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Substance Name: Thiostrepton [USP]
RN: 1393-48-2
UNII: HR4S203Y18
InChIKey: NSFFHOGKXHRQEW-AIHSUZKVSA-N

Note

  • One of the CYCLIC PEPTIDES from Streptomyces that is active against gram-positive bacteria. In veterinary medicine, it has been used in mastitis caused by gram-negative organisms and in dermatologic disorders.

Molecular Formula

  • C72-H85-N19-O18-S5

Molecular Weight

  • 1664.9085
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial (Veterinary)
  • Drug / Therapeutic Agent
  • Natural Product
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Names and Synonyms

Name of Substance

  • Thiostrepton
  • Thiostrepton [USP]

MeSH Heading

  • Thiostrepton

Synonyms

  • A-8506
  • Alaninamide,
  • Antibiotic 6761-31
  • Antibiotic A 8506
  • Antibiotic X 146
  • Bryamycin
  • EINECS 215-734-9
  • NSC 170365
  • NSC 81722
  • Thiactin
  • Thiostrepton
  • UNII-HR4S203Y18
  • X 146

Systematic Name

  • Thiostrepton

Mixture Name

  • Panolog Cream (Veterinary)

Registry Numbers

CAS Registry Number

  • 1393-48-2

FDA UNII

  • HR4S203Y18

System Generated Number

  • 0001393482

Structure Descriptors

InChI

1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15-/t26-,30-,31-,32-,33+,34+,35+,39+,45+,47-,48-,49-,51-,52+,53+,71+,72+/m0/s1

InChIKey

NSFFHOGKXHRQEW-AIHSUZKVSA-N

Smiles

CC[C@H](C)[C@@H]1N[C@@H]2C=Cc3c(cc(nc3[C@H]2O)C(=O)O[C@H](C)[C@@H]4NC(=O)c5csc(n5)[C@@H](NC(=O)[C@H]6CSC(=N6)\C(=C\C)\NC(=O)[C@@H](NC(=O)c7csc(n7)[C@]8(CCC(=N[C@@H]8c9csc4n9)c%10nc(cs%10)C(=O)NC(=C)C(=O)NC(=C)C(=O)N)NC(=O)[C@H](C)NC(=O)C(=C)NC(=O)[C@H](C)NC1=O)[C@@H](C)O)[C@](C)(O)[C@@H](C)O)[C@H](C)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intramuscular 1gm/kg (1000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 4(1), Pg. 397, 1980.
mouse LD50 intraperitoneal 2gm/kg (2000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 4(1), Pg. 396, 1980.
mouse LD50 intravenous 41mg/kg (41mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 4(1), Pg. 396, 1980.
mouse LD50 oral > 1gm/kg (1000mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 63, 1956.