(2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol
- Product Name
- (2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol
- CAS No.
- 167354-41-8
- Chemical Name
- (2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol
- Synonyms
- CS-251;Zosuquidar;Unii-ab5K82X98y;Zosuquidar [inn];LY335979; ZOSUQUIDAR;LY335979; LY 335979; LY-335979;(2R)-Anti-5-[3-[4-(10,11-difluoromethanodibenzosuber-5-yl)piperazin-1-yl]-2-hydroxypropoxy]quinoline hydrochloride;(2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol;1-Piperazineethanol, 4-[(1aα,6α,10bα)-1,1-difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]-α-[(5-quinolinyloxy)methyl]-, (αR)-;1-Piperazineethanol, 4-[(1aα,6α,10bα)-1,1-difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]-α-[(5-quinolinyloxy)methyl]-, (αR)-
- CBNumber
- CB12128765
- Molecular Formula
- C32H31F2N3O2
- Formula Weight
- 527.6
- MOL File
- 167354-41-8.mol
(2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol Property
- Boiling point:
- 690.5±55.0 °C(Predicted)
- Density
- 1.36
- storage temp.
- -20°C
- solubility
- H2O: soluble4mg/mL, clear (warmed)
- form
- powder
- pka
- 13.94±0.20(Predicted)
- color
- white to beige
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- SML1044
- Product name
- Zosuquidar hydrochloride
- Purity
- ≥98% (HPLC)
- Packaging
- 5mg
- Price
- $209
- Updated
- 2024/03/01
- Product number
- SML1044
- Product name
- Zosuquidar hydrochloride
- Purity
- ≥98% (HPLC)
- Packaging
- 25mg
- Price
- $741
- Updated
- 2024/03/01
- Product number
- A3956
- Product name
- Zosuquidar
- Packaging
- 50mg
- Price
- $1024
- Updated
- 2021/12/16
- Product number
- A3956
- Product name
- Zosuquidar
- Packaging
- 100mg
- Price
- $1733
- Updated
- 2021/12/16
- Product number
- CS-0921
- Product name
- Zosuquidar
- Purity
- 98.33%
- Packaging
- 50mg
- Price
- $420
- Updated
- 2021/12/16
(2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol Chemical Properties,Usage,Production
Uses
Treatment of multidrug resistance (modulator of Pgp resistance).
Definition
ChEBI: LSM-5782 is a carbopolycyclic compound.
Biological Activity
zosuquidar (ly335979) 3hcl is a novel and potent modulator of p-glycoprotein (p-gp) [1]. p-gp is wildly expressed in brain, liver, small intestine and tumor cells and acts as an efflux pump responsible for multidrug resistance in tumor cells. overexpression of pgp in tumors results in multidrug resistance (mdr) to structurally unrelated oncolytics [2].
Biochem/physiol Actions
Zosuqidar is a potent inhibitor of P-glycoprotein (P-gp, MDR1) a transporter protein that is a key modulator of cellular drug efflux. Zosuquidar sensitizes AML, and other cancer cell lines to cytotoxic drugs.
in vitro
in cem/vlb100 cells, ly335979 treatment (0.1 μm) fully restored the sensitivity to vinblastine, doxorubicin (dox), etoposide, and taxol. in cem/vlb100 plasma membranes, ly335979 blocked [3h]azidopinephotoaffinity labeling of the m(r) approximately 170,000 pgp and competitively inhibited equilibrium binding of [3h]vinblastine to pgp with the ki value of approximately 0.06 μm [3]. in all p-gp-expressing leukemia cell linesincluding k562/hht40, k562/hht90, k562/dox and hl60/dnr, zosuquidar completely or partially restored drug sensitivity. in primary aml blasts with active p-gp, zosuquidar enhanced the cytotoxicity of anthracyclines (daunorubicin, idarubicin, mitoxantrone) and gemtuzumabozogamicin (mylotarg)[4].
in vivo
in mice bearing p388/adr murine leukemia cells,treatment with ly335979 in combination with dox or etoposide significantly increased in life span with no apparent alteration of pharmacokinetics. in a mdr human non-small cell lung carcinoma nude mouse xenograft model, ly335979 enhanced the antitumor activity of taxol [3].
References
[1] cripe l d, uno h, paietta e m, et al. zosuquidar, a novel modulator of p-glycoprotein, does not improve the outcome of older patients with newly diagnosed acute myeloid leukemia: a randomized, placebo-controlled trial of the eastern cooperative oncology group 3999[j]. blood, 2010, 116(20): 4077-4085.
[2] chaudhary p m, roninson i b. expression and activity of p-glycoprotein, a multidrug efflux pump, in human hematopoietic stem cells[j]. cell, 1991, 66(1): 85-94.
[3] dantzig a h, shepard r l, cao j, et al. reversal of p-glycoprotein-mediated multidrug resistance by a potent cyclopropyldibenzosuberane modulator, ly335979[j]. cancer research, 1996, 56(18): 4171-4179.
[3] tang r, faussat a m, perrot j y, et al. zosuquidar restores drug sensitivity in p-glycoprotein expressing acute myeloid leukemia (aml)[j]. bmc cancer, 2008, 8(1): 1.
[4] morschhauser f, zinzani p l, burgess m, et al. phase i/ii trial of a p-glycoprotein inhibitor, zosuquidar. 3hcl trihydrochloride (ly335979), given orally in combination with the chop regimen in patients with non-hodgkin's lymphoma[j]. leukemia & lymphoma, 2007, 48(4): 708-715.
[5] lê l h, moore m j, siu l l, et al. phase i study of the multidrug resistance inhibitor zosuquidar administered in combination with vinorelbine in patients with advanced solid tumours[j]. cancer chemotherapy and pharmacology, 2005, 56(2): 154-160.
(2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from (2R)-1-{4-[(1aR,6r,10bS)-1,1-Difluoro-1,1a,6,10b-tetrahydrodibenzo[a,e]cyclopropa[c]cyclohepten-6-yl]piperazin-1-yl}-3-(quinolin-5-yloxy)propan-2-ol manufacturers
- Product
- Zosuquidar 167354-41-8
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-10
- Product
- Zosuquidar 167354-41-8
- Price
- US $15.00-10.00/KG
- Min. Order
- 1KG
- Purity
- 99%+ HPLC
- Supply Ability
- Monthly supply of 1 ton
- Release date
- 2021-07-09