MAROPITANT CITRATE ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H40N2O.C6H8O7
Molecular Weight	660.7963
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of MAROPITANT CITRATE ANHYDROUS

Structure Search

SMILES

OC(=O)CC(O)(CC(O)=O)C(O)=O.COC1=C(CN[C@H]2C3CCN(CC3)[C@H]2C(C4=CC=CC=C4)C5=CC=CC=C5)C=C(C=C1)C(C)(C)C

InChI

InChIKey=XDZPFSKCXRGRIO-PNXDLZEOSA-N

InChI=1S/C32H40N2O.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h5-16,21,25,29-31,33H,17-20,22H2,1-4H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t30-,31-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C32H40N2O
Molecular Weight	468.6728
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C6H8O7
Molecular Weight	192.1235
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Motion sickness in dogs 3 Sources: http://cerenia.com/	Preventing		Approved 8583	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
In vivo assessment of antiemetic drugs and mechanism of lycorine-induced nausea and emesis.	2011-12	21626407
Efficacy of maropitant in the prevention of delayed vomiting associated with administration of doxorubicin to dogs.	2010-11-03	21039869
Acute vomiting in cats: rational treatment selection.	2010-03	20193913
Acute pancreatitis attributed to dietary indiscretion in a female mixed breed canine.	2010-02	20436868
Effect of refrigeration of the antiemetic Cerenia (maropitant) on pain on injection.	2009	20037963
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.	2008-12	19000277
Comparative efficacy of maropitant and selected drugs in preventing emesis induced by centrally or peripherally acting emetogens in dogs.	2008-12	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.	2008-12	19000275
Safety, pharmacokinetics and use of the novel NK-1 receptor antagonist maropitant (Cerenia) for the prevention of emesis and motion sickness in cats.	2008-06	18471143
Efficacy of maropitant for preventing vomiting associated with motion sickness in dogs.	2007-09-29	17906225
The pharmacokinetics of maropitant, a novel neurokinin type-1 receptor antagonist, in dogs.	2007-08	17610407
The neurokinin-1 antagonist activity of maropitant, an antiemetic drug for dogs, in a gerbil model.	2007-08	17610400
[New antiemetics: maropitant citrate].	2007-05-15	17578239
Efficacy of injectable maropitant (Cerenia) in a randomized clinical trial for prevention and treatment of cisplatin-induced emesis in dogs presented as veterinary patients.	2007-03	19754800
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.	2007-02	17286662
Efficacy of maropitant for treatment and prevention of emesis caused by intravenous infusion of cisplatin in dogs.	2007-01	17199418

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:29:42 GMT 2025` Edited by `admin` on `Mon Mar 31 21:29:42 GMT 2025`
Record UNII	19364RWW06
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MAROPITANT CITRATE ANHYDROUS

Common Name

English

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

Preferred Name

English

Code System Code Type Description

EPA CompTox

DTXSID20235458