OMAVELOXOLONE

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 Search

SMILES

CC(F)(F)C(=O)N[C@]12CCC(C)(C)C[C@H]1[C@H]3C(=O)C=C4[C@@]5(C)C=C(C#N)C(=O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC2

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25897966 | http://adisinsight.springer.com/drugs/800039652 | https://reatapharma.com/

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nuclear factor erythroid 2-related factor 2 15 Target ID: CHEMBL1075094 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26170027 \| https://www.ncbi.nlm.nih.gov/pubmed/25897966	Activator 1447
Nuclear factor NF-kappa-B complex 11 Target ID: CHEMBL2094258 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25897966	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Friedreich ataxia 12 Sources: http://adisinsight.springer.com/drugs/800039652	Primary	Phase II 1147	Unknown Approved Use Unknown
Mitochondrial myopathy 1 Sources: http://adisinsight.springer.com/drugs/800039652	Primary	Phase II 1147	Unknown Approved Use Unknown
Melanoma 88 Sources: http://adisinsight.springer.com/drugs/800039652	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
112 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31118567/	160 mg 1 times / day steady-state, oral dose: 160 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		OMAVELOXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
15.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28919776	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		OMAVELOXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1.26 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31118567/	160 mg 1 times / day steady-state, oral dose: 160 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		OMAVELOXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
114.4 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28919776	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		OMAVELOXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31118567/	160 mg 1 times / day steady-state, oral dose: 160 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	OMAVELOXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
57 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/216718Orig1s000lbl.pdf	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:	OMAVELOXOLONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FASTED
9.2 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28919776	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	OMAVELOXOLONE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
3% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2023/216718Orig1s000lbl.pdf	150 mg 1 times / day multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered:		OMAVELOXOLONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: FASTED

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/30656180	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/30656180	Sources: https://pubmed.ncbi.nlm.nih.gov/30656180

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00AC1P	https://www.1pchem.com/search?query=1P00AC1P
ApexBio Technology	B3576	https://www.apexbt.com/catalogsearch/result/?q=B3576
AstaTech	40810	http://astatechinc.com/CPSResult.php?CRNO=40810
Axon MedChem	2497	https://www.axonmedchem.com/product/2497
Cayman Chemical	17854	http://www.caymanchem.com/app/template/Product.vm/catalog/17854
Chem Scene	CS-3078	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3078
ChemShuttle	169578	https://www.chemshuttle.com/catalogsearch/result/?q=169578
eMolecules	50283346	https://orderbb.emolecules.com/search/#?query=50283346
eMolecules	75224124	https://orderbb.emolecules.com/search/#?query=75224124
Excenen	EX-A541	http://www.excenen.com/searchresultlist.php?id=EX-A541
mcule	MCULE-2178019155	https://mcule.com/MCULE-2178019155/
MedChem Express	HY-12212	https://www.medchemexpress.com/search.html?q=HY-12212&ft=&fa=&fp=
MolPort	MolPort-039-193-839	https://www.molport.com/shop/molecule-link/MolPort-039-193-839
MolPort	MolPort-042-665-881	https://www.molport.com/shop/molecule-link/MolPort-042-665-881
MuseChem	I001800	https://www.musechem.com/product/I001800.html
Selleck Chemicals	S7672	http://www.selleckchem.com/search.html?searchDTO.searchParam=S7672
ShangHai Biochempartner	BCP28609	http://www.biochempartner.com/search_BCP28609
Toronto Research Chemicals	D292465	https://www.trc-canada.com/product-detail/?CatNum=D292465
Toronto Research Chemicals	R700990	https://www.trc-canada.com/product-detail/?CatNum=R700990

PubMed

Title	Date	PubMed
RTA 408, A Novel Synthetic Triterpenoid with Broad Anticancer and Anti-Inflammatory Activity.	2015	25897966
Topical application of the synthetic triterpenoid RTA 408 activates Nrf2 and induces cytoprotective genes in rat skin.	2014-07	24362512
Topical application of the synthetic triterpenoid RTA 408 protects mice from radiation-induced dermatitis.	2014-05	24720753
Molecular mechanisms of Nrf2-mediated antioxidant response.	2009-02	18618599

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 23:46:54 GMT 2025` Edited by `admin` on `Mon Mar 31 23:46:54 GMT 2025`
Record UNII	G69Z98951Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

omaveloxolone [INN]

Preferred Name

English

OMAVELOXOLONE

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

RTA-408

Code

English

Omaveloxolone [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2080