7-Epi-Taxol

HCID 184492

Basic information

CAS
105454-04-4
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
Molecular formula
C47H51NO14
Average molar mass
853.9 g/mol
Monoisotopic mass
853.3309553

Names & identifiers

Preferred 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
English name
7-Epitaxol
Molecular formula
C47H51NO14
Molecular weight
853.91

Names & synonyms

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
Show more names
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

Database identifiers

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

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
221 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
14
Rotatable bonds
14
Heavy atoms
62

Physicochemical properties

Melting point
168 · 168-170C
Boiling point
957.1 · 957.1±65.0 °C(Predicted)
Density
1.39 · 1.39±0.1 g/cm3 (20 ºC 760 Torr)
storage temp.
2 · Inert atmosphere,2-8°C
solubility
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
form
A crystalline solid

Safety & regulation

GHS classification

GHS Classification · 5 items

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.

Hazard information

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%)

Toxicology

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 item

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.

Safety data

hs_code
29329990
Signal word
Danger
Symbol(GHS)
GHS08,GHS06
Hazard statements
H360-H372-H351-H340-H301
Precautionary statements
P264-P270-P301+P310-P321-P330-P405-P501-P201-P202-P281-P308+P313-P405-P501-P260-P264-P270-P314-P501

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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 items

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

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

Uses & manufacturing

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.

Applications

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

Uses7-Epitaxol has been isolated from Taxus brevifolia. It is an antineoplastic that is currently being used in cancer research. Paclitaxel EP Impurity E.

Suppliers100 total

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
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]

Related reactions

10 records

Compound notes

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