text:
I Put a Spell on You
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"I Put a Spell on You"
A-side label of the 1956 U.S. 7-inch vinyl single
Single by Screamin' Jay Hawkins
from the album At Home with Screamin' Jay Hawkins
B-side
"Little Demon"
Released
November 1956 (1956-11)
Format
Seven-inch 45 rpm record
Genre
Rhythm and blues[1]
shock rock[2]
Length
2:25
Label
Okeh
Songwriter(s)
Jay Hawkins
Herb Slotkin
Producer(s)
Arnold Maxin
Screamin' Jay Hawkins singles chronology
"Even Though"
(1956) "I Put a Spell on You"
(1956) "You Made Me Love You"
(1957)
"Even Though"
(1956) "I Put a Spell on You"
(1956) "You Made Me Love You"
(1957)
"I Put a Spell on You" is a 1956 song written by Jay Hawkins, whose recording was selected as one of the Rock and Roll Hall of Fame's 500 Songs that Shaped Rock and Roll. It was also ranked No. 313 on Rolling Stone magazine's list of The 500 Greatest Songs of All Time. The track became a classic cult song covered by a variety of artists and was his greatest commercial success, reportedly surpassing a million copies in sales,[3][4] although it failed to make the Billboard pop or R&B charts.[5][6]
Contents
[hide]
1 The original composition
2 Personnel
3 Covers and samples
4 References
The original composition[edit]
Hawkins had originally intended to record "I Put a Spell on You" as "a refined love song, a blues ballad". However, the producer "brought in ribs and chicken and got everybody drunk, and we came out with this weird version ... I don't even remember making the record. Before, I was just a normal blues singer. I was just Jay Hawkins. It all sort of just fell in place. I found out I could do more destroying a song and screaming it to death."[7]
Hawkins first recorded "I Put a Spell on You" as a ballad during his stint with Grand Records in late 1955. However, that version was not released at the time (it has since been reissued on Hawkins' UK Rev-Ola CD The Whamee 1953–55). The following year, Hawkins re-recorded the song for Columbia's Okeh Records – the notorious screaming version, which was released in October 1956. This version was banned from radio for its outrageous style. A truncated version was released but the ban remained. The record still sold over a million copies.[8]
The hit brought Hawkins together with Cleveland disc jockey Alan Freed who promptly added him to his "Rock and Roll Revue." Up to this time, Hawkins had been a blues performer: emotional, but not wild. Freed suggested a gimmick to capitalize on the "demented" sound of "I Put a Spell on You": Hawkins wore a long cape, and appeared onstage by rising out of a coffin in the midst of smoke and fog.[9] The act was a sensation, later bolstered by tusks worn in Hawkins' nose, on-stage snakes and fireworks, and a cigarette-smoking skull named "Henry".
This theatrical act was one of the first shock rock performances.[10]
Personnel[edit]
Guitar – Mickey Baker
Piano – Ernie Hayes
Tenor Saxophone – Sam "The Man" Taylor
Baritone Saxophone – Bud Johnson
Bass – Al Lucas
Drums – David "Panama" Francis
Arranged By – Leroy Kirkland
Recorded 12 September 1956[11]
Covers and samples[edit]
"I Put a Spell on You" has been covered by other artists extensively; there are several hundred versions available on online stores like iTunes. Most of the covers treat the song seriously; few attempt to duplicate Hawkins's bravura performance. Although Hawkins' version did not make any charts, several later cover versions have.
Nina Simone's version reached No. 23 on the U.S. Billboard R&B chart in 1965; it also reached No. 49 on the UK singles chart that year, and No. 28 when it was reissued in 1969.[12]
The version by The Alan Price Set reached No. 9 in the UK in 1966[13] and No. 80 on the Billboard Hot 100.
Creedence Clearwater Revival's version reached No. 58 on the U.S. Hot 100 in 1968. The band later performed it at the Woodstock Festival in 1969.[14]
A disco version by Dutch singer Dee Dee (Anna Dekkers) reached No. 16 on the Dutch charts in 1978 and was also released in Belgium (where it peaked on No. 12), France, Germany, Spain, and Australia.
In the UK, Bryan Ferry's version reached No. 18 in 1993.[15]
The version by Sonique reached No. 36 in 1998 and No. 5 on reissue in 2000.[16][17][18]
Other versions of note:
Manfred Mann released a version on their U.K. EP No Living Without Loving in November 1965 (also appeared on the band's 1966 U.S. album 'Pretty Flamingo').
The 2010 version by Jeff Beck featuring Joss Stone was nominated for the Grammy Award for Best Rock Performance by a Duo or Group with Vocal at the 53rd Grammy Awards.[19]
Bette Midler covered the song in the film Hocus Pocus in an elaborate song and dance sequence. Midler performed the song again during her 2015 Divine Intervention Tour, wearing a costume similar to the one she wore in Hocus Pocus.
