MAROPITANT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H40N2O
Molecular Weight	468.6728
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1CN[C@H]2C3CCN(CC3)[C@H]2C(C4=CC=CC=C4)C5=CC=CC=C5)C(C)(C)C

InChI

InChIKey=OMPCVMLFFSQFIX-CONSDPRKSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/pro/cerenia.html
Curator's Comment: Description was created based on several sources, including http://cerenia.com/ http://www.fda.gov/downloads/AnimalVeterinary/ucm062313.pdf

Maropitant (trade name Cerenia in the U.S. and other countries), used as maropitant citrate is a neurokinin (NK1) 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 was later approved for use in cats. Maropitant also has anti-nociceptive (analgesic) properties. Maropitant inhibits binding of substance P to NK-1 receptors. Substance P is an emetogen experimentally, and is found endogenously, along with NK-1 receptors, in the emetic center, chemoreceptor trigger zone, and in vagal afferent nerves in the gastrointestinal tract.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Substance-P receptor 8 Target ID: Q5DUB3 Gene ID: 403815.0 Gene Symbol: TACR1 Target Organism: Canis lupus familiaris (Dog) (Canis familiaris) Sources: https://www.drugs.com/pro/cerenia.html \| https://www.ncbi.nlm.nih.gov/pubmed/17610407	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Motion sickness in dogs 3 Sources: http://cerenia.com/	Preventing		Approved 8429	Cerenia Approved Use Cerenia is indicated for the prevention of acute vomiting and the prevention of vomiting due to motion sickness in dogs. Launch Date 2007

PubMed

Title	Date	PubMed
The pharmacokinetics of maropitant, a novel neurokinin type-1 receptor antagonist, in dogs.	2007 Aug	17610407
The neurokinin-1 antagonist activity of maropitant, an antiemetic drug for dogs, in a gerbil model.	2007 Aug	17610400
The anti-emetic efficacy of maropitant (Cerenia) in the treatment of ongoing emesis caused by a wide range of underlying clinical aetiologies in canine patients in Europe.	2007 Feb	17286662
Efficacy of maropitant for treatment and prevention of emesis caused by intravenous infusion of cisplatin in dogs.	2007 Jan	17199418
Efficacy of injectable maropitant (Cerenia) in a randomized clinical trial for prevention and treatment of cisplatin-induced emesis in dogs presented as veterinary patients.	2007 Mar	19754800
[New antiemetics: maropitant citrate].	2007 May 15	17578239
Efficacy of maropitant for preventing vomiting associated with motion sickness in dogs.	2007 Sep 29	17906225
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.	2008 Dec	19000277
Comparative efficacy of maropitant and selected drugs in preventing emesis induced by centrally or peripherally acting emetogens in dogs.	2008 Dec	19000276
Efficacy and safety of maropitant, a selective neurokinin 1 receptor antagonist, in two randomized clinical trials for prevention of vomiting due to motion sickness in dogs.	2008 Dec	19000275
Safety, pharmacokinetics and use of the novel NK-1 receptor antagonist maropitant (Cerenia) for the prevention of emesis and motion sickness in cats.	2008 Jun	18471143
Effect of refrigeration of the antiemetic Cerenia (maropitant) on pain on injection.	2009 Fall	20037963
Acute pancreatitis attributed to dietary indiscretion in a female mixed breed canine.	2010 Feb	20436868
Acute vomiting in cats: rational treatment selection.	2010 Mar	20193913
Efficacy of maropitant in the prevention of delayed vomiting associated with administration of doxorubicin to dogs.	2010 Nov-Dec	21039869
In vivo assessment of antiemetic drugs and mechanism of lycorine-induced nausea and emesis.	2011 Dec	21626407

Patents

Sample Use Guides

In Vivo Use Guide

For Prevention of Vomiting Due to Motion Sickness Administer Cerenia (Maropitant) Tablets orally at a minimum dose of 8 mg/kg (3.6 mg/lb) body weight once daily for up to 2 consecutive days. Dogs should be fasted 1 hour prior to administration of Cerenia Tablets. Administer Cerenia Tablets 2 hours prior to travel.

Route of Administration: Oral

In Vitro Use Guide

Maropitant (0.1-10 uM) increased frequency of whole murine intestine contraction, decreased amplitude of contraction and totally inhibited motility index in a concentration-dependent manner.

Name

Type

Language

MAROPITANT

Official Name

English

1-AZABICYCLO(2.2.2)OCTAN-3-AMINE, N-((5-(1,1-DIMETHYLETHYL)-2-METHOXYPHENYL)METHYL)-2-(DIPHENYLMETHYL)-, (2S,3S)-

Systematic Name

English

(2S,3S)-N-(5-(1,1-DIMETHYLETHYL)-2-METHOXYBENZYL)-2-(DIPHENYLMETHYL)-1-AZABICYCLO(2.2.2)OCTAN-3-AMINE

Systematic Name

English

MAROPITANT [GREEN BOOK]

Common Name

English

maropitant [INN]

Common Name

English

MAROPITANT [MI]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 520.1315