OSI-930
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MedKoo CAT#: 202100

CAS#: 728033-96-3

Description: OSI-930 is a selective thiophene-derived tyrosine kinase inhibitor with potential antineoplastic activity. Tyrosine kinase inhibitor OSI-930 inhibits stem cell factor receptor (c-Kit) and the vascular endothelial growth factor receptor 2 (VEGFR2), which may result in the inhibition of both tumor cell proliferation and tumor angiogenesis. Both c-Kit and VEGFR2 are overexpressed in a variety of cancers. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Chemical Structure

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OSI-930
CAS# 728033-96-3
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 202100
Name: OSI-930
CAS#: 728033-96-3
Chemical Formula: C22H16F3N3O2S
Exact Mass: 443.09
Molecular Weight: 443.444
Elemental Analysis: C, 59.59; H, 3.64; F, 12.85; N, 9.48; O, 7.22; S, 7.23

Price and Availability

Size Price Availability Quantity
500mg USD 2950
1g USD 3950
2g USD 5450
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Synonym: OSI-930; OSI 930; OSI930.

IUPAC/Chemical Name: 3-((quinolin-4-ylmethyl)amino)-N-(4-(trifluoromethoxy)phenyl)thiophene-2-carboxamide

InChi Key: FGTCROZDHDSNIO-UHFFFAOYSA-N

InChi Code: InChI=1S/C22H16F3N3O2S/c23-22(24,25)30-16-7-5-15(6-8-16)28-21(29)20-19(10-12-31-20)27-13-14-9-11-26-18-4-2-1-3-17(14)18/h1-12,27H,13H2,(H,28,29)

SMILES Code: O=C(C1=C(NCC2=CC=NC3=CC=CC=C23)C=CS1)NC4=CC=C(OC(F)(F)F)C=C4

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: >5 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: OSI-930 is a novel inhibitor of the receptor tyrosine kinases Kit and kinase insert domain receptor (KDR), which is currently being evaluated in clinical studies. OSI-930 selectively inhibits Kit and KDR with similar potency in intact cells and also inhibits these targets in vivo following oral dosing.    

Product Data:
Product Data
Instruction:
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Biological target: OSI-930 is an orally selective inhibitor of Kit, KDR and CSF-1R (c-Fms) with IC50s of 80 nM, 9 nM and 15 nM.
In vitro activity: Results showed that OSI-930 inactivated purified, recombinant cytochrome P450 (P450) 3A4 in the reconstituted system in a mechanism-based manner. The inactivation of 3A4 by OSI-930 was time- and concentration-dependent. Modeling studies on the binding of OSI-930 to the active site of the P450 3A4 indicated that OSI-930 would be oriented properly in the active site for oxidation of the thiophene sulfur to give the sulfoxide, which has previously been shown to be a significant metabolite of OSI-930. Reference: Drug Metab Dispos. 2011 Feb;39(2):345-50. https://pubmed.ncbi.nlm.nih.gov/21068193/
In vivo activity: The data suggest that antitumor activity of OSI-930 in mouse xenograft models is observed at dose levels that maintain a significant level of inhibition of the molecular targets of OSI-930 for a prolonged period. Furthermore, pharmacokinetic evaluation of the plasma exposure levels of OSI-930 at these effective dose levels provides an estimate of the target plasma concentrations that may be required to achieve prolonged inhibition of Kit and KDR in humans and which would therefore be expected to yield a therapeutic benefit in future clinical evaluations of OSI-930. Reference: Cancer Res. 2006 Jan 15;66(2):1015-24. https://pubmed.ncbi.nlm.nih.gov/16424037/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 56.3 127.04
DMSO:PBS (pH 7.2) (1:1) 0.3 0.74
Ethanol 3.0 6.77

