Maropitant

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

Identification

Generic Name
Maropitant
DrugBank Accession Number
DB11427
Background

Maropitant, used as maropitant citrate, is a neurokinin receptor antagonist, which was developed by Zoetis specifically for the treatment of motion sickness and vomiting in dogs. It was approved by the FDA in 2007 for use in dogs, and more recently has also been approved for use in cats.

Type
Small Molecule
Groups
Vet approved
Structure
Weight
Average: 468.685
Monoisotopic: 468.314063916
Chemical Formula
C32H40N2O
Synonyms
  • Maropitant

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.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Maropitant citrateLXN6S3999X359875-09-5PGVSXRHFXJOMGW-YBZGWEFGSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Phenylpropanes / Quinuclidines / Phenylmethylamines / Phenoxy compounds / Methoxybenzenes / Benzylamines / Anisoles / Aralkylamines / Aminopiperidines / Alkyl aryl ethers
show 5 more
Substituents
3-aminopiperidine / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzylamine / Diphenylmethane / Ether
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
4XE2T9H4DH
CAS number
147116-67-4
InChI Key
OMPCVMLFFSQFIX-CONSDPRKSA-N
InChI
InChI=1S/C32H40N2O/c1-32(2,3)27-15-16-28(35-4)26(21-27)22-33-30-25-17-19-34(20-18-25)31(30)29(23-11-7-5-8-12-23)24-13-9-6-10-14-24/h5-16,21,25,29-31,33H,17-20,22H2,1-4H3/t30-,31-/m0/s1
IUPAC Name
(2S,3S)-N-[(5-tert-butyl-2-methoxyphenyl)methyl]-2-(diphenylmethyl)-1-azabicyclo[2.2.2]octan-3-amine
SMILES
[H][C@]1(NCC2=CC(=CC=C2OC)C(C)(C)C)C2CCN(CC2)[C@@]1([H])C(C1=CC=CC=C1)C1=CC=CC=C1

References

General References
  1. van Noort R: [New antiemetics: maropitant citrate]. Tijdschr Diergeneeskd. 2007 May 15;132(10):411-2. [Article]
  2. Benchaoui HA, Siedek EM, De La Puente-Redondo VA, Tilt N, Rowan TG, Clemence RG: Efficacy of maropitant for preventing vomiting associated with motion sickness in dogs. Vet Rec. 2007 Sep 29;161(13):444-7. [Article]
  3. Benchaoui HA, Cox SR, Schneider RP, Boucher JF, Clemence RG: The pharmacokinetics of maropitant, a novel neurokinin type-1 receptor antagonist, in dogs. J Vet Pharmacol Ther. 2007 Aug;30(4):336-44. [Article]
  4. de la Puente-Redondo V, Tingley FD 3rd, Schneider RP, Hickman MA: The neurokinin-1 antagonist activity of maropitant, an antiemetic drug for dogs, in a gerbil model. J Vet Pharmacol Ther. 2007 Aug;30(4):281-7. [Article]
  5. Narishetty ST, Galvan B, Coscarelli E, Aleo M, Fleck T, Humphrey W, McCall RB: Effect of refrigeration of the antiemetic Cerenia (maropitant) on pain on injection. Vet Ther. 2009 Fall;10(3):93-102. [Article]
  6. Rau SE, Barber LG, Burgess KE: Efficacy of maropitant in the prevention of delayed vomiting associated with administration of doxorubicin to dogs. J Vet Intern Med. 2010 Nov-Dec;24(6):1452-7. doi: 10.1111/j.1939-1676.2010.0611.x. Epub 2010 Oct 12. [Article]
  7. Williams-Fritze MJ, Carlson Scholz JA, Zeiss C, Deng Y, Wilson SR, Franklin R, Smith PC: Maropitant citrate for treatment of ulcerative dermatitis in mice with a C57BL/6 background. J Am Assoc Lab Anim Sci. 2011 Mar;50(2):221-6. [Article]
  8. Lorenzutti AM, Martin-Flores M, Litterio NJ, Himelfarb MA, Zarazaga MP: Evaluation of the antiemetic efficacy of maropitant in dogs medicated with morphine and acepromazine. Vet Anaesth Analg. 2016 Mar;43(2):195-8. doi: 10.1111/vaa.12286. Epub 2015 Jun 19. [Article]
  9. Johnson RA: Maropitant prevented vomiting but not gastroesophageal reflux in anesthetized dogs premedicated with acepromazine-hydromorphone. Vet Anaesth Analg. 2014 Jul;41(4):406-10. doi: 10.1111/vaa.12120. Epub 2013 Dec 16. [Article]
  10. Hay Kraus BL: Efficacy of orally administered maropitant citrate in preventing vomiting associated with hydromorphone administration in dogs. J Am Vet Med Assoc. 2014 May 15;244(10):1164-9. doi: 10.2460/javma.244.10.1164. [Article]
ChemSpider
176805
RxNav
715869
ChEMBL
CHEMBL2111099
ZINC
ZINC000040664622
Wikipedia
Maropitant

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 Solubility6.27e-05 mg/mLALOGPS
logP6.27ALOGPS
logP6.87Chemaxon
logS-6.9ALOGPS
pKa (Strongest Basic)9.43Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area24.5 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity146.01 m3·mol-1Chemaxon
Polarizability54.92 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
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/MSsplash10-014i-0000900000-0381802637eccd2a63e0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0010900000-5e1237f265a162206e69
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-07vl-5021900000-9f3690a790aa7a034e78
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0010900000-125571f12a05b94bb253
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9504200000-82117f1d1f25fd8cc067
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00xr-0932200000-7e4b5812210136c11d12
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-229.8267949
predicted
DarkChem Lite v0.1.0
[M-H]-210.9788
predicted
DeepCCS 1.0 (2019)
[M+H]+229.5639949
predicted
DarkChem Lite v0.1.0
[M+H]+213.90996
predicted
DeepCCS 1.0 (2019)
[M+Na]+228.4057949
predicted
DarkChem Lite v0.1.0
[M+Na]+221.22661
predicted
DeepCCS 1.0 (2019)

Drug created at February 25, 2016 18:41 / Updated at February 21, 2021 18:53