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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 of MAROPITANT

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
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

Description
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

CNS Active
3897
Curator's Comment: Maropitant, a lipophilic compound, crosses the blood-brain barrier http://veterinarymedicine.dvm360.com/maropitants-pharmacokinetics-and-pharmacology Maropitant is a neurokinin (NK1) receptor antagonist that blocks the pharmacological action of substance P in the central nervous system (CNS).

Originator

Approval Year

2007
181
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substance-P receptor
8
Target ID: Q5DUB3
Gene ID: 403815.0
Gene Symbol: TACR1
Target Organism: Canis lupus familiaris (Dog) (Canis familiaris)
Antagonist
2737
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8307
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

1.16994238E12
PubMed

PubMed

TitleDatePubMed
The pharmacokinetics of maropitant, a novel neurokinin type-1 receptor antagonist, in dogs.
2007 Aug
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
Efficacy of maropitant for preventing vomiting associated with motion sickness in dogs.
2007 Sep 29
Effect of refrigeration of the antiemetic Cerenia (maropitant) on pain on injection.
2009 Fall
Efficacy of maropitant in the prevention of delayed vomiting associated with administration of doxorubicin to dogs.
2010 Nov-Dec
In vivo assessment of antiemetic drugs and mechanism of lycorine-induced nausea and emesis.
2011 Dec
Patents

Patents

20010006972
5
20090192325
4
6562335
3
WO2003009848A1
3
WO2004067703A2
3
WO2007030307A2
3

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can also be injected subcutaneously http://www.fda.gov/downloads/AnimalVeterinary/ucm062313.pdf
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 16 20:07:31 UTC 2022
Edited
by admin
on Fri Dec 16 20:07:31 UTC 2022
Record UNII
4XE2T9H4DH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MAROPITANT
GREEN BOOK   INN   MI  
INN  
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
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
WHO-VATC QA04AD90
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
CFR 21 CFR 522.1315
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
NCI_THESAURUS C267
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
Code System Code Type Description
DAILYMED
4XE2T9H4DH
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
NCI_THESAURUS
C81500
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
ChEMBL
CHEMBL2111099
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
MESH
C518176
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
RXCUI
715869
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY RxNorm
CAS
147116-67-4
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
EPA CompTox
DTXSID1057874
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
PUBCHEM
204108
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
WIKIPEDIA
MAROPITANT
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
MERCK INDEX
M7089
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY Merck Index
FDA UNII
4XE2T9H4DH
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
INN
8421
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
DRUG BANK
DB11427
Created by admin on Fri Dec 16 20:07:32 UTC 2022 , Edited by admin on Fri Dec 16 20:07:32 UTC 2022
PRIMARY
Related Record Type Details
SUBSTANCE-P RECEPTOR
TARGET -> INHIBITOR
CYTOCHROME P450 3A12 (CANINE)
METABOLIC ENZYME -> SUBSTRATE
MAJOR
CYTOCHROME P450 1A2 (CANINE)
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Structure of MAROPITANT CITRATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of MAROPITANT
ACTIVE MOIETY
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