Selamectin

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

Identification

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Name
Selamectin
Accession Number
DB11459
Type
Small Molecule
Groups
Vet approved
Description

Selamectin is a topical parasiticide and antihelminthic used on dogs and cats to treat and prevent infections of heartworms, fleas, ear mites, sarcoptic mange, and certain types of ticks in dogs as well as prevent heartworms, fleas, ear mites, hookworms, and roundworms in cats. It also removes 2 types of lungworm in cats and one type of lungworm in dogs. It is distributed by Zoetis, a former Pfizer subsidiary. It is structurally related to ivermectin and milbemycin. Selamectin is not approved for human use.

Structure
Thumb
Synonyms
Not Available
External IDs
UK-124,114 / UK-124114
Categories
UNII
A2669OWX9N
CAS number
Not Available
Weight
Average: 769.973
Monoisotopic: 769.440111853
Chemical Formula
C43H63NO11
InChI Key
AFJYYKSVHJGXSN-XHKIUTQPSA-N
InChI
InChI=1S/C43H63NO11/c1-24-11-10-14-30-23-50-40-36(44-48)27(4)19-33(43(30,40)47)41(46)52-32-20-31(16-15-25(2)38(24)53-35-21-34(49-6)37(45)28(5)51-35)54-42(22-32)18-17-26(3)39(55-42)29-12-8-7-9-13-29/h10-11,14-15,19,24,26,28-29,31-35,37-40,45,47-48H,7-9,12-13,16-18,20-23H2,1-6H3/b11-10+,25-15+,30-14+,44-36-/t24-,26-,28-,31+,32-,33-,34-,35-,37-,38-,39-,40+,42+,43+/m0/s1
IUPAC Name
(1'R,2R,4'S,5S,6S,8'R,10'E,12'S,13'S,14'E,20'R,21'Z,24'S)-6-cyclohexyl-24'-hydroxy-12'-{[(2R,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-21'-(hydroxyimino)-5,11',13',22'-tetramethyl-3',7',19'-trioxaspiro[oxane-2,6'-tetracyclo[15.6.1.1⁴,⁸.0²⁰,²⁴]pentacosane]-10',14',16',22'-tetraen-2'-one
SMILES
[H]\C1=C(C)/[C@@]([H])(O[C@@]2([H])C[C@]([H])(OC)[C@@]([H])(O)[C@]([H])(C)O2)[C@@]([H])(C)\C([H])=C(/[H])\C(\[H])=C2/CO[C@]3([H])\C(=N/O)C(C)=C[C@@]([H])(C(=O)O[C@@]4([H])C[C@@]([H])(C1)O[C@@]1(CC[C@]([H])(C)[C@]([H])(O1)C1CCCCC1)C4)[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
DrugInteraction
(R)-warfarinThe serum concentration of (R)-warfarin can be increased when it is combined with Selamectin.
(S)-WarfarinThe serum concentration of (S)-Warfarin can be increased when it is combined with Selamectin.
3-isobutyl-1-methyl-7H-xanthineThe metabolism of 3-isobutyl-1-methyl-7H-xanthine can be decreased when combined with Selamectin.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Selamectin.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Selamectin.
7-DeazaguanineThe metabolism of 7-Deazaguanine can be decreased when combined with Selamectin.
7,9-DimethylguanineThe metabolism of 7,9-Dimethylguanine can be decreased when combined with Selamectin.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Selamectin.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Selamectin.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be decreased when combined with Selamectin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

References

General References
  1. Krautmann MJ, Novotny MJ, De Keulenaer K, Godin CS, Evans EI, McCall JW, Wang C, Rowan TG, Jernigan AD: Safety of selamectin in cats. Vet Parasitol. 2000 Aug 23;91(3-4):393-403. [PubMed:10940537]
  2. Novotny MJ, Krautmann MJ, Ehrhart JC, Godin CS, Evans EI, McCall JW, Sun F, Rowan TG, Jernigan AD: Safety of selamectin in dogs. Vet Parasitol. 2000 Aug 23;91(3-4):377-91. [PubMed:10940536]
  3. Gupta RC, Masthay MB, Canerdy TD, Acosta TM, Provost RJ, Britton DM, Atieh BH, Keller RJ: Human exposure to selamectin from dogs treated with revolution: methodological consideration for selamectin isolation. Toxicol Mech Methods. 2005;15(4):317-21. doi: 10.1080/15376520590968860. [PubMed:20021097]
  4. Jacobs DE: Selamectin - a novel endectocide for dogs and cats. Vet Parasitol. 2000 Aug 23;91(3-4):161-2. [PubMed:10940518]
  5. Shanks DJ, Gautier P, McTier TL, Evans NA, Pengo G, Rowan TG: Efficacy of selamectin against biting lice on dogs and cats. Vet Rec. 2003 Feb 22;152(8):234-7. [PubMed:12625538]
  6. Bishop BF, Bruce CI, Evans NA, Goudie AC, Gration KA, Gibson SP, Pacey MS, Perry DA, Walshe ND, Witty MJ: Selamectin: a novel broad-spectrum endectocide for dogs and cats. Vet Parasitol. 2000 Aug 23;91(3-4):163-76. [PubMed:10940519]
  7. Schnabl B, Bettenay S, Glos N, Linek M, Loewenstein C, Mueller RS: Oral selamectin in the treatment of canine generalised demodicosis. Vet Rec. 2010 Jun 5;166(23):710-4. doi: 10.1136/vr.4850. [PubMed:20525946]
  8. Dupuy J, Derlon AL, Sutra JF, Cadiergues MC, Franc M, Alvinerie M: Pharmacokinetics of selamectin in dogs after topical application. Vet Res Commun. 2004 Jul;28(5):407-13. [PubMed:15379435]
  9. Itoh N, Muraoka N, Aoki M, Itagaki T: Treatment of Notoedres cati infestation in cats with selamectin. Vet Rec. 2004 Mar 27;154(13):409. [PubMed:15083980]
  10. Mueller RS, Bettenay SV: Efficacy of selamectin in the treatment of canine cheyletiellosis. Vet Rec. 2002 Dec 21-28;151(25):773. [PubMed:12521253]
External Links
ChemSpider
16738655
ChEMBL
CHEMBL1908325
Wikipedia
Selamectin

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 Solubility0.00425 mg/mLALOGPS
logP5.09ALOGPS
logP6.21ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)9.58ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area154.73 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity206.75 m3·mol-1ChemAxon
Polarizability85.75 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 milbemycins. These are a group of macrolides with a structure containing a 16-membered lactone ring fused to a 1,7-dioxaspiroundecane ring system and to either a benzofuran (or hydrogenated derivative thereof). In some cases (e.g. Milbemycin E), the tetrahydrofuranyl ring is missing. Milbemycins can be o-glycosylated at C13 to form Avermectins. Milbemycins are produced by Streptomyces species.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolides and analogues
Sub Class
Milbemycins
Direct Parent
Milbemycins
Alternative Parents
O-glycosyl compounds / Ketals / Monosaccharides / Oxanes / Tertiary alcohols / Ketoximes / Tetrahydrofurans / Lactones / Carboxylic acid esters / Secondary alcohols
show 7 more
Substituents
Milbemycin / Glycosyl compound / O-glycosyl compound / Ketal / Monosaccharide / Oxane / Tetrahydrofuran / Tertiary alcohol / Ketoxime / Carboxylic acid ester
show 20 more
Molecular Framework
Aliphatic heteropolycyclic compounds
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 11:55 / Updated on June 04, 2019 07:22