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
Eprinomectin
Accession Number
DB11405
Type
Small Molecule
Groups
Vet approved
Description
Not Available
Structure
Thumb
Synonyms
  • Eprinomectin
Categories
UNII
75KP30FD8O
CAS number
Not Available
Weight
Average: 1814.259
Monoisotopic: 1813.021862134
Chemical Formula
C99H148N2O28
InChI Key
VBPOFUHCXIRECN-SXLRFJQHSA-N
InChI
InChI=1S/C50H75NO14.C49H73NO14/c1-12-26(2)45-29(5)18-19-49(65-45)24-36-21-35(64-49)17-16-28(4)44(27(3)14-13-15-34-25-58-47-43(53)30(6)20-37(48(54)61-36)50(34,47)55)62-41-23-39(57-11)46(32(8)60-41)63-40-22-38(56-10)42(31(7)59-40)51-33(9)52;1-25(2)43-28(5)17-18-48(64-43)23-35-20-34(63-48)16-15-27(4)44(26(3)13-12-14-33-24-57-46-42(52)29(6)19-36(47(53)60-35)49(33,46)54)61-40-22-38(56-11)45(31(8)59-40)62-39-21-37(55-10)41(30(7)58-39)50-32(9)51/h13-16,18-20,26-27,29,31-32,35-47,53,55H,12,17,21-25H2,1-11H3,(H,51,52);12-15,17-19,25-26,28,30-31,34-46,52,54H,16,20-24H2,1-11H3,(H,50,51)/b14-13+,28-16+,34-15+;13-12+,27-15+,33-14+/t26-,27-,29-,31-,32-,35+,36-,37-,38-,39-,40-,41-,42+,43+,44-,45+,46-,47+,49+,50+;26-,28-,30-,31-,34+,35-,36-,37-,38-,39-,40-,41+,42+,43+,44-,45-,46+,48+,49+/m00/s1
IUPAC Name
N-[(2S,3R,4S,6S)-6-{[(2S,3S,4S,6R)-6-[(1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,20'R,21'R,24'S)-21',24'-dihydroxy-5,11',13',22'-tetramethyl-6-(propan-2-yl)-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-oneoxy]-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]ethanimidic acid; N-[(2S,3R,4S,6S)-6-{[(2S,3S,4S,6R)-6-[(1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,20'R,21'R,24'S)-6-[(2S)-butan-2-yl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-5,6-dihydro-3',7',19'-trioxaspiro[pyran-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-oneoxy]-4-methoxy-2-methyloxan-3-yl]oxy}-4-methoxy-2-methyloxan-3-yl]ethanimidic acid
SMILES
[H]\C1=C(C)/[C@@]([H])(O[C@@]2([H])C[C@]([H])(OC)[C@@]([H])(O[C@@]3([H])C[C@]([H])(OC)[C@]([H])(N=C(C)O)[C@]([H])(C)O3)[C@]([H])(C)O2)[C@@]([H])(C)\C([H])=C(/[H])\C(\[H])=C2/CO[C@]3([H])[C@]([H])(O)C(C)=C[C@@]([H])(C(=O)O[C@@]4([H])C[C@@]([H])(C1)O[C@@]1(C4)O[C@]([H])(C(C)C)[C@@]([H])(C)C=C1)[C@]23O.[H]\C1=C(C)/[C@@]([H])(O[C@@]2([H])C[C@]([H])(OC)[C@@]([H])(O[C@@]3([H])C[C@]([H])(OC)[C@]([H])(N=C(C)O)[C@]([H])(C)O3)[C@]([H])(C)O2)[C@@]([H])(C)\C([H])=C(/[H])\C(\[H])=C2/CO[C@]3([H])[C@]([H])(O)C(C)=C[C@@]([H])(C(=O)O[C@@]4([H])C[C@@]([H])(C1)O[C@@]1(C4)O[C@]([H])([C@@]([H])(C)CC)[C@@]([H])(C)C=C1)[C@]23O

