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Prestwick3_000307

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35 API Suppliers, 16 USDMF, 16 CEP/COS, 1 EU WC, 10 NDC API, 17 VMF, 7 Listed Suppliers, $ API Reference Price

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Suanfarma Oxytetracycline Dihydrate

Synopsis

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Chemistry

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Also known as: 79-57-2, Terramycin, Oxyterracine, Oxytetracyclin, Adamycin, Oxymycin

Molecular Formula

C₂₂H₂₄N₂O₉

Molecular Weight

460.4 g/mol

InChI Key

OWFJMIVZYSDULZ-PXOLEDIWSA-N

FDA UNII

SLF0D9077S

A TETRACYCLINE analog isolated from the actinomycete STREPTOMYCES rimosus and used in a wide variety of clinical conditions.

Oxytetracycline anhydrous is a Tetracycline-class Antimicrobial.

1 2D Structure

Oxytetracycline Dihydrate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4S,4aR,5S,5aR,6S,12aR)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide

2.1.2 InChI

InChI=1S/C22H24N2O9/c1-21(32)7-5-4-6-8(25)9(7)15(26)10-12(21)17(28)13-14(24(2)3)16(27)11(20(23)31)19(30)22(13,33)18(10)29/h4-6,12-14,17,25-26,28,30,32-33H,1-3H3,(H2,23,31)/t12-,13-,14+,17+,21-,22+/m1/s1

2.1.3 InChI Key

OWFJMIVZYSDULZ-PXOLEDIWSA-N

2.1.4 Canonical SMILES

CC1(C2C(C3C(C(=O)C(=C(C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O

2.1.5 Isomeric SMILES

C[C@@]1([C@H]2[C@@H]([C@H]3[C@@H](C(=O)C(=C([C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)O)C(=O)N)N(C)C)O)O

2.2 Other Identifiers

2.2.1 UNII

SLF0D9077S

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bisolvomycin

2. Geomycin

3. Hydroxytetracycline

4. Oxyterracin

5. Oxyterracine

6. Oxytetracid

7. Oxytetracycline Anhydrous

8. Oxytetracycline Calcium

9. Oxytetracycline Dihydrate

10. Oxytetracycline Hydrochloride

11. Oxytetracycline Monohydrochloride

12. Oxytetracycline Sulfate (2:1)

13. Oxytetracycline, (4a Beta,5 Beta,5a Beta,12a Beta)-isomer

14. Oxytetracycline, (5 Beta)-isomer

15. Oxytetracycline, Anhydrous

16. Oxytetracycline, Calcium (1:1) Salt

17. Oxytetracycline, Disodium Salt, Dihydrate

18. Oxytetracycline, Sodium Salt

19. Terramycin

2.3.2 Depositor-Supplied Synonyms

1. 79-57-2

2. Terramycin

3. Oxyterracine

4. Oxytetracyclin

5. Adamycin

6. Oxymycin

7. Terrafungine

8. Oxyterracin

9. Oxytetracycline Anhydrous

10. Oxitetraciclina

11. Oxitetracyclin

12. Biostat

13. Geomycin

14. Ryomycin

15. Oxytetracycline (anhydrous)

16. Oxitetracyclinum

17. Oxytetracyclinum

18. Oxyterracyne

19. Solkaciclina

20. Dabicycline

21. Fanterrin

22. Geotilin

23. Imperacin

24. Lenocycline

25. Oksisyklin

26. Proteroxyna

27. Riomitsin

28. Terramitsin

29. Ursocyclin

30. Ursocycline

31. Oxypam

32. Tarocyn

33. Tarosin

34. Teravit

35. Tetran

36. Antibiotic Tm 25

37. Oxytetracycline Amphoteric

38. 5-hydroxytetracycline

39. Liquamycin La 200

40. Biostat Pa

41. Oxytetracycline [inn]

42. Bisolvomycin

43. Oxysteclin

44. Oxymykoin

45. Vendarcin

46. Ossitetraciclina

47. Pennox 200

48. Oxy-kesso-tetra

49. Oxytetracycline (terramycin)

50. Berkmycen

51. Mycoshield Tmqthc 20

52. Dalimycin

53. Oxacycline

54. Unimycin

55. Nsc-9169

56. Oxytetracycline Calcium

57. Stevacin

58. Macocyn

59. Medamycin

60. Mepatar

61. (4s,4ar,5s,5ar,6s,12as)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

62. Otc (antibiotic)

63. Mls000069429

64. Nsc 9169

65. Slf0d9077s

66. Tetracycline, 5-hydroxy-

67. Chebi:27701

68. Oxitetracycline

69. Terramycine

70. Nitox

71. Oxytetracycline (internal Use)

72. Stecsolin

73. Oxydon

74. Tm 5

75. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-

76. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4s,4ar,5s,5ar,6s,12as)-

77. Oxytetracid

78. E703

79. Nci-c56473

80. Smr000059000

81. Terramycin Im

82. Terramycin Q50

83. Ossitetraciclina [dcit]

84. (4s,4ar,5s,5ar,6s,12as)-4-(dimethylamino)-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide

