WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 203210
CAS#: 305841-29-6
Description: Sagopilone is a fully synthetic low-molecular-weight epothilone with potential antineoplastic activity. Sagopilone binds to tubulin and induces microtubule polymerization while stabilizing microtubules against depolymerization, which may result in the inhibition of cell division, the induction of G2/M arrest, and apoptosis. The agent is not a substrate for the P-glycoprotein (P-gp) efflux pump and so may exhibit activity in multidrug-resistant (MDR) tumors. The epothilone class of metabolites was originally isolated from the myxobacterium Solangium cellulosum.
MedKoo Cat#: 203210
Name: Sagopilone
CAS#: 305841-29-6
Chemical Formula: C30H41NO6S
Exact Mass: 543.26546
Molecular Weight: 543.71
Elemental Analysis: C, 66.27; H, 7.60; N, 2.58; O, 17.66; S, 5.90
Synonym: ZK-Epothilone; ZK 219477; ZK-219477; ZK219477; ZK-EPO; DE 03757; DE-03757; DE03757; Sagopilone.
IUPAC/Chemical Name: (1S,3S,7S,10R,11S,12S,16R)-10-allyl-7,11-dihydroxy-8,8,12,16-tetramethyl-3-(2-methylbenzo[d]thiazol-5-yl)-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
InChi Key: BFZKMNSQCNVFGM-UCEYFQQTSA-N
InChi Code: InChI=1S/C30H41NO6S/c1-7-9-20-27(34)17(2)10-8-13-30(6)25(37-30)15-22(19-11-12-23-21(14-19)31-18(3)38-23)36-26(33)16-24(32)29(4,5)28(20)35/h7,11-12,14,17,20,22,24-25,27,32,34H,1,8-10,13,15-16H2,2-6H3/t17-,20+,22-,24-,25-,27-,30+/m0/s1
SMILES Code: O=C(C[C@H](O)C1(C)C)O[C@H](C2=CC=C(SC(C)=N3)C3=C2)C[C@]4([H])O[C@]4(C)CCC[C@H](C)[C@H](O)[C@@H](CC=C)C1=O
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 soluble 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
The following data is based on the product molecular weight 543.71 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.
| 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. Galmarini, Carlos M. Sagopilone, a microtubule stabilizer for the potential treatment of cancer. Current Opinion in Investigational Drugs (BioMed Central) (2009), 10(12), 1359-1371. CODEN: COIDAZ ISSN:2040-3429. AN 2010:726309
2. Richter, Annett; Olbrich, Carsten; Krause, Michael; Hoffmann, Jens; Kissel, Thomas. Polymeric Micelles for parenteral delivery of Sagopilone: Physicochemical characterization, novel formulation approaches and their toxicity assessment in vitro as well as in vivo. European Journal of Pharmaceutics and Biopharmaceutics (2010), 75(2), 80-89. CODEN: EJPBEL ISSN:0939-6411. AN 2010:643014
3. Richter, Annett; Wiedekind, Achim; Krause, Michael; Kissel, Thomas; Haag, Rainer; Olbrich, Carsten. Non-ionic dendritic glycerol-based amphiphiles: Novel excipients for the solubilization of poorly water-soluble anticancer drug Sagopilone. European Journal of Pharmaceutical Sciences (2010), 40(1), 48-55. CODEN: EPSCED ISSN:0928-0987. CAN 153:69993 AN 2010:465236
4. Eschenbrenner, Julia. Mode of action analysis of the synthetic epothilone Sagopilone. (2009), No pp. CAN 152:397468 AN 2010:438250
5. Richter, Annett; Olbrich, Carsten; Krause, Michael; Kissel, Thomas. Solubilization of Sagopilone, a poorly water-soluble anticancer drug, using polymeric micelles for parenteral delivery. International Journal of Pharmaceutics (2010), 389(1-2), 244-253.
6. Hammer, Stefanie; Sommer, Anette; Fichtner, Iduna; Becker, Michael; Rolff, Jana; Merk, Johannes; Klar, Ulrich; Hoffmann, Jens. Comparative Profiling of the Novel Epothilone, Sagopilone, in Xenografts Derived from Primary Non-Small Cell Lung Cancer. Clinical Cancer Research (2010), 16(5), 1452-1465.
7. Qi, Wenyuan; Meng, Zhiyun; Dou, Guifang. Clinical research progress of epothilone analogues. Guoji Yaoxue Yanjiu Zazhi (2009), 36(5), 336-339. CODEN: GYYZBO ISSN:1674-0440. CAN 152:559866 AN 2010:145484
8. Koitka, Matthias; Hochel, Joachim; Gieschen, Hille; Borchert, Hans-Hubert. Improving the ex vivo stability of drug ester compounds in rat and dog serum: Inhibition of the specific esterases and implications on their identity. Journal of Pharmaceutical and Biomedical Analysis (2010), 51(3), 664-678.
9. Arnold, D.; Voigt, W.; Kiewe, P.; Behrmann, C.; Lindemann, S.; Reif, S.; Wiesinger, H.; Giurescu, M.; Thiel, E.; Schmoll, H.-J. Weekly administration of sagopilone (ZK-EPO), a fully synthetic epothilone, in patients with refractory solid tumours: results of a phase I trial. British Journal of Cancer (2009), 101(8), 1241-1247.