Annie Lennox included a version of the song on her 2014 album Nostalgia.
References[edit]
Jump up ^ Bush, John. Screamin' Jay Hawkins - I Put a Spell on You at AllMusic. Retrieved 7 November 2015.
Jump up ^ Mike McPadden (1 May 2012). If You Like Metallica ... : Here Are Over 200 Bands, CDs, Movies, and Other Oddities That You Will Love. Backbeat Books. p. 37. ISBN 978-1-4768-1357-8. Retrieved 7 November 2015.
Jump up ^ Edward M. Komara (2006). Encyclopedia of the Blues: A-J. Routledge. p. 415. Retrieved 2008-12-04.
Jump up ^ Ed Sikov (1996). Laughing Hysterically: American Screen Comedy of the 1950s. Columbia University Press. p. 17. Retrieved 2008-12-04.
Jump up ^ Whitburn, Joel (2003). Top Pop Singles 1955–2002 (1st ed.). Menomonee Falls, Wisconsin: Record Research Inc. ISBN 0-89820-155-1.
Jump up ^ Whitburn, Joel (1996). Top R&B/Hip-Hop Singles: 1942–2004. Menomonee Falls, Wisconsin: Record Research. ISBN 0-89820-115-2.
Jump up ^ Julia Rubiner, Contemporary Musicians: Profiles of the People in Music, Volume 8, Gale, 1992, p.117
Jump up ^ Colin Larkin (2011), The Encyclopedia of Popular Music, Omnibus Press, p. 2680, ISBN 978-0-85712-595-8
Jump up ^ Chris Morris (Feb 26, 2000), "Legendary Screamin' Jay Hawkins Dies At 70", Billboard
Jump up ^ Gillespie, Paula, and Neal Lerner. The Allyn and Bacon Guide to Peer Tutoring. Boston: Allyn, 2000. Print.
Jump up ^ https://www.discogs.com/Screamin-Jay-Hawkins-I-Put-A-Spell-On-You-The-Singles-1954-1957/release/3181566
Jump up ^ Brown, Tony, Jon Kutner & Neil Warwick, The Complete Book of the British Charts: Singles and Albums, Omnibus Press, London, 2002 p. 911
Jump up ^ Brown, Tony, Jon Kutner & Neil Warwick, The Complete Book of the British Charts: Singles and Albums, Omnibus Press, London, 2002 p. 795
Jump up ^ https://www.setlist.fm/setlist/creedence-clearwater-revival/1969/max-yasgurs-farm-bethel-ny-13d6b529.html
Jump up ^ Brown, Tony, Jon Kutner & Neil Warwick, The Complete Book of the British Charts: Singles and Albums, Omnibus Press, London, 2002 p. 371
Jump up ^ Whitburn, Joel (2003). Top Pop Singles 1955–2002 (1st ed.). Menomonee Falls, Wisconsin: Record Research Inc. ISBN 0-89820-155-1.
Jump up ^ Whitburn, Joel (1996). Top R&B/Hip-Hop Singles: 1942–2004. Menomonee Falls, Wisconsin: Record Research. ISBN 0-89820-115-2.
Jump up ^ Betts, Graham (2004). Complete UK Hit Singles 1952–2004 (1st ed.). London: Collins. ISBN 0-00-717931-6.
Jump up ^ "Nominees And Winners – GRAMMY.com". National Academy of Recording Arts and Sciences.
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Yakety Yak
From Wikipedia, the free encyclopedia
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This article is about the song. For other uses, see Yakety Yak (disambiguation).
