Misplaced Pages

Surotomycin

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Investigational oral antibiotic
Surotomycin
Names
IUPAC name (3S)-3-{-24-(3-aminopropyl)-15,21-bis(carboxymethyl)-6--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-propanamido]propanamido]propanoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: 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/s1Key: DYNMYYRPPFVAKR-CWXHRMTKBW
SMILES
  • CCCCCc1ccc(cc1)/C(=C/C(=O)N(Cc2cc3c2cccc3)C(=O)N(CC(=O)N)C(=O)N(CC(=O)O)C(=O)N4(OC(=O)(NC(=O)(NC(=O)(NC(=O)CNC(=O)(NC(=O)(NC(=O)(NC(=O)(NC(=O)CNC4=O)CCCN)CC(=O)O)C)CC(=O)O)CO)(C)CC(=O)O)CC(=O)c5ccccc5N)C)/C
Properties
Chemical formula C77H101N17O26
Molar mass 1680.748 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. After reaching phase III in clinical trials, its production was discontinued in 2017 due to its non-superiority to current therapies.

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.


Stub icon

This systemic antibiotic-related article is a stub. You can help Misplaced Pages by expanding it.

Categories: