NAV

Sparsomycin

Identification

Generic Name
Sparsomycin
DrugBank Accession Number
DB04222
Background

An antitumor antibiotic produced by Streptomyces sparsogenes. It inhibits protein synthesis in 70S and 80S ribosomal systems. [PubChem]

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 361.437
Monoisotopic: 361.076612113
Chemical Formula
C13H19N3O5S2
Synonyms
  • Esparsomicina
  • Sparsomycin
  • Sparsomycine
  • Sparsomycinum
External IDs
  • NSC-59729
  • SKI 28430
  • U 19183
  • U-19183
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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
Integrate drug-drug
interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Sparsomycin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Sparsomycin is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Sparsomycin is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Sparsomycin is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Sparsomycin is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Pyrimidones
Alternative Parents
Hydropyrimidines / Vinylogous amides / Heteroaromatic compounds / Ureas / Sulfoxides / Secondary carboxylic acid amides / Lactams / Sulfinyl compounds / Sulfenyl compounds / Azacyclic compounds
show 7 more
Substituents
Alcohol / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Dialkylthioether / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
6C940P63E7
CAS number
1404-64-4
InChI Key
XKLZIVIOZDNKEQ-CLQLPEFOSA-N
InChI
InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23+/m0/s1
IUPAC Name
(2E)-N-[(2S)-1-hydroxy-3-[(R)-(methylsulfanyl)methanesulfinyl]propan-2-yl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-enamide
SMILES
CSC[S@+]([O-])C[C@H](CO)NC(=O)\C=C\C1=C(C)NC(=O)NC1=O

References

Synthesis Reference

Henricus C. J. Ottenheijm, "Sparsomycin (SC-RS) compounds having antitumor activity, a process for their preparation and pharmaceutical compositions containing sparsomycin (SC-RS) compounds." U.S. Patent US4820712, issued April, 1986.

US4820712
General References
Not Available
PubChem Compound
9543443
PubChem Substance
46505251
ChemSpider
7822406
ChEMBL
CHEMBL105720
ZINC
ZINC000004742520
PDBe Ligand
SPS
Wikipedia
Sparsomycin
PDB Entries
1m90 / 1njm / 1njn / 1vq8 / 1vq9 / 5dge / 5dgf / 5dgv / 5tgm

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.59 mg/mLALOGPS
logP-1.3ALOGPS
logP-2.5Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)8.97Chemaxon
pKa (Strongest Basic)-0.34Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area124.6 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity91.67 m3·mol-1Chemaxon
Polarizability36.61 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8944
Blood Brain Barrier-0.8279
Caco-2 permeable-0.6471
P-glycoprotein substrateSubstrate0.5232
P-glycoprotein inhibitor INon-inhibitor0.8592
P-glycoprotein inhibitor IINon-inhibitor0.9974
Renal organic cation transporterNon-inhibitor0.9232
CYP450 2C9 substrateNon-substrate0.7127
CYP450 2D6 substrateNon-substrate0.8125
CYP450 3A4 substrateSubstrate0.5161
CYP450 1A2 substrateNon-inhibitor0.7752
CYP450 2C9 inhibitorNon-inhibitor0.8087
CYP450 2D6 inhibitorNon-inhibitor0.8899
CYP450 2C19 inhibitorNon-inhibitor0.7924
CYP450 3A4 inhibitorNon-inhibitor0.6771
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9919
Ames testNon AMES toxic0.623
CarcinogenicityNon-carcinogens0.8003
BiodegradationNot ready biodegradable0.7831
Rat acute toxicity2.5203 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8591
hERG inhibition (predictor II)Non-inhibitor0.8647
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-03di-9576000000-3b088e5e9dc843f8367e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ue9-0492000000-9cb4a0660aad61ec6300
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-1297000000-5854ffeb7426ff771728
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01q9-4595000000-433d3123de0b583a6785
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-7692000000-991687423f2774c091d9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dj-9640000000-804ed5bfb540cef13beb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-9220000000-1683df886d19f8665b08
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-194.950907
predicted
DarkChem Lite v0.1.0
[M-H]-187.90617
predicted
DeepCCS 1.0 (2019)
[M+H]+195.314907
predicted
DarkChem Lite v0.1.0
[M+H]+190.26418
predicted
DeepCCS 1.0 (2019)
[M+Na]+195.444907
predicted
DarkChem Lite v0.1.0
[M+Na]+197.13112
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51