Maduramicin

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

Identification

Generic Name
Maduramicin
DrugBank Accession Number
DB11525
Background

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.

Type
Small Molecule
Groups
Vet approved
Structure
Weight
Average: 934.171
Monoisotopic: 933.566100217
Chemical Formula
C47H83NO17
Synonyms
  • Maduramicin
External IDs
  • CL 273,703
  • CL-273703

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
AcenocoumarolThe risk or severity of bleeding can be increased when Maduramicin is combined with Acenocoumarol.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Maduramicin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Maduramicin is combined with Articaine.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Maduramicin.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Maduramicin is combined with Benzocaine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Maduramicin ammoniumNot AvailableNot AvailableNot applicable

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Acetal / Alcohol / Aliphatic heteropolycyclic compound / C-glycosyl compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl ether / Ether / Hemiacetal
show 12 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
5U912U22T2
CAS number
84878-61-5
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

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. [Article]
  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. [Article]
  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. [Article]
  4. Sanford SE, McNaughton C: Ontario. Inonophore (maduramicin) toxicity in pigs. Can Vet J. 1991 Sep;32(9):567. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
KEGG Drug
D04830
ChemSpider
61862
ChEMBL
CHEMBL2105807
Wikipedia
Maduramicin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Drug created at February 26, 2016 17:34 / Updated at February 21, 2021 18:53