NAV

Streptolydigin

Identification

Generic Name
Streptolydigin
DrugBank Accession Number
DB04785
Background

Streptolydigin is an antibiotic isolated from culture filtrates of Streptomyces lydicus. It is active against gram-postive bacteria except micrococci.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 600.6998
Monoisotopic: 600.304681016
Chemical Formula
C32H44N2O9
Synonyms
  • Afragilimycin A
  • Portamycin
External IDs
  • Antibiotic D-45
  • NSC-3360

Pharmacology

Indication

Not Available

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Pharmacodynamics

Streptolydigin is an antibiotic which works by blocking nucleic acid chain elongation by binding to the polymerase, thus stopping RNA polymerase activity inside a cell. Specifically, it inhibits the assembly of the RNA polymerase II transcription complex and DNA polymerase III transcription. It is active against a number of gram positive bacteria.

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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AcenocoumarolThe risk or severity of bleeding can be increased when Streptolydigin is combined with Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Streptolydigin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Streptolydigin is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Streptolydigin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Streptolydigin is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Streptolydigin is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Streptolydigin is combined with Bupivacaine.
ButacaineThe risk or severity of methemoglobinemia can be increased when Streptolydigin is combined with Butacaine.
ButambenThe risk or severity of methemoglobinemia can be increased when Streptolydigin is combined with Butamben.
CapsaicinThe risk or severity of methemoglobinemia can be increased when Streptolydigin is combined with Capsaicin.
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Food Interactions
Not Available

Products

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International/Other Brands
Portamycin

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Beta amino acids and derivatives
Alternative Parents
Ketals / Pyrrolidine-3-ones / Pyrrolidine-2-ones / Pyrans / Oxanes / 1,3-dioxanes / N-alkylpyrrolidines / Vinylogous acids / Tertiary carboxylic acid amides / Secondary carboxylic acid amides
show 12 more
Substituents
2-pyrrolidone / 3-pyrrolidone / Acetal / Alcohol / Aliphatic heteropolycyclic compound / Azacycle / Beta amino acid or derivatives / Carbonyl group / Carboxamide group / Cyclic ketone
show 26 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
pyrrolidinone, monocarboxylic acid amide, organic heterotricyclic compound, epoxide, N-glycosyl compound, bridged compound, enol, cyclic ketal, oxaspiro compound (CHEBI:45773)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
6MON4029Q8
CAS number
7229-50-7
InChI Key
KVTPRMVXYZKLIG-NCAOFHFGSA-N
InChI
InChI=1S/C32H44N2O9/c1-16(14-17(2)28-18(3)23-12-13-32(15-40-32)31(6,42-23)43-28)8-9-22(36)25-27(37)26(19(4)29(38)33-7)34(30(25)39)24-11-10-21(35)20(5)41-24/h8-9,12-14,17-21,23-24,26,28,35-36H,10-11,15H2,1-7H3,(H,33,38)/b9-8+,16-14+,25-22+/t17-,18+,19+,20+,21+,23-,24+,26+,28-,31-,32-/m1/s1
IUPAC Name
(2S)-2-[(2S,4E)-4-[(2E,4E,6R)-6-[(1R,2R,5R,6S,7R)-1,6-dimethyl-8,9-dioxaspiro[bicyclo[3.3.1]nonane-2,2'-oxiran]-3-en-7-yl]-1-hydroxy-4-methylhepta-2,4-dien-1-ylidene]-1-[(2S,5S,6S)-5-hydroxy-6-methyloxan-2-yl]-3,5-dioxopyrrolidin-2-yl]-N-methylpropanamide
SMILES
[H][C@@]1([C@H](C)C(=O)NC)N([C@@H]2CC[C@H](O)[C@H](C)O2)C(=O)\C(=C(\O)/C=C/C(/C)=C/[C@@H](C)[C@@]2([H])O[C@@]3(C)O[C@H](C=C[C@@]33CO3)[C@@H]2C)C1=O

References

General References
Not Available
PubChem Compound
54708748
PubChem Substance
46505558
ChemSpider
21270076
ChEBI
45773
ChEMBL
CHEMBL1236068
ZINC
ZINC000169363256
PDBe Ligand
STD
Wikipedia
Streptolydigin
PDB Entries
1zyr / 2a6h / 2ppb

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 Solubility0.0386 mg/mLALOGPS
logP1.78ALOGPS
logP2.09Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)5.29Chemaxon
pKa (Strongest Basic)-0.48Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area147.16 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity160.29 m3·mol-1Chemaxon
Polarizability63.96 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8435
Blood Brain Barrier-0.9824
Caco-2 permeable-0.632
P-glycoprotein substrateSubstrate0.7381
P-glycoprotein inhibitor INon-inhibitor0.5781
P-glycoprotein inhibitor IINon-inhibitor0.6987
Renal organic cation transporterNon-inhibitor0.8953
CYP450 2C9 substrateNon-substrate0.7662
CYP450 2D6 substrateNon-substrate0.85
CYP450 3A4 substrateSubstrate0.7436
CYP450 1A2 substrateNon-inhibitor0.8165
CYP450 2C9 inhibitorNon-inhibitor0.7315
CYP450 2D6 inhibitorNon-inhibitor0.9006
CYP450 2C19 inhibitorNon-inhibitor0.7712
CYP450 3A4 inhibitorNon-inhibitor0.7387
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9076
Ames testAMES toxic0.5386
CarcinogenicityNon-carcinogens0.9381
BiodegradationNot ready biodegradable0.9488
Rat acute toxicity2.8753 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9972
hERG inhibition (predictor II)Non-inhibitor0.8705
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at September 11, 2007 17:49 / Updated at June 12, 2020 16:52