THIOSTREPTON

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 Search

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

Description
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

Approval Year

Targets

Primary Target	Pharmacology	Potency
Forkhead box protein M1 1 Target ID: Q08050 Gene ID: 2305.0 Gene Symbol: FOXM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/25093142 \| https://www.ncbi.nlm.nih.gov/pubmed/25391371 \| https://www.ncbi.nlm.nih.gov/pubmed/25231007	Inhibitor 8297
Daoy 1 Target ID: CHEMBL612519 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23912794	Inhibitor 8297	1.69 µM [IC50]
Toll-like receptor 9 4 Target ID: CHEMBL5804 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26371257	Inhibitor 8297
Babesia bovis 1 Target ID: Babesia bovis Sources: https://www.ncbi.nlm.nih.gov/pubmed/22391527	Inhibitor 8297	11.5 µM [IC50]
Plasmodium falciparum 74 Target ID: CHEMBL364 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17289168	Inhibitor 8297
23S ribosomal RNA 1 Target ID: 23S ribosomal RNA Sources: https://www.ncbi.nlm.nih.gov/pubmed/12954336 \| https://www.ncbi.nlm.nih.gov/pubmed/8127673	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dermatologic disorders in dogs and cats 1 Sources: https://www.drugs.com/vet/derma-vet-cream.html	Primary		Approved 8429	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

Title	Date	PubMed
Inhibition of mitochondrial protein translation sensitizes melanoma cells to arsenic trioxide cytotoxicity via a reactive oxygen species dependent mechanism.	2008 Dec	18297286
Thiostrepton is an inducer of oxidative and proteotoxic stress that impairs viability of human melanoma cells but not primary melanocytes.	2012 May 1	22321511
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1.	2013 Sep 5	23769903

Patents

Sample Use Guides

In Vivo Use Guide

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

Treatment with 1.75 uM thiostrepton completely abolished the colony formation ability of Daoy cells

Name

Type

Language

THIOSTREPTON

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