Basic information
- CAS
152044-53-6- Standard SMILES
C/C(=C\c1csc(C)n1)[C@@H]1C[C@@H]2O[C@@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1- InChIKey
HESCAJZNRMSMJG-KKQRBIROSA-N- Molecular formula
- C26H39NO6S
- Average molar mass
- 493.7 g/mol
- Monoisotopic mass
- 493.24980897
Overview
Epothilone A is an epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer). It has a role as a metabolite, an antineoplastic agent, a tubulin modulator and a microtubule-stabilising agent. It is an epoxide and an epothilone.
Names & identifiers
- Preferred name
- Epothilone A
- IUPAC
- (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12-tetramethyl-3-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
- English name
- Epothilone A
- Molecular formula
- C26H39NO6S
- Molecular weight
- 493.66
Names & synonyms
Show more names
Database identifiers
- CAS
152044-53-6- PubChem CID
- 448799
- DTXSID
DTXSID10332288- ChEMBL
CHEMBL329993- ChEBI
CHEBI:31549- UNII
- 51E07YBX96
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 137 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 2
- Heavy atoms
- 34
- Formal charge
- 0
- Complexity
- 770
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 95 ℃ · 95℃
- alpha
- 21 · D21 -47.1° (c = 1.0 in methanol)
- Boiling point
- 683.3 · 683.3±55.0 °C(Predicted)
- Density
- 1.143 · 1.143
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- form
- solid
- pka
- 13.57 · 13.57±0.70(Predicted)
- color
- White to Off-White
- Stability
- Stable under recommended storage conditions., Stable Under Recommended Storage C
- InChIKey
- HESCAJZNRMSMJG-KKQRBIROSA-N
- SMILES
- [C@]12([H])[C@]([H])(O1)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O[C@H](/C(/C)=C/C1=CSC(C)=N1)C2
- FDA UNII
- 51 E07YBX96 · 51E07YBX96
- WGK Germany
- 3 · 3
Safety & regulation
Hazard information
Regulatory Information
4,17-Dioxabicyclo14.1.0heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12-tetramethyl-3-(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl-, (1S,3S,7S,10R,11S,12S,16R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Safety & protection
Toxicology
Treatment
EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Toxicity Summary
The exact mechanism of toxicty of PBBs varies depending on the specific congener. The predominant interaction is believed to involve the aryl hydrocarbon receptor (AhR). PBBs bind to and activate the AhR, which in turn initiates the transcriptional upregulation of a number of genes, affecting biochemical and endocrine pathways, cell cycle regulation, morphogenesis, oxidative stress response, and various other processes. This results in the numerous toxic responses characteristic of PBBs. Some of the known induced genes include the cytochrome P-450-dependent monooxygenases CYP1A1 and CYP1A2. (L628)
Safety data
- wgk
- 3
Chemistry & industry
Pharmacology
Metabolism/Metabolites
PBBs can be absorbed via oral, inhalation, and dermal routes. Due to their lipophilic nature, PBBs, especially the highly brominated congeners, tend to accumulate in lipid-rich tissues such as the liver, adipose, skin, and breast milk. Certain PBB compounds are metabolized by the microsomal monooxygenase system catalyzed by cytochrome P-450 of the type induced by phenobarbital. The rate of metabolism may depends on the bromine substitution pattern. PBB congeners of low bromine content are transformed into hydroxylated derivatives that are predominately eliminated in the urine. Highly brominated congeners are either retained or excreted unchanged in the feces. (L628)
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES.
Uses & manufacturing
Uses
PBBs can be used as flame retardants and may be added to the plastics used to make products like computer monitors, televisions, textiles, and plastic foams to make them difficult to burn. However, the use of PBBs is banned or restricted in most areas due to their toxicity and persistence in the environment. (L628, L629)
Applications
UsesThe epothilones are a novel class of antineoplastic agents possessing antitubulin activity. Epothilone A, B isolated from Sorangium cellulosum was associated with cell cycle arrest at G2/M transition and apoptosis that was resisted with overexpression of β-tubulin and P-glycoprotein in human bladder carcinoma cell.
UsesEpothilone A is a microtubule inhibitor isolated from the myxobacteria, Sorangium cellulosum. Epothilone A acts by stabilising microtubule formation at the taxol binding site, and causes cell cycle arrest at the G2/M transition, leading to cytotoxicity. Epothilone A has been investigated in clinical trials as an antitumour agent.
Suppliers100 total
Additional notes
DefinitionChEBI: An epithilone that is epothilone C in which the double bond in the macrocyclic lactone ring has been oxidised to the corresponding epoxide (the 13R,14S diastereoisomer).
Related reactions
Compound notes
Loading…