U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

SMILES

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=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 C6H8O7
Molecular Weight 192.1235
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

1.16994238E12
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:27:08 UTC 2023
Edited
by admin
on Sat Dec 16 05:27:08 UTC 2023
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)
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID20235458
Created by admin on Sat Dec 16 05:27:08 UTC 2023 , Edited by admin on Sat Dec 16 05:27:08 UTC 2023
PRIMARY
FDA UNII
19364RWW06
Created by admin on Sat Dec 16 05:27:08 UTC 2023 , Edited by admin on Sat Dec 16 05:27:08 UTC 2023
PRIMARY
PUBCHEM
11319809
Created by admin on Sat Dec 16 05:27:08 UTC 2023 , Edited by admin on Sat Dec 16 05:27:08 UTC 2023
PRIMARY
SMS_ID
300000023723
Created by admin on Sat Dec 16 05:27:08 UTC 2023 , Edited by admin on Sat Dec 16 05:27:08 UTC 2023
PRIMARY
CAS
862543-54-2
Created by admin on Sat Dec 16 05:27:08 UTC 2023 , Edited by admin on Sat Dec 16 05:27:08 UTC 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY