6-(4-Dimethylamino-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-14-ethyl-7,12,13-trihydroxy-4-(5-hydroxy-4-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yloxy)-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione

ID: ALA532

Cas Number: 114-07-8

PubChem CID: 12560

Product Number: E105346, Order Now?

Max Phase: Approved

First Approval: 1964

Molecular Formula: C37H67NO13

Molecular Weight: 733.94

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Benzamycin | Bristamycin | E-Base | E-Glades | E-Mycin | ERY-TAB | Erypar | Erythro-Statin | Erythrocin | Erythromycin | PCE | Pfizer-E | J01FA01 | NSC-55929 | erythromycin|114-07-8|Erythromycin A|E-Mycin|Abomacetin|Erythromycinum|Emgel|Erymax|Ilotycin|Robimycin|Torlamicina|Eryderm|Erythro-Statin|Erythrocin|E-Glades|Ery-Tab|Erythromycine|Eritromicina|Pantomicina|Erygel|Sansac|E-Base|Erythra-Derm|Erythromycin base|ERYC|Dumotrycin|Mephamycin|Ermycin|Eryacne|Stiemycin|Aknin|Erycen|Wemid|Erycette|R-Show More⌵

Synonyms from Alternative Forms(23): Erythromycin lactobionate | Erythromycini lactobionas | Erythrocin | Erythromycin | Sterile erythromycin lactobionate | Erythromycin stearate | Abboticine | Erythromycin octadecanoate (salt) | Erythromycini stearas | Sk-erythromycin | NSC-756747 | Bristamycin | Erypar | Erythrocin 500 | Erythrocin acne pack | Erythrocin stearate | Ethril 250 | Ethril 500 | Pfizer-e | Wyamycin s | Erythromycin gluceptate | Erythromycin glucoheptonate | Ilotycin gluceptate

Trade Names(43): A/t/s | Akne-mycin | Aknemycin plus | C-solve-2 | E-base | E-glades | E-mycin | E-solve 2 | Emgel | Ery-tab | Eryacne 2 | Eryacne 4 | Eryc | Eryc 125 | Eryc sprinkles | Erycette | Eryderm | Erygel | Erymax | Erymax sprinkle | Erythra-derm | Erythro 200 | Erythro-statin | Erythrocin | Erythromycin | Gallimycin | Ilotycin | Isotrexin | Kerymax | Oftalmolosa cusi eritromicina | Paediathrocin | R-p mycin | Retcin | Robimycin | Rommix 250 ec | Rommix 500 ec | Sansac | Staticin | Stiemycin | T-stat | Tiloryth | Wyamycin | Zineryt

Canonical SMILES:  CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O

Standard InChI:  InChI=1S/C37H67NO13/c1-14-25-37(10,45)30(41)20(4)27(39)18(2)16-35(8,44)32(51-34-28(40)24(38(11)12)15-19(3)47-34)21(5)29(22(6)33(43)49-25)50-26-17-36(9,46-13)31(42)23(7)48-26/h18-26,28-32,34,40-42,44-45H,14-17H2,1-13H3/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1

Standard InChI Key:  ULGZDMOVFRHVEP-RWJQBGPGSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA532

   ERYTHROMYCIN

2. Alternative Forms:

   

   ALA532

   Oxacyclotetradecane
3. 

   ALA532

   Erythromycin lactobionate
4. 

   ALA532

   ERYTHROMYCIN STEARATE
5. 

   ALA532

   ERYTHROMYCIN GLUCEPTATE
6. 

