Thiostrepton
Star0
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
- Weight
- Average: 1664.89
Monoisotopic: 1663.492352843 - Chemical Formula
- C72H85N19O18S5
- Synonyms
- Thiostrepton
Pharmacology
- Indication
Not Available
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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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Thiostrepton is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Thiostrepton is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Thiostrepton is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Thiostrepton. Benzocaine The 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
- Bodanszky M, Scozzie JA, Muramatsu I: Dehydroalanine residues in thiostrepton. J Antibiot (Tokyo). 1970 Jan;23(1):9-12. [Article]
- Godoy-Alcantar C, Rivera IL, Yatsimirsky AK: Anion recognition by thiostrepton. Bioorg Med Chem Lett. 2001 Mar 12;11(5):651-4. [Article]
- Anderson B, Hodgkin DC, Viswamitra MA: The structure of thiostrepton. Nature. 1970 Jan 17;225(5229):233-5. [Article]
- COHN I Jr, LONGACRE AB: Thiostrepton and thiostrepton-neomycin for preoperative preparation of the colon. Surgery. 1957 Nov;42(5):865-73. [Article]
- Cundliffe E, Thompson J: Ribose methylation and resistance to thiostrepton. Nature. 1979 Apr 26;278(5707):859-61. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- External Links
- ChemSpider
- 10469505
- 1365970
- ChEMBL
- CHEMBL410968
- Wikipedia
- Thiostrepton
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1, 2 Recruiting Treatment Malignant Pleural Effusion / Malignant Pleural Mesothelioma (MPM) / Mesothelioma / Pleural Mesotheliomas 1
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
Property Value Source Water Solubility 0.032 mg/mL ALOGPS logP 3.23 ALOGPS logP 7.2 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 2.28 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 36 Chemaxon Hydrogen Donor Count 18 Chemaxon Polar Surface Area 598.63 Å2 Chemaxon Rotatable Bond Count 12 Chemaxon Refractivity 430.74 m3·mol-1 Chemaxon Polarizability 164.21 Å3 Chemaxon Number of Rings 10 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 393.30835 predictedDeepCCS 1.0 (2019) [M+H]+ 395.01782 predictedDeepCCS 1.0 (2019) [M+Na]+ 401.17468 predictedDeepCCS 1.0 (2019)
Drug created at February 25, 2016 18:59 / Updated at February 21, 2021 18:53