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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 17 / 17
E/Z Centers 3
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
1.69 µM [IC50]
11.5 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Derma-Vet Cream

PubMed

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
Substance Class Chemical
Record UNII
HR4S203Y18
Record Status Validated (UNII)
Record Version