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Details

Stereochemistry ABSOLUTE
Molecular Formula C72H85N19O18S5
Molecular Weight 1664.887
Optical Activity UNSPECIFIED
Defined Stereocenters 17 / 17
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of THIOSTREPTON

SMILES

[H][C@]12CSC(=N1)\C(NC(=O)[C@@H](NC(=O)C3=CSC(=N3)[C@@]45CCC(=N[C@]4([H])C6=CSC(=N6)[C@@H](NC(=O)C7=CSC(=N7)[C@@H](NC2=O)[C@](C)(O)[C@@H](C)O)[C@@H](C)OC(=O)C8=NC9=C(C=C[C@@H](N[C@@]([H])([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)NC(=C)C(=O)N[C@@H](C)C(=O)N5)[C@@H]9O)C(=C8)[C@H](C)O)C%10=NC(=CS%10)C(=O)NC(=C)C(=O)NC(=C)C(N)=O)[C@@H](C)O)=C\C

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

Molecular Formula C72H85N19O18S5
Molecular Weight 1664.887
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 17 / 17
E/Z Centers 3
Optical Activity UNSPECIFIED

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

1999
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:32:55 GMT 2023
Edited
by admin
on Fri Dec 15 20:32:55 GMT 2023
Record UNII
HR4S203Y18
Record Status Validated (UNII)
Record Version
  • Download
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 Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
FDA ORPHAN DRUG 851321
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
CFR 21 CFR 524.1600A
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
Code System Code Type Description
NSC
81722
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
DRUG BANK
DB11467
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
215-734-9
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
RS_ITEM_NUM
1663700
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
NCI_THESAURUS
C187031
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
SMS_ID
300000023712
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID5040625
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
DAILYMED
HR4S203Y18
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
WIKIPEDIA
THIOSTREPTON
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
PUBCHEM
16154490
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL2303629
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
CAS
1393-48-2
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
CHEBI
29693
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
MERCK INDEX
m10787
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY Merck Index
RXCUI
1365970
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY RxNorm
FDA UNII
HR4S203Y18
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
NSC
170365
Created by admin on Fri Dec 15 20:32:56 GMT 2023 , Edited by admin on Fri Dec 15 20:32:56 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY