Abstract
The tetracyclines are a group of antibiotics having an identical 4-ring carbocyclic structure as a basic skeleton and differing from each other chemically only by substituent variation. The popularity of the tetracyclines with the medical practitioners and the very large number of prescriptions written for them testifies eloquently to their importance to modern medicine. In addition, certain of these antibiotics have been used in very large quantities as additives to the food of meat-producing animals where they improve the efficiency of converting animal feeds to meat protein.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
R. W. Broschard, A. C. Dornbush, S. Gordon, B. L. Hutchings, A. R. Kohler, G. Krupka, S. Kushner, D. V. Lefemine and C. Pidacks, Science 109, 199 (1949); B. M. Duggar, Ann. N.Y. Acad. Sci. 51, 177 (1948).
A. C. Finlay, G. L. Hobby, S. Y. Fan, P. P. Regna, J. B. Routien, D. B. Seeley, G. M. Shull, B. A. Sobin, I. A. Solomons, J. W. Vinson and J. H. Kane, Science 111, 85 (1950); P. P. Regna, I. A. Solomons, K. Murai, A. E. Timreck, K. J. Brünings and W. A. Lazier, J. Am. chem. Soc. 73, 4211 (1951).
J. H. Boothe, J. Morton, J. P. Petisi, G. R. Wilkinson and J. H. Williams, J. Am. chem. Soc. 75, 4621 (1953).
L. H. Conover, W. T. Moreland, A. R. English, C. R. Stephens and F. J. Pilgrim, J. Am. chem. Soc. 75, 4622 (1953).
P. P. Minieri, M. C. Firman, A. G. Mistretta, A. Abbey, C. E. Bricker, N. E. Rigler and H. Sokol, Antibiotics Ann. 1953–54, 81.
J. R. D. McCormick, N. O. Sjolander, U. Hirsch, E. R. Jensen and A. P. Doer- Schuk, J. Am. chem. Soc. 79, 4561 (1957).
R. K. Blackwood, J. J. Beereboom, H. H. Rennhard, M. SchacH Von Wittenau and C. R. Stephens, J. Amer. chem. Soc. 85, 3943 (1963).
C. R. Stephens, J. J. Beereboom, H. H. Rennhard, P. N. Gordon, K. Murai, R. K. Blackwood and M. Schach Von Wittenau, J. Am. chem. Soc. 85, 2643 (1963).
M. J. Martell. 10, 44 (1967); G. S. Redin, Antimicrobial Agents and Chemotherapy (Ed. G. L. Hobby; William & Wilkens, Baltimore, Md. 1966 ), p. 371.
N. H. Steigbigel, C. W. Reid and M. Finland, Am. J. med. Sci. 255, 179 (1968).
F. A. Hochstein, C. R. Stephens, L. H. Conover, P. P. Regna, R. Pasternack, P. N. Gordon, F. J. Pilgrim, K. J. Brünings and R. B. Woodward, J. Am. chem. Soc. 75, 5455 (1953).
S. Hirokawa, Y. Okaya, F. M. Lovell and R. Pepinsky, Z. Kristallogr. 772, 439 (1959); J. Donohue, J. D, Dunitz, K. N. Trueblood and M. S. Webster, J. Am. chem. Soc. 85, 851 (1963).
M. Pearson, The Million Dollar Bugs (Putnam, New York, N.Y. 1969 ).
Med. World News 70, 18 (1969).
C. R. Stephens, L. H. Conover, R. Pasternack, F. A. Hochstein, W. T. Moreland, P. P. Regna, F. J. Pilgrim, K. J. Brünings and R. B. Woodward, J. Am. chem. SOC. 76, 3568 (1954); 74, 4976 (1952).
C. W. Waller, B. L. Hutchings, C. F. Wolf, A. A. Goldman, R. W. Broshard and J. H. Williams, J. Am. chem. Soc. 74, 4981 (1952).
