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Details

Stereochemistry ABSOLUTE
Molecular Formula C33H44F2N2O3
Molecular Weight 554.7109
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OMAVELOXOLONE

SMILES

[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]3(C)[C@]2([H])C(=O)C=C4[C@@]5(C)C=C(C#N)C(=O)C(C)(C)[C@]5([H])CC[C@@]34C)NC(=O)C(C)(F)F

InChI

InChIKey=RJCWBNBKOKFWNY-IDPLTSGASA-N
InChI=1S/C33H44F2N2O3/c1-27(2)11-13-33(37-26(40)32(8,34)35)14-12-31(7)24(20(33)17-27)21(38)15-23-29(5)16-19(18-36)25(39)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3,(H,37,40)/t20-,22-,24-,29-,30+,31+,33-/m0/s1

HIDE SMILES / InChI

Molecular Formula C33H44F2N2O3
Molecular Weight 554.7109
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Omaveloxolone (RTA-408) is a synthetic triterpenoid exerting antioxidant inflammation modulator properties. It activates the transcription factor Nrf2 and inhibits NF-κB signaling. Omaveloxolone demonstrated antioxidant, anti-inflammatory, and anticancer activities. Reata Pharmaceuticals is developing omaveloxolone for the treatment of cancers, Friedreich's ataxia and mitochondrial disorders.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day multiple, oral
Highest studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources: Page: p.19
unhealthy, ADULT
n = 10
Health Status: unhealthy
Condition: Friedreich ataxia
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 10
Sources: Page: p.19
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Molecular mechanisms of Nrf2-mediated antioxidant response.
2009 Feb
Patents

Patents

Sample Use Guides

Phase 2 study investigated oral omaveloxolone (RTA-408) (2.5-300 mg capsules) in patients with Friedreich's Ataxia. A Phase 1 healthy volunteer clinical study with RTA 408 Lotion (NCT02029716) consisted of 3 sequential parts. In Part A, RTA 408 Lotion (0.5 %, 1 %, and 3 %) and lotion vehicle were applied to individual 4-cm(2) sites twice daily for 14 days. In Parts B and C, separate groups of subjects had 3 % RTA 408 Lotion applied twice daily to a 100-cm(2) site for 14 days or a 500-cm(2) site for 28 days.
Route of Administration: Other
At low concentrations (≤ 25 nM), omaveloxolone (RTA-408) activated Nrf2 and suppressed nitric oxide and pro-inflammatory cytokine levels in interferon-γ-stimulated RAW 264.7 macrophage cells. At higher concentrations, RTA 408 inhibited tumor cell growth (GI50 = 260 ± 74 nM) and increased caspase activity in tumor cell lines, but not in normal primary human cells.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:19:22 UTC 2023
Edited
by admin
on Sat Dec 16 11:19:22 UTC 2023
Record UNII
G69Z98951Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OMAVELOXOLONE
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
PROPANAMIDE, N-(2-CYANO-3,12-DIOXO-28-NOROLEANA-1,9(11)-DIEN-17-YL)-2,2-DIFLUORO-
Systematic Name English
SKYCLARYS
Brand Name English
OMAVELOXOLONE [USAN]
Common Name English
RTA 408
Code English
omaveloxolone [INN]
Common Name English
RTA-408
Code English
Omaveloxolone [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2080
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
FDA ORPHAN DRUG 461214
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
EU-Orphan Drug EU/3/18/2037
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
FDA ORPHAN DRUG 461114
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
Code System Code Type Description
FDA UNII
G69Z98951Q
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
USAN
CD-116
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
DRUG BANK
DB12513
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
INN
10135
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
CAS
1474034-05-3
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
PUBCHEM
71811910
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
EVMPD
SUB179300
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL3707273
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
DAILYMED
G69Z98951Q
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID101138251
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
SMS_ID
100000164733
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
NCI_THESAURUS
C113443
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
WIKIPEDIA
RTA 408
Created by admin on Sat Dec 16 11:19:22 UTC 2023 , Edited by admin on Sat Dec 16 11:19:22 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> ACTIVATOR
TARGET -> INHIBITOR
suppresses activity
Related Record Type Details
ACTIVE MOIETY