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Pralidoxime

Systematic (IUPAC) name
2-[(hydroxyimino)methyl]-1-methylpyridin-1-ium
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy cat.	C
Legal status	RX-only
Identifiers
CAS number	6735-59-7 Y
ATC code	V03AB04
PubChem	CID 6789253
DrugBank	DB00733
ChemSpider	5193737 Y
UNII	P7MU9UTP52 Y
KEGG	C07400 Y
ChEBI	CHEBI:8354 Y
ChEMBL	CHEMBL1420 Y
Synonyms	1-methylpyridine-6-carbaldehyde oxime
Chemical data
Formula	C7H9N2O+
Mol. mass	137.159 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C7H8N2O/c1-9-5-3-2-4-7(9)6-8-10/h2-6H,1H3/p+1 Y Key:JBKPUQTUERUYQE-UHFFFAOYSA-O Y
Y (what is this?)  (verify)

Pralidoxime (2-pyridine aldoxime methyl chloride,) or 2-PAM, usually as the chloride or methiodide salts, belongs to a family of compounds called oximes that bind to organophosphate-inactivated acetylcholinesterase. It is used to combat poisoning by organophosphates^[1] or acetylcholinesterase inhibitors (nerve agents), in conjunction with atropine and diazepam. In India, it is marketed by Nucleus Inc. with the brand names LyoPAM and PurePAM.

Mechanism of action[link]

Pralidoxime, typically used in cases of organophosphate poisoning (which causes AChase inhibition), attaches to the site where a cholinesterase inhibitor has attached, then attaches to the inhibitor, removing the organophosphate from cholinesterase, allowing it to work normally again. This is known as "regenerating" or "reactivating" acetylcholinesterase allowing the breakdown of Ach at the synapse. After some time though, some inhibitors can develop a permanent bond with cholinesterase, known as aging, where oximes such as pralidoxime can not reverse the bond.^{[citation needed]} Pralidoxime is often used with atropine (a muscarinic antagonist) to help reduce the parasympathetic effects of organophosphate poisoning. Pralidoxime can also be used to treat neostigmine or pyridostigmine (both ACHase inhibitors) overdoses due to its ACHase regenerating capacities.

Pralidoxime has an important role in reversing paralysis of the respiratory muscles but due to its poor blood–brain barrier penetration, it has little effect on centrally-mediated respiratory depression. This is why atropine which has excellent blood–brain barrier penetration, is concomitantly administered with pralidoxime during the treatment of organophosphate poisoning.

Dosage[link]

• Adults: 30 mg/kg (typically 1-2 g), administered by intravenous therapy over 15–30 minutes or intramuscular injection or subcutaneous injection, repeated 60 minutes later. It can also be given as a 500 mg/hr continuous IV infusion.
• Children: 20–50 mg/kg followed by a maintenance infusion at 5–10 mg/kg/hr.

Intravenous infusions can lead to respiratory or cardiac arrest if given too quickly.^[2]

Interactions[link]

When atropine and pralidoxime are used together, the signs of atropinization (flushing, mydriasis, tachycardia, dryness of the mouth and nose) may occur earlier than might be expected when atropine is used alone. This is especially true if the total dose of atropine has been large and the administration of pralidoxime has been delayed.

The following precautions should be kept in mind in the treatment of anticholinesterase poisoning, although they do not bear directly on the use of pralidoxime: since barbiturates are potentiated by the anticholinesterases, they should be used cautiously in the treatment of convulsions; morphine, theophylline, aminophylline, succinylcholine, reserpine, and phenothiazine-type tranquilizers should be avoided in patients with organophosphate poisoning.

Contraindications[link]

There are no known absolute contraindications for the use of pralidoxime. Relative contraindications include known hypersensitivity to the drug and other situations in which the risk of its use clearly outweighs possible benefit.

Chemistry[link]

Pralidoxime, 2-pyridinaldoxime methylchloride, is synthesized by reacting picolinaldehyde (2-formyl pyridine) with hydroxylamine, giving pyridine-2-aldoxime, which is further reacted with methyl iodide, giving the desired pralidoxime.

• D. Nachmansonn, S. Ginsburg, U.S. Patent 2,816,113 (1957).
• L.P. Black, U.S. Patent 3,123,613 (1964).
• D.E. Easterday, A.A. Kondritzer, U.S. Patent 3,140,289 (1964).
• W.B. McDowell, U.S. Patent 3,155,674 (1964).