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
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
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Eprinomectin.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Eprinomectin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Eprinomectin.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Eprinomectin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Eprinomectin.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Eprinomectin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Eprinomectin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Eprinomectin.
7-ethyl-10-hydroxycamptothecinThe metabolism of 7-ethyl-10-hydroxycamptothecin can be decreased when combined with Eprinomectin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Eprinomectin.
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. Zeng Z, Andrew NW: Characterization of eprinomectin N-deacetylase in rats. Drug Metab Dispos. 1999 Feb;27(2):269-73. [PubMed:9929515]
  2. Lespine A, Sutra JF, Dupuy J, Alvinerie M: Eprinomectin in goat: assessment of subcutaneous administration. Parasitol Res. 2003 Jan;89(2):120-2. Epub 2002 Sep 24. [PubMed:12489011]
  3. Halley BA, Winter R, Yoon S, Marley SE, Rehbein S: The environmental safety of eprinomectin to earthworms. Vet Parasitol. 2005 Mar 10;128(1-2):109-14. Epub 2004 Dec 21. [PubMed:15725539]
  4. Yazwinski TA, Johnson EG, Thompson DR, Drag MD, Zimmerman GL, Langholff WK, Holste JE, Eagleson JS: Nematocidal efficacy of eprinomectin, delivered topically, in naturally infected cattle. Am J Vet Res. 1997 Jun;58(6):612-4. [PubMed:9185967]
  5. Cramer LG, Pitt SR, Rehbein S, Gogolewski RP, Kunkle BN, Langhoff WK, Bond KG, Maciel AE: Persistent efficacy of topical eprinomectin against nematode parasites in cattle. Parasitol Res. 2000 Nov;86(11):944-6. [PubMed:11097305]
  6. Barth D, Hair JA, Kunkle BN, Langholff WK, Lowenstein M, Rehbein S, Smith LL, Eagleson JS, Kutzer E: Efficacy of eprinomectin against mange mites in cattle. Am J Vet Res. 1997 Nov;58(11):1257-9. [PubMed:9361888]
  7. Avcioglu H, Balkaya I: Efficacy of eprinomectin against Toxocara vitulorum in calves. Trop Anim Health Prod. 2011 Feb;43(2):283-6. doi: 10.1007/s11250-010-9699-7. Epub 2010 Oct 7. [PubMed:20927587]
  8. Rehbein S, Winter R, Visser M, Maciel AE, Marley SE: Chorioptic mange in dairy cattle: treatment with eprinomectin pour-on. Parasitol Res. 2005 Dec;98(1):21-5. Epub 2005 Oct 21. [PubMed:16240128]
  9. Holste JE, Colwell DD, Kumar R, Lloyd JE, Pinkall NP, Sierra MA, Waggoner JW, Langholff WK, Barrick RA, Eagleson JS: Efficacy of eprinomectin against Hypoderma spp in cattle. Am J Vet Res. 1998 Jan;59(1):56-8. [PubMed:9442244]
  10. Litskas VD, Karamanlis XN, Batzias GC, Kamarianos AP: Sorption of the antiparasitic drug eprinomectin in three soils. Chemosphere. 2011 Jan;82(2):193-8. doi: 10.1016/j.chemosphere.2010.10.024. Epub 2010 Nov 4. [PubMed:21055791]
External Links
ChemSpider
16738624
Wikipedia
Eprinomectin

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 Solubility0.00462 mg/mLALOGPS
logP4.4ALOGPS
logP6.38ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)5.74ChemAxon
pKa (Strongest Basic)2.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area182.42 Å2ChemAxon
Rotatable Bond Count17ChemAxon
Refractivity242.8 m3·mol-1ChemAxon
Polarizability100.01 Å3ChemAxon
Number of Rings14ChemAxon
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 macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolides and analogues
Sub Class
Not Available
Direct Parent
Macrolides and analogues
Alternative Parents
O-glycosyl compounds / Ketals / Monosaccharides / Oxanes / Pyrans / Tertiary alcohols / Acetamides / Tetrahydrofurans / Lactones / Carboxylic acid esters
show 10 more
Substituents
Macrolide / Glycosyl compound / O-glycosyl compound / Ketal / Monosaccharide / Pyran / Oxane / Acetamide / Tetrahydrofuran / Tertiary alcohol
show 22 more
Molecular Framework
Not Available
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kuper JI, D'Aprile M: Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14. [PubMed:11020135]

Drug created on February 25, 2016 11:27 / Updated on September 02, 2019 19:23