Maduramicin

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
Maduramicin
Accession Number
DB11525
Type
Small Molecule
Groups
Vet approved
Description

Maduramicin is an antiprotozoal agent used in veterinary medicine as prophylaxis against coccidiosis. It is a naturally occurring compound which was first isolated from the actinomycete, Actinomadura rubra.

Structure
Thumb
Synonyms
Not Available
External IDs
CL 273,703 / CL-273703
Product Ingredients
IngredientUNIICASInChI Key
Maduramicin ammoniumNot AvailableNot AvailableNot applicable
Categories
UNII
5U912U22T2
CAS number
84878-61-5
Weight
Average: 934.171
Monoisotopic: 933.566100217
Chemical Formula
C47H83NO17
InChI Key
WQGJEAMPBSZCIF-HKSLRPGUSA-N
InChI
InChI=1S/C47H80O17.H3N/c1-23-18-24(2)45(9,51)61-36(23)31-19-32(58-35-20-30(53-10)40(55-12)28(6)57-35)42(59-31)44(8)15-14-33(60-44)43(7)16-17-46(64-43)21-29(48)25(3)37(62-46)26(4)38-41(56-13)39(54-11)27(5)47(52,63-38)22-34(49)50;/h23-33,35-42,48,51-52H,14-22H2,1-13H3,(H,49,50);1H3/t23-,24+,25+,26+,27-,28-,29-,30-,31+,32-,33+,35+,36-,37-,38-,39-,40-,41-,42+,43-,44-,45-,46+,47+;/m0./s1
IUPAC Name
2-[(2R,3S,4S,5R,6S)-6-[(1R)-1-[(2S,5R,7S,8R,9S)-2-[(2S,2'R,3'S,5R,5'R)-3'-{[(2R,4S,5S,6S)-4,5-dimethoxy-6-methyloxan-2-yl]oxy}-5'-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-2-methyl-[2,2'-bioxolane]-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]ethyl]-2-hydroxy-4,5-dimethoxy-3-methyloxan-2-yl]acetic acid amine
SMILES
N.[H][C@@](C)([C@@]1([H])O[C@@]2(CC[C@](C)(O2)[C@@]2([H])CC[C@](C)(O2)[C@]2([H])O[C@]([H])(C[C@]2([H])O[C@]2([H])C[C@]([H])(OC)[C@@]([H])(OC)[C@]([H])(C)O2)[C@@]2([H])O[C@](C)(O)[C@]([H])(C)C[C@]2([H])C)C[C@]([H])(O)[C@@]1([H])C)[C@]1([H])O[C@](O)(CC(O)=O)[C@@]([H])(C)[C@]([H])(OC)[C@@]1([H])OC

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 Maduramicin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Maduramicin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Maduramicin is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Maduramicin 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 Maduramicin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Maduramicin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Maduramicin.
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 Maduramicin.
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 Maduramicin.
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 Maduramicin.
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. Sharma N, Bhalla A, Varma S, Jain S, Singh S: Toxicity of maduramicin. Emerg Med J. 2005 Dec;22(12):880-2. [PubMed:16299200]
  2. Gutierrez-Lugo MT, Lotina-Hennsen B, Farres A, Sanchez S, Mata R: Phytotoxic and photosynthetic activities of maduramicin and maduramicin methyl ester. Z Naturforsch C. 1999 May-Jun;54(5-6):325-32. [PubMed:10431386]
  3. Shlosberg A, Perl S, Harmelin A, Hanji V, Bellaiche M, Bogin E, Cohen R, Markusfeld-Nir O, Shpigel N, Eisenberg Z, Furman M, Brosh A, Holzer Z, Aharoni Y: Acute maduramicin toxicity in calves. Vet Rec. 1997 Jun 21;140(25):643-6. [PubMed:9226847]
  4. Sanford SE, McNaughton C: Ontario. Inonophore (maduramicin) toxicity in pigs. Can Vet J. 1991 Sep;32(9):567. [PubMed:17423864]
  5. Badiola JJ, Luco DF, Perez V, Vargas MA, Lujan L, Marin JF: Maduramicin and tiamulin compatibility in broiler chickens. Avian Pathol. 1994 Mar;23(1):3-17. [PubMed:18671068]
  6. Arrowood MJ, Xie LT, Hurd MR: In vitro assays of maduramicin activity against Cryptosporidium parvum. J Eukaryot Microbiol. 1994 Sep-Oct;41(5):23S. [PubMed:7804225]
  7. McGahren WJ, Morton GO, Siegel MM, Borders DB, James JC, Ellestad GA: Chemistry of maduramicin. II. Decarboxylation, abnormal ketalization and dehydration. J Antibiot (Tokyo). 1986 Nov;39(11):1541-50. [PubMed:3793623]
  8. Ellestad GA, Canfield N, Leese RA, Morton GO, James JC, Siegel MM, McGahren WJ: Chemistry of maduramicin. I. Salt formation and normal ketalization. J Antibiot (Tokyo). 1986 Mar;39(3):447-56. [PubMed:3700246]
  9. Tsou HR, Rajan S, Chang TT, Fiala RR, Stockton GW, Bullock MW: The utilization of molecular oxygen during the biosynthesis of maduramicin. J Antibiot (Tokyo). 1987 Jan;40(1):94-9. [PubMed:3558121]
  10. Kennedy DG, Blanchflower WJ, O'Dornan BC: Development of an ELISA for maduramicin and determination of the depletion kinetics of maduramicin residues in poultry. Food Addit Contam. 1997 Jan;14(1):27-33. [PubMed:9059580]
External Links
KEGG Drug
D04830
ChemSpider
61862
ChEMBL
CHEMBL2105807
Wikipedia
Maduramicin

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 Solubility0.0157 mg/mLALOGPS
logP2.22ALOGPS
logP4.77ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.01ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area208.75 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity227.28 m3·mol-1ChemAxon
Polarizability99.84 Å3ChemAxon
Number of Rings7ChemAxon
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/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

Taxonomy

Description
This compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
O-glycosyl compounds
Alternative Parents
C-glycosyl compounds / Ketals / Oxanes / Monosaccharides / Tetrahydrofurans / Secondary alcohols / Hemiacetals / Oxacyclic compounds / Monocarboxylic acids and derivatives / Dialkyl ethers
show 5 more
Substituents
C-glycosyl compound / O-glycosyl compound / Ketal / Monosaccharide / Oxane / Tetrahydrofuran / Hemiacetal / Secondary alcohol / Acetal / Carboxylic acid derivative
show 12 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on February 26, 2016 10:34 / Updated on June 04, 2019 07:23