DRUG SPOTLIGHT…LEVETIRACETAM

New Drug Approvals

LEVETIRACETAM, etiracetam

(-)-(S)-α-ethyl-2-oxo-1-pyrrolidine acetamide

(−)-(S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide

CAS…102767-28-2

(aS)-a-Ethyl-2-oxo-1-pyrrolidineacetamide

Names: 2(S)-(2-oxopyrrolidin-1-yl)butyramide

Manufacturers’ Codes: UCB-L059; SIB-S1

Trademarks: Keppra (UCB)

FDA UNII: 44YRR34555

UNII-44YRR34555

MF: C8H14N2O2

MW 170.21

Percent Composition: C 56.45%, H 8.29%, N 16.46%, O 18.80%

Crystals from ethyl acetate, mp 117°. [a]25D -90.0° (c = 1 in acetone). Soly (g/100 ml): water 104.0; chloroform 65.3; methanol 53.6; ethanol 16.5; acetonitrile 5.7. Practically insol in n-hexane. LD50 in male mice, male rats (mg/kg): 1081, 1038 i.v. (Gobert, 1990).

Mp: mp 117°C

O’Neil, M.J. (ed.). The Merck Index – An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 978

Optical Rotation: [a]25D -90.0° (c = 1 in acetone)

Specific optical rotation: -90 deg at 25 deg C/D (c = 1 in acetone)

Toxicity data: LD50 in male mice, male rats (mg/kg): 1081, 1038 i.v. (Gobert, 1990)

Therap-Cat: Anticonvulsant.

Very…

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Temsirolimus

New Drug Approvals

TEMSIROLIMUS

Proline CCI-779

Torisel, NCGC00167518-01

LAUNCHED 2007

PFIZER

• CCI 779
• CCI-779
• HSDB 7931
• Temsirolimus
• Torisel
• UNII-624KN6GM2T
• WAY-CCI 779

Inhibits mTOR protein

For the treatment of renal cell carcinoma (RCC). Also investigated for use/treatment in breast cancer, lymphoma (unspecified), rheumatoid arthritis, and multiple myeloma.

An ester analog of rapamycin. Temsirolimus binds to and inhibits the mammalian target of rapamycin (mTOR), resulting in decreased expression of mRNAs necessary for cell cycle progression and arresting cells in the G1 phase of the cell cycle. mTOR is a serine/threonine kinase which plays a role in the PI3K/AKT pathway that is upregulated in some tumors

(1R,2R,4S)-4-{(2R)-2-[(3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,27-dihydroxy-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-1,5,11,28,29-pentaoxo-1,4,5,6,9,10,11,12,13,14,21,22,23,24,25,26,27,28,29,31,32,33,34,34a-tetracosahydro-3H-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontin-3-yl]propyl}-2-methoxycyclohexyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate

cas 162635-04-3 

Temsirolimus is an…

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TAK 733 » All About Drugs

TAK 733 » All About Drugs

Asymmetric [2+2]

Naturalproductman's Blog

Thorsten Bach and colleague have reported in Science on a Lewis acid catalyzed [2+2] reaction.

 

Science paper

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Chiral Tin Participates in Radical Cyclizations

 

Chiral tin hydrides generate radicals and transfer chirality in the cyclization of aldehydes
This offers an insight for the future design of catalytic asymmetric radical reactions.

Read more

http://www.chemistryviews.org/details/ezine/5446641/Chiral_Tin_Participates_in_Radical_Cyclizations.html

ORGANIC SPECTROSCOPY INTERNATIONAL: Mix and Shake NMR Method

ORGANIC SPECTROSCOPY INTERNATIONAL: Mix and Shake NMR Method

Rapid Wolff-Kishner reductions in a silicon carbide microreactor

Green Chem., 2013, Advance Article
DOI: 10.1039/C3GC41942H, Paper

Stephen G. Newman, Lei Gu, Christoph Lesniak, Georg Victor, Frank Meschke, Lahbib Abahmane, Klavs F. Jensen
Wolff-Kishner reductions are performed continuously in a silicon carbide microreactor. Short reactions times and safe operation are achieved, giving high yields without reactor corrosion issues using just 1.5 equivalents of hydrazine.

Rapid Wolff-Kishner reductions in a silicon carbide microreactor

http://pubs.rsc.org/en/Content/ArticleLanding/2013/GC/C3GC41942H?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

Wolff–Kishner reductions are performed in a novel silicon carbide microreactor. Greatly reduced reaction times and safer operation are achieved, giving high yields without requiring a large excess of hydrazine. The corrosion resistance of silicon carbide avoids the problematic reactor compatibility issues that arise when Wolff–Kishner reductions are done in glass or stainless steel reactors. With only nitrogen gas and water as by-products, this opens the possibility of performing selective, large scale ketone reductions without the generation of hazardous waste streams

Thank you Sir Chesebrough

The Organic Solution

I have a lot of favourite chemicals, including caffeine and paracetamol. Lately, though, my favourite chemical has become soft paraffin. Soft paraffin (petroleum jelly or petrolatum) is a non-polar, hydrophobic hydrocarbon mixture. It is not one chemical structure but a mixture of hydrocarbon chains (around 25 carbons in length) with a melting point similar to that of the human body’s temperature.

n-Pentacosane

I suffer from excruciatingly itchy legs, mostly in the winter months. It keeps me (and my poor other half) awake at night. I can even draw blood without realising. Various creams keep my itching at bay but what most of these creams/lotions/balms have in common is that they contain soft paraffin. This works by forming a layer that prevents loss of moisture from my skin and also protects my skin from harsh conditions.

This stuff saves me from having sleepless nights and scarred legs, so thank you Sir Chesebrough for…

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Taking Medicines

The Organic Solution

Is it just me, or do all chemists guess the structure of a medicine before they take it? After having a guess, I then Google it and look up the synthesis, where possible.

I am currently using Ketoconazole for a skin condition (over-share, sorry). Immediately I knew there was a ketone (keto) and a nitrogen containing heterocycle (azole = five-membered nitrogen ring containing at least one other heteroatom) in there.  Conazoles are a common type of fungicide containing an imidazole or triazole ring so that narrowed it down further for me. I could not predict any thing more so looked up the structure (DOI: 10.1021/jm00194a023). It is actually a lot more complex than I expected.

Ketoconazole

Similarly, a few years ago I took Metronidazole and, as usual, I tried to predict the structure from the name. I guessed there was a nitrogen heterocycle, probably an imidazole ring and possibly nitro…

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