Preparing Stock Solutions

The following data is based on the product molecular weight 443.44 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. Lin HL, Zhang H, Medower C, Hollenberg PF, Johnson WW. Inactivation of cytochrome P450 (P450) 3A4 but not P450 3A5 by OSI-930, a thiophene-containing anticancer drug. Drug Metab Dispos. 2011 Feb;39(2):345-50. doi: 10.1124/dmd.110.034074. Epub 2010 Nov 10. PMID: 21068193; PMCID: PMC3033695. 2. Sugita Y, Takada S, Tanigaki K, Muraki K, Uemura M, Hojo M, Miyamoto S. Inhibition of VEGF receptors induces pituitary apoplexy: An experimental study in mice. PLoS One. 2023 Mar 16;18(3):e0279634. doi: 10.1371/journal.pone.0279634. PMID: 36928058; PMCID: PMC10019612. 3. Garton AJ, Crew AP, Franklin M, Cooke AR, Wynne GM, Castaldo L, Kahler J, Winski SL, Franks A, Brown EN, Bittner MA, Keily JF, Briner P, Hidden C, Srebernak MC, Pirrit C, O'Connor M, Chan A, Vulevic B, Henninger D, Hart K, Sennello R, Li AH, Zhang T, Richardson F, Emerson DL, Castelhano AL, Arnold LD, Gibson NW. OSI-930: a novel selective inhibitor of Kit and kinase insert domain receptor tyrosine kinases with antitumor activity in mouse xenograft models. Cancer Res. 2006 Jan 15;66(2):1015-24. doi: 10.1158/0008-5472.CAN-05-2873. PMID: 16424037.
In vitro protocol: 1. Lin HL, Zhang H, Medower C, Hollenberg PF, Johnson WW. Inactivation of cytochrome P450 (P450) 3A4 but not P450 3A5 by OSI-930, a thiophene-containing anticancer drug. Drug Metab Dispos. 2011 Feb;39(2):345-50. doi: 10.1124/dmd.110.034074. Epub 2010 Nov 10. PMID: 21068193; PMCID: PMC3033695.
In vivo protocol: 1. Sugita Y, Takada S, Tanigaki K, Muraki K, Uemura M, Hojo M, Miyamoto S. Inhibition of VEGF receptors induces pituitary apoplexy: An experimental study in mice. PLoS One. 2023 Mar 16;18(3):e0279634. doi: 10.1371/journal.pone.0279634. PMID: 36928058; PMCID: PMC10019612. 2. Garton AJ, Crew AP, Franklin M, Cooke AR, Wynne GM, Castaldo L, Kahler J, Winski SL, Franks A, Brown EN, Bittner MA, Keily JF, Briner P, Hidden C, Srebernak MC, Pirrit C, O'Connor M, Chan A, Vulevic B, Henninger D, Hart K, Sennello R, Li AH, Zhang T, Richardson F, Emerson DL, Castelhano AL, Arnold LD, Gibson NW. OSI-930: a novel selective inhibitor of Kit and kinase insert domain receptor tyrosine kinases with antitumor activity in mouse xenograft models. Cancer Res. 2006 Jan 15;66(2):1015-24. doi: 10.1158/0008-5472.CAN-05-2873. PMID: 16424037.

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 1. Dihel, Larry; Kittleson, Christine; Mulvihill, Kristen; Johnson, William W. Oxidative metabolism of the trifluoromethoxy moiety of OSI-930. Drug Metabolism and Drug Interactions (2009), 24(2-4), 95-121. CODEN: DMDIEQ ISSN:0792-5077. AN 2010:437994

2. Gruber, Harry E.; Jolly, Douglas; Perez, Omar. Recombinant replication-competent retroviral vectors expressing therapeutic products for treatment of proliferative disorders. PCT Int. Appl. (2010), 194pp. CODEN: PIXXD2 WO 2010036986 A2 20100401 CAN 152:423197 AN 2010:402977

3. Patel, Jay; Korlipara, Vijaya L. Design, synthesis, and evaluation of OSI-930 analogs as dual c-Kit and KDR (VEGFR-2) tyrosine kinase inhibitors. Abstracts of Papers, 238th ACS National Meeting, Washington, DC, United States, August 16-20, 2009 (2009), MEDI-144. CODEN: 69LVCL AN 2009:984314

4. Steinberg, Joyce L.; Gupta, Neeraj; Pradhan, Rajendra S.; Enschede, Sari H.; Humerickhouse, Rod A. Pharmaceutical dosage form for oral administration of tyrosine kinase inhibitor. PCT Int. Appl. (2009), 38pp. CODEN: PIXXD2 WO 2009100176 A2 20090813 CAN 151:253972 AN 2009:976624

5. Bosch Genover, Jaime; Fernandez Lobato, Mercedes. Treatment of portal hypertension and related conditions by combined inhibition of the VEGF and PDGF signaling pathways. PCT Int. Appl. (2009), 30pp. CODEN: PIXXD2 WO 2009092442 A1 20090730 CAN 151:212495 AN 2009:918301

6. Garton, Andrew J.; Franklin, Maryland. Combined treatment with an EGFR kinase inhibitor and an inhibitor of c-kit. U.S. Pat. Appl. Publ. (2009), 40 pp. CODEN: USXXCO US 2009136517 A1 20090528 CAN 151:1315 AN 2009:652406

7. Haley, John; Thomson, Stuart. Biological markers predictive of anti-cancer response to kinase inhibitors. PCT Int. Appl. (2008), 106pp. CODEN: PIXXD2 WO 2008127719 A1 20081023 CAN 149:486833 AN 2008:1281025

8. Bradner, James Elliot; Shen, John Paul; Perlstein, Ethan Oren; Rubinsztein, David; Sarkar, Sovan; Schreiber, Stuart L. Modulators for regulating autophagy, and therapeutic uses and combinations. PCT Int. Appl. (2008), 159pp. CODEN: PIXXD2 WO 2008122038 A1 20081009 CAN 149:440403 AN 2008:1211287

9. Medower, Christine; Wen, Lian; Johnson, William W. Cytochrome P450 Oxidation of the Thiophene-Containing Anticancer Drug 3-[(Quinolin-4-ylmethyl)-amino]-thiophene-2-carboxylic Acid (4-Trifluoromethoxy-phenyl)-amide to an Electrophilic Intermediate. Chemical Research in Toxicology (2008), 21(8), 1570-1577. CODEN: CRTOEC ISSN:0893-228X. CAN 149:298699 AN 2008:932957

10. Tiollier, Jerome; Sicard, Helene; Bonnafous, Cecile. Improved methods of using phosphoantigen for the treatment of cancer. PCT Int. Appl. (2008), 107pp. CODEN: PIXXD2 WO 2008059052 A1 20080522 CAN 148:577360 AN 2008:614166
0080515 CAN 148:546116 AN 2008:586637