   ALA532

   (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;(2R,3

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: No

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 733.94

Molecular Weight (Monoisotopic): 733.4612

AlogP: 1.79

#Rotatable Bonds: 7

Polar Surface Area: 193.91

Molecular Species: NEUTRAL

HBA: 14

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.45

CX Basic pKa: 8.38

CX LogP: 2.60

CX LogD: 1.57

Aromatic Rings: ┄

Heavy Atoms: 51

QED Weighted: 0.24

Np Likeness Score: 1.89

References

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38. Yong H, Gu YG, Clark RF, Marron T, Ma Z, Soni N, Stone GG, Nilius AM, Marsh K, Djuric SW..  (2005)  Design, synthesis and structure-activity relationships of 6-O-arylpropargyl diazalides with potent activity against multidrug-resistant Streptococcus pneumoniae.,  15  (10): [PMID:15863336] [10.1016/j.bmcl.2005.03.011]

39. Li J, Kim IH, Roche ED, Beeman D, Lynch AS, Ding CZ, Ma Z..  (2006)  Design, synthesis, and biological evaluation of BODIPY-erythromycin probes for bacterial ribosomes.,  16  (4): [PMID:16309904] [10.1016/j.bmcl.2005.11.028]

40. Zhu B, Marinelli BA, Abbanat D, Foleno BD, Henninger TC, Bush K, Macielag MJ..  (2006)  Synthesis and antibacterial activity of 3-O-acyl-6-O-carbamoyl erythromycin A derivatives.,  16  (4): [PMID:16289812] [10.1016/j.bmcl.2005.10.074]

41. Fu H, Marquez S, Gu X, Katz L, Myles DC..  (2006)  Synthesis and in vitro antibiotic activity of 16-membered 9-O-arylalkyloxime macrolides.,  16  (5): [PMID:16343900] [10.1016/j.bmcl.2005.11.061]

42. Sherman D, Xiong L, Mankin AS, Melman A..  (2006)  Synthesis and biological investigation of new 4''-malonyl tethered derivatives of erythromycin and clarithromycin.,  16  (6): [PMID:16387493] [10.1016/j.bmcl.2005.12.033]

43. Voets M, Antes I, Scherer C, Müller-Vieira U, Biemel K, Marchais-Oberwinkler S, Hartmann RW..  (2006)  Synthesis and evaluation of heteroaryl-substituted dihydronaphthalenes and indenes: potent and selective inhibitors of aldosterone synthase (CYP11B2) for the treatment of congestive heart failure and myocardial fibrosis.,  49  (7): [PMID:16570918] [10.1021/jm060055x]

44. Grant EB, Guiadeen D, Abbanat D, Foleno BD, Bush K, Macielag MJ..  (2006)  Synthesis and antibacterial activity of 6-O-heteroarylcarbamoyl-11,12-lactoketolides.,  16  (7): [PMID:16446089] [10.1016/j.bmcl.2005.12.097]

45. Mereu A, Moriggi E, Napoletano M, Regazzoni C, Manfredini S, Mercurio TP, Pellacini F..  (2006)  Design, synthesis and in vivo activity of 9-(S)-dihydroerythromycin derivatives as potent anti-inflammatory agents.,  16  (22): [PMID:16982191] [10.1016/j.bmcl.2006.08.076]

46. Tennakoon MA, Henninger TC, Abbanat D, Foleno BD, Hilliard JJ, Bush K, Macielag MJ..  (2006)  Synthesis and antibacterial activity of C6-carbazate ketolides.,  16  (24): [PMID:16997549] [10.1016/j.bmcl.2006.09.036]

47. Baker SJ, Akama T, Zhang YK, Sauro V, Pandit C, Singh R, Kully M, Khan J, Plattner JJ, Benkovic SJ, Lee V, Maples KR..  (2006)  Identification of a novel boron-containing antibacterial agent (AN0128) with anti-inflammatory activity, for the potential treatment of cutaneous diseases.,  16  (23): [PMID:16997550] [10.1016/j.bmcl.2006.08.130]

48. Nielsen EI, Viberg A, Löwdin E, Cars O, Karlsson MO, Sandström M..  (2007)  Semimechanistic pharmacokinetic/pharmacodynamic model for assessment of activity of antibacterial agents from time-kill curve experiments.,  51  (1): [PMID:17060524] [10.1128/aac.00604-06]

49. Obert CA, Miller ML, Montgomery J, Adamkiewicz T, Tuomanen EI..  (2007)  Quinupristin-dalfopristin nonsusceptibility in pneumococci from sickle cell disease patients.,  51  (1): [PMID:17060526] [10.1128/aac.01016-06]

50. Kheadr E, Dabour N, Le Lay C, Lacroix C, Fliss I..  (2007)  Antibiotic susceptibility profile of bifidobacteria as affected by oxgall, acid, and hydrogen peroxide stress.,  51  (1): [PMID:17060530] [10.1128/aac.00261-06]

51. Kamysz W, Silvestri C, Cirioni O, Giacometti A, Licci A, Della Vittoria A, Okroj M, Scalise G..  (2007)  In vitro activities of the lipopeptides palmitoyl (Pal)-Lys-Lys-NH(2) and Pal-Lys-Lys alone and in combination with antimicrobial agents against multiresistant gram-positive cocci.,  51  (1): [PMID:17060532] [10.1128/aac.00344-06]

52. Weigel LM, Donlan RM, Shin DH, Jensen B, Clark NC, McDougal LK, Zhu W, Musser KA, Thompson J, Kohlerschmidt D, Dumas N, Limberger RJ, Patel JB..  (2007)  High-level vancomycin-resistant Staphylococcus aureus isolates associated with a polymicrobial biofilm.,  51  (1): [PMID:17074796] [10.1128/aac.00576-06]

53. Duewelhenke N, Krut O, Eysel P..  (2007)  Influence on mitochondria and cytotoxicity of different antibiotics administered in high concentrations on primary human osteoblasts and cell lines.,  51  (1): [PMID:17088489] [10.1128/aac.00729-05]

54. Foleno BD, Abbanat D, Goldschmidt RM, Flamm RK, Paget SD, Webb GC, Wira E, Macielag MJ, Bush K..  (2007)  In vitro antibacterial activity of the pyrrolopyrazolyl-substituted oxazolidinone RWJ-416457.,  51  (1): [PMID:17101672] [10.1128/aac.01017-06]

55. Szczepanowski R, Krahn I, Bohn N, Pühler A, Schlüter A..  (2007)  Novel macrolide resistance module carried by the IncP-1beta resistance plasmid pRSB111, isolated from a wastewater treatment plant.,  51  (2): [PMID:17101677] [10.1128/aac.00802-06]

56. Szumowski JD, Cohen DE, Kanaya F, Mayer KH..  (2007)  Treatment and outcomes of infections by methicillin-resistant Staphylococcus aureus at an ambulatory clinic.,  51  (2): [PMID:17116664] [10.1128/aac.01244-06]

57. Chan YY, Ong YM, Chua KL..  (2007)  Synergistic interaction between phenothiazines and antimicrobial agents against Burkholderia pseudomallei.,  51  (2): [PMID:17145801] [10.1128/aac.01033-06]

58. Wolter N, Smith AM, Low DE, Klugman KP..  (2007)  High-level telithromycin resistance in a clinical isolate of Streptococcus pneumoniae.,  51  (3): [PMID:17210764] [10.1128/aac.01153-06]

59. Elkins CA, Mullis LB..  (2007)  Substrate competition studies using whole-cell accumulation assays with the major tripartite multidrug efflux pumps of Escherichia coli.,  51  (3): [PMID:17210767] [10.1128/aac.01048-06]

60. Izdebski R, Sadowy E, Fiett J, Grzesiowski P, Gniadkowski M, Hryniewicz W..  (2007)  Clonal diversity and resistance mechanisms in tetracycline-nonsusceptible Streptococcus pneumoniae isolates in Poland.,  51  (4): [PMID:17210772] [10.1128/aac.01384-06]

61. Gaudreau C, Girouard Y, Ringuette L, Tsimiklis C..  (2007)  Comparison of disk diffusion and agar dilution methods for erythromycin and ciprofloxacin susceptibility testing of Campylobacter jejuni subsp. jejuni.,  51  (4): [PMID:17261628] [10.1128/aac.00905-06]

62. Brenciani A, Bacciaglia A, Vecchi M, Vitali LA, Varaldo PE, Giovanetti E..  (2007)  Genetic elements carrying erm(B) in Streptococcus pyogenes and association with tet(M) tetracycline resistance gene.,  51  (4): [PMID:17261630] [10.1128/aac.01484-06]

