemSpider 4981055
ChEMBL CHEMBL218650
Synonyms OPC-67683
Chemical data
Formula C25H25F3N4O6
Molecular mass 534.48 g/mol
  • FC(F)(F)Oc5ccc(OC4CCN(c3ccc(OC[C@@]2(Oc1nc(cn1C2)[N+]([O-])=O)C)cc3)CC4)cc5
  • 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
  • Key:XDAOLTSRNUSPPH-XMMPIXPASA-N

Delamanid (USAN, INN) is an experimental 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.[1][2][3] The drug is approved in the EU under the trade name Deltyba (made by Otsuka Pharmaceutical).

It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[4]

Adverse effects

Delamanid prolongs QT time.[5]

Interactions

Delamanid is metabolised by the liver enzyme CYP3A4, wherefore strong inducers of this enzyme can reduce its effectiveness.[5]

History

In phase II clinical trials, the drug was used in combination with standard treatments, such as four or five of the drugs ethambutol, isoniazid, pyrazinamide, rifampicin, aminoglycoside antibiotics, and quinolones. Healing rates (measured as sputum culture conversion) were significantly better in patients who additionally took delamanid.[3][6]

The European Medicines Agency (EMA) recommended conditional marketing authorization for delamanid in adults with multidrug-resistant pulmonary tuberculosis without other treatment options because of resistance or tolerability. The EMA considered the data show that the benefits of delamanid outweigh the risks, but that additional studies were needed on the long-term effectiveness.[7]

See also

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 Pharmazeutische Zeitung: Delamanid: Neuer Wirkstoff gegen multiresistente TB, 9 May 2014. (German)
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Drug Discovery & Development. EMA Recommends Two New Tuberculosis Treatments. November 22, 2013.
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