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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

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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q5DUB3
Gene ID: 403815.0
Gene Symbol: TACR1
Target Organism: Canis lupus familiaris (Dog) (Canis familiaris)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
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

PubMed

TitleDatePubMed
[New antiemetics: maropitant citrate].
2007 May 15
Comparative efficacy of maropitant and selected drugs in preventing emesis induced by centrally or peripherally acting emetogens in dogs.
2008 Dec
Patents

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
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 16:25:30 GMT 2023
Edited
by admin
on Fri Dec 15 16:25:30 GMT 2023
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 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
WHO-VATC QA04AD90
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
CFR 21 CFR 522.1315
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
NCI_THESAURUS C267
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
Code System Code Type Description
DAILYMED
4XE2T9H4DH
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
NCI_THESAURUS
C81500
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL2111099
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
MESH
C518176
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
RXCUI
715869
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY RxNorm
CAS
147116-67-4
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
SMS_ID
300000023688
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID1057874
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
PUBCHEM
204108
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
WIKIPEDIA
MAROPITANT
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
MERCK INDEX
m7089
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY Merck Index
FDA UNII
4XE2T9H4DH
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
INN
8421
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
DRUG BANK
DB11427
Created by admin on Fri Dec 15 16:25:31 GMT 2023 , Edited by admin on Fri Dec 15 16:25:31 GMT 2023
PRIMARY
Related Record Type Details
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METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
MAJOR
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY