7-Epi-Taxol

HCID 184492CAS 105454-04-4

Grundinformationen

Standard-SMILES
CC(=O)O[C@H]1C(=O)[C@]2(C)[C@H](O)C[C@H]3OC[C@@]3(OC(C)=O)[C@H]2[C@H](OC(=O)c2ccccc2)[C@]2(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c3ccccc3)c3ccccc3)C(C)=C1C2(C)C
InChIKey
RCINICONZNJXQF-LYTKHFMESA-N
Summenformel
C47H51NO14
Durchschnittliche Molmasse
853,9 g/mol
Monoisotopische Masse
853,3309553

Namen und Bezeichner

Bevorzugter Name
7-Epi-Taxol
IUPAC
[(1S,2S,3R,4S,7R,9R,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
Englischer Name
7-Epitaxol
Summenformel
C47H51NO14
Molmasse
853.91

Namen und Synonyme

7-Epitaxol7-epi-Taxol105454-04-4EpitaxolVRA3UAZ8BLDTXSID201318105[(1S,2S,3R,4S,7R,9R,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate((1S,2S,3R,4S,7R,9R,10S,12R,15S)-4,12-diacetyloxy-15-((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo(11.3.1.03,10.04,7)heptadec-13-en-2-yl) benzoateRefChem:546330DTXCID7017478947-Epipaclitaxel7-epi-Paclitaxel
Weitere Namen anzeigen
EPITAXOL, 7-7-Epitaxol ,S9265Paclitaxel Impurity E7-Epipaclitaxel(crude)Paclitaxel 7-Epi-Impurity7-Epitaxol 7-Epipaclitaxel7-epi-Taxol, 10 mM in DMSO7-epi-Paclitaxel(7-Epitaxol)
Paclitaxel EP Impurity EMFCD077837137-Epi Paclitaxel(2aR,4R,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-Benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diyl diacetateC47H51NO147-Epipaclitaxel?CHEMBL503883orb1303347

Datenbank-Bezeichner

CAS
105454-04-4
PubChem CID
184492
DTXSID
DTXSID201318105
ChEMBL
CHEMBL503883
UNII
VRA3UAZ8BL
EC Number
630-563-3
Nikkaji
J624.351G

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,5
Polarare Oberfläche (TPSA)
221 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
14
Frei drehbare Bindungen
14
Schwere Atome
62

Physikochemische Eigenschaften

Schmelzpunkt
168 · 168-170C
Siedepunkt
957.1 · 957.1±65.0 °C(Predicted)
Dichte
1.39 · 1.39±0.1 g/cm3 (20 ºC 760 Torr)
storage temp.
2 · Inert atmosphere,2-8°C
Löslichkeit
25 mg/ml; · DMF: 25 mg/ml; DMF:PBS (pH 7.2)(1:3): 0.25 mg/ml; DMSO: 10 mg/ml; Ethanol: 5 mg/ml
Aggregatzustand
A crystalline solid

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Danger

H301 (33.3%): Toxic if swallowed [Danger Acute toxicity, oral];H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation];H317 (33.3%): May cause an allergic skin reaction [Warning Sensitization, Skin];H318 (33.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H334 (33.3%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory];H335 (33.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H340 (33.3%): May cause genetic defects [Danger Germ cell mutagenicity];H341 (66.7%): Suspected of causing genetic defects [Warning Germ cell mutagenicity];H351 (33.3%): Suspected of causing cancer [Warning Carcinogenicity];H360 (33.3%): May damage fertility or the unborn child [Danger Reproductive toxicity];H360FD (33.3%): May damage fertility; May damage the unborn child [Danger Reproductive toxicity];H361 (33.3%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity];H372 (33.3%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

P203, P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P354+P338, P317, P318, P319, P321, P330, P332+P317, P333+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (33.3%);Skin Irrit. 2 (33.3%);Skin Sens. 1 (33.3%);Eye Dam. 1 (33.3%);Resp. Sens. 1 (33.3%);STOT SE 3 (33.3%);Muta. 1B (33.3%);Muta. 2 (66.7%);Carc. 2 (33.3%);Repr. 1B (33.3%);Repr. 1B (33.3%);Repr. 2 (33.3%);STOT RE 1 (33.3%)

Toxikologische Informationen

Exposure RoutesWhen a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the maximum plasma concentration (Cmax) is 195 ng/mL, while the AUC is 6300 ng*h/mL.
Toxicity Summary · 1 Eintrag

Paclitaxel interferes with the normal function of microtubule growth. Whereas drugs like colchicine cause the depolymerization of microtubules in vivo, paclitaxel arrests their function by having the opposite effect; it hyper-stabilizes their structure. This destroys the cell's ability to use its cytoskeleton in a flexible manner. Specifically, paclitaxel binds to the β subunit of tubulin. Tubulin is the 'building block' of mictotubules, and the binding of paclitaxel locks these building blocks in place. The resulting microtubule/paclitaxel complex does not have the ability to disassemble. This adversely affects cell function because the shortening and lengthening of microtubules (termed dynamic instability) is necessary for their function as a transportation highway for the cell. Chromosomes, for example, rely upon this property of microtubules during mitosis. Further research has indicated that paclitaxel induces programmed cell death (apoptosis) in cancer cells by binding to an apoptosis stopping protein called Bcl-2 (B-cell leukemia 2) and thus arresting its function.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataRat (ipr) LD<sub>50</sub>=32530 &micro;g/kg.

Sicherheitsdaten

hs_code
29329990

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Hepatic. In vitro studies with human liver microsomes and tissue slices showed that paclitaxel was metabolized primarily to 6a-hydrox-ypaclitaxel by the cytochrome P450 isozyme CYP2C8; and to two minor metabolites, 3&rsquo;-p-hydroxypaclitaxel and 6a, 3&rsquo;-p-dihydroxypaclitaxel, by CYP3A4. Route of Elimination: In 5 patients administered a 225 or 250 mg/m2 dose of radiolabeled paclitaxel as a 3-hour infusion, a mean of 71% of the radioactivity was excreted in the feces in 120 hours, and 14% was recovered in the urine. Half Life: When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the elimination half=life is 52.7 hours.

MeSH Pharmacological Classification · 2 Einträge

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.

Verwendung und Herstellung

UsesUsed in the treatment of Kaposi's sarcoma and cancer of the lung, ovarian, and breast. Abraxane&#8482; is specfically indicated for the treatment of metastatic breast cancer and locally advanced or metastatic non-small cell lung cancer.

Anwendungen

Verwenden7-Epitaxol has been isolated from Taxus brevifolia. It is an antineoplastic that is currently being used in cancer research. Paclitaxel EP Impurity E.

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南京普怡生物科技有限公司13814510036 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]

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