Ravoxertinib
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MedKoo CAT#: 206065

CAS#: 1453848-26-4 (free base)

Description: Ravoxertinib also known as GDC-0994, GDC994 and RG7842, is an orally available inhibitor of extracellular signal-regulated kinase (ERK), with potential antineoplastic activity. Upon oral administration, GDC-0994 inhibits both ERK phosphorylation and activation of ERK-mediated signal transduction pathways. This prevents ERK-dependent tumor cell proliferation and survival. The mitogen-activated protein kinase (MAPK)/ERK pathway is upregulated in a variety of tumor cell types and plays a key role in tumor cell proliferation, differentiation and survival.

Chemical Structure

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Ravoxertinib
CAS# 1453848-26-4 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 206065
Name: Ravoxertinib
CAS#: 1453848-26-4 (free base)
Chemical Formula: C21H18ClFN6O2
Exact Mass: 440.12
Molecular Weight: 440.860
Elemental Analysis: C, 57.21; H, 4.12; Cl, 8.04; F, 4.31; N, 19.06; O, 7.26

Price and Availability

Size Price Availability Quantity
5mg USD 90 Ready to ship
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 400 Ready to ship
100mg USD 650 Ready to ship
200mg USD 1150 Ready to ship
500mg USD 2750 Ready to ship
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Related CAS #: 1453848-26-4 (free base)   1817728-45-2 (besylate)   1817728-47-4 (tosylate)   2070009-58-2 (HCl)  

Synonym: GDC0994; GDC 0994; GDC-0994; RG7842; RG-7842; RG 7842; GDC994; GDC 994; GDC-994; Ravoxertinib

IUPAC/Chemical Name: (S)-1-(1-(4-chloro-3-fluorophenyl)-2-hydroxyethyl)-4-(2-((1-methyl-1H-pyrazol-5-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one

InChi Key: RZUOCXOYPYGSKL-GOSISDBHSA-N

InChi Code: InChI=1S/C21H18ClFN6O2/c1-28-19(5-8-25-28)27-21-24-7-4-17(26-21)13-6-9-29(20(31)11-13)18(12-30)14-2-3-15(22)16(23)10-14/h2-11,18,30H,12H2,1H3,(H,24,26,27)/t18-/m1/s1

SMILES Code: O=C1C=C(C2=NC(NC3=CC=NN3C)=NC=C2)C=CN1[C@@H](C4=CC=C(Cl)C(F)=C4)CO

Appearance: 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

More Info:         

Biological target: Ravoxertinib is an orally active ERK kinase inhibitor with an IC50 of 6.1 nM and 3.1 nM for ERK1 and ERK2, respectively. It inhibits ERK-dependent p90RSK serine 380 phosphorylation in PMA-stimulated HepG2 cells with an IC50 value of 12 nM.
In vitro activity: This article describes the discovery and characterization of ravoxertinib. Reference: J Med Chem. 2016 Jun 23;59(12):5650-60. https://pubmed.ncbi.nlm.nih.gov/27227380/
In vivo activity: Ravoxertinib (RAH) treatment attenuates neurobehavioral deficits, the blood-brain barrier damage, and cerebral edema after subarachnoid hemorrhage (SAH). RAH treatment decreases the SAH-elevated apoptosis-related factor active caspase-3 and RIPK1 expression. RAH attenuated neuronal apoptosis in the basal cortex at 72 h after SAH in rats. These results suggest that RAH improves long-term neurologic deficits through early inhibition of Erk1/2 in experimental SAH. Reference: ACS Omega. 2023 May 23;8(22):19692-19704. https://pubmed.ncbi.nlm.nih.gov/37305289/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 68.45