J. R. D. McCormick, S. Fox, L. Smith, B. Bitler, J. ReichenthaL, V. Origoni, W. Müller, R. Winterbottom and A. Doerschük, J. Am. chem. Soc. 79, 2849 (1957).
C. R. Stephens, L. H. Conover, P. N. Gordon, F. C. Pennington, R. L. Wagner, K. J. Brünings and F. J. Pilgrim, J. Am. chem. Soc. 78, 1515 (1956).
A. P. Doerschük, B. A. Bitler and J. R. D. McCormick, J. Am. chem. Soc. 77, 4687 (1955).
E. G. Remers, G. Steiger and A. Doerschük, J. pharm. Sci. 52, 753 (1963).
M. Noseworthy, U.S. Patent 3,009,956 (11/21/61).
C. R. Stephens, J.J. Beereboom, H. H. Rennhard, P. N. Gordon, K. Murai, R. K. Blackwood and M. Schach Von Wittenaü, J. Am. chem. Soc. 85, 2643 (1963); U. S. Patent 3,028,409 (1962); C.R.Stephens (to Chas. Plizer & Co.).
M. J. Martell Jr., A. S. Ross and J. H. Boothe J. Med. Chem. 70, 485 (1967).
G.C. Barrett, J. pharm. Sci. 52, 309 (1963).
A. Brünzell, Acta chem. scand. 76, 245 (1962).
R. Hültenraüch and J. Keiner, Naturwissenschaften 53, 552 (1966).
W. J. Gottstein, W. F. Minor and L. C. Cheney, J. Am. chem. Soc. 87, 1198 (1959).
W. Seidel, A. Söder and F. Linder, Münch, med. Wschr. 77, 661 (1958); S. Afr. Pat. Spec. 3169 /57 (1957).
J. H. Boothe, G. E. Bonvicino, C. W. Waller, J. P. Petisi, R. W. Wilkinson and R. B. Roschard, J. Am. chem. Soc. 80, 1654 (1958).
L. H. Conover, Symp. Antihio. Mold Metabolites, Spec. Publ. No. 5 ( The Chemical Society, London 1956 ).
J. J. Hlavka and P. Bitha, Tetrahedron Lett. 32, 3843 (1966).
J. J. Hlavka and P. Bitha, J. Am. chem. Soc. 87, 1795 (1965).
J. R. McCormick, J. Hirsch, E. Jensen, S. Johnson and N. Sjolander, J. Am. chem. SOC. 87, 1793 (1965).
R. C. Esse, J. A. Lowery, C. R. Tamorria and G. M. Sieger, J. Am. chem. Soc. 86, 3874, 3875 (1964); S. Afr. Pat. Appl. 63/4791, (to American Cyanamid Co.); J. H. Van Den HendE, J. Am. chem. Soc. 87, 929 (1965).
R. K. Blackwood and C. R. Stephens, J. Am. chem. Soc. 86, 2736 (1964); Can. J. Chem. 43, 1382 (1965).
M. Schach Von Wittenaü, F. Hochstein and C. Stephens, J. org. Chem. 28, 2454 (1963).
M. Kolosov, M. Shemyakin, A. Khoklov and Y. Berlin, Chemistry of Antibiotics, Vol. 1 (U.S.S.R. Acad. Sci., Moscow), p. 180.
J. R. D. McCormick, P. A. Miller, J. A. Growich, N. O. Sjolander and A. P. Doerschük, J. Am. chem. Soc. 80, 5572 (1958).
M. J. Martell, Jr., A. S. Ross and J. H. Boothe, J. Am. chem. Soc. 89, 6780 (1967).
J. McCormick, R. Winterbottom and P. Bitha, U.S. Patent 3, 226, 435.
M. Schach Von Wittenau, F. A. Hochstein and C. R. Stephens, J. org. Chem. 28, 2454 (1963).
K. Koschel, G.Hartmann, W. Kersten and H. Kersten, Biochem. Z. 344, 76 (1966).
J. McCormick, E. Jensen, P. Miller and A. Doerschuk, J. Am. chem. Soc. 82, 3331 (1960); S. Afr. Pat. Appi. 513/58 (to American Cyanamid Co.).
