Surotomycin

Last updated
Surotomycin
Structure of surotomycin.png
Names
IUPAC name
(3S)-3-{[(3S,6S,9R,15S,18R,21S,24S,30S,31R)-3-[2-(2-aminophenyl)-2-oxoethyl]-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6-[(2R)-1-carboxypropan-2-yl]-9-(hydroxymethyl)-18,31-dimethyl-2,5,8,11,14,17,20,23,26,29-decaoxo-1-oxa-4,7,10,13,16,19,22,25,28-nonaazacyclohentriacontan-30-yl]carbamoyl}-3-[(2R)-3-carbamoyl-2-[(2R)-3-(1H-indol-3-yl)-2-[(2E)-3-(4-pentylphenyl)but-2-enamido]propanamido]propanamido]propanoic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C77H101N17O26/c1-6-7-8-14-41-20-22-42(23-21-41)37(2)25-58(98)86-49(27-43-33-81-47-18-12-10-15-44(43)47)71(113)89-50(29-57(80)97)72(114)91-53(32-64(107)108)73(115)94-66-40(5)120-77(119)54(28-56(96)45-16-9-11-17-46(45)79)92-76(118)65(38(3)26-61(101)102)93-74(116)55(36-95)87-60(100)34-82-68(110)51(30-62(103)104)88-67(109)39(4)84-70(112)52(31-63(105)106)90-69(111)48(19-13-24-78)85-59(99)35-83-75(66)117/h9-12,15-18,20-23,25,33,38-40,48-55,65-66,81,95H,6-8,13-14,19,24,26-32,34-36,78-79H2,1-5H3,(H2,80,97)(H,82,110)(H,83,117)(H,84,112)(H,85,99)(H,86,98)(H,87,100)(H,88,109)(H,89,113)(H,90,111)(H,91,114)(H,92,118)(H,93,116)(H,94,115)(H,101,102)(H,103,104)(H,105,106)(H,107,108)/b37-25+/t38-,39-,40-,48+,49+,50-,51+,52+,53+,54+,55-,65+,66+/m1/s1
    Key: DYNMYYRPPFVAKR-CWXHRMTKSA-N
  • InChI=1/C77H101N17O26/c1-6-7-8-14-41-20-22-42(23-21-41)37(2)25-58(98)86-49(27-43-33-81-47-18-12-10-15-44(43)47)71(113)89-50(29-57(80)97)72(114)91-53(32-64(107)108)73(115)94-66-40(5)120-77(119)54(28-56(96)45-16-9-11-17-46(45)79)92-76(118)65(38(3)26-61(101)102)93-74(116)55(36-95)87-60(100)34-82-68(110)51(30-62(103)104)88-67(109)39(4)84-70(112)52(31-63(105)106)90-69(111)48(19-13-24-78)85-59(99)35-83-75(66)117/h9-12,15-18,20-23,25,33,38-40,48-55,65-66,81,95H,6-8,13-14,19,24,26-32,34-36,78-79H2,1-5H3,(H2,80,97)(H,82,110)(H,83,117)(H,84,112)(H,85,99)(H,86,98)(H,87,100)(H,88,109)(H,89,113)(H,90,111)(H,91,114)(H,92,118)(H,93,116)(H,94,115)(H,101,102)(H,103,104)(H,105,106)(H,107,108)/b37-25+/t38-,39-,40-,48+,49+,50-,51+,52+,53+,54+,55-,65+,66+/m1/s1
    Key: DYNMYYRPPFVAKR-CWXHRMTKBW
  • CCCCCc1ccc(cc1)/C(=C/C(=O)N[C@@H](Cc2c[nH]c3c2cccc3)C(=O)N[C@H](CC(=O)N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H]4[C@H](OC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)CNC4=O)CCCN)CC(=O)O)C)CC(=O)O)CO)[C@H](C)CC(=O)O)CC(=O)c5ccccc5N)C)/C
Properties
C77H101N17O26
Molar mass 1680.748 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Surotomycin was an investigational oral antibiotic. This macrolide antibiotic was under investigation by Merck & Co (who acquired Cubist Pharmaceuticals) for the treatment of life-threatening diarrhea, commonly caused by the bacterium Clostridioides difficile . [1] After reaching phase III in clinical trials, its production was discontinued in 2017 due to its non-superiority to current therapies. [2] [3]

See also

References

  1. ↑ "Surotomycin Fact Sheet" (PDF). cubist.com.
  2. ↑ P Daley; T Louie; J E Lutz; S Khanna; U Stoutenburgh; M Jin; A Adedoyin; L Chesnel; D Guris; K B Larson; Y Murata (December 2017). "Surotomycin versus vancomycin in adults with Clostridium difficile infection: primary clinical outcomes from the second pivotal, randomized, double-blind, Phase 3 trial". Journal of Antimicrobial Chemotherapy. 72 (12): 3462–3470. doi: 10.1093/jac/dkx299 . PMID   28961905.
  3. ↑ Jenna Payesko. "Surotomycin Fails To Show Benefit Over Vancomycin in C. Difficile Treatment in Phase 3 Trial". MD magazines. Retrieved 24 September 2019.


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