85. Oxytetracycline Base

86. Oxytetracyclinum [inn-latin]

87. Oxitetraciclina [inn-spanish]

88. Terramicina Oftalmica

89. Geomycin (streptomyces Vimosus)

90. Hsdb 3145

91. Nsc-757262

92. Oxytetracycline Dehydrate

93. Einecs 201-212-8

94. La 200

95. Brn 2714587

96. Unii-slf0d9077s

97. Embryostat

98. Galsenomycin

99. Sr-01000003006

100. Hydroxytetracyclinum

101. (4s,4ar,5s,5ar,6s,12ar)-4-(dimethylamino)-1,5,6,10,11,12a-hexahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide

102. Oxytetracycline,(s)

103. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4s-(4alpha,4aalpha,5alpha,5aalpha,6beta,12aalpha))-

104. 5-hydroxy-tetracycline

105. Spectrum_001055

106. Opera_id_661

107. Oxytetracyclinum Dihydras

108. Prestwick0_000307

109. Prestwick1_000307

110. Prestwick2_000307

111. Prestwick3_000307

112. Spectrum2_000988

113. Spectrum3_000536

114. Spectrum4_000466

115. Spectrum5_001148

116. Oxytetracycline(terramycin)

117. Schembl2899

118. Chembl1517

119. Dsstox_cid_14260

120. Dsstox_rid_79133

121. Oxytetracycline [mi]

122. Dsstox_gsid_34260

123. Bspbio_000274

124. Bspbio_002151

125. Doxycycline Impurity E

126. Kbiogr_000912

127. Kbioss_001535

128. 4-14-00-02633 (beilstein Handbook Reference)

129. Divk1c_000225

130. Schembl560497

131. Spbio_001055

132. Spbio_002493

133. Bpbio1_000302

134. Chembl461529

135. Chembl1401333

136. Chembl4280957

137. Nsc9169 (hcl)

138. Oxytetracycline [who-dd]

139. Schembl13169109

140. Schembl13782651

141. Gtpl10919

142. Kbio1_000225

143. Kbio2_001535

144. Kbio2_004103

145. Kbio2_006671

146. Kbio3_001651

147. 6153-64-6 (di-hydrate)

148. Ninds_000225

149. Bdbm241973

150. 2-naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-, (4s-(4.alpha.,4a.alpha.,5.alpha.,5a.alpha.,6.beta.,12a.alpha.))-

151. 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-2-naphthacenecarboxamide

152. 79-57-2 (anhydrous)

153. Hy-b0275

154. 2058-46-0 (mono-hydrochloride)

155. Tox21_302380

156. Lmpk07000005

157. Mfcd00003700

158. S1773

159. Zinc95626782

160. Akos015951277

161. Akos015961254

162. Zinc100026355

163. Zinc100303028

164. Ccg-269334

165. Db00595

166. Cas-79-57-2

167. Idi1_000225

168. Ncgc00091268-04

169. Ncgc00091268-05

170. Ncgc00091268-06

171. Ncgc00091268-07

172. Ncgc00091268-08

173. Ncgc00091268-09

174. Ncgc00091268-10

175. Ncgc00091268-11

176. Ncgc00091268-12

177. Ncgc00188956-01

178. Ncgc00255168-01

179. Ac-12777

180. Ac-13466

181. 7179-50-2 (calcium (1:1) Salt)

182. Oxytetracycline (anhydrous) [hsdb]

183. Sbi-0051473.p003

184. Sw196796-3

185. 3,5,6,10,12,12a-hexahydroxy-6-methyl-

186. C06624

187. E75911

188. Oxytetra Selective Supplement, For Microbiology

189. Oxytetracycline 1000 Microg/ml In Acetonitrile

190. Ab00053514_04

191. Ab00053514_05

192. Ab01274728-01

193. Ab01274728_02

194. 6153-65-7 (di-hydrochloride Salt, Di-hydrate)

