MAROPITANT CITRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H40N2O.C6H8O7.H2O
Molecular Weight	678.8116
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.OC(=O)CC(O)(CC(O)=O)C(O)=O.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=PGVSXRHFXJOMGW-YBZGWEFGSA-N

InChI=1S/C32H40N2O.C6H8O7.H2O/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);1H2/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	H2O
Molecular Weight	18.0153
Charge	0
Count

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

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 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 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
Comparative efficacy of maropitant and selected drugs in preventing emesis induced by centrally or peripherally acting emetogens in dogs.	2008 Dec	19000276
Acute pancreatitis attributed to dietary indiscretion in a female mixed breed canine.	2010 Feb	20436868
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:10:02 GMT 2023` Edited by `admin` on `Fri Dec 15 16:10:02 GMT 2023`
Record UNII	LXN6S3999X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MAROPITANT CITRATE

Official Name

English

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

Common Name

English

CJ-11,972

Code

English

MAROPITANT CITRATE MONOHYDRATE [MI]

Common Name

English

CJ-11972

Code

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), monohydrate

Common Name

English

MAROPITANT CITRATE MONOHYDRATE

Common Name

English

MAROPITANT CITRATE [USAN]

Common Name

English

CERENIA

Brand Name

English

MAROPITANT CITRATE [EMA EPAR VETERINARY]

Common Name

English

Classification Tree Code System Code

EMA VETERINARY ASSESSMENT REPORTS

CERENIA (AUTHORISED)