See also[link]

• Mark I NAAK

References[link]

External links[link]

• Chemical Bioweapons website
• Drugs.com

This biographical article needs additional citations for verification. Please help by adding reliable sources. Contentious material about living persons that is unsourced or poorly sourced must be removed immediately, especially if potentially libelous or harmful. (December 2010)

Deniz Tek is an American singer, guitarist and songwriter and a founding member of Australian group Radio Birdman who broke up, for the last time, after their last European tour in 2007. He has played in many of the underground rock bands of the 1970s including Australian bands The Visitors, and New Race but is most known for exerting his burning Detroit style guitar influence over the punk rock genre in Australia. Legend has it that Tek's navy codename 'Iceman' was appropriated by visiting screenwriters for a character in the hit movie Top Gun.

Tek was raised in Ann Arbor, Michigan, USA. He spent 1967 in Sydney, Australia with his family and was greatly attracted to the Australian landscape, moving there permanently in 1972 to commence his medical studies at The University of NSW in Sydney. Deniz Tek is a trained ER doctor and ex-navy flight surgeon who currently splits his time working in emergency departments in hospitals in NSW, Australia and Hawaii, USA while still taking time to record and tour.^[1]

Biography[link]

Early years[link]

Tek was born to a Turkish father and an American mother and grew up in Ann Arbor, Michigan a university town near Detroit where Tek was exposed to Motor City music icons such as MC5, The Stooges and The Rationals. In the late '60s Ann Arbor became somewhat of a nexus for rock music, hosting festivals which drew performers from all around the world such as Pink Floyd, Janis Joplin, Johnny Winter, Captain Beefheart, and a personal favourite of Tek's, The Rolling Stones. Headlining world acts such The Rolling Stones aside, Tek was heavily influenced by the mushrooming local underground scene of Ann Arbor, which included bands such as The Frost, Mitch Ryder, Carnal Kitchen with Steve Mackay, The Up, The SRC plus jazz greats Pharaoh Sanders, Sun Ra, Archie Shepp and Yusef Lateef. In 1971 Tek left the rock metropolis of Ann Arbor to pursue his medical studies in Sydney, Australia.

1972-73 with TV Jones[link]

In late 1972 Tek had joined the band TV Jones as lead singer/guitarist along with Chris Jones on guitar, Gerry Jones on drums (brother of the now successful jazz trumpet player Vince Jones), Giles Vanderwerf on bass. TV Jones had a fanatical cult following in Wollongong, to the point where things got crazed and dangerous where by in 1974, the group fled north of the city. The band was hopeful of success, but amid disastrous engagements at Chequers and the Whisky A Go Go, ran afoul of both the police and organised crime simultaneously. After unsuccessful album recording sessions in North Sydney, the group began to disintegrate, sacking Tek from TV Jones as a negative influence.

1974-78 with Radio Birdman[link]

After being dismissed from TV Jones, Tek proceeded to form a new band with long time friend Rob Younger, with the addition of Chris Masuak, Warwick Gilbert, Pip Hoyle and Ron Keeley, and called themselves Radio Birdman, after a misheard Stooges lyric. Radio Birdman were arguably the most successful band that Tek was associated with, despite the bands initial shunning from the Australian music scene. The Radio Birdman sound was unconventional and raw and echos the Motor City influences of Tek's youth. Birdman are often attributed with the initiation of the Australian indie rock scene, as after being repeatedly rejected from various clubs and bars in the Sydney area, Birdman took it upon themselves to record and release their first recording Radios Appear, and distribute it out the back of the band members station wagons. Radio Birdman began a world tour in 1977 travelling to England and playing a few shows around London as well as recording their second album Living Eyes, until in 1978 the band broke up mid-tour due to "personality conflict".

1978-81 with The Visitors, Angie Pepper Band, and the New Race tour[link]

Following the demise of Radio Birdman, Tek proceeded to experiment musically in several different bands. From 1978 to 1979 Deniz dabbled in a band called The Visitors with Deniz on guitar, Mark Sisto on vocals, Ron Keeley on drums, Pip Hoyle on keyboards and Steve Harris on bass. The band being 3/5ths Birdman members was often compared to the early sound that Birdman had, but with a new twist of the Sisto vocal which likened the sound to that of The Doors. During these years Tek had also committed to writing the songs for Angie Pepper's new band The Angie Pepper Band after the breakup of her more successful band The Passengers.