"Yakety Yak"
A-side label of the U.S. vinyl single
Single by The Coasters and Johnny Cash
B-side
"Zing! Went the Strings of My Heart"
Released
April 1958
Format
45 rpm, 78 rpm
Recorded
March 17, 1958
Genre
Rock and roll
Length
1:52
Label
Atco 6116
Songwriter(s)
Jerry Leiber, Mike Stoller
Producer(s)
Jerry Leiber, Mike Stoller
The Coasters and Johnny Cash singles chronology
"Gee, Golly"
(1958) "Yakety Yak"
(1958) "The Shadow Knows"
(1958)
"Gee, Golly"
(1958) "Yakety Yak"
(1958) "The Shadow Knows"
(1958)
"Yakety Yak" is a song written, produced, and arranged by Jerry Leiber and Mike Stoller for The Coasters and released on Atco Records in 1958, spending seven weeks as #1 on the R&B charts and a week as number one on the Top 100 pop list.[1] This song was one of a string of singles released by The Coasters between 1957 and 1959 that dominated the charts, one of the biggest performing acts of the rock and roll era.[2]
Contents
1 Song
2 Popular culture
3 See also
4 References
5 External links
Song[edit]
The song is a "playlet," a word Stoller used for the glimpses into teenage life that characterized the songs Leiber and Stoller wrote and produced.[3] The lyrics describe the listing of household chores to a kid, presumably a teenager, the teenager's response ("yakety yak") and the parents' retort ("don't talk back") — an experience very familiar to a middle-class teenager of the day. Leiber has said the Coasters portrayed "a white kid’s view of a black person’s conception of white society."[2] The serio-comic street-smart “playlets” etched out by the songwriters were sung by the Coasters with a sly clowning humor, while the saxophone of King Curtis filled in, in the up-tempo doo-wop style. The group was openly "theatrical" in style—they were not pretending to be expressing their own experience.[4]
The threatened punishment for not taking out the garbage and sweeping the floor is, in the song's humorous lyrics:[5]
"You ain't gonna rock and roll no more,"
And the refrain is:
"Yakety yak; don't talk back."[6]
Popular culture[edit]
Québécois duo Les Jérolas recorded in 1959 a French version "Rouspet' pas"
The sax solo by King Curtis inspired the 1963 Boots Randolph song "Yakety Sax"[7]
Sha Na Na performed this as part of their set at the original Woodstock Festival and recorded 2 live covers of the song in 1971 and 1972
The song was covered by Jan & Dean and was planned to be released on their album Carnival of Sound in 1968. Carnival of Sound was not released until 2010.
Lee Perry released a cover version in 1969 (as Lee Perry and the Upsetters), altering the lyric "You ain't gonna rock and roll no more" to "You ain't gonna reggae reggae reggae no more"
The Pipkins covered their song in 1970, produced by John Burgess.
Electronic/disco group El Coco covered this song in 1975 with some comedy elements, taken from their debut album, Mondo Disco, released on AVI Records.
Vince Vance & The Valiants, one of multiple groups parodying Barbara Ann as "Bomb Iran" in 1980, created a similarly themed 2005 parody called "Yakety Yak (Bomb Iraq)".[8]
Stand by Me, the 1986 classic coming of age drama included "Yakety Yak" on its iconic soundtrack.
The song has also been mixed & recorded by 2 Live Crew for the 1988 movie Twins. In the same film, Julius (Arnold Schwarzenegger) sings along, with hilarious results, as the song plays in his earphones while flying to the United States.
The song is sung by the Coasters in the 1988 horror-comedy Phantom of the Ritz which the four-man group makes a cameo appearance.
It has also served as the theme to Clive Anderson's chat-show Clive Anderson Talks Back during the 1990s, and as the opening theme of the 1988 movie The Great Outdoors.[9]
It was the inspiration and theme song for the 2002-2003 Canadian/Australian animated series, Yakkity Yak.[10]
A modified version, "Yakety Yak, Take it Back", was used in a 1990 all-star PSA for the Take It Back Foundation.[11]
A music video starring Plucky Duck as the kid tasked with chores, and a group of anthropomorphic yaks in police officer suits, aired on the 90th episode of Tiny Toon Adventures and used in The Plucky Duck Show.
The song was parodied for use in adverts for Radox bath soak and McCain Micro Chips in the 1980s and 1990s respectively.
The song name was used for the code name of Ubuntu 16.10, a Linux operating system with its versions all named after animals.[12]
Phantom Planet covered this song for the soundtrack of the 1999 film Mumford.
See also[edit]
List of number-one R&B singles of 1958 (U.S.)
List of number-one singles of 1958 (U.S.)
References[edit]
Jump up ^ Whitburn, Joel (2004). Top R&B/Hip-Hop Singles: 1942-2004. Record Research. p. 125.
^ Jump up to: a b "The Coasters". Rock Hall of Fame. Archived from the original on 2006-10-17. Retrieved 2006-11-08.
Jump up ^ Anthony DeCurtis, & James Henke (eds) (1980). The RollingStone: The Definitive History of the Most Important Artists and Their Music ((3rd Ed.) ed.). New York, N.Y.: Random House, Inc. p. 98. ISBN 0-679-73728-6. CS1 maint: Extra text: authors list (link)
Jump up ^ Matos, Michaelangelo (April 13, 2005). "Yakety Yak". Seattle Weekly. Retrieved 2006-11-08.
Jump up ^ Friedlander, Paul (1996). Rock and Roll: A social history. Boulder, CO: Westview Press (Harper Collins). p. 66. ISBN 0-8133-2725-3.
Jump up ^ Leiber & Stoller interviewed on the Pop Chronicles (1969)
Jump up ^ Boots Randolph, Boots Randolph's Yakety Sax! Retrieved February 6, 2015
Jump up ^ "The Show Band that Wouldn't Die". Houston Press, June 30, 2005.
Jump up ^ "The Great Outdoors (1988) - Soundtracks". IMDb. Retrieved 2009-03-13.
