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Thechemicalengineer.com


tce CHEMENGERS WHO CHANGED THE WORLD
EFINING, reactor design, bulk
plastics – the kind of world-

" no one initially realised that progesterone,
changing developments featured
especially when combined with oestrogen,
thus far in this series include many of the
stereotypical activities one would imagine

was an effective contraceptive
chemical engineers to be involved in.
But the influence of chemical engineering
reaches much further. How many would
straightforward – not to mention the social the relevant patents were held by European have suspected that the work of chemical resistances that would have to be overcome. companies, giving them a competitive engineers could have contributed directly At the time, research on contraceptives was stranglehold over US-based research. to feminism and women's liberation, the illegal in many countries and even where it Marker's process brought the price down by swinging 60s and the sexual revolution? wasn't, established medical science largely two thirds straight away and imploded the It's an easily-forgotten fact, because refused to participate in this ‘disreputable' European hormone cartel, and the price fell the people in question have often been area of research.
from anywhere between $80–1000/g to less conveniently mislabelled as "chemists", During the course of the 1930s it became than $2/g. A new company – Syntex – but two of the key people responsible for clear that oestrogen and progesterone had a was formed in Mexico to commercialise developing the contraceptive pill were in fact role in preventing ovulation. But all hormones the process.
chemical engineers. at the time had to be extracted from animal They are George Rosenkranz, who in sources, a laborious process which made any educated guesswork the early 1950s was research director at hormone-based treatments horrendously Within a year, Marker left the company the Mexican chemicals company Syntex, over a commercial disagreement, and it fell and research student Luis Miramontes. to the Hungarian Jewish emigrant George Enter Russell Marker, professor of organic Working with chemist Carl Djerassi, in 1951 Rosenkranz – a chemical engineering chemistry at Pennsylvania State College and they synthesised a substance they called graduate from the Technische Hochschule a real maverick of the field – much to the norethindrone – the progesterone that was Zurich who'd fled the war to Cuba and disdain of some colleagues, he didn't even to be used in one of the first two combined later Mexico – to recreate Marker's process have a PhD to his name. However, Marker did oral contraceptive pills, and is still used by and re-start the large-scale production of succeed in revolutionising the progesterone millions of women around the world, production process by synthesising progesterone from sapogenins, natural Marker had not made it easy for him – the This is the story of how they developed it.
steroids found in Mexican yams. Marker lab was a "shambles" and Marker's notes on developed a process for turning diogenin, a starting materials and intermediates were all mavericks and renegades kind of sapogenin, into progesterone via a in code, so Rosenkranz had to use his own The idea of a contraceptive pill based on five-step process. Until his research became knowledge on steroids and a combination hormones was first proposed in 1921 by the known in the mid-1940s, progesterone was of detective work and educated guesses to Austrian physiologist Ludwig Haberlandt. recreate the progesterone production process. prepared in a laborious process from animal However, identifying, synthesising and He succeeded. Within two months, Syntex's glands, which limited the quantities available correctly dosing the right hormones was not progesterone production was back on track and kept prices sky-high. Moreover all of and production soon reached levels never known before. winning the cortisone race Engineering the Syntex first gained international recognition
by being the first company to develop an industrially-viable synthesis process for cortisone, another steroid which attracted sexual revolution huge interest as a treatment for rheumatoid
arthritis.
Syntex chemist Carl Djerassi writes in his Chemical engineers have a lot to answer autobiography, This man's pill: "Until 1951, for – including the Summer of Love. the only source of cortisone was through an extraordinarily complex process of 36 Claudia Flavell-While explains
different chemical transformations starting from animal bile acids – for many years, the longest and most complicated synthesis of any chemical on an industrial scale. Now that cortisone had emerged as a wonder drug, however, such a process looked less like a tour de force and more like a bottleneck." The race for cortisone captured public interest so much it's been compared to the space race, and Syntex was up against many much larger and better-funded rivals in North America. When Syntex beat the competition, the country was ecstatic. Ironically, it took only a few months before 46 www.tcetoday.com june 2010