63. Istuk ZM, Mutak S, Kujundzić N, Kragol G..  (2007)  Novel 9a-carbamoyl- and 9a-thiocarbamoyl-3-decladinosyl-6-hydroxy and 6-methoxy derivatives of 15-membered macrolides.,  15  (13): [PMID:17467993] [10.1016/j.bmc.2007.04.021]

64. Villain-Guillot P, Gualtieri M, Bastide L, Roquet F, Martinez J, Amblard M, Pugniere M, Leonetti JP..  (2007)  Structure-activity relationships of phenyl-furanyl-rhodanines as inhibitors of RNA polymerase with antibacterial activity on biofilms.,  50  (17): [PMID:17665895] [10.1021/jm0703183]

65. Zhu B, Marinelli BA, Abbanat D, Foleno BD, Bush K, Macielag MJ..  (2007)  Synthesis and antibacterial activity of 3-keto-6-O-carbamoyl-11,12-cyclic thiocarbamate erythromycin A derivatives.,  17  (14): [PMID:17502142] [10.1016/j.bmcl.2007.04.104]

66. Sugawara A, Sunazuka T, Hirose T, Nagai K, Yamaguchi Y, Hanaki H, Sharpless KB, Omura S..  (2007)  Design and synthesis via click chemistry of 8,9-anhydroerythromycin A 6,9-hemiketal analogues with anti-MRSA and -VRE activity.,  17  (22): [PMID:17869508] [10.1016/j.bmcl.2007.08.068]

67. Moda TL, Montanari CA, Andricopulo AD..  (2007)  Hologram QSAR model for the prediction of human oral bioavailability.,  15  (24): [PMID:17870541] [10.1016/j.bmc.2007.08.060]

68. Hirokawa Y, Kinoshita H, Tanaka T, Nakata K, Kitadai N, Fujimoto K, Kashimoto S, Kojima T, Kato S..  (2008)  Water-soluble pleuromutilin derivative with excellent in vitro and in vivo antibacterial activity against gram-positive pathogens.,  51  (7): [PMID:18330977] [10.1021/jm8000136]

69. Ekins S, Mankowski DC, Hoover DJ, Lawton MP, Treadway JL, Harwood HJ..  (2007)  Three-dimensional quantitative structure-activity relationship analysis of human CYP51 inhibitors.,  35  (3): [PMID:17194716] [10.1124/dmd.106.013888]

70. Heller S, Kellenberger L, Shapiro S..  (2007)  Antipropionibacterial activity of BAL19403, a novel macrolide antibiotic.,  51  (6): [PMID:17387155] [10.1128/aac.00062-07]

71. Ayer V, Tewodros W, Manoharan A, Skariah S, Luo F, Bessen DE..  (2007)  Tetracycline resistance in group a streptococci: emergence on a global scale and influence on multiple-drug resistance.,  51  (5): [PMID:17307980] [10.1128/aac.01341-06]

72. Rantala M, Nyberg S, Lindgren M, Huovinen P, Jalava J, Skyttä R, Teirilä L, Vainio A, Virolainen-Julkunen A, Kaijalainen T..  (2007)  Molecular epidemiology of telithromycin-resistant pneumococci in Finland.,  51  (5): [PMID:17325224] [10.1128/aac.00187-07]

73. Kwon DH, Lu CD..  (2007)  Polyamine effects on antibiotic susceptibility in bacteria.,  51  (6): [PMID:17438056] [10.1128/aac.01472-06]

74. Llull D, Rivas L, García E..  (2007)  In vitro bactericidal activity of the antiprotozoal drug miltefosine against Streptococcus pneumoniae and other pathogenic streptococci.,  51  (5): [PMID:17353242] [10.1128/aac.01428-06]

75. Lin J, Yan M, Sahin O, Pereira S, Chang YJ, Zhang Q..  (2007)  Effect of macrolide usage on emergence of erythromycin-resistant Campylobacter isolates in chickens.,  51  (5): [PMID:17353243] [10.1128/aac.01411-06]

76. Yasuda Y, Kasahara K, Mizuno F, Nishi K, Mikasa K, Kita E..  (2007)  Roxithromycin favorably modifies the initial phase of resistance against infection with macrolide-resistant Streptococcus pneumoniae in a murine pneumonia model.,  51  (5): [PMID:17353244] [10.1128/aac.01459-06]

77. Fang W, Ruan J, Wang Z, Zhao Z, Zou J, Zhou D, Cai Y..  (2006)  Acetylated flavanone glycosides from the rhizomes of Cyclosorus acuminatus.,  69  (11): [PMID:17125239] [10.1021/np060334n]

78. Onuki H, Yamazaki M, Nakamura A, Hanai R, Kuroda C, Gong X, Shen Y, Hirota H..  (2008)  Chemical constituents and diversity of Ligularia lankongensis in Yunnan Province of China.,  71  (4): [PMID:18260639] [10.1021/np070195p]

79. Gai Y, Tang D, Xu G, Chen Z, Polemeropoulos A, Wang Z, Or YS..  (2008)  Synthesis of 3,6-bicyclolides: a novel class of macrolide antibiotics.,  18  (24): [PMID:18996692] [10.1016/j.bmcl.2008.10.109]

80. Santana L, González-Díaz H, Quezada E, Uriarte E, Yáñez M, Viña D, Orallo F..  (2008)  Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.,  51  (21): [PMID:18834112] [10.1021/jm800656v]

81. Lewis CA, Merkel J, Miller SJ..  (2008)  Catalytic site-selective synthesis and evaluation of a series of erythromycin analogs.,  18  (22): [PMID:18819795] [10.1016/j.bmcl.2008.09.019]

82. Westaway SM, Brown SL, Fell SC, Johnson CN, MacPherson DT, Mitchell DJ, Myatt JW, Stanway SJ, Seal JT, Stemp G, Thompson M, Lawless K, McKay F, Muir AI, Barford JM, Cluff C, Mahmood SR, Matthews KL, Mohamed S, Smith B, Stevens AJ, Bolton VJ, Jarvie EM, Sanger GJ..  (2009)  Discovery of N-(3-fluorophenyl)-1-[(4-([(3S)-3-methyl-1-piperazinyl]methyl)phenyl)acetyl]-4-piperidinamine (GSK962040), the first small molecule motilin receptor agonist clinical candidate.,  52  (4): [PMID:19191554] [10.1021/jm801332q]

83. Appendino G, Maxia L, Bettoni P, Locatelli M, Valdivia C, Ballero M, Stavri M, Gibbons S, Sterner O..  (2006)  Antibacterial galloylated alkylphloroglucinol glucosides from myrtle (Myrtus communis).,  69  (2): [PMID:16499325] [10.1021/np050462w]

84. Savikin-Fodulović K, Aljancić I, Vajs V, Menković N, Macura S, Gojgić G, Milosavljević S..  (2003)  Hyperatomarin, an antibacterial prenylated phloroglucinol from Hypericumatomarium ssp. degenii.,  66  (9): [PMID:14510605] [10.1021/np030131o]

85. Li XC, Dunbar DC, ElSohly HN, Jacob MR, Nimrod AC, Walker LA, Clark AM..  (2001)  A new naphthopyrone derivative from Cassia quinquangulata and structural revision of quinquangulin and its glycosides.,  64  (9): [PMID:11575947] [10.1021/np010173h]

86. Meehl M, Herbert S, Götz F, Cheung A..  (2007)  Interaction of the GraRS two-component system with the VraFG ABC transporter to support vancomycin-intermediate resistance in Staphylococcus aureus.,  51  (8): [PMID:17502406] [10.1128/aac.00209-07]

87. Ahlin G, Karlsson J, Pedersen JM, Gustavsson L, Larsson R, Matsson P, Norinder U, Bergström CA, Artursson P..  (2008)  Structural requirements for drug inhibition of the liver specific human organic cation transport protein 1.,  51  (19): [PMID:18788725] [10.1021/jm8003152]

