Maropitant
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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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- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Maropitant citrate LXN6S3999X 359875-09-5 PGVSXRHFXJOMGW-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
- van Noort R: [New antiemetics: maropitant citrate]. Tijdschr Diergeneeskd. 2007 May 15;132(10):411-2. [Article]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- External Links
- ChemSpider
- 176805
- 715869
- ChEMBL
- CHEMBL2111099
- ZINC
- ZINC000040664622
- Wikipedia
- Maropitant
Clinical Trials
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
Property Value Source Water Solubility 6.27e-05 mg/mL ALOGPS logP 6.27 ALOGPS logP 6.87 Chemaxon logS -6.9 ALOGPS pKa (Strongest Basic) 9.43 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 24.5 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 146.01 m3·mol-1 Chemaxon Polarizability 54.92 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0000900000-0381802637eccd2a63e0 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0010900000-5e1237f265a162206e69 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-07vl-5021900000-9f3690a790aa7a034e78 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0010900000-125571f12a05b94bb253 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9504200000-82117f1d1f25fd8cc067 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00xr-0932200000-7e4b5812210136c11d12 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 229.8267949 predictedDarkChem Lite v0.1.0 [M-H]- 210.9788 predictedDeepCCS 1.0 (2019) [M+H]+ 229.5639949 predictedDarkChem Lite v0.1.0 [M+H]+ 213.90996 predictedDeepCCS 1.0 (2019) [M+Na]+ 228.4057949 predictedDarkChem Lite v0.1.0 [M+Na]+ 221.22661 predictedDeepCCS 1.0 (2019)
Drug created at February 25, 2016 18:41 / Updated at February 21, 2021 18:53