What has often been hailed as the ultimate Motor City supergroup New Race, was formed by Tek with fellow Birdman members Rob Younger, and Warwick Gilbert, along with guitarist from The Stooges, Ron Asheton, and the drummer of MC5, Dennis Thompson, for a once off tour along the east coast of Australia in 1981. The band performed to sold out shows and many bootleg recordings of the shows were made, which resulted in the formation of several bootleg releases. The only official live recording of the shows was released in 1982 by Birdman's Trafalgar Studios under the appropriate title of The First and Last.

The between years[link]

He then moved back to America where he became a licensed physician, specialising his qualifications in emergency and aerospace medicine. When in America he is based in Montana. He served time as a Navy flight surgeon with the Marines, and flew back seat in F4 Phantoms in the squadrons VMFA212 and VMFA232. His callsign of "Iceman" was noticed by producers of the Top Gun film during a research visit to the squadron and may have been appropriated for Val Kilmer's character in the film. [1]

1991 with The Deniz Tek Group[link]

Encouraged by his friend and ex-Birdman compadre Chris Masuak, Deniz came back to Australia in 1991, intent on renewing himself musically. He began extensive touring in 1992 and, following a near career destroying disaster on the Take It To The Vertical tour of 1992 initiated a line-up that became known as The Deniz Tek Group. This line-up spent the next few years touring Europe, Australia and the USA, while releasing an EP and several albums (Outside, 444 The Number Of The Beat, La Bonne Route) Geographical difficulties became untenable in late '96 and the group split up. Deniz then continued with US based lineups and recorded albums with Wayne Kramer(MC5)(Dodge Main), skateboard stars Art and Steve Godoy (Golden Breed, The Last Of The Bad Men), a Montana based trio (Equinox), an experimental electronic duo with Jimi Hendrix's sidekick and amplifier designer Dave Weyer (Glass Insects), east coast hard rockers (Deep Reduction and DR2 featuring Rob Younger), and live work including tours and live albums with the Rationals' Scott Morgan (Three Assassins, Powertrane) and surviving members of Sonic's Rendezvous Band (Getting There Is Half The Fun). Deniz and wife Angie Pepper (Passengers) recorded her album Res Ipsa Loquitor in 2001. Deniz continued to record and tour extensively in the late '90s, while Radio Birdman reunified and began to work again.

The re-unification of Radio Birdman[link]

Radio Birdman reformed in January 1996, with all original members, touring Australia extensively- including their headlining of the 1996 Big Day Out Tour. Critics and fans old and new expressed the belief that they more than lived up to the legend.

They recorded a "live" album, performed to an exclusive, invited audience of 24 and released this on CD as Ritualism. Initially it was only available by mail order on their own Crying Sun Records label, a low budget, but high quality DIY project which is perfectly consistent with their earlier work both sonically and philosophically.

Radio Birdman played and toured sporadically over the next ten years, losing the original drummer and bass player along the way. With Jim Dickson on bass and Rusty Hopkinson (You Am I) on drums, they played shows around Australia, returned to the recording studio in 2006, and released their first new studio album in 25 years, Zeno Beach Zeno Beach was accompanied by a national tour of Australia and an extensive world tour, which included New Zealand, Europe, and for the first time ever, the United States. Radio Birdman again toured the world in 2007. In July 2007 Radio Birdman was inducted into the ARIA Australian Music Hall of Fame.^[2]

Current projects[link]

The Soul Movers is one of Deniz's latest musical projects (commenced 2008) with ex-Birdman member Pip Hoyle on keys, Andy Newman and Calvin Welch on drums with co-songwriter Lizzie Mack on vocals. 'On the INside' (Career/ Cool Time Records) was released September 2009. In April 2011 Deniz joined with Iggy and the Stooges, as a special guest, for a tribute performance in Ann Arbor. The remainder of 2011 saw Deniz recording a new solo album and touring with Art and Steve Godoy as the Golden Breed.^{[citation needed]}

Discography[link]

This list is incomplete; you can help by expanding it.

Radio Birdman[link]