88. Westaway SM, Brown SL, Conway E, Heightman TD, Johnson CN, Lapsley K, Macdonald GJ, MacPherson DT, Mitchell DJ, Myatt JW, Seal JT, Stanway SJ, Stemp G, Thompson M, Celestini P, Colombo A, Consonni A, Gagliardi S, Riccaboni M, Ronzoni S, Briggs MA, Matthews KL, Stevens AJ, Bolton VJ, Boyfield I, Jarvie EM, Stratton SC, Sanger GJ..  (2008)  The discovery of biaryl carboxamides as novel small molecule agonists of the motilin receptor.,  18  (24): [PMID:19006669] [10.1016/j.bmcl.2008.10.072]

89. Heightman TD, Conway E, Corbett DF, Macdonald GJ, Stemp G, Westaway SM, Celestini P, Gagliardi S, Riccaboni M, Ronzoni S, Vaidya K, Butler S, McKay F, Muir A, Powney B, Winborn K, Wise A, Jarvie EM, Sanger GJ..  (2008)  Identification of small molecule agonists of the motilin receptor.,  18  (24): [PMID:18980843] [10.1016/j.bmcl.2008.10.071]

90. Hu JF, Garo E, Hough GW, Goering MG, O'Neil-Johnson M, Eldridge GR..  (2006)  Antibacterial, partially acetylated oligorhamnosides from Cleistopholis patens.,  69  (4): [PMID:16643031] [10.1021/np050438i]

91. Sidhu AB, Sun Q, Nkrumah LJ, Dunne MW, Sacchettini JC, Fidock DA..  (2007)  In vitro efficacy, resistance selection, and structural modeling studies implicate the malarial parasite apicoplast as the target of azithromycin.,  282  (4): [PMID:17110371] [10.1074/jbc.m608615200]

92. Pedersen JM, Matsson P, Bergström CA, Norinder U, Hoogstraate J, Artursson P..  (2008)  Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).,  51  (11): [PMID:18457386] [10.1021/jm7015683]

93. Bavikar SN, Salunke DB, Hazra BG, Pore VS, Dodd RH, Thierry J, Shirazi F, Deshpande MV, Kadreppa S, Chattopadhyay S..  (2008)  Synthesis of chimeric tetrapeptide-linked cholic acid derivatives: impending synergistic agents.,  18  (20): [PMID:18805690] [10.1016/j.bmcl.2008.09.013]

94. Tang D, Gai Y, Polemeropoulos A, Chen Z, Wang Z, Or YS..  (2008)  Design, synthesis, and antibacterial activities of novel 3,6-bicyclolide oximes: length optimization and zero carbon linker oximes.,  18  (18): [PMID:18762418] [10.1016/j.bmcl.2008.07.118]

95. Yamane K, Wachino J, Suzuki S, Kimura K, Shibata N, Kato H, Shibayama K, Konda T, Arakawa Y..  (2007)  New plasmid-mediated fluoroquinolone efflux pump, QepA, found in an Escherichia coli clinical isolate.,  51  (9): [PMID:17548499] [10.1128/aac.00339-07]

96. Calatayud L, Ardanuy C, Cercenado E, Fenoll A, Bouza E, Pallares R, Martín R, Liñares J..  (2007)  Serotypes, Clones, and Mechanisms of Resistance of Erythromycin-Resistant Streptococcus pneumoniae Isolates Collected in Spain.,  51  (9): [PMID:17606677] [10.1128/aac.00157-07]

97. Antunes NT, Tavío MM, Mercier P, Ayling RD, Al-Momani W, Assunção P, Rosales RS, Poveda JB..  (2007)  In vitro susceptibilities of Mycoplasma putrefaciens field isolates.,  51  (9): [PMID:17638695] [10.1128/aac.00420-07]

98. Gibreel A, Wetsch NM, Taylor DE..  (2007)  Contribution of the CmeABC efflux pump to macrolide and tetracycline resistance in Campylobacter jejuni.,  51  (9): [PMID:17606685] [10.1128/aac.01592-06]

99. Pérez A, Canle D, Latasa C, Poza M, Beceiro A, Tomás Mdel M, Fernández A, Mallo S, Pérez S, Molina F, Villanueva R, Lasa I, Bou G..  (2007)  Cloning, nucleotide sequencing, and analysis of the AcrAB-TolC efflux pump of Enterobacter cloacae and determination of its involvement in antibiotic resistance in a clinical isolate.,  51  (9): [PMID:17638702] [10.1128/aac.00072-07]