M. Schach Von Wittenau, J. J. Beereboom, R. K. Blackwood and C. R. Stephens, J. Am. chem. Soc. 84, 2645 (1962).
P. Bitha, J. Hlavka and J. H. Boothe, J. Med. Chem. 1, 89 (1970).
J. J. Hlavka, A. Schneller, H. Krazinski and J. H. Boothe, J. Am. chem. Soc. 84, 1426 (1962).
J. J. Hlavka and H.M. Krazinski, J. org. Chem. 28, 1422 (1963).
J. J. Hlavka, H. M. Krazinski and J. H. Boothe, J. org. Chem. 27, 3674 (1962).
J. H. Boothe, J. J. Hlavka, J. P. Petisi and J. L. Spencer, J. Am. chem. Soc. 82, 1253 (1960).
J. Petisi, J.L. Spencer, J. J. Hlavka and J. H. Boothe, J. med. pharm. Chem. 5, 538 (1962).
J. L. Spencer, J. J. Hlavka, J. Petisi, H. M. Krazinski and J. H. Boothe, J. Med. Chem. 6, 405 (1963).
J. J. Beereboom, J. J. Ursprung, H. H. Rennhard and C. R. Stephens, J. Am. chem. Soc. 82, 1003 (1960).
M. J. Martell, Jr., A. S. Ross and J. H. Boothe, J. Med. Chem. 10, 359 (1967).
J. Hlavka and D. Buyske, Nature 186, 1064 (1960).
A. Green and J. H. Boothe, J. Am. chem. Soc. 82, 3950 (1960).
R. K. Blackwood, H. H. Rennhard and C. R. Stephens, J. Am. chem. Soc. 82 745 (1960).
C. E. Holmlund, W. W. Andres and A. J. Shay, J. Am. chem. Soc. 81, 4748, 4750 (1959).
H. Muxfeldt, G. Hardtmann, F. Kathawale, E. Vedejs and J. B. Mooberry, J. Am. chem. Soc. 90, 6534 (1968).
M. Burstall, Manufact. Chem.,p. 474 (1960).
J. Doluisio and A. Martin, J. Med. Chem. 6, 16 (1963).
P. Brown, Ph.D. Dissertation (S3nracuse University, June 1965 ).
Private communication from G. Redin (American Cyanamid Co.; Le. lerle Laboratories Division, Pearl River, New York).
A. Cammarata, S. J. Yau, J. Collett and A. Martin, Molec. Pharmio. 6, 61 (1970).
F. Peradejordi, A. Martin and A. Cammarata, J. pharm. Sci. 60, 5 /7 (1971).
J. Colaizzi and P. Klink, J. pharm. Sci. 58, 1185 (1969); M. Schach Von Wittenau, Chemotherapy (Suppl. ad.) 13, 41 (1968).
J. R. D. McCormick, P. A. Miller, J. A. Growich, N. O. Sjolander and A. P. Doerschuk, J. Am. chem. Soc. 80, 5572 (1958).
R. C. Evans, The Technology of the Tetracyclines ( Quadrangele Press, New York 1968 ).
Tetracycline Manufacturing Processes (Noyes Development Corp., Park Ridge, N.J. 1969).
J. C. Sheehan, K. R. Hennery-Logan, J. Am. chem. Soc. 79, 1262 (1957); 81, 3089 (1959).
G. N. Robinson, F. R. Batchelor, D. Butterworth, J. Cameron-wood, M. Cole, G. C. Eustace, M. V. Hart, M. Richards and E. B. Chain, Nature 187, 236 (1960).