CHEMENGERS WHO CHANGED THE WORLD tce
Gregory Pincus, John Hammond and Min-Chueh Chang, biologists at the Worcester Foundation for Experimental Biology in Massachusetts, who drove the development of the contraceptive pill Syntex' prized process was obsolete, thanks Syntex team used toluene as a solvent instead to a biochemical fermentation developed by of benzene, the industry standard in what Upjohn that shortened the process to a single Djerassi calls "those pre-oncophobic years". step. Luckily for Syntex, Upjohn's process Benzene was not only a carcinogen (though relied on progesterone as a raw material, so this was not known at the time), but its low the company was certainly not out of pocket. boiling point made it unsuitable for the 2.4 km high altitude of Mexico City. "This was high-altitude chemical the type of high altitude chemical cookery that most gringos working in the fancy sea- Working with Rosenkranz were Carl Djerassi, level laboratories of Harvard or Merck never another European refugee of Jewish ancestry even had to consider," Djerassi says.
patents almost two years ahead of their who'd fled his native Austria and Luis The substance was as good as the team North American rival, thus proving it was the Miramontes, a 26-year-old student from had hoped, proving to be the most active oral Universidad Nacional Autónoma de México, progestational hormone of its time.
Ultimately, both would make it to market working on his chemical engineering PhD.
as the first combined oral contraceptive pills, Djerassi and Rosenkranz returned their the pill that nobody wanted though Searle ultimately launched two years attention to progesterone. Together with Not that anyone thought of using it as a earlier. Indeed, the pill has just celebrated its Miramontes, they set out to synthesise a contraceptive, at least to begin with. The main 50th birthday: it was on 9 May 1960 that the progesterone steroid that would combine two use of progesterone at the time was to treat Food and Drug Administration first licensed previously observed effects: that replacing the certain menstrual disorders and infertility. it for contraceptive use.
carbon 19 atom with hydrogen would greatly No one initially realised that progesterone, Mexicans still take a huge amount of pride increase the compound's activity, while especially when combined with oestrogen, from the fact that it was their researchers, adding an acetylene group to position 17 was an effective contraceptive – and even in a country normally regarded as a quiet would allow it to survive absorption through when they did, fear of religiously-motivated backwater in the world of cutting edge the digestive tract.
boycotts caused companies to veer away science, who were the first to synthesise It fell to Miramontes to do most of the from the drug. Rosenkranz recalled: "I went progesterone for the contraceptive pill, practical work, and so, on 15 October 1951, around Europe and the world offering the and the Syntex researchers involved in the Miramontes completed the synthesis of contraceptive, but nobody wanted it." development have received just about every 19-nor-17α-ethynyltestosterone or, for short In the end it was two women, Margaret scientific honour Mexico has to bestow. ‘norethindrone', which turned out to be the Sanger and Katharine Dexter McCormick sex and sustainability first oral contraceptive to be synthesised.
– both passionate campaigners for the "Lecture audiences are always intrigued contraceptive pill and women's rights – The impact and importance of the when I display a slide showing (Miramontes') funding Gregory Pincus and Min-Chueh contraceptive pill can hardly be overstated. carefully-dated and hand-written lab protocol Chang, two independent-minded biologists While it did cause some social upset initially, of the very last step in that synthesis," he at the Worcester Foundation for Experimental it was a huge success from the outset. Today, added. Most of the intrigue centres on the Biology in Massachusetts, who drove the over 100m women worldwide take the pill choice of solvent used in the final step, adding development of the contraceptive pill. the acetylene to impart oral activity: the They tested a range of steroids for efficacy, Women's liberation owes a huge debt and settled on two to the pill. The sexual revolution would (Clockwise from right) , stand-out versions: have been impossible without a method of Miramontes and Rosenkranz Syntex' norethindrone, contraception that was under the woman's in 2001, Luis Miramontes and norethynodrel, an control and divorced from the sex act. and the hand-written lab isomer of norethindrone Effective family planning meant there were protocol detailing the final synthesised by Frank far fewer unwanted pregnancies and a synthesis step Corlton at the Chicago sharp drop in risky abortions and in health drugs manufacturer GD problems due to constant pregnancies. Searle. Controversy still Moreover, being able to plan pregnancies rages about whether finally enabled women to have careers and Searle's progesterone is work towards the equality of the sexes. a case of independent Gender equality and sex without fear parallel research, or weren't all of it though: the runaway success of the pill preceded a sharp decline in the birth rate in countries where the pill was available and affordable. One might argue that this has made the pill team's – Corlton the greatest ever force for sustainability there ever was – and chemical engineers were at former, Djerassi the heart of this development. tce
Next month: Thomas Midgeley
– climate killer or energy saver? june 2010 www.tcetoday.com 47

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Bronchiolitis in children. (sign guideline no 91)

Scottish Intercollegiate Guidelines Network Bronchiolitis in children 91 A national clinical guideline diagnosis risk factors for severe disease Assessment and referral treatment symptom duration and hospital discharge chronic symptoms and follow up limiting disease transmission

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(Metyrapone Capsules) Diagnostic Test of Pituitary Adrenocorticotropic Function Rx only Prescribing Information DESCRIPTION Metopirone (metyrapone Capsules) 250 mg is an inhibitor of endogenous adrenal corticosteroid synthesis, available as 250‑mg capsules for oral administration. Its chemical name is 2‑methyl‑1, 2‑di‑3‑pyridyl‑1‑propanone, and its structural formula is