100. Jansen WT, Verel A, Verhoef J, Milatovic D..  (2007)  In vitro activity of telavancin against gram-positive clinical isolates recently obtained in Europe.,  51  (9): [PMID:17606689] [10.1128/aac.00100-07]

101. Simor AE, Stuart TL, Louie L, Watt C, Ofner-Agostini M, Gravel D, Mulvey M, Loeb M, McGeer A, Bryce E, Matlow A, Canadian Nosocomial Infection Surveillance Program..  (2007)  Mupirocin-resistant, methicillin-resistant Staphylococcus aureus strains in Canadian hospitals.,  51  (11): [PMID:17724154] [10.1128/aac.00846-07]

102. Shin JH, Jung HJ, Kim HR, Jeong J, Jeong SH, Kim S, Lee EY, Lee JN, Chang CL..  (2007)  Prevalence, characteristics, and molecular epidemiology of macrolide and fluoroquinolone resistance in clinical isolates of Streptococcus pneumoniae at five tertiary-care hospitals in Korea.,  51  (7): [PMID:17502407] [10.1128/aac.00107-07]

103. Yum JH, Kim CK, Yong D, Lee K, Chong Y, Kim CM, Kim JM, Ro S, Cho JM..  (2007)  In vitro activities of CG400549, a novel FabI inhibitor, against recently isolated clinical staphylococcal strains in Korea.,  51  (7): [PMID:17420210] [10.1128/aac.01562-06]

104. Chow VC, Hawkey PM, Chan EW, Chin ML, Au TK, Fung DK, Chan RC..  (2007)  High-level gentamicin resistance mediated by a Tn4001-like transposon in seven nonclonal hospital isolates of Streptococcus pasteurianus.,  51  (7): [PMID:17371822] [10.1128/aac.00603-06]

105. Appendino G, Gibbons S, Giana A, Pagani A, Grassi G, Stavri M, Smith E, Rahman MM..  (2008)  Antibacterial cannabinoids from Cannabis sativa: a structure-activity study.,  71  (8): [PMID:18681481] [10.1021/np8002673]

106. Diwakar SD, Bhagwat SS, Shingare MS, Gill CH..  (2008)  Substituted 3-((Z)-2-(4-nitrophenyl)-2-(1H-tetrazol-5-yl) vinyl)-4H-chromen-4-ones as novel anti-MRSA agents: synthesis, SAR, and in-vitro assessment.,  18  (16): [PMID:18650090] [10.1016/j.bmcl.2008.07.007]

107. Abou-Shoer MI, Shaala LA, Youssef DT, Badr JM, Habib AA..  (2008)  Bioactive brominated metabolites from the red sea sponge Suberea mollis.,  71  (8): [PMID:18656986] [10.1021/np800142n]

108. Binet R, Maurelli AT..  (2007)  Frequency of development and associated physiological cost of azithromycin resistance in Chlamydia psittaci 6BC and C. trachomatis L2.,  51  (12): [PMID:17908942] [10.1128/aac.00962-07]

109. Zhang C, Herath K, Jayasuriya H, Ondeyka JG, Zink DL, Occi J, Birdsall G, Venugopal J, Ushio M, Burgess B, Masurekar P, Barrett JF, Singh SB..  (2009)  Thiazomycins, thiazolyl peptide antibiotics from Amycolatopsis fastidiosa.,  72  (5): [PMID:19334707] [10.1021/np800783b]

110. Morio F, Jean-Pierre H, Dubreuil L, Jumas-Bilak E, Calvet L, Mercier G, Devine R, Marchandin H..  (2007)  Antimicrobial susceptibilities and clinical sources of Dialister species.,  51  (12): [PMID:17923492] [10.1128/aac.00538-07]

111. Dreier J, Amantea E, Kellenberger L, Page MG..  (2007)  Activity of the novel macrolide BAL19403 against ribosomes from erythromycin-resistant Propionibacterium acnes.,  51  (12): [PMID:17923495] [10.1128/aac.00672-07]