Preparing Stock Solutions

The following data is based on the product molecular weight 440.86 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. Blake JF, Burkard M, Chan J, Chen H, Chou KJ, Diaz D, Dudley DA, Gaudino JJ, Gould SE, Grina J, Hunsaker T, Liu L, Martinson M, Moreno D, Mueller L, Orr C, Pacheco P, Qin A, Rasor K, Ren L, Robarge K, Shahidi-Latham S, Stults J, Sullivan F, Wang W, Yin J, Zhou A, Belvin M, Merchant M, Moffat J, Schwarz JB. Discovery of (S)-1-(1-(4-Chloro-3-fluorophenyl)-2-hydroxyethyl)-4-(2-((1-methyl-1H-pyrazol-5-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (GDC-0994), an Extracellular Signal-Regulated Kinase 1/2 (ERK1/2) Inhibitor in Early Clinical Development. J Med Chem. 2016 Jun 23;59(12):5650-60. doi: 10.1021/acs.jmedchem.6b00389. Epub 2016 Jun 7. PMID: 27227380. 2. Yang MF, Sun SY, Lv HG, Wang WQ, Li HX, Sun JY, Zhang ZY. Ravoxertinib Improves Long-Term Neurologic Deficits after Experimental Subarachnoid Hemorrhage through Early Inhibition of Erk1/2. ACS Omega. 2023 May 23;8(22):19692-19704. doi: 10.1021/acsomega.3c01296. PMID: 37305289; PMCID: PMC10249378. 3. Janardhan HP, Dresser K, Hutchinson L, Trivedi CM. Pathological MAPK activation-mediated lymphatic basement membrane disruption causes lymphangiectasia that is treatable with ravoxertinib. JCI Insight. 2022 Sep 8;7(17):e153033. doi: 10.1172/jci.insight.153033. PMID: 36073544; PMCID: PMC9536262.
In vitro protocol: 1. Blake JF, Burkard M, Chan J, Chen H, Chou KJ, Diaz D, Dudley DA, Gaudino JJ, Gould SE, Grina J, Hunsaker T, Liu L, Martinson M, Moreno D, Mueller L, Orr C, Pacheco P, Qin A, Rasor K, Ren L, Robarge K, Shahidi-Latham S, Stults J, Sullivan F, Wang W, Yin J, Zhou A, Belvin M, Merchant M, Moffat J, Schwarz JB. Discovery of (S)-1-(1-(4-Chloro-3-fluorophenyl)-2-hydroxyethyl)-4-(2-((1-methyl-1H-pyrazol-5-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (GDC-0994), an Extracellular Signal-Regulated Kinase 1/2 (ERK1/2) Inhibitor in Early Clinical Development. J Med Chem. 2016 Jun 23;59(12):5650-60. doi: 10.1021/acs.jmedchem.6b00389. Epub 2016 Jun 7. PMID: 27227380.
In vivo protocol: 1. Yang MF, Sun SY, Lv HG, Wang WQ, Li HX, Sun JY, Zhang ZY. Ravoxertinib Improves Long-Term Neurologic Deficits after Experimental Subarachnoid Hemorrhage through Early Inhibition of Erk1/2. ACS Omega. 2023 May 23;8(22):19692-19704. doi: 10.1021/acsomega.3c01296. PMID: 37305289; PMCID: PMC10249378. 2. Janardhan HP, Dresser K, Hutchinson L, Trivedi CM. Pathological MAPK activation-mediated lymphatic basement membrane disruption causes lymphangiectasia that is treatable with ravoxertinib. JCI Insight. 2022 Sep 8;7(17):e153033. doi: 10.1172/jci.insight.153033. PMID: 36073544; PMCID: PMC9536262.

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 1: Blake JF, Burkard M, Chan J, Chen H, Chou KJ, Diaz D, Dudley DA, Gaudino JJ, Gould SE, Grina J, Hunsaker T, Liu L, Martinson M, Moreno D, Mueller L, Orr C, Pacheco P, Qin A, Rasor K, Ren L, Robarge K, Shahidi-Latham S, Stults J, Sullivan F, Wang W, Yin J, Zhou A, Belvin M, Merchant M, Moffat J, Schwarz JB. Discovery of (S)-1-(1-(4-Chloro-3-fluorophenyl)-2-hydroxyethyl)-4-(2-((1-methyl-1H-pyrazol-5-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (GDC-0994), an Extracellular Signal-Regulated Kinase 1/2 (ERK1/2) Inhibitor in Early Clinical Development. J Med Chem. 2016 Jun 23;59(12):5650-60. doi: 10.1021/acs.jmedchem.6b00389. Epub 2016 Jun 7. PubMed PMID: 27227380.