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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
2588
Curator's Comment: Delamanid is brain penetrant in rats. No human data available.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
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

2014
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.31 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/33378452/
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DELAMANID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2.9 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/33378452/
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DELAMANID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/33378452/
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DELAMANID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.5%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/33378452/
100 mg 2 times / day multiple, oral
dose: 100 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DELAMANID plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
200 mg 2 times / day multiple, oral
Higher than recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22670901/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/22670901/
Disc. AE: Psychiatric symptom, Respiratory failure...
AEs leading to
discontinuation/dose reduction:
Psychiatric symptom (1.88%)
Respiratory failure (0.63%)
Skin disorder (0.63%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/22670901/
AEs

AEs

AESignificanceDosePopulation
Respiratory failure 0.63%
Disc. AE
200 mg 2 times / day multiple, oral
Higher than recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22670901/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/22670901/
Skin disorder 0.63%
Disc. AE
200 mg 2 times / day multiple, oral
Higher than recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22670901/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/22670901/
Psychiatric symptom 1.88%
Disc. AE
200 mg 2 times / day multiple, oral
Higher than recommended
Dose: 200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 200 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/22670901/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/22670901/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inducer
1087

substrate
1946

inhibitor
2252
inducer
440

inhibitor
2438
substrate
1388

inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
BSEP
550

CYP2A6
879

CYP1A1
132

P-gp
1741

CYP1A2
2153

BCRP
910

OAT1
725

OAT3
747

OATP1B1
1079

OATP1B3
961

CYP2B6
926

OCT1
620

OCT2
779

CYP2C19
2057

CYP2C8
1057
CYP1A1
389

OATP1B1
503

CYP2E1
729

BCRP
697

P-gp
2052

OATP1B3
435

OCT1
393
CYP1A1
151

CYP3A5
92
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A1
272
 no
CYP1A1
272
 no
CYP1A2
2333
 no
CYP2A6
911
 no
CYP2B6
1160
 no
CYP2C19
2141
 no
CYP2C8
1117
 no
CYP2C9
2497
 no
CYP2C9
2497
 no
CYP2D6
2546
 no
CYP3A4
2633
 no
CYP3A4
2633
 no
CYP3A5
201
 no
P-gp
1932
 no
BCRP
985
 weak
BSEP
554
 weak
OAT1
730
 weak
OAT3
749
 weak
OATP1B1
1095
 weak
OATP1B3
970
 weak
OCT1
656
 weak
OCT2
782
 weak
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1946
 minor
yes (co-administration study)
Comment: Rifampicin decreased the concentrations of delamanid by about 50%
Page: 19 | 36 | 41
P-gp
2052
 no
CYP1A1
389
 unlikely
CYP2D6
1388
 unlikely
CYP2E1
729
 unlikely
BCRP
697
 yes
OATP1B1
503
 yes
OATP1B3
435
 yes
OCT1
393
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Pentacyclic nitrofurans with in vivo efficacy and activity against nonreplicating Mycobacterium tuberculosis.
2014
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).
2011-08-25
A microbiological assessment of novel nitrofuranylamides as anti-tuberculosis agents.
2008-11
Synthesis and antituberculosis activity of a novel series of optically active 6-nitro-2,3-dihydroimidazo[2,1-b]oxazoles.
2006-12-28
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 Mon Mar 31 18:41:38 GMT 2025
Edited
by admin
on Mon Mar 31 18:41:38 GMT 2025
Record UNII
8OOT6M1PC7
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OPC-67683
Preferred Name English
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
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 Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
EU-Orphan Drug EU/3/07/524
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
WHO-VATC QJ04AK06
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
WHO-ATC J04AK06
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C157406
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
FDA UNII
8OOT6M1PC7
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
USAN
XX-14
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
INN
9401
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
MERCK INDEX
m11734
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
CAS
681492-22-8
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID60218326
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
DRUG BANK
DB11637
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
PUBCHEM
6480466
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
ChEMBL
CHEMBL218650
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
SMS_ID
100000127700
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
DRUG CENTRAL
4819
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
WIKIPEDIA
Delamanid
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
JAPANESE REVIEW
DELTYBA
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY APPROVED JULY 2014
EVMPD
SUB33761
Created by admin on Mon Mar 31 18:41:38 GMT 2025 , Edited by admin on Mon Mar 31 18:41:38 GMT 2025
PRIMARY
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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
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Structure of (5S)-2-AMINO-5-METHYL-5-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-4(5H)-OXAZOLONE
METABOLITE -> PARENT
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Structure of (4R,5S)-4-HYDROXY-5-METHYL-5-((4-(4-(4-(TRIFLUOROMETHOXY)PHENOXY)-1-PIPERIDINYL)PHENOXY)METHYL)-2-OXAZOLIDINONE
METABOLITE -> PARENT
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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
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ACTIVE MOIETY
NIH
NCATS
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