NAV

Thiostrepton

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

Identification

Generic Name
Thiostrepton
DrugBank Accession Number
DB11467
Background

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.

Type
Small Molecule
Groups
Vet approved
Structure
Similar Structures
Weight
Average: 1664.89
Monoisotopic: 1663.492352843
Chemical Formula
C72H85N19O18S5
Synonyms
  • Thiostrepton
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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interactions in your software
AcenocoumarolThe risk or severity of bleeding can be increased when Thiostrepton is combined with Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Thiostrepton is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Thiostrepton is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Thiostrepton.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Thiostrepton is combined with Benzocaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2,4-disubstituted 1,3-thiazole / Alcohol / Amine / Amino acid or derivatives / Aralkylamine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Azole / Carboximidic acid
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
HR4S203Y18
CAS number
Not Available
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

References

General References
  1. Bodanszky M, Scozzie JA, Muramatsu I: Dehydroalanine residues in thiostrepton. J Antibiot (Tokyo). 1970 Jan;23(1):9-12. [Article]
  2. Godoy-Alcantar C, Rivera IL, Yatsimirsky AK: Anion recognition by thiostrepton. Bioorg Med Chem Lett. 2001 Mar 12;11(5):651-4. [Article]
  3. Anderson B, Hodgkin DC, Viswamitra MA: The structure of thiostrepton. Nature. 1970 Jan 17;225(5229):233-5. [Article]
  4. COHN I Jr, LONGACRE AB: Thiostrepton and thiostrepton-neomycin for preoperative preparation of the colon. Surgery. 1957 Nov;42(5):865-73. [Article]
  5. Cundliffe E, Thompson J: Ribose methylation and resistance to thiostrepton. Nature. 1979 Apr 26;278(5707):859-61. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
ChemSpider
10469505
RxNav
1365970
ChEMBL
CHEMBL410968
Wikipedia
Thiostrepton

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2RecruitingTreatmentMalignant Pleural Effusion / Malignant Pleural Mesothelioma (MPM) / Mesothelioma / Pleural Mesotheliomas1

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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ot-0000019000-684fbb69a50ab881195d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-0000009000-f1aef2c84485199e92d1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0000092000-81b4ef7b9cbec556b2fd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0h00-2000089000-15de65b1f8e846cf8c57
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01qc-4000139000-48fd1a4da915fe01be1a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fb9-2000129000-a4e4e78b99f712ead402
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-393.30835
predicted
DeepCCS 1.0 (2019)
[M+H]+395.01782
predicted
DeepCCS 1.0 (2019)
[M+Na]+401.17468
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:59 / Updated at February 21, 2021 18:53