J. H. Boothe, A. S. Kende, T. L. Fields and G. R. Wilkinson, J. Am. chem. Soc. 81, 1006 (1959).
T. L. Fields, A. S. Kende and J. H. Boothe, J. Am. chem. Soc. 82, 1250 (1960).
R. G. Wilkinson, T. L. Fields and J. H. Boothe, J. org. Chem. 26, 637 (1961).
A. S. Kende, T. L. Fields, J. H. Boothe and S. Kushner, J. Am. chem. Soc. 83, 439 (1961).
T. L. Fields, A. S. Kende and J. H. Boothe, J. Am. chem. Soc. 83, 4612 (1961).
H. Muxfeldt, Chem. Ber. 92, 3122 (1959).
H. Muxfeldt, H. Rogalsky and K. Striegler, Angew. Chem. 72, 170 (1960).
H. Muxfeldt, Angew. Chem. Int. Ed. Engl. 7, 372 (1962).
H. Muxfeldt and A. Kreutzer, Chem. Ber. 94, 881 (1961).
L. H. Conover, K. Butler, J. D. Johnston, J. J. Korst and R. B. Woodward, J. Am. chem. Soc. 84, 3222 (1962).
R. B. Woodward, Pure appi. Chem. 6, 561 (1963).
J. J. Korst, J. D. Johnston, K. Butler, E. J. Bianco, L. H. Conover and R. B. Woodward, J. Am. chem. Soc. 90, 439 (1968).
H. Muxfeldt and W. Rogalsky, J. Am. chem. Soc. 87, 933 (1965).
A. I. Gurevich, M. G. Karapetyan, M. N. Kolosov, V. G. Korobko, V. V. Onoprienko, S. A. Popravko and M. M. Shemyakin, Tetrahedron Lett. 1967, 131.
M. Schach Von Wittenau, J. org. Chem. 29, 2746 (1964).
A. I. Scott, C. T. Bedford, J. Am. chem. Soc. 84, 2271 (1962).
H.Muxfeldt, G.Hardtman, F. Kathawale, E. Vedejs and J. B.Mooberry, J. Am. chem. Soc. 90, 6534 (1968).
D. H. R. Barton et al., J. chem. Soc. 1971, 2164.
R. Robinson, Structural Relations of Natural Products ( Oxford University Press, London 1955 ), p. 58.
J. F. Snell, R. Wagner and F. A. Hochstein, Proc. Int. Conf. Peaceful Uses of At. Energy 12, 431 (1955).
P.A.Miller, J. R. D. McCormick and A. P. Doerschuk, Science 123, 1030 (1956).
S. Gatenbeck, Biochem. biophys. Res. Commun. 6, 422 (1961).
A. S. Buch, Fortschr. Chem. org. Naturstoffe 14, 186 (1957).
J. R.D. McCormick, Biogenesis, Vol.2 of Antibiotics (Ed. D.Gottlieb and P.D. Shaw; Springer-Verlag, Berlin 1967 ).
J. R. D. McCormick, Genetics and Breeding of Streptomyces ( Yugoslav Academy of Arts and Sciences, Zagreb 1969 ).
J. R. D. McCormick, P. A. Miller, S. Johnson, N. H. Arnold and N. O. Sjolander, J. Am. chem. Soc. 84, 3023 (1962); J. R.D. McCormick, The Biogenesis of Antibiotic Substances (Academic Press, Inc., New York 1965), p. 83; L. A. Mitscher, J. pharm. Sci. 57, 1633 (1968); J. R. D. McCormick, E. R. Jensen, S. Johnson and N. O. Sjolander, J. Am. chem. Soc. 90, 2201 (1968); J. R. D. McCormick and E. R. Jensen, J. Am. chem. Soc. 90, 7126 (1968); J. R. D. McCormick, S. Johnson and N. O. Sjolander, J. Am. chem. Soc. 85, 1692 (1963).
J. R. D. McCormick, U. Hirsch, E. Jensen, S. Johnson and N. O. Sjolander, J. Am. chem. Soc. 87, 1793 (1965).
This material was synithesized by Dr. R. ESSE, Lederle Laboratories, Division of American Cyanamid Company, private communication.