112. Starner TD, Shrout JD, Parsek MR, Appelbaum PC, Kim G..  (2008)  Subinhibitory concentrations of azithromycin decrease nontypeable Haemophilus influenzae biofilm formation and Diminish established biofilms.,  52  (1): [PMID:17954687] [10.1128/aac.00607-07]

113. Morozumi M, Iwata S, Hasegawa K, Chiba N, Takayanagi R, Matsubara K, Nakayama E, Sunakawa K, Ubukata K, Acute Respiratory Diseases Study Group..  (2008)  Increased macrolide resistance of Mycoplasma pneumoniae in pediatric patients with community-acquired pneumonia.,  52  (1): [PMID:17954691] [10.1128/aac.00779-07]

114. Zhu W, Clark NC, McDougal LK, Hageman J, McDonald LC, Patel JB..  (2008)  Vancomycin-resistant Staphylococcus aureus isolates associated with Inc18-like vanA plasmids in Michigan.,  52  (2): [PMID:18056272] [10.1128/aac.00908-07]

115. Varma MV, Feng B, Obach RS, Troutman MD, Chupka J, Miller HR, El-Kattan A..  (2009)  Physicochemical determinants of human renal clearance.,  52  (15): [PMID:19445515] [10.1021/jm900403j]

116. Roy K, Pratim Roy P..  (2009)  Comparative chemometric modeling of cytochrome 3A4 inhibitory activity of structurally diverse compounds using stepwise MLR, FA-MLR, PLS, GFA, G/PLS and ANN techniques.,  44  (7): [PMID:19128860] [10.1016/j.ejmech.2008.12.004]

117. Wolter N, Smith AM, Farrell DJ, Northwood JB, Douthwaite S, Klugman KP..  (2008)  Telithromycin resistance in Streptococcus pneumoniae is conferred by a deletion in the leader sequence of erm(B) that increases rRNA methylation.,  52  (2): [PMID:18056269] [10.1128/aac.01074-07]

118. Jiang X, Yu P, Jiang J, Zhang Z, Wang Z, Yang Z, Tian Z, Wright SC, Larrick JW, Wang Y..  (2009)  Synthesis and evaluation of antibacterial activities of andrographolide analogues.,  44  (7): [PMID:19152987] [10.1016/j.ejmech.2008.12.014]

119. Damier-Piolle L, Magnet S, Brémont S, Lambert T, Courvalin P..  (2008)  AdeIJK, a resistance-nodulation-cell division pump effluxing multiple antibiotics in Acinetobacter baumannii.,  52  (2): [PMID:18086852] [10.1128/aac.00732-07]

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145. Shakya T, Wright GD..  (2010)  Nucleotide selectivity of antibiotic kinases.,  54  (5): [PMID:20231391] [10.1128/aac.01570-09]

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156. Urich SK, Petersen JM..  (2008)  In vitro susceptibility of isolates of Francisella tularensis types A and B from North America.,  52  (6): [PMID:18411318] [10.1128/aac.01584-07]

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158. Sader HS, Fritsche TR, Jones RN..  (2008)  Antimicrobial activities of Ceftaroline and ME1036 tested against clinical strains of community-acquired methicillin-resistant Staphylococcus aureus.,  52  (3): [PMID:18180353] [10.1128/aac.01351-07]

159. Gentry DR, Holmes DJ..  (2008)  Selection for high-level telithromycin resistance in Staphylococcus aureus yields mutants resulting from an rplB-to-rplV gene conversion-like event.,  52  (3): [PMID:18195060] [10.1128/aac.00923-07]

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Source

Source(17):

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• PubChem BioAssays
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• DrugMatrix
• TP-search Transporter Database
• Curated Drug Metabolism Pathways
• HeCaToS Compounds
• Patent Bioactivity Data
• CO-ADD antimicrobial screening data
• WHO Anatomical Therapeutic Chemical Classification
• British National Formulary
• SARS-CoV-2 Screening Data 2020-21
• Active Ingredient of a Prodrug
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6