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MedKoo Cat#: 328035 | Name: Apomine

Description:

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

Apomine, also known as APB-231-A-2; SK&F-99085; SR-45023A; SR-9223i, is an inhibitor of HMG-CoA-reductase, promotes apoptosis of myeloma cells in vitro and is associated with a modulation of myeloma in vivo. Apomine enhances the antitumor effects of lovastatin on myeloma cells by down-regulating 3-hydroxy-3-methylglutaryl-coenzyme A reductase. Apomine accelerates degradation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase and stimulates low density lipoprotein receptor activity.

Chemical Structure

Apomine
Apomine
CAS#126411-13-0

Theoretical Analysis

MedKoo Cat#: 328035

Name: Apomine

CAS#: 126411-13-0

Chemical Formula: C28H52O7P2

Exact Mass: 562.3188

Molecular Weight: 562.66

Elemental Analysis: C, 59.77; H, 9.32; O, 19.90; P, 11.01

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 #
No Data
Synonym
Apomine; APB-231-A-2; SK&F-99085; SR-45023A; SR-9223i; APB-231-A2; SK&F99085; SR45023A; SR9223i.
IUPAC/Chemical Name
tetraisopropyl (2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethane-1,1-diyl)bis(phosphonate)
InChi Key
YLJOVCWVJCDPLN-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H52O7P2/c1-18(2)32-36(30,33-19(3)4)25(37(31,34-20(5)6)35-21(7)8)17-22-15-23(27(9,10)11)26(29)24(16-22)28(12,13)14/h15-16,18-21,25,29H,17H2,1-14H3
SMILES Code
OC1=C(C(C)(C)C)C=C(CC(P(OC(C)C)(OC(C)C)=O)P(OC(C)C)(OC(C)C)=O)C=C1C(C)(C)C
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

Preparing Stock Solutions

The following data is based on the product molecular weight 562.66 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: Ang ZY, Boddy M, Liu Y, Sunderland B. Stability of apomorphine in solutions containing selected antioxidant agents. Drug Des Devel Ther. 2016 Oct 3;10:3253-3265. PubMed PMID: 27757015. 2: Moriceau G, Roelofs AJ, Brion R, Redini F, Ebetion FH, Rogers MJ, Heymann D. Synergistic inhibitory effect of apomine and lovastatin on osteosarcoma cell growth. Cancer. 2012 Feb 1;118(3):750-60. doi: 10.1002/cncr.26336. PubMed PMID: 21751201. 3: Kuehl PJ, Stratton SP, Powell MB, Myrdal PB. Preformulation, formulation, and in vivo efficacy of topically applied apomine. Int J Pharm. 2009 Dec 1;382(1-2):104-10. doi: 10.1016/j.ijpharm.2009.08.016. PubMed PMID: 19699284; PubMed Central PMCID: PMC2783960. 4: Roelofs AJ, Edwards CM, Russell RG, Ebetino FH, Rogers MJ, Hulley PA. Apomine enhances the antitumor effects of lovastatin on myeloma cells by down-regulating 3-hydroxy-3-methylglutaryl-coenzyme A reductase. J Pharmacol Exp Ther. 2007 Jul;322(1):228-35. PubMed PMID: 17412884; PubMed Central PMCID: PMC2820734. 5: Edwards CM, Mueller G, Roelofs AJ, Chantry A, Perry M, Russell RG, Van Camp B, Guyon-Gellin Y, Niesor EJ, Bentzen CL, Vanderkerken K, Croucher PI. Apomine, an inhibitor of HMG-CoA-reductase, promotes apoptosis of myeloma cells in vitro and is associated with a modulation of myeloma in vivo. Int J Cancer. 2007 Apr 15;120(8):1657-63. PubMed PMID: 17230522. 6: Pourpak A, Dorr RT, Meyers RO, Powell MB, Stratton SP. Cytotoxic activity of Apomine is due to a novel membrane-mediated cytolytic mechanism independent of apoptosis in the A375 human melanoma cell line. Invest New Drugs. 2007 Apr;25(2):107-14. PubMed PMID: 17024575. 7: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2006 Sep;28(7):451-95. Review. PubMed PMID: 17003851. 8: Lewis KD, Thompson JA, Weber JS, Robinson WA, O'Day S, Lutzky J, Legha SS, Floret S, Ruvuna F, Gonzalez R. A phase II open-label trial of apomine (SR-45023A) in patients with refractory melanoma. Invest New Drugs. 2006 Jan;24(1):89-94. PubMed PMID: 16379038. 9: Kuehl PJ, Angersbach BS, Stratton SP, Myrdal PB. Development of an HPLC method for the analysis of Apomine in a topical cream formulation. J Pharm Biomed Anal. 2006 Mar 3;40(4):975-80. PubMed PMID: 16181759. 10: Elmore E, Siddiqui S, Navidi M, Steele VE, Redpath JL. Correlation of in vitro chemopreventive efficacy data from the human epidermal cell assay with animal efficacy data and clinical trial plasma levels. J Cell Biochem. 2005 Jun 1;95(3):571-88. PubMed PMID: 15786488. 11: Lowe LC, Senaratne SG, Colston KW. Induction of apoptosis in breast cancer cells by apomine is mediated by caspase and p38 mitogen activated protein kinase activation. Biochem Biophys Res Commun. 2005 Apr 8;329(2):772-9. PubMed PMID: 15737653. 12: Bonate PL, Floret S, Bentzen C. Population pharmacokinetics of APOMINE: a meta-analysis in cancer patients and healthy males. Br J Clin Pharmacol. 2004 Aug;58(2):142-55. PubMed PMID: 15255796; PubMed Central PMCID: PMC1884594. 13: Roitelman J, Masson D, Avner R, Ammon-Zufferey C, Perez A, Guyon-Gellin Y, Bentzen CL, Niesor EJ. Apomine, a novel hypocholesterolemic agent, accelerates degradation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase and stimulates low density lipoprotein receptor activity. J Biol Chem. 2004 Feb 20;279(8):6465-73. PubMed PMID: 14627708. 14: Alberts DS, Hallum AV 3rd, Stratton-Custis M, Garcia DJ, Gleason-Guzman M, Salmon SE, Santabarbara P, Niesor EJ, Floret S, Bentzen CL. Phase I pharmacokinetic trial and correlative in vitro phase II tumor kinetic study of Apomine (SR-45023A), a novel oral biphosphonate anticancer drug. Clin Cancer Res. 2001 May;7(5):1246-50. PubMed PMID: 11350890. 15: Niesor EJ, Flach J, Lopes-Antoni I, Perez A, Bentzen CL. The nuclear receptors FXR and LXRalpha: potential targets for the development of drugs affecting lipid metabolism and neoplastic diseases. Curr Pharm Des. 2001 Mar;7(4):231-59. Review. PubMed PMID: 11254888. 16: Jackson B, Gee AN, Guyon-Gellin Y, Niesor E, Bentzen CL, Kerns WD, Suckling KE. Hypocholesterolaemic and antiatherosclerotic effects of tetra-iso-propyl 2-(3,5-di-tert-butyl-4-hydroxyphenyl)ethyl-1,1-diphosphonate (SR-9223i). Arzneimittelforschung. 2000 Apr;50(4):380-6. PubMed PMID: 10800637. 17: Flach J, Antoni I, Villemin P, Bentzen CL, Niesor EJ. The mevalonate/isoprenoid pathway inhibitor apomine (SR-45023A) is antiproliferative and induces apoptosis similar to farnesol. Biochem Biophys Res Commun. 2000 Apr 2;270(1):240-6. PubMed PMID: 10733934.