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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

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
The pharmacokinetics of maropitant, a novel neurokinin type-1 receptor antagonist, in dogs.
2007 Aug
The neurokinin-1 antagonist activity of maropitant, an antiemetic drug for dogs, in a gerbil model.
2007 Aug
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
Efficacy of maropitant for treatment and prevention of emesis caused by intravenous infusion of cisplatin in dogs.
2007 Jan
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
[New antiemetics: maropitant citrate].
2007 May 15
Efficacy of maropitant for preventing vomiting associated with motion sickness in dogs.
2007 Sep 29
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
Comparative efficacy of maropitant and selected drugs in preventing emesis induced by centrally or peripherally acting emetogens in dogs.
2008 Dec
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
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
Effect of refrigeration of the antiemetic Cerenia (maropitant) on pain on injection.
2009 Fall
Acute pancreatitis attributed to dietary indiscretion in a female mixed breed canine.
2010 Feb
Acute vomiting in cats: rational treatment selection.
2010 Mar
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

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.
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
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WHO-VATC QA04AD90
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CFR 21 CFR 522.1315
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NCI_THESAURUS C267
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Code System Code Type Description
DAILYMED
4XE2T9H4DH
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NCI_THESAURUS
C81500
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ChEMBL
CHEMBL2111099
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MESH
C518176
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RXCUI
715869
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CAS
147116-67-4
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SMS_ID
300000023688
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EPA CompTox
DTXSID1057874
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PUBCHEM
204108
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WIKIPEDIA
MAROPITANT
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MERCK INDEX
m7089
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FDA UNII
4XE2T9H4DH
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INN
8421
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DRUG BANK
DB11427
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