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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H25F3N4O6
Molecular Weight 534.4844
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DELAMANID

SMILES

C[C@]4(COC1=CC=C(C=C1)N2CCC(CC2)OC3=CC=C(OC(F)(F)F)C=C3)CN5C=C(N=C5O4)[N+]([O-])=O

InChI

InChIKey=XDAOLTSRNUSPPH-XMMPIXPASA-N
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

HIDE SMILES / InChI
Molecular Formula C25H25F3N4O6
Molecular Weight 534.4844
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24923253

Delamanid (OPC-67683, Deltyba™) is a nitro-dihydro-imidazooxazoles derivative. It is a mycolic acid biosynthesis inhibitor, an essential component of the cell wall of M. tuberculosis. Delamanid possess highly potent activity against tuberculosis, as shown by its exceptionally low minimum inhibitory concentration range in vitro and highly effective therapeutic activity at low doses in vivo. Delamanid has been developed by Otsuka Pharmaceutical for the treatment of multidrug-resistant tuberculosis. Delamanid received its first global approval for the treatment of MDR-TB in the European Union (EU), for use in combination with optimised background therapy. It is also under review for marketing in Japan for MDR-TB, the first drug application filed in Japan for this indication. Delamanid has been granted orphan drug status in both the EU and Japan.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Delamanid is brain penetrant in rats. No human data available.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
DELTYBA

Approved Use

Deltyba is indicated for use as part of an appropriate combination regimen for pulmonary multi-drug resistant tuberculosis (MDR-TB) in adult patients when an effective treatment regimen cannot otherwise be composed for reasons of resistance or tolerability

Launch Date

1.39855685E12
PubMed

PubMed

TitleDatePubMed
Synthesis and antituberculosis activity of a novel series of optically active 6-nitro-2,3-dihydroimidazo[2,1-b]oxazoles.
2006 Dec 28
A microbiological assessment of novel nitrofuranylamides as anti-tuberculosis agents.
2008 Nov
Structure-activity relationships of antitubercular nitroimidazoles. 3. Exploration of the linker and lipophilic tail of ((s)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yl)-(4-trifluoromethoxybenzyl)amine (6-amino PA-824).
2011 Aug 25
Pentacyclic nitrofurans with in vivo efficacy and activity against nonreplicating Mycobacterium tuberculosis.
2014
Patents

Patents

07262212
2
07368579
2
07807843
1
08129544
1
08598358
1
20060079697
2
20060094767
10
20070219374
2
20080097107
1
20080200689
1

Sample Use Guides

In Vivo Use Guide
The recommended dose for adults is 100 mg twice daily for 24 weeks.
Route of Administration: Oral
In Vitro Use Guide
Delamanid exhibited significant bactericidal activity against replicating and dormant bacilli at or above the concentrations of 0.016 and 0.4 mg/L, respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:10:56 UTC 2023
Edited
by admin
on Fri Dec 15 17:10:56 UTC 2023
Record UNII
8OOT6M1PC7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DELAMANID
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
IMIDAZO(2,1-B)OXAZOLE, 2,3-DIHYDRO-2-METHYL-6-NITRO-2-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-, (2R)-
Systematic Name English
OPC67683
Code English
Delamanid [WHO-DD]
Common Name English
OPC-67683
Code English
DELAMANID [MI]
Common Name English
DELAMANID [USAN]
Common Name English
DELAMANID [JAN]
Common Name English
(2R)-2-METHYL-6-NITRO-2-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)PIPERIDIN-1- YL)PHENOXY)METHYL)-2,3-DIHYDROIMIDAZO(2,1-B)OXAZOLE
Systematic Name English
delamanid [INN]
Common Name English
DELTYBA
Brand Name English
(2R)-2-METHYL-6-NITRO-2-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)PIPERIDIN-1-YL)PHENOXY)METHYL)-2,3-DIHYDROIMIDAZO(2,1-B)(1,3)OXAZOLE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 244007
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
EU-Orphan Drug EU/3/07/524
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
WHO-VATC QJ04AK06
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
WHO-ATC J04AK06
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C157406
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
FDA UNII
8OOT6M1PC7
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
USAN
XX-14
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
INN
9401
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
MERCK INDEX
m11734
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
CAS
681492-22-8
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID60218326
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
DRUG BANK
DB11637
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
PUBCHEM
6480466
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
ChEMBL
CHEMBL218650
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
SMS_ID
100000127700
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
DRUG CENTRAL
4819
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
WIKIPEDIA
Delamanid
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
JAPANESE REVIEW
DELTYBA
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY APPROVED JULY 2014
EVMPD
SUB33761
Created by admin on Fri Dec 15 17:10:56 UTC 2023 , Edited by admin on Fri Dec 15 17:10:56 UTC 2023
PRIMARY
Related Record Type Details
MYCOBACTERIUM TUBERCULOSIS
TARGET ORGANISM->INHIBITOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
Structure of (5S)-2-AMINO-4,5-DIHYDRO-5-METHYL-5-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-4-OXAZOLOL
METABOLITE -> PARENT
PLASMA
Structure of (5R)-4,5-DIHYDRO-5-METHYL-5-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-2-OXAZOLAMINE
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of (5R)-5-METHYL-5-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-2-OXAZOLIDINONE
METABOLITE -> PARENT
PLASMA
Structure of (4S,5S)-4-HYDROXY-5-METHYL-5-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-2-OXAZOLIDINONE
METABOLITE -> PARENT
PLASMA
Structure of (5S)-5-METHYL-5-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-2,4-OXAZOLIDINEDIONE
METABOLITE -> PARENT
PLASMA
Structure of (5S)-2-AMINO-5-METHYL-5-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-4(5H)-OXAZOLONE
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of (4R,5S)-4-HYDROXY-5-METHYL-5-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-2-OXAZOLIDINONE
METABOLITE -> PARENT
PLASMA
Structure of N-((2R)-2-HYDROXY-2-METHYL-3-(4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)PROPYL)UREA
METABOLITE -> PARENT
PLASMA
Related Record Type Details
Structure of DELAMANID
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