Jump up ^ Yakkity Yak Intro. YouTube. January 12, 2011.
Jump up ^ "'Yakety Yak – Take It Back!' Music Video". Take It Back Foundation. Retrieved 2012-02-08.
Jump up ^ "Mark Shuttleworth » Blog Archive » Y is for…". www.markshuttleworth.com. Retrieved 2016-11-02.
External links[edit]
Lyrics of this song at MetroLyrics
hide
v
t
e
The Coasters
Carl Gardner
Billy Guy
Bobby Nunn
Leon Hughes
Adolph Jacobs
Young Jessie
Cornell Gunter
Will "Dub" Jones
Vernon Harrell
Earl "Speedo" Carroll
Ronnie Bright
Jimmy Norman
Thomas "Curly" Palmer
Albert "Sonny" Forriest
Alvin Morse
Carl Gardner Jr
J.W. Lance
Primotivo Candelara
Eddie Whitfield
Dennis Anderson
Studio albums
The Coasters
The Coasters One By One
Coast Along with The Coasters
It Ain't Sanitary (with Billy Guy)
Other albums
The Coasters' Greatest Hits
Greatest Hits
That Is Rock & Roll
All Time Greatest Hits
Their Greatest Recordings: The Early Years
The Coasters On Broadway
This Is the Coasters
The World Famous Coasters
20 Great Originals
16 Greatest Hits
What Is the Secret of Your Success?
Young Blood
The Ultimate Coasters
20 Greatest Hits
The Greatest Hits
50 Coastin' Classics: Anthology
The Very Best of the Coasters
Golden Hits
Great
Yakety Yak & Other Favorites
All Our Best
The Best of the Coasters
Yakety Yak: The Platinum Collection
The Definitive Soul: The Coasters
There's a Riot Goin' On: The Coasters on Atco
Only the Best of the Coasters
Singles
"Down in Mexico"
"One Kiss Led to Another"
"Young Blood"
"Idol With The Golden Head"
"Sweet Georgia Brown"
"Gee, Golly"
"Yakety Yak"
"The Shadow Knows"
"Charlie Brown"
"Along Came Jones"
"Poison Ivy"
"What About Us"
"Besame Mucho (Part I)"
"Wake Me, Shake Me"
"Shoppin' for Clothes"
"Wait A Minute"
"Little Egypt (Ying-Yang)"
"Girls Girls Girls (Part I)"
"(Ain't That) Just Like Me"
"Ridin´ Hood"
"The Climb (vocal)"
"The P.T.A."
"T'ain't Nothin' to Me"
"Bad Detective"
"Wild One"
"Lady Like"
"Let's Go Get Stoned"
"Crazy Baby"
"She's A Yum Yum"
"Soul Pad"
"She Can"
"D. W. Washburn"
"Act Right"
"Love Potion Number Nine"
"Cool Jerk"
"Hush Don't Talk About It"
B-sides
"Turtle Dovin"
"Brazil"
"Searchin'"
"(When She Wants Good Lovin´) My Baby Comes To Me"
"What Is The Secret Of Your Success?"
"Dance!"
"Zing! Went the Strings of My Heart"
"Sorry But I'm Gonna Have To Pass"
"Three Cool Cats"
"That Is Rock & Roll"
"I'm A Hog For You"
"Run Red Run"
"Besame Mucho (Part II)"
"Stewball"
"The Snake And The Book Worm"
"Thumbin´ A Ride"
"Keep On Rolling"
"Girls Girls Girls (Part II)"
"Bad Blood"
"Teach Me How To Shimmy"
"The Climb (instrumental)"
"Bull Tick Waltz"
"Speedo's Back In Town"
"Lovey Dovey"
"I Must Be Dreaming"
"Hongry"
"Money Honey"
"Bell Bottom Slacks And A Chinese Kimono (She's My Little Spodee-O)"
"Saturday Night Fish Fry"
"Down Home Girl"
"Everybody's Woman"
"The World Is Changing"
"Talkin´ ´Bout A Woman"
Cover songs
"Autumn Leaves"
"But Beautiful"
"Don't Get Around Much Anymore"
"Easy Living"
"Frosty the Snowman"
"Gee, Baby, Ain't I Good to You"
"I Love Paris"
"If I Had a Hammer" (by WIll Jones)
"The 'In' Crowd"
"Moonglow"
"Moonlight in Vermont"
"Mustang Sally"
"My Babe"
"On Broadway"
"On the Sunny Side of the Street"
"Satin Doll"
"The Way You Look Tonight"
"Willow Weep for Me"
"You'd Be So Nice to Come Home To"
Retrieved from "https://en.wikipedia.org/w/index.php?title=Yakety_Yak&oldid=858769087"
Categories:
Songs written by Jerry Leiber and Mike Stoller
Jan and Dean songs
1958 singles
The Coasters songs
Billboard Top 100 number-one singles
Billboard Hot R&B/Hip-Hop Songs number-one singles
Novelty songs
1958 songs
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Sulfonamide (medicine)
From Wikipedia, the free encyclopedia
Jump to: navigation, search
Sulfonamide functional group
Hydrochlorothiazide is a sulfonamide and a thiazide.