P. A. Miller, A. Saturnelli, J. Martin, L. Mithcer and N. BohonoS, Biochem. biophys. Res. Commun. 16, 285 (1964).
J. R. D. McCormick and E. R. Jensen, J. Am. chem. Soc. 91, 206 (1969).
J. R. D. McCormick, P. A. Miller, J. A. Growich, N. O. Sjolander and A. P. Doerschuk, J. Am. chem. Soc. 80, 5572 (1958).
J. J. Hlavka, P. Bitha and J. H. Boothe, J. Am. chem. Soc. 87, 1795 (1965); J. Am. chem. Soc. 90, 1034 (1968).
D.H.R. BArton and A.I Scott, J. chem. 1958, 1767.
G. Stork, Chem. Ind., Lond. 1955, 915.
A. Dornbush and E. Pelcak, Ann. N.Y. Acad. Sci. 51, 218 (1948).
J. R. McMahon, J. biol. Chem. 153, 249 (1944).
S. Waksman and S. Reilly, Ind. Eng. Chem. 17, 556 (1945).
G. S. Redin, Antimicrob. Ag. Chemother. 1966, 371.
G. Suarez and D. NathanS, Biochem. biophys. Res. Commun. 18, 743 (1965).
A. Cammarata et al., Molec. Pharmac. 6, 61 (1970).
R. Rendi and S. Ochoa, J. biol. Chem. 237, 3711 (1962); Science 133, 1367 (1961).
T. J. Franklin, Biochem. J. 87, 449 (1963); 84, HOP (1962).
T. Akiba and T. Yokota, Igaku To Seibutsugaku 64, 34, 39 (1962).
J. Park, Biochem. J. 70, 2P (1958).
A. I. Laskin, Antibiotics, Mechanism of Action I ( Springer-Verlag, New York 1967 ), p. 331.
J. Snell and L. Cheng, Develop, ind. Microbiol. 2, 107 (1961).
G. Suarez and D. Nathans, Biochem. biophys. Res. Commun. 18, 743 (1965).
R. Connamacher and H. Mandel, Biochim. biophys. Acta 166, 475 (1968).
A. Larkin and J. Lard, Antibiot. Chemother. 17, 1 (1971).
Z. Vogel, Biochemistry 8, 5161 (1969).
R. Kaempfer, Proc. nat. Acad. Sci. 61, 106 (1968).
M. Barker and L. Garrod, Antibiotics and Chemotherapy (E S Livingstone Ltd., Edinburg, Scotland).
M. Finland, New Engl. J. Med. 253, 909 (1955).
J. Dexter and H. Bates, Minn. Med. 53, 205 (1970).
O. Jessen and K. Rosendal, New Engl. J. Med. 281, 627 (1969).
R. McCormack, R. Kaye and E. Hook, New Engl. J. Med. 267, 323 (1966).
Ragsdale and J. Sanford, Antimicrob. Ag. Chemother. 1964, 164.
A. Percival and E. Armstrong, Lancet 7, 998 (1969).
T. J. Franklin, Symposia of the Society for General Microbiology, Number X VI (1966).
T. J. Franklin and A. Godfrey, Biochem. J. 94, 54 (1965).
S. Mitsuhashi, J. infect. Dis. 119, 89 (1969).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1973 Birkhäuser Verlag Basel
About this chapter
Cite this chapter
Hlavka, J.J., Boothe, J.H. (1973). The Tetracyclines. In: Jucker, E. (eds) Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques. Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des Recherches Pharmaceutiques, vol 17. Birkhäuser Basel. https://doi.org/10.1007/978-3-0348-7084-9_5
Download citation
DOI: https://doi.org/10.1007/978-3-0348-7084-9_5
Publisher Name: Birkhäuser Basel
Print ISBN: 978-3-0348-7086-3
Online ISBN: 978-3-0348-7084-9
eBook Packages: Springer Book Archive