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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/mesh/68013883 | https://www.ncbi.nlm.nih.gov/pubmed/24952196Curator'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
Sources: https://www.ncbi.nlm.nih.gov/mesh/68013883 | https://www.ncbi.nlm.nih.gov/pubmed/24952196
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13355325
Curator's Comment: Thiostrepton was discovered by Donovick et al. who described its antibacterial properties in 1955.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q08050 Gene ID: 2305.0 Gene Symbol: FOXM1 Target Organism: Homo sapiens (Human) |
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Target ID: CHEMBL612519 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23912794 |
1.69 µM [IC50] | ||
Target ID: CHEMBL5804 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26371257 |
|||
Target ID: Babesia bovis Sources: https://www.ncbi.nlm.nih.gov/pubmed/22391527 |
11.5 µM [IC50] | ||
Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17289168 |
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Target ID: 23S ribosomal RNA |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Derma-Vet Cream Approved UseNystatin-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 Date1999 |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vivo Use Guide
Sources: https://www.drugs.com/vet/derma-vet-cream.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23912794
Treatment with 1.75 uM thiostrepton completely abolished the colony
formation ability of Daoy cells
Substance Class |
Chemical
Created
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Record UNII |
HR4S203Y18
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Validated (UNII)
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CFR |
21 CFR 524.1600B
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FDA ORPHAN DRUG |
851321
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CFR |
21 CFR 524.1600A
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C187031
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THIOSTREPTON
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1365970
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170365
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