Omaveloxolone
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MedKoo CAT#: 206147

CAS#: 1474034-05-3

Description: Omaveloxolone, also known as RTA-408, is a member of the synthetic oleanane triterpenoid class of compounds and an activator of nuclear factor erythroid 2 [NF-E2]-related factor 2 (Nrf2, Nfe2l2), with potential chemopreventive activity. Upon administration, RTA 408 activates the cytoprotective transcription factor Nrf2. In turn, Nrf2 translocates to the nucleus, dimerizes with a small Maf protein (sMaf), and binds to the antioxidant response element (ARE). This induces the expression of a number of cytoprotective genes, including NAD(P)H quinone oxidoreductase 1 (NQO1), sulfiredoxin 1 (Srxn1), heme oxygenase-1 (HO1, HMOX1), superoxide dismutase 1 (SOD1), gamma-glutamylcysteine synthetase (gamma-GCS), thioredoxin reductase-1 (TXNRD1), glutathione S-transferase (GST), glutamate-cysteine ligase catalytic subunit (Gclc) and glutamate-cysteine ligase regulatory subunit (Gclm), and increases the synthesis of the antioxidant glutathione (GSH).


Chemical Structure

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Omaveloxolone
CAS# 1474034-05-3

Theoretical Analysis

MedKoo Cat#: 206147
Name: Omaveloxolone
CAS#: 1474034-05-3
Chemical Formula: C33H44F2N2O3
Exact Mass: 554.332
Molecular Weight: 554.71
Elemental Analysis: C, 71.45; H, 8.00; F, 6.85; N, 5.05; O, 8.65

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Ready to ship
25.0mg USD 250.0 Ready to ship
50.0mg USD 450.0 Ready to ship
100.0mg USD 650.0 Ready to ship
200.0mg USD 950.0 Ready to ship
500.0mg USD 1850.0 Ready to ship
1.0g USD 3250.0 Ready to ship
2.0g USD 5450.0 Ready to ship
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Synonym: RTA408; RTA408; RTA-408. Omaveloxolone

IUPAC/Chemical Name: N-((4aR,6aR,6bS,12aS,14aR,14bR)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicen-4a-yl)-2,2-difluoropropanamide

InChi Key: RJCWBNBKOKFWNY-HGNIWHNWSA-N

InChi Code: 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-/m1/s1

SMILES Code: CC(F)(F)C(N[C@]1(CCC(C)(C[C@@]1([C@]23[H])[H])C)CC[C@@]2(C)[C@]4(C)CCC5C(C)(C)C(C(C#N)=C[C@]5(C)C4=CC3=O)=O)=O

Appearance: White solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Omaveloxolone (RTA 408) is an antioxidant inflammation modulator (AIM), which activates Nrf2 and suppresses nitric oxide (NO).
In vitro activity: RTA-408 activated Nrf2 expression during RANKL-induced osteoclastogenesis (Fig. 1A). To explore the effect of this compound on RANKL-induced osteoclast differentiation, this study treated BMMs with RANKL and M-CSF in the presence of RTA-408 at various concentrations (0, 5, 10, and 20 nM). RTA-408 significantly inhibited osteoclast differentiation in a dose-dependent manner as indicated by TRAP staining (Fig. 1C). TRAP-positive cells with more than three nuclei were considered osteoclasts. The number of osteoclasts decreased from approximately 233/well (no RTA-408) to 21/well (20 nM RTA-408). Further, osteoclasts with more than eight nuclei were scarcely observed upon treatment with 20 nM RTA-408 (Fig. 1D). Reference: Redox Biol. 2020 Jan; 28: 101309. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6728880/
In vivo activity: RTA‐408 pretreatment significantly reduced propofol‐induced apoptosis of hippocampus neurons of mice (p < .05, Figure 6a,b). Besides, expression of Caspase‐3 was tested in the CA1 area of hippocampus via immunohistochemistry, which showed Caspase‐3 expression was increased significantly in other three groups compared with intralipid group, but when compared to vehicle + propofol group, its expression was decreased significantly in RTA‐408 + propofol group (all p < .05, Figure 6c,d). Moreover, the activities of GPx, SOD, and CAT in the hippocampus of mice from propofol group and vehicle + propofol group were lower than those from intralipid group, while RTA‐408 can significantly improve propofol‐induced oxidative stress in hippocampus (all p < .05, Figure 6e–g). Reference: Brain Behav. 2021 Jan; 11(1): e01918. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7821557/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 35.0 63.1

Preparing Stock Solutions

The following data is based on the product molecular weight 554.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Sun X, Xie Z, Hu B, Zhang B, Ma Y, Pan X, Huang H, Wang J, Zhao X, Jie Z, Shi P, Chen Z. The Nrf2 activator RTA-408 attenuates osteoclastogenesis by inhibiting STING dependent NF-κb signaling. Redox Biol. 2020 Jan;28:101309. doi: 10.1016/j.redox.2019.101309. Epub 2019 Aug 27. PMID: 31487581; PMCID: PMC6728880. 2. Liu X, Ward K, Xavier C, Jann J, Clark AF, Pang IH, Wu H. The novel triterpenoid RTA 408 protects human retinal pigment epithelial cells against H2O2-induced cell injury via NF-E2-related factor 2 (Nrf2) activation. Redox Biol. 2016 Aug;8:98-109. doi: 10.1016/j.redox.2015.12.005. Epub 2015 Dec 19. PMID: 26773873; PMCID: PMC4731949. 3. Zhang L, Zhou Q, Zhou CL. RTA-408 protects against propofol-induced cognitive impairment in neonatal mice via the activation of Nrf2 and the inhibition of NF-κB p65 nuclear translocation. Brain Behav. 2021 Jan;11(1):e01918. doi: 10.1002/brb3.1918. Epub 2020 Dec 9. PMID: 33295701; PMCID: PMC7821557. 4. Tsai TH, Lin SH, Wu CH, Tsai YC, Yang SF, Lin CL. Mechanisms and therapeutic implications of RTA 408, an activator of Nrf2, in subarachnoid hemorrhage-induced delayed cerebral vasospasm and secondary brain injury. PLoS One. 2020 Oct 5;15(10):e0240122. doi: 10.1371/journal.pone.0240122. PMID: 33017422; PMCID: PMC7535038.
In vitro protocol: 1. Sun X, Xie Z, Hu B, Zhang B, Ma Y, Pan X, Huang H, Wang J, Zhao X, Jie Z, Shi P, Chen Z. The Nrf2 activator RTA-408 attenuates osteoclastogenesis by inhibiting STING dependent NF-κb signaling. Redox Biol. 2020 Jan;28:101309. doi: 10.1016/j.redox.2019.101309. Epub 2019 Aug 27. PMID: 31487581; PMCID: PMC6728880. 2. Liu X, Ward K, Xavier C, Jann J, Clark AF, Pang IH, Wu H. The novel triterpenoid RTA 408 protects human retinal pigment epithelial cells against H2O2-induced cell injury via NF-E2-related factor 2 (Nrf2) activation. Redox Biol. 2016 Aug;8:98-109. doi: 10.1016/j.redox.2015.12.005. Epub 2015 Dec 19. PMID: 26773873; PMCID: PMC4731949.
In vivo protocol: 1. Zhang L, Zhou Q, Zhou CL. RTA-408 protects against propofol-induced cognitive impairment in neonatal mice via the activation of Nrf2 and the inhibition of NF-κB p65 nuclear translocation. Brain Behav. 2021 Jan;11(1):e01918. doi: 10.1002/brb3.1918. Epub 2020 Dec 9. PMID: 33295701; PMCID: PMC7821557. 2. Tsai TH, Lin SH, Wu CH, Tsai YC, Yang SF, Lin CL. Mechanisms and therapeutic implications of RTA 408, an activator of Nrf2, in subarachnoid hemorrhage-induced delayed cerebral vasospasm and secondary brain injury. PLoS One. 2020 Oct 5;15(10):e0240122. doi: 10.1371/journal.pone.0240122. PMID: 33017422; PMCID: PMC7535038.

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1: Alexeev V, Lash E, Aguillard A, Corsini L, Bitterman A, Ward K, Dicker AP, Linnenbach A, Rodeck U. Radiation protection of the gastrointestinal tract and growth inhibition of prostate cancer xenografts by a single compound. Mol Cancer  Ther. 2014 Dec;13(12):2968-77. doi: 10.1158/1535-7163.MCT-14-0354. Epub 2014 Nov  14. PubMed PMID: 25398830; PubMed Central PMCID: PMC4258451.



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