Thiostrepton

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Thiostrepton
Accession Number
DB11467
Type
Small Molecule
Groups
Vet approved
Description

Thiostrepton is a natural cyclic oligopeptide antibiotic, derived from several strains of streptomycetes including Streptomyces azureus and Streptomyces laurentii. Thiostrepton is a natural product of the ribosomally synthesized and post-translationally modified peptide class.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
HR4S203Y18
CAS number
Not Available
Weight
Average: 1664.89
Monoisotopic: 1663.492352843
Chemical Formula
C72H85N19O18S5
InChI Key
NSFFHOGKXHRQEW-DVRIZHICSA-N
InChI
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+
IUPAC Name
2-[({2-[(11E)-37-(butan-2-yl)-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-6,9,16,23,38,41,44,47,59-nonahydroxy-8,60-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-28-oxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,30,36,39,42,45,48,52,58,62,63,64-pentadecaazanonacyclo[23.23.9.2²⁹,³².1²,⁵.1¹²,¹⁵.1¹⁹,²².1³¹,³⁵.1⁵⁴,⁵⁷.0¹,⁵³]tetrahexaconta-2(64),4,6,9,12(63),16,19(62),21,23,29,31,33,38,41,44,47,51,54,57,60-icosaen-51-yl]-1,3-thiazol-4-yl}(hydroxy)methylidene)amino]-N-[1-(C-hydroxycarbonimidoyl)eth-1-en-1-yl]prop-2-enimidic acid
SMILES
[H]\C(C)=C1/N=C(O)C(N=C(O)C2=CSC(=N2)C23CCC(=NC2C2=CSC(=N2)C(N=C(O)C2=CSC(=N2)C(N=C(O)C2CSC1=N2)C(C)(O)C(C)O)C(C)OC(=O)C1=NC2=C(C=CC(NC(C(C)CC)C(O)=NC(C)C(O)=NC(=C)C(O)=NC(C)C(O)=N3)C2O)C(=C1)C(C)O)C1=NC(=CS1)C(O)=NC(=C)C(O)=NC(=C)C(O)=N)C(C)O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Thiostrepton is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Thiostrepton is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Thiostrepton is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Thiostrepton is combined with Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Thiostrepton.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Thiostrepton.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Thiostrepton.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Thiostrepton.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Thiostrepton.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Thiostrepton.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Bodanszky M, Scozzie JA, Muramatsu I: Dehydroalanine residues in thiostrepton. J Antibiot (Tokyo). 1970 Jan;23(1):9-12. [PubMed:5416649]
  2. Godoy-Alcantar C, Rivera IL, Yatsimirsky AK: Anion recognition by thiostrepton. Bioorg Med Chem Lett. 2001 Mar 12;11(5):651-4. [PubMed:11266162]
  3. Anderson B, Hodgkin DC, Viswamitra MA: The structure of thiostrepton. Nature. 1970 Jan 17;225(5229):233-5. [PubMed:5409975]
  4. COHN I Jr, LONGACRE AB: Thiostrepton and thiostrepton-neomycin for preoperative preparation of the colon. Surgery. 1957 Nov;42(5):865-73. [PubMed:13486397]
  5. Cundliffe E, Thompson J: Ribose methylation and resistance to thiostrepton. Nature. 1979 Apr 26;278(5707):859-61. [PubMed:440414]
  6. Clough B, Strath M, Preiser P, Denny P, Wilson IR: Thiostrepton binds to malarial plastid rRNA. FEBS Lett. 1997 Apr 7;406(1-2):123-5. [PubMed:9109400]
  7. Trejo WH, Dean LD, Pluscec J, Meyers E, Brown WE: Streptomyces laurentii, a new species producing thiostrepton. J Antibiot (Tokyo). 1977 Aug;30(8):639-43. [PubMed:908663]
  8. Cameron DM, Thompson J, Gregory ST, March PE, Dahlberg AE: Thiostrepton-resistant mutants of Thermus thermophilus. Nucleic Acids Res. 2004 Jun 15;32(10):3220-7. Print 2004. [PubMed:15199170]
  9. Nicolaou KC: How thiostrepton was made in the laboratory. Angew Chem Int Ed Engl. 2012 Dec 7;51(50):12414-36. doi: 10.1002/anie.201205576. Epub 2012 Dec 3. [PubMed:23208736]
  10. Gartel AL: Thiostrepton, proteasome inhibitors and FOXM1. Cell Cycle. 2011 Dec 15;10(24):4341-2. doi: 10.4161/cc.10.24.18544. Epub 2011 Dec 15. [PubMed:22134246]
External Links
ChemSpider
10469505
ChEMBL
CHEMBL410968
Wikipedia
Thiostrepton

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 mg/mLALOGPS
logP3.23ALOGPS
logP7.2ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)2.28ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count36ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area598.63 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity430.74 m3·mol-1ChemAxon
Polarizability164.21 Å3ChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Cyclic peptides
Alternative Parents
Pyridinecarboxylic acids / Tetrahydropyridines / 2,4-disubstituted thiazoles / Aralkylamines / Imidothiolactones / Thiazolines / Tertiary alcohols / Cyclic carboximidic acids / Heteroaromatic compounds / Secondary alcohols
show 14 more
Substituents
Cyclic alpha peptide / Pyridine carboxylic acid / 2,4-disubstituted 1,3-thiazole / Tetrahydropyridine / Aralkylamine / Pyridine / Imidothiolactone / Azole / Heteroaromatic compound / Tertiary alcohol
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on February 25, 2016 11:59 / Updated on June 04, 2019 07:22