Furosemide is a sulfonamide, but not a thiazide.
Sulfamethoxazole is an antibacterial sulfonamide
Sulfonamide (also called sulphonamide, sulfa drugs or sulpha drugs) is the basis of several groups of drugs. The original antibacterial sulfonamides are synthetic antimicrobial agents that contain the sulfonamide group. Some sulfonamides are also devoid of antibacterial activity, e.g., the anticonvulsant sultiame. The sulfonylureas and thiazide diuretics are newer drug groups based on the antibacterial sulfonamides.[1][2]
Allergies to sulfonamide are common. According to data the overall incidence of adverse drug reactions to sulfa antibiotics is approximately 3%, close to penicillin;[3] hence medications containing sulfonamides are prescribed carefully. It is important to make a distinction between sulfa drugs and other sulfur-containing drugs and additives, such as sulfates and sulfites, which are chemically unrelated to the sulfonamide group, and do not cause the same hypersensitivity reactions seen in the sulfonamides.
Contents
[hide]
1 Function
1.1 Antimicrobial
1.2 Other uses
2 History
3 Preparation
4 List of sulfonamides
4.1 Children's antibacterial drugs
4.2 Antimicrobials
4.3 Sulfonylureas (anti-diabetic agents)
4.4 Diuretics
4.5 Anticonvulsants
4.6 Dermatologicals
4.7 Antiretrovirals
4.8 Hepatitis C antivirals
4.9 Stimulant
4.10 Other
5 Side effects
6 See also
7 References
8 External links
Function[edit]
Antimicrobial[edit]
Main article: Dihydropteroate synthase inhibitor
In bacteria, antibacterial sulfonamides act as competitive inhibitors of the enzyme dihydropteroate synthase (DHPS), an enzyme involved in folate synthesis. Sulfonamides are therefore bacteriostatic and inhibit growth and multiplication of bacteria, but do not kill them. Humans, in contrast to bacteria, acquire folate (vitamin B9) through the diet.[4]
Structural similarity between sulfonamide (left) and PABA (center) is the basis for the inhibitory activity of sulfa drugs on tetrahydrofolate(right) biosynthesis
Other uses[edit]
Sulfonamides are used to treat allergies and cough, as well as antifungal and antimalarial functions. The moiety is also present in other medications that are not antimicrobials, including thiazide diuretics (including hydrochlorothiazide, metolazone, and indapamide, among others), loop diuretics (including furosemide, bumetanide, and torsemide), acetazolamide, sulfonylureas (including glipizide, glyburide, among others), and some COX-2 inhibitors (e.g., celecoxib).
Sulfasalazine, in addition to its use as an antibiotic, is also used in the treatment of inflammatory bowel disease.
History[edit]
Sulfonamide drugs were the first antibiotics to be used systemically, and paved the way for the antibiotic revolution in medicine. The first sulfonamide, trade-named Prontosil, was a prodrug. Experiments with Prontosil began in 1932 in the laboratories of Bayer AG, at that time a component of the huge German chemical trust IG Farben. The Bayer team believed that coal-tar dyes which are able to bind preferentially to bacteria and parasites might be used to attack harmful organisms in the body. After years of fruitless trial-and-error work on hundreds of dyes, a team led by physician/researcher Gerhard Domagk[5] (working under the general direction of Farben executive Heinrich Hörlein) finally found one that worked: a red dye synthesized by Bayer chemist Josef Klarer that had remarkable effects on stopping some bacterial infections in mice.[6] The first official communication about the breakthrough discovery was not published until 1935, more than two years after the drug was patented by Klarer and his research partner Fritz Mietzsch.
Prontosil, as Bayer named the new drug, was the first medicine ever discovered that could effectively treat a range of bacterial infections inside the body. It had a strong protective action against infections caused by streptococci, including blood infections, childbed fever, and erysipelas, and a lesser effect on infections caused by other cocci. However, it had no effect at all in the test tube, exerting its antibacterial action only in live animals. Later, it was discovered by Bovet,[7] Federico Nitti and J. and Th. Jacques Tréfouël, a French research team led by Ernest Fourneau at the Pasteur Institute, that the drug was metabolized into two pieces inside the body, releasing from the inactive dye portion a smaller, colorless, active compound called sulfanilamide.[8] The discovery helped establish the concept of "bioactivation" and dashed the German corporation's dreams of enormous profit; the active molecule sulfanilamide (or sulfa) had first been synthesized in 1906 and was widely used in the dye-making industry; its patent had since expired and the drug was available to anyone.[9]
The result was a sulfa craze.[10] For several years in the late 1930s, hundreds of manufacturers produced tens of thousands of tons of myriad forms of sulfa. This and nonexistent testing requirements led to the elixir sulfanilamide disaster in the fall of 1937, during which at least 100 people were poisoned with diethylene glycol. This led to the passage of the Federal Food, Drug, and Cosmetic Act in 1938 in the United States. As the first and only effective antibiotic available in the years before penicillin, sulfa drugs continued to thrive through the early years of World War II.[11] They are credited with saving the lives of tens of thousands of patients, including Franklin Delano Roosevelt Jr. (son of US President Franklin Delano Roosevelt) and Winston Churchill. Sulfa had a central role in preventing wound infections during the war. American soldiers were issued a first-aid kit containing sulfa pills and powder, and were told to sprinkle it on any open wound.
The sulfanilamide compound is more active in the protonated form. The drug has very low solubility and sometimes can crystallize in the kidneys, due to its first pKa of around 10. This is a very painful experience, so patients are told to take the medication with copious amounts of water. Newer analogous compounds prevent this complication because they have a lower pKa, around 5–6,[citation needed] making them more likely to remain in a soluble form.
Many thousands of molecules containing the sulfanilamide structure have been created since its discovery (by one account, over 5,400 permutations by 1945), yielding improved formulations with greater effectiveness and less toxicity. Sulfa drugs are still widely used for conditions such as acne and urinary tract infections, and are receiving renewed interest for the treatment of infections caused by bacteria resistant to other antibiotics.
Preparation[edit]
Sulfonamides are prepared by the reaction of a sulfonyl chloride with ammonia or an amine. Certain sulfonamides (sulfadiazine or sulfamethoxazole) are sometimes mixed with the drug trimethoprim, which acts against dihydrofolate reductase. As of 2013, the Republic of Ireland is the largest exporter worldwide of Sulfonamides, accounting for approximately 32% of total exports.[12]
List of sulfonamides[edit]
Children's antibacterial drugs[edit]
Sulfafurazole (in Pediazole)[13]
Antimicrobials[edit]
Short-acting[14]
Sulfacetamide
Sulfadiazine
Sulfadimidine
Sulfafurazole (sulfisoxazole)
Sulfisomidine (sulfaisodimidine)
Intermediate-acting
Sulfadoxine
Sulfamethoxazole
Sulfamoxole
Sulfanitran
Long-acting
Sulfadimethoxine
Sulfamethoxypyridazine
Sulfametoxydiazine
Ultra long-acting
Sulfadoxine
Sulfametopyrazine
Terephtyl
Sulfonylureas (anti-diabetic agents)[edit]
Acetohexamide
Carbutamide
Chlorpropamide
Glibenclamide (glyburide)
Glibornuride
Gliclazide
Glyclopyramide
Glimepiride
Glipizide
Gliquidone
Glisoxepide
Tolazamide
Tolbutamide
Diuretics[edit]
Acetazolamide
Bumetanide
Chlorthalidone
Clopamide
Furosemide
Hydrochlorothiazide
Indapamide
Mefruside
Metolazone
Xipamide
Anticonvulsants[edit]
Ethoxzolamide
Sultiame
Zonisamide
Dermatologicals[edit]
Mafenide
Antiretrovirals[edit]
Amprenavir (HIV protease inhibitor)
Darunavir (HIV protease inhibitor)
Delavirdine (non-nucleoside reverse transcriptase inhibitor)
Fosamprenavir (HIV protease inhibitor)
Tipranavir (HIV protease inhibitor)
Hepatitis C antivirals[edit]
Asunaprevir (NS3/4A protease inhibitor)
Beclabuvir (NS5B RNA polymerase inhibitor)
Dasabuvir (NS5B RNA polymerase inhibitor)
Grazoprevir (NS3/4A protease inhibitor)
Paritaprevir (NS3/4A protease inhibitor)
Simeprevir (NS3/4A protease inhibitor)
Stimulant[edit]
Azabon
Other[edit]
Apricoxib (COX-2 inhibitor)
Bosentan (endothelin receptor antagonist)
