SAGOPILONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C30H41NO6S
Molecular Weight	543.715
Optical Activity	( - )
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12C[C@]([H])(OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](CC=C)[C@@H](O)[C@@H](C)CCC[C@@]1(C)O2)C3=CC=C4SC(C)=NC4=C3

InChI

InChIKey=BFZKMNSQCNVFGM-UCEYFQQTSA-N

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

HIDE SMILES / InChI

Molecular Formula	C30H41NO6S
Molecular Weight	543.715
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00246688 | https://clinicaltrials.gov/ct2/show/NCT00397072 | https://www.ncbi.nlm.nih.gov/pubmed/23522488 | https://www.ncbi.nlm.nih.gov/pubmed/18593931

Sagopilone (BAY86-5302; ZK 219477; ZK-EPO) is a synthetic epothilone, an analog of patupilone that was developed by Bayer HealthCare as an anticancer agent. Epothilones are 16-member ring macrolides have demonstrated potent antiproliferative activity in several different multidrug-resistant and paclitaxel-resistant tumor cell lines in vitro and in vivo. Sagopilone binds to tubulin and induces microtubule polymerization, which may result in the induction of G2/M arrest, and apoptosis. Sagopilone is not a substrate for the P-glycoprotein efflux pump and so may exhibit activity in multidrug-resistant tumors. This drug was studied in clinical trials phase II in patients with recurrent ovarian cancer, in metastatic melanoma patients, for the treatment of advanced stage breast cancer and in the treatment of Glioblastoma patients. However, the development of this drug was discontinued, because of its adverse effects, including peripheral neuropathy.

CNS Activity

Approval Year

PubMed

Title	Date	PubMed
New therapeutic options for chemotherapy-resistant metastatic breast cancer: the epothilones.	2008	18197722
Novel therapies in genitourinary cancer: an update.	2008 Aug 11	18694493
Novel microtubule-targeting agents - the epothilones.	2008 Dec	19707459
Improved cellular pharmacokinetics and pharmacodynamics underlie the wide anticancer activity of sagopilone.	2008 Jul 1	18593931
Gateways to Clinical Trials.	2008 Nov	19229381
Sagopilone (ZK-EPO): from a natural product to a fully synthetic clinical development candidate.	2008 Nov	18922109
Sagopilone crosses the blood-brain barrier in vivo to inhibit brain tumor growth and metastases.	2009 Apr	18780814
Sagopilone, a microtubule stabilizer for the potential treatment of cancer.	2009 Dec	19943207
The epothilones: how pharmacology relates to clinical utility.	2009 Jul	19584389
Gateways to clinical trials.	2009 Jun	19649342
Sagopilone inhibits breast cancer bone metastasis and bone destruction due to simultaneous inhibition of both tumor growth and bone resorption.	2009 Jun 1	19470728
Systemic sagopilone (ZK-EPO) treatment of patients with recurrent malignant gliomas.	2009 Oct	19381446
Weekly administration of sagopilone (ZK-EPO), a fully synthetic epothilone, in patients with refractory solid tumours: results of a phase I trial.	2009 Oct 20	19773753
Management of advanced breast cancer with the epothilone B analog, ixabepilone.	2009 Sep 21	19920932
Solubilization of sagopilone, a poorly water-soluble anticancer drug, using polymeric micelles for parenteral delivery.	2010 Apr 15	20100557
Non-ionic dendritic glycerol-based amphiphiles: novel excipients for the solubilization of poorly water-soluble anticancer drug Sagopilone.	2010 Apr 16	20188825
Treatment of cutaneous melanoma: current approaches and future prospects.	2010 Aug 17	21188111
Improving the ex vivo stability of drug ester compounds in rat and dog serum: inhibition of the specific esterases and implications on their identity.	2010 Feb 5	19850433
Gateways to clinical trials.	2010 Jan-Feb	20383346
Polymeric micelles for parenteral delivery of sagopilone: physicochemical characterization, novel formulation approaches and their toxicity assessment in vitro as well as in vivo.	2010 Jun	20188169
Phase I study of the novel, fully synthetic epothilone sagopilone (ZK-EPO) in patients with solid tumors.	2010 Mar	19880436
Comparative profiling of the novel epothilone, sagopilone, in xenografts derived from primary non-small cell lung cancer.	2010 Mar 1	20179216
Exon array analysis using re-defined probe sets results in reliable identification of alternatively spliced genes in non-small cell lung cancer.	2010 Nov 30	21118496
Phase II trial of sagopilone, a novel epothilone analog in metastatic melanoma.	2010 Nov 9	20924376
Phase II study evaluating the efficacy and safety of sagopilone (ZK-EPO) in patients with metastatic breast cancer that has progressed following chemotherapy.	2010 Oct	20697802

Patents

Sample Use Guides

In Vivo Use Guide

Subjects received one infusion (for 0.5 h) of sagopilone every 3 weeks at a dose of 16 mg/m2 (maximum up to 32 mg) for approximately 18 weeks. 10.5 mg lyophilized sagopilone per vial

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:25:40 GMT 2023` Edited by `admin` on `Fri Dec 15 16:25:40 GMT 2023`
Record UNII	KY72JU32FO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SAGOPILONE

Official Name

English

(1S,3S,7S,10R,11S,12S,16R)-10-ALLYL-7,11-DIHYDROXY-8,8,12,16-TETRAMETHYL-3-(2-METHYLBENZOTHIAZOL-5-YL)-4,17-DIOXABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE

Systematic Name

English

DE-03757

Code

English

4,17-DIOXABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE, 7,11-DIHYDROXY-8,8,12,16-TETRAMETHYL-3-(2-METHYL-5-BENZOTHIAZOLYL)-10-(2-PROPENYL)-, (1S,3S,7S,10R,11S,12S,16R)-

Common Name

English

ZK-219477

Code

English

Sagopilone [WHO-DD]

Common Name

English

(1S,3S,7S,10R,11S,12S,16R)-10-ALLYL-7,11-DIHYDROXY-8,8,12,16-TETRAMETHYL-3-(2-METHYL-1,3-BENZOTHIAZOL-5-YL)-4,17-DIOXABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE

Systematic Name

English

ZK-EPO

Code

English

(1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,12,16-TETRAMETHYL-3-(2-METHYL-1,3- BENZOTHIAZOL-5-YL)-10-(PROP-2-ENYL)-4,17-DIOXABICYCLO(14.1.0)HEPTADECANE-5,9-DIONE

Common Name

English

SAGOPILONE [USAN]

Common Name

English

ZK219477

Code

English

sagopilone [INN]

Common Name

English

BAY86-5302

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C67437