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Details

Stereochemistry ABSOLUTE
Molecular Formula C72H85N19O18S5
Molecular Weight 1664.895
Optical Activity UNSPECIFIED
Defined Stereocenters 17 / 17
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of THIOSTREPTON

SMILES

CC[C@]([H])(C)[C@@]1([H])C(=N[C@@]([H])(C)C(=NC(=C)C(=N[C@@]([H])(C)C(=N[C@@]23CCC(=N[C@]3([H])c4csc([C@]([H])([C@@]([H])(C)OC(=O)c5cc([C@]([H])(C)O)c6C=C[C@]([H])([C@@]([H])(c6n5)O)N1)N=C(c7csc([C@]([H])([C@@](C)([C@@]([H])(C)O)O)N=C([C@@]8([H])CSC(=N8)/C(=C(\[H])/C)/N=C([C@]([H])([C@@]([H])(C)O)N=C(c9csc2n9)O)O)O)n7)O)n4)c%10nc(cs%10)C(=NC(=C)C(=NC(=C)C(=N)O)O)O)O)O)O)O

InChI

InChIKey=NSFFHOGKXHRQEW-AIHSUZKVSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/vet/entederm-ointment.html | https://www.ncbi.nlm.nih.gov/pubmed/23912794

Thiostrepton is a natural antibiotic produced by bacteria of Streptomyces genus. Thiostrepton has been used in veterinary medicine in mastitis caused by gram-negative organisms and in dermatologic disorders. It is mostly used in complex ointments containing neomycin, nystatin, Thiostrepton and topical steroids. It is also active against gram-positive bacteria. It is notable that ointments for human usage contain neomycin, nystatin, and topical steroids, but no Thiostrepton. It can induce apoptotic cell death in human cancer cells. Thiostrepton was reported (in 2008) to exhibit activity against breast cancer cells through targeting the transcription factor forkhead box M1 (FOXM1). It has also been shown to circumvent acquired cisplatin resistance in breast cancer cells under in invitro conditions. Thiostrepton is used in molecular biology as a reagent for both positive and negative selection of genes involved in nucleotide metabolism. It is protein synthesis inhibitor.

Originator

Curator's Comment:: Thiostrepton was discovered by Donovick et al. who described its antibacterial properties in 1955.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Derma-Vet Cream

Approved Use

Nystatin-Neomycin Sulfate-Thiostrepton-Triamcinolone Acetonide Cream is indicated in the management of dermatologic disorders in dogs and cats, characterized by inflammation and dry or exudative dermatitis, particularly those caused, complicated or threatened by bacterial or candidal (Candida albicans) infections. It is also of value in eczematous dermatitis; contact dermatitis, and seborrheic dermatitis, and as an adjunct in the treatment of dermatitis due to parasitic infestation.

Launch Date

9.2283837E11
PubMed

PubMed

TitleDatePubMed
Inhibition of mitochondrial protein translation sensitizes melanoma cells to arsenic trioxide cytotoxicity via a reactive oxygen species dependent mechanism.
2008 Dec
Thiostrepton is an inducer of oxidative and proteotoxic stress that impairs viability of human melanoma cells but not primary melanocytes.
2012 May 1
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.
2013 Sep 5
Patents

Sample Use Guides

Nystatin-Neomycin Sulfate-Thiostrepton-Triamcinolone Acetonide cream (ach gram contains: Nystatin 100,000 units, Neomycin sulfate equivalent to neomycin base 2.5 mg, Thiostrepton 2500 units, Triamcinolone acetonide 1.0 mg) Dogs and cats:Clean affected areas, removing any encrusted discharge or exudate. Apply Nystatin-Neomycin Sulfate-Thiostrepton-Triamcinolone Acetonide Cream sparingly in a thin film.
Route of Administration: Topical
Treatment with 1.75 uM thiostrepton completely abolished the colony formation ability of Daoy cells
Name Type Language
THIOSTREPTON
GREEN BOOK   MART.   MI   USP   USP-RS  
Common Name English
NSC-81722
Code English
THIACTIN
Common Name English
THIOSTREPTON [USP MONOGRAPH]
Common Name English
GARGON
Common Name English
THIOSTREPTON [GREEN BOOK]
Common Name English
THIOSTREPTON [MART.]
Common Name English
NSC-170365
Code English
THIOSTREPTON A
Common Name English
BRYAMYCIN
Brand Name English
THIOSTREPTON [MI]
Common Name English
THIOSTREPTON (ANTIBIOTIC OF A STREPTOMYCES SPECIES)
Common Name English
THIOSTREPTON [USP-RS]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 524.1600B
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
CFR 21 CFR 524.1600A
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
Code System Code Type Description
DRUG BANK
DB11467
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
ECHA (EC/EINECS)
215-734-9
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
EPA CompTox
1393-48-2
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
WIKIPEDIA
THIOSTREPTON
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
PUBCHEM
16154490
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
ChEMBL
CHEMBL2303629
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
CAS
1393-48-2
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
MERCK INDEX
M10787
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY Merck Index
RXCUI
1365970
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY RxNorm
FDA UNII
HR4S203Y18
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY
USP_CATALOG
1663700
Created by admin on Fri Jun 25 20:56:11 UTC 2021 , Edited by admin on Fri Jun 25 20:56:11 UTC 2021
PRIMARY USP-RS