195. A839720

196. Q411646

197. (4s,4ar,5s,5ar,6s,12as)-4-(dimethylamino)-

198. Doxycycline Hyclate Impurity E [ep Impurity]

199. Sr-01000003006-5

200. Q63393012

201. Doxycycline Monohydrate Impurity E [ep Impurity]

202. 1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene

203. Oxytetracycline, British Pharmacopoeia (bp) Reference Standard

204. Oxytetracycline, European Pharmacopoeia (ep) Reference Standard

205. (4s,4ar,5s,5ar,6s,12as)-4-(dimethylamino)-3,5,6,10,12,12ahexahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide

206. 2z,4s,4ar,5s,5ar,6s,12as)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-5,6,10,11,12a-pentahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione

2.4 Create Date

2011-12-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₄N₂O₉
Molecular Weight	460.4 g/mol
XLogP3	-1.6
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	2
Exact Mass	460.14818035 g/mol
Monoisotopic Mass	460.14818035 g/mol
Topological Polar Surface Area	202 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	1000
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Mesh Heading: anti-bacterial agents

National Library of Medicine, SIS; ChemIDplus Record for Oxytetracycline (79-57-2). Available from, as of April 13, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp

Antibiotics, Tetracycline

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

... Possess wide range of antimicrobial activity against gram-positive and gram-negative bacteria ... some microorganisms innately insensitive to many chemotherapeutic agents, such as rickettsiae, mycoplasma, chlamydia agents of lymphogranuloma venerum, psittacosis, inclusion conjunctivitis, and trachoma and amebae. /Tetracyclines/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1117

The tetracyclines are active against a wide range of aerobic and anaerobic gram-positive and gram-negative bacteria. They also are effective against some microorganisms that are resistant to cell-wall-active antimicrobial agents, such as Rickettsiae, Coxiella burnetii, Mycoplasma pneumoniae, Chlamydia spp, Legionella spp, Ureaplasma, some atypical mycobacteria, and Plasmodium spp. They are not active against fungi. /Tetracyclines/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1240

For more Therapeutic Uses (Complete) data for OXYTETRACYCLINE (28 total), please visit the HSDB record page.

4.2 Drug Warning

GENERIC INEQUIVALENCE HAS BEEN DEMONSTRATED FOR SOME OXYTETRACYCLINE FORMULATIONS, ALTHOUGH INDIVIDUAL VARIATION PREVENTED SIGNIFICANT DIFFERENCES BEING SHOWN IN ALL BUT MOST EXTREME CASES.

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 172

FOOD, MILK, NONSYSTEMIC ANTACIDS & IRON PREPN INTERFERE WITH ORAL ABSORPTION.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1142

... Not active against any true viruses, yeasts, or fungi. /Tetracyclines/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 1184

Topical admin is best avoided because of high risk of sensitization, except for use in eye ... Should never be injected intrathecally. /Tetracyclines/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1120

For more Drug Warnings (Complete) data for OXYTETRACYCLINE (38 total), please visit the HSDB record page.

4.3 Drug Indication

Oxytetracycline is indicated for treatment of infections caused by a variety of Gram positive and Gram negative microorganisms including Mycoplasma pneumoniae, Pasteurella pestis, Escherichia coli, Haemophilus influenzae (respiratory infections), and Diplococcus pneumoniae.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Oxytetracycline is known as a broad-spectrum antibiotic due to its activity against such a wide range of infections. It was the second of the tetracyclines to be discovered. Oxytetracycline, like other tetracyclines, is used to treat many infections common and rare. Its better absorption profile makes it preferable to tetracycline for moderately severe acne, but alternatives sould be sought if no improvement occurs by 3 months.

5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

OXYTETRACYCLINE ANHYDROUS

5.3.2 FDA UNII

SLF0D9077S

5.3.3 Pharmacological Classes

Chemical Structure [CS] - Tetracyclines

5.4 ATC Code

D - Dermatologicals

D06 - Antibiotics and chemotherapeutics for dermatological use

D06A - Antibiotics for topical use

D06AA - Tetracycline and derivatives

D06AA03 - Oxytetracycline

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AA - Antibiotics

G01AA07 - Oxytetracycline

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01A - Tetracyclines

J01AA - Tetracyclines

J01AA06 - Oxytetracycline

S - Sensory organs

S01 - Ophthalmologicals

S01A - Antiinfectives

S01AA - Antibiotics

S01AA04 - Oxytetracycline

5.5 Absorption, Distribution and Excretion

Absorption

Readily absorbed following oral administration.

SERUM HALF-LIFE ... IN HORSES IS ... 15.7 HR & 10.5 HR AFTER IV & IM INJECTIONS, RESPECTIVELY. ... /A FACTOR/ MAY BE THE INFLUENCE OF DOSE-DEPENDENT KINETICS ... .

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 174

The percentage of an oral dose that is absorbed (when the stomach is empty) ... for oxytetracycline /is/ 60 to 80% ... After a single oral dose, the peak plasma concn /of oxytetracycline/ is attained in 2 to 4 hr. /It has a half-life/ in the range of 6 to 12 hr and ... frequently admin 2 to 4 times daily ... The admin of 250 mg every 6 hr produces peak plasma concn of 2 to 2.5 ug/mL ... Increasing the dosage above 1 g every 6 hr does not produce significantly higher plasma concn ... Approx 10 to 35% of a dose of oxytetracycline is excreted in active form in urine, in which it is detectable within 30 min and reaches a peak concn about 5 hr after it is admin.

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1242

/Oxytetracycline is/ bound to plasma proteins ... approx ... 20-25%.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1119

/Absorption is/ much less complete from lower ... tract ... Biliary concn ... /is/ 5 to 10 times higher than ... plasma. /Tetracyclines/

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1119

For more Absorption, Distribution and Excretion (Complete) data for OXYTETRACYCLINE (20 total), please visit the HSDB record page.

5.6 Biological Half-Life

BIOLOGIC HALF-LIFE ... MAY BE 3-4 DAYS IN ANURIA.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1142

The serum half-life of oxytetracycline is 6 to 10 hours in adults with normal renal function and is reported to be 47 to 66 hours in patients with severe renal impairment. In patients with normal renal function, approximately 60 to 70 percent of a single oral dose of oxytetracycline is excreted in urine within 72 hours as active drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 319

A two-way crossover study was conducted in crossbred male calves (6-8 months old) to determine the bioavailability, pharmacokinetics and dosage regimens for a long-acting formulation of oxytetracycline (OTC-LA). The half-lives of oxytetracycline after intravenous and intramuscular administration were 7.8 hr and 24 hr, respectively. ....

PMID:10066127 Kumar R, Malik JK; Vet Res Commun 22 (8): 533-44 (1998)

The pharmacokinetic properties of oxytetracycline were studied following a single injection of a long-acting formulation (20 mg/kg body weight) into the semimembranosus muscle of healthy dogs and of dogs that had been experimentally infected with Ehrlichia canis. ... The mean apparent elimination half-life (t(1/2) beta) was significantly increased following infection. ... The absorption half-life (t(1/2) ab) was significantly decreased after infection.

PMID:11469510 Kikuvi GM et al; Vet Res Commun 25 (5): 391-400 (2001)

SERUM HALF-LIFE ... IN HORSES IS ... 15.7 HR & 10.5 HR AFTER IV & IM INJECTIONS, RESPECTIVELY. ... /A FACTOR/ MAY BE THE INFLUENCE OF DOSE-DEPENDENT KINETICS ... .

The Chemical Society. Foreign Compound Metabolism in Mammals Volume 3. London: The Chemical Society, 1975., p. 174

5.7 Mechanism of Action

Oxytetracycline inhibits cell growth by inhibiting translation. It binds to the 30S ribosomal subunit and prevents the amino-acyl tRNA from binding to the A site of the ribosome. The binding is reversible in nature. Oxytetracycline is lipophilic and can easily pass through the cell membrane or passively diffuses through porin channels in the bacterial membrane.

Tetracyclines inhibit bacterial protein synthesis by binding to the 30 S bacterial ribosome and preventing access of aminoacyl tRNA to the acceptor (A) site on the mRNA-ribosome complex. They enter gram-negative bacteria by passive diffusion through the hydrophilic channels formed by the porin proteins of the outer cell membrane, and active transport by an energy-dependent system that pumps all tetracyclines across cytoplasmic membrane. Although permeation of these drugs into gram-positive bacteria is less well understood, it also is energy requiring. At high concn, these cmpd impair protein synthesis in mammalian cells. However, because mammalian cells lack the active transport system found in bacteria, and the ribosomal target is less sensitive, tetracyclines are selectively active against bacteria. /Tetracyclines/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1241

The tetracycline antibiotics ... can produce neuromuscular blockade, possibly by chelation of Ca+2. /Tetracyclines/

Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 203

API SUPPLIERS