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Maropitan (CJ11972; CJ11972) is a novel, potent, selective and orally bioactive antagonist of neurokinin (NK1) receptor. Maropitant functions by preventing substance P from binding to the chemoreceptor trigger zone (CRTZ) and the emetic center. Maropitant was created by Zoetis expressly to treat motion sickness and vomiting in dogs, and it works incredibly well at preventing vomiting. The FDA approved it for use in dogs in 2007; cats were added to the list of approved uses more recently.
Physicochemical Properties
| Molecular Formula | C32H40N2O |
| Molecular Weight | 468.6728 |
| Exact Mass | 468.314 |
| Elemental Analysis | C, 82.01; H, 8.60; N, 5.98; O, 3.41 |
| CAS # | 147116-67-4 |
| Related CAS # | Maropitant-13C,d3; 359875-09-5 (citrate hydrate); 862543-54-2 (citrate) |
| PubChem CID | 204108 |
| Appearance | White solid powder |
| LogP | 6.706 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 8 |
| Heavy Atom Count | 35 |
| Complexity | 620 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CC(C)(C)C1=CC=C(OC)C(CN[C@@H]2[C@H](C(C3=CC=CC=C3)C4=CC=CC=C4)N5CCC2CC5)=C1 |
| InChi Key | OMPCVMLFFSQFIX-CONSDPRKSA-N |
| InChi Code | 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 |
| Chemical Name | (2S,3S)-2-benzhydryl-N-[(5-tert-butyl-2-methoxyphenyl)methyl]-1-azabicyclo[2.2.2]octan-3-amine |
| Synonyms | Maropitant; CJ-11972; CJ 11972; CJ11972; CJ-11,972; CJ 11,972; CJ11,972; brand name: Cerenia |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vivo | Mice treated with 1 mg/kg Maropitant citrate have much smaller ulcerative dermatitis (UD) lesions. Intravenous maropitant reduces MAC by sixteen percent. By contrast, the MAC (2.17% and 1.92%, respectively) remains unchanged following the epidural injection of either saline or Maropitant. |
| References |
[1]. Efficacy of maropitant in preventing vomiting in dogs premedicated with hydromorphone. Vet Anaesth Analg. 2013 Jan;40(1):28-34. [2]. The pharmacokinetics of maropitant citrate dosed orally to dogs at 2 mg/kg and 8 mg/kg once daily for 14 days consecutive days. J Vet Pharmacol Ther. 2012 Nov 20. [3]. Effect of epidural and intravenous use of the neurokinin-1 (NK-1) receptor antagonist maropitant on the sevoflurane minimum alveolar concentration (MAC) in dogs. Vet Anaesth Analg. 2012 Mar;39(2):201-5. [4]. Safety and efficacy of injectable and oral maropitant, a selective neurokinin 1 receptor antagonist, in a randomized clinical trial for treatment of vomiting in dogs. J Vet Pharmacol Ther. 2008 Dec;31(6):538-43. [5]. The pharmacokinetics of maropitant, a novel neurokinin type-1 receptor antagonist, in dogs. J Vet Pharmacol Ther. 2007 Aug;30(4):336-44. [6]. Maropitant. |
| Additional Infomation |
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. See also: Maropitant Citrate (has salt form); maropitant citrate anhydrous (is active moiety of). Drug Indication Dogs: For the treatment and prevention of nausea induced by chemotherapyFor the prevention of vomiting except that induced by motion sicknessFor the treatment of vomiting, in combination with other supportive measuresFor the prevention of perioperative nausea and vomiting and improvement in recovery from general anaesthesia after use of the μ-opiate receptor agonist morphineCats: For the prevention of vomiting and the reduction of nausea, except that induced by motion sicknessFor the treatment of vomiting, in combination with other supportive measures. Tablets Dogs: For the prevention of nausea induced by chemotherapy. For the prevention of vomiting induced by motion sickness. For the prevention and treatment of vomiting, in conjunction with Cerenia solution for injection and in combination with other supportive measures. Solution for injectionDogs: For the treatment and prevention of nausea induced by chemotherapy. For the prevention of vomiting except that induced by motion sickness. For the treatment of vomiting, in combination with other supportive measures. For the prevention of perioperative nausea and vomiting and improvement in recovery from general anaesthesia after use of the μ-opiate receptor agonist morphine. Cats: For the prevention of vomiting and the reduction of nausea, except that induced by motion sickness. For the treatment of vomiting, in combination with other supportive measures. |
Solubility Data
| Solubility (In Vitro) | DMSO: ~25 mg/mL (~53.3 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.33 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.1337 mL | 10.6685 mL | 21.3370 mL | |
| 5 mM | 0.4267 mL | 2.1337 mL | 4.2674 mL | |
| 10 mM | 0.2134 mL | 1.0668 mL | 2.1337 mL |