Brinzolamide (carbonic anhydrase inhibitor for glaucoma)
Celecoxib (COX-2 inhibitor)
Dofetilide (class III antiarrhythmic)
Dorzolamide (anti-glaucoma carbonic anhydrase inhibitor)
Dronedarone (class III antiarrhythmic)
Ibutilide (class III antiarrhythmic)
Parecoxib (COX-2 inhibitor)
Probenecid (uricosuric)
Sotalol (β blocker)
Sulfasalazine (anti-inflammatory agent and a DMARD)
Sumatriptan (antimigraine triptan)
Tamsulosin (α blocker)
Udenafil (PDE5 inhibitor)
Side effects[edit]
Patient suffering from Stevens–Johnson syndrome
Allergic urticaria on the skin induced by an antibiotic
Sulfonamides have the potential to cause a variety of untoward reactions, including urinary tract disorders, haemopoietic disorders, porphyria, and hypersensitivity reactions. When used in large doses, they may cause a strong allergic reaction. Two of the most serious are Stevens–Johnson syndrome and toxic epidermal necrolysis (also known as Lyell syndrome).[3]
Approximately 3% of the general population have adverse reactions when treated with sulfonamide antimicrobials. Of note is the observation that patients with HIV have a much higher prevalence, at about 60%.[15]
Hypersensitivity reactions are less common in nonantibiotic sulfonamides, and, though controversial, the available evidence suggests those with hypersensitivity to sulfonamide antibiotics do not have an increased risk of hypersensitivity reaction to the nonantibiotic agents.[16] A key component to the allergic response to sulfonamide antibiotics is the arylamine group at N4, found in sulfamethoxazole, sulfasalazine, sulfadiazine, and the anti-retrovirals amprenavir and fosamprenavir. Other sulfonamide drugs do not contain this arylamine group; available evidence suggests that patients who are allergic to arylamine sulfonamides do not cross-react to sulfonamides that lack the arylamine group, and may therefore safely take non-arylamine sulfonamides.[17] It has therefore been argued that the terms 'sulfonamide allergy' or 'sulfa allergy' are misleading, and should be replaced by a reference to a specific drug (e.g. 'cotrimoxazole allergy').[18]
Two regions of the sulfonamide antibiotic chemical structure are implicated in the hypersensitivity reactions associated with the class.
The first is the N1 heterocyclic ring, which causes a type I hypersensitivity reaction.
The second is the N4 amino nitrogen that, in a stereospecific process, forms reactive metabolites that cause either direct cytotoxicity or immunologic response.
The nonantibiotic sulfonamides lack both of these structures.[19]
The most common manifestations of a hypersensitivity reaction to sulfa drugs are rash and hives. However, there are several life-threatening manifestations of hypersensitivity to sulfa drugs, including Stevens–Johnson syndrome, toxic epidermal necrolysis, agranulocytosis, hemolytic anemia, thrombocytopenia, fulminant hepatic necrosis, and acute pancreatitis, among others.[20]
See also[edit]
Antibiotic
Timeline of antibiotics
Elixir sulfanilamide
Dihydropteroate synthase
PABA
References[edit]
Jump up ^ Henry RJ (1943). "The Mode of Action of Sulfonamides". Bacteriological reviews. 7 (4): 175–262. PMC 440870  . PMID 16350088.
Jump up ^ "SULFONAMIDE CLASS ANTIBIOTICS". chemicalland21.com. Retrieved 17 January 2014.
^ Jump up to: a b "Sulfa Drugs Allergy -- Sulfa Bactrim Drug Allergies". allergies.about.com. Retrieved 17 January 2014.
Jump up ^ M. Madigan, J. Martinko, D. Stahl, D. Clark, Brock Biology of Microorganisms (13th ed.), Pearson Education, 2012, p. 797 ISBN 9780321735515
Jump up ^ Otten H (1986). "Domagk and the development of the sulphonamides". Journal of Antimicrobial Chemotherapy. 17 (6): 689–696. PMID 3525495. doi:10.1093/jac/17.6.689.
Jump up ^ Hager, Thomas (2006-09-01). "The Demon Under the Microscope: From Battlefield Hospitals to Nazi Labs, One Doctor's Heroic Search for the World's First Miracle Drug". ISBN 978-0-307-35228-6.
Jump up ^ Cf. Daniel Bovet, Une chimie qui guérit : Histoire de la découverte des sulfamides, Paris, Payot, coll. « Médecine et sociétés », 1988 (ISBN 2-228-88108-2).
Jump up ^ J. et Th. Tréfouël, F. Nitti et D. Bovet, « Activité du p.aminophénylsulfamide sur l’infection streptococcique expérimentale de la souris et du lapin », dans C. R. Soc. Biol., vol. 120, 23 novembre 1935, p. 756.
Jump up ^ "history of medicine :: Medicine in the 20th century -- Encyclopædia Britannica". britannica.com. Retrieved 17 January 2014.
Jump up ^ "BAD HEALTH – Elixir Sulfanilamide | The Blog of Bad". blogofbad.wordpress.com. Retrieved 17 January 2014.
Jump up ^ "History of WWII Medicine". Archived from the original on 1999-10-14. Retrieved 2014-04-04.
Jump up ^ "Trade of Sulfonamides". Massachusetts Institute of Technology. Retrieved 26 October 2013.
Jump up ^ "Pediazole: Indications, Side Effects, Warnings - Drugs.com". drugs.com. Retrieved 17 January 2014.
