Isocycloheximide
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| Category | Antibiotics |
| Catalog number | BBF-01512 |
| CAS | 6746-42-5 |
| Molecular Weight | 281.35 |
| Molecular Formula | C15H23NO4 |
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Description
It is produced by the strain of Str. griseus. Isocycloheximide has antifungal effect, and its activity to Barbiturates is only 30% of that of actinomyces.
Specification
| Synonyms | D-Isocycloheximide; Caswell No. 504C; (+)-3-(2-(3,5-Dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide; Aktidion |
| IUPAC Name | 4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]piperidine-2,6-dione |
| Canonical SMILES | CC1CC(C(=O)C(C1)C(CC2CC(=O)NC(=O)C2)O)C |
| InChI | InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19) |
| InChI Key | YPHMISFOHDHNIV-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Diamond Crystalline |
| Antibiotic Activity Spectrum | fungi; yeast |
| Melting Point | 101-102°C |
Reference Reading
1. High-pressure liquid chromatographic determination of cycloheximide in ointment and suspension formulations
L W Brown J Pharm Sci. 1978 May;67(5):669-72. doi: 10.1002/jps.2600670526.
A high-pressure liquid chromatographic procedure is described for the assay of the antibiotic cycloheximidein bulk drug and two experimental formulations. The method utilizes a reversed-phase C18 chromatographic column and refractive index detection. Possible impurities or degradation products, isocycloheximide, anhydrocycloheximide, and dimethylcyclohexone, are well separated from cycloheximide by this procedure. Complete extraction of cycloheximide from the formulations was obtained. The assay has a relative standard deviation of approximately 1%.
2. Cycloheximide congeners produced by Streptomyces sp. SC0581 and photoinduced interconversion between ( E) - and ( Z)-2,3-dehydroanhydrocycloheximides
Li Yang, Ping Wu, Jinghua Xue, Huitong Tan, Zheng Zhang, Xiaoyi Wei Beilstein J Org Chem. 2017 May 30;13:1039-1049. doi: 10.3762/bjoc.13.103. eCollection 2017.
Three new cycloheximide congeners, 2,3-dehydro-α-epi-isocycloheximide (1), (E)- and (Z)-2,3-dehydroanhydrocycloheximides (2 and 3), together with three known compounds, anhydroisoheximide (4), cycloheximide (5), and isocycloheximide (6), were obtained from the cultures of Streptomyces sp. SC0581. Their structures were elucidated by extensive spectroscopic analysis in combination with theoretical conformational analysis and ECD computations. The photoinduced interconversion between 2 and 3 was observed and verified and the possible reaction path and mechanism were proposed by theoretical computations. The antifungal and cytotoxic activities of 1-6 were evaluated and suggested that 2,3-dehydrogenation results in the loss of the activities and supported that the OH-α is important to the activities of cycloheximide congeners.
3. [Askostatin--a fungicide from Streptomyces viridovulgaris]
Iu D Shenin, L F Kruglikova, I V Boĭkova, Iu E Konev, E G Karpov Antibiot Khimioter. 1994 Jun;39(6):8-12.
Askostatin is a fungicide isolated from the culture of Streptomyces viridovulgaris. It was separated by the countercurrent distribution procedure into components A and B. By the mass and NMR spectra and the biological findings the components were identified with cycloheximide and isocycloheximide respectively.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
