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MedKoo Cat#: 413251 | Name: OXI-4503 Free Base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

OXI-4503 Free Base is a diphosphate prodrug of cambretastatin A1.

Chemical Structure

OXI-4503 Free Base
OXI-4503 Free Base
CAS#288847-35-8 (free base)

Theoretical Analysis

MedKoo Cat#: 413251

Name: OXI-4503 Free Base

CAS#: 288847-35-8 (free base)

Chemical Formula: C18H22O12P2

Exact Mass: 492.0586

Molecular Weight: 492.31

Elemental Analysis: C, 43.92; H, 4.50; O, 39.00; P, 12.58

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
288847-35-8 (free acid) 288847-34-7 (sodium) 1014615-46-3 (potassium)
Synonym
OXI-4503; OXI 4503; OXI4503
IUPAC/Chemical Name
1,2-Benzenediol, 3-methoxy-6-((1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl)-, 1,2-bis(dihydrogen phosphate)
InChi Key
GSOXMQLWUDQTNT-WAYWQWQTSA-N
InChi Code
InChI=1S/C18H22O12P2/c1-25-13-8-7-12(16(29-31(19,20)21)18(13)30-32(22,23)24)6-5-11-9-14(26-2)17(28-4)15(10-11)27-3/h5-10H,1-4H3,(H2,19,20,21)(H2,22,23,24)/b6-5-
SMILES Code
COC1=C(OC)C(OC)=CC(/C=C\C2=C(OP(O)(O)=O)C(OP(O)(O)=O)=C(OC)C=C2)=C1
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
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
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 492.31 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
1: Hill SA, Toze GM, Pettit GR, Chaplin DJ. Preclinical evaluation of the antitumour activity of the novel vascular targeting agent Oxi 4503. Anticancer Res. 2002 May-Jun;22(3):1453-8. Erratum in: Anticancer Res. 2003;23:5369. PMID: 12168822. 2: Chan LS, Daruwalla J, Christophi C. Selective targeting of the tumour vasculature. ANZ J Surg. 2008 Nov;78(11):955-67. doi: 10.1111/j.1445-2197.2008.04712.x. PMID: 18959693. 3: Thorpe PE. Vascular targeting agents as cancer therapeutics. Clin Cancer Res. 2004 Jan 15;10(2):415-27. doi: 10.1158/1078-0432.ccr-0642-03. PMID: 14760060. 4: Cai SX. Small molecule vascular disrupting agents: potential new drugs for cancer treatment. Recent Pat Anticancer Drug Discov. 2007 Jan;2(1):79-101. doi: 10.2174/157489207779561462. PMID: 18221055. 5: Shaked Y, Tang T, Woloszynek J, Daenen LG, Man S, Xu P, Cai SR, Arbeit JM, Voest EE, Chaplin DJ, Smythe J, Harris A, Nathan P, Judson I, Rustin G, Bertolini F, Link DC, Kerbel RS. Contribution of granulocyte colony-stimulating factor to the acute mobilization of endothelial precursor cells by vascular disrupting agents. Cancer Res. 2009 Oct 1;69(19):7524-8. doi: 10.1158/0008-5472.CAN-09-0381. Epub 2009 Sep 8. PMID: 19738066; PMCID: PMC2758166. 6: Johnson SP, Ogunlade O, Lythgoe MF, Beard P, Pedley RB. Longitudinal Photoacoustic Imaging of the Pharmacodynamic Effect of Vascular Targeted Therapy on Tumors. Clin Cancer Res. 2019 Dec 15;25(24):7436-7447. doi: 10.1158/1078-0432.CCR-19-0360. Epub 2019 Sep 24. PMID: 31551349. 7: Quatrale AE, Porcelli L, Gnoni A, Numico G, Paradiso A, Azzariti A. New vascular disrupting agents in upper gastrointestinal malignancies. Curr Med Chem. 2014;21(8):1039-49. doi: 10.2174/09298673113209990233. PMID: 23992324. 8: Cogle CR, Collins B, Turner D, Pettiford LC, Bossé R, Hawkins KE, Beachamp Z, Wise E, Cline C, May WS, Moreb JS, Hsu J, Hiemenz J, Brown R, Norkin M, Wingard JR, Uckun F. Safety, feasibility and preliminary efficacy of single agent combretastatin A1 diphosphate (OXi4503) in patients with relapsed or refractory acute myeloid leukemia or myelodysplastic syndromes. Br J Haematol. 2020 Jun;189(5):e211-e213. doi: 10.1111/bjh.16629. Epub 2020 Apr 1. PMID: 32236943. 9: Wittenborn TR, Horsman MR. Targeting tumour hypoxia to improve outcome of stereotactic radiotherapy. Acta Oncol. 2015;54(9):1385-92. doi: 10.3109/0284186X.2015.1064162. Epub 2015 Sep 2. PMID: 26329662. 10: d'Esposito A, Sweeney PW, Ali M, Saleh M, Ramasawmy R, Roberts TA, Agliardi G, Desjardins A, Lythgoe MF, Pedley RB, Shipley R, Walker-Samuel S. Computational fluid dynamics with imaging of cleared tissue and of in vivo perfusion predicts drug uptake and treatment responses in tumours. Nat Biomed Eng. 2018 Oct;2(10):773-787. doi: 10.1038/s41551-018-0306-y. Epub 2018 Oct 10. PMID: 31015649.

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