Jump up ^ Brayfield, A, ed. (2 February 2011). "Sulfonamides and diaminopyrimidines". Martindale: The Complete Drug Reference. Pharmaceutical Press. Retrieved 28 March 2014.
Jump up ^ Tilles SA (August 2001). "Practical issues in the management of hypersensitivity reactions: sulfonamides". Southern Medical Journal. 94 (8): 817–24. PMID 11549195. doi:10.1097/00007611-200108000-00013.
Jump up ^ Slatore CG, Tilles SA (2004). "Sulfonamide hypersensitivity". Immunology and Allergy Clinics of North America. 24 (3): 477–490, vii. PMID 15242722. doi:10.1016/j.iac.2004.03.011.
Jump up ^ Knowles S, Shapiro L, Shear NH (2001). "Should Celecoxib Be Contraindicated in Patients Who Are Allergic to Sulfonamides?". Drug Safety. 24 (4): 239–247. PMID 11330653. doi:10.2165/00002018-200124040-00001.
Jump up ^ Veroni M. "ALLERGIES TO SULFONAMIDE ANTIBIOTICS AND CROSS-REACTIVITIES" (PDF). Western Australian Therapeutic Advisory Group. Retrieved 2014-02-07.
Jump up ^ Brackett CC, Singh H, Block JH (July 2004). "Likelihood and mechanisms of cross-allergenicity between sulfonamide antibiotics and other drugs containing a sulfonamide functional group". Pharmacotherapy. 24 (7): 856–70. PMID 15303450. doi:10.1592/phco.24.9.856.36106.
Jump up ^ Harrison's Principles of Internal Medicine, 13th Ed. McGraw-Hill Inc. 1994. p. 604.
External links[edit]
List of sulfonamides
Author of "The Demon under the Microscope," a history of the discovery of the sulfa drugs
A History of the Fight Against Tuberculosis in Canada (Chemotherapy)
Presentation speech, Nobel Prize in Physiology and Medicine, 1939
The History of WW II Medicine
"Five Medical Miracles of the Sulfa Drugs." Popular Science, June 1942, pp. 73–78.
http://www.life.umd.edu/classroom/bsci424/Chemotherapy/AntibioticsHistory.htm - A history of antibiotics
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(inhibits
purine metabolism,
thereby inhibiting
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DHFR inhibitor
2,4-Diaminopyrimidine
Trimethoprim#
Brodimoprim
Tetroxoprim
Iclaprim†
Sulfonamides
(DHPS inhibitor)
Short-
acting
Sulfaisodimidine
Sulfamethizole
Sulfadimidine
Sulfapyridine
Sulfafurazole
Sulfanilamide
Prontosil
Sulfathiazole
Sulfathiourea
Intermediate-
acting
Sulfamethoxazole
Sulfadiazine#
Sulfamoxole
Long-
acting
Sulfadimethoxine
Sulfadoxine
Sulfalene
Sulfametomidine
Sulfametoxydiazine
Sulfamethoxypyridazine
Sulfaperin
Sulfamerazine
Sulfaphenazole
Sulfamazone
Other/ungrouped
Sulfacetamide
Sulfadicramide
Sulfametrole
Sulfanitran
Combinations
Trimethoprim/sulfamethoxazole#
Ormetoprim/sulfadimethoxine
Other DHPS inhibitors
Dapsone
Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)
1st g.
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Flumequine‡
Nalidixic acid‡
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Rosoxacin‡
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quinolones
2nd g.
Ciprofloxacin#
Ofloxacin
Enoxacin‡
Fleroxacin‡
Lomefloxacin‡
Nadifloxacin‡
Norfloxacin‡
Pefloxacin‡
Rufloxacin‡
3rd g.
Levofloxacin#
Balofloxacin‡
Grepafloxacin‡
Pazufloxacin‡
Sparfloxacin‡
Temafloxacin‡
Tosufloxacin‡
4th g.
Besifloxacin
Gatifloxacin
Finafloxacin
Gemifloxacin
Moxifloxacin
Clinafloxacin†
Garenoxacin‡
Prulifloxacin‡
Sitafloxacin‡
Trovafloxacin‡/Alatrofloxacin‡
Vet.
Danofloxacin
Difloxacin
Enrofloxacin
Ibafloxacin
Marbofloxacin
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Pradofloxacin
Sarafloxacin‡
Newer non-fluorinated
Nemonoxacin
Related (DG)
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inhibitors
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RNA polymerase
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Rifalazil§
#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
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#WHO-EM
‡Withdrawn from market
Clinical trials:
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§Never to phase III
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#WHO-EM
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Clinical trials:
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§Never to phase III
Retrieved from "https://en.wikipedia.org/w/index.php?title=Sulfonamide_(medicine)&oldid=804750303"
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