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Details

Stereochemistry ACHIRAL
Molecular Formula C22H27N3O3S2
Molecular Weight 445.598
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METOPIMAZINE

SMILES

CS(=O)(=O)C1=CC=C2SC3=C(C=CC=C3)N(CCCN4CCC(CC4)C(N)=O)C2=C1

InChI

InChIKey=BQDBKDMTIJBJLA-UHFFFAOYSA-N
InChI=1S/C22H27N3O3S2/c1-30(27,28)17-7-8-21-19(15-17)25(18-5-2-3-6-20(18)29-21)12-4-11-24-13-9-16(10-14-24)22(23)26/h2-3,5-8,15-16H,4,9-14H2,1H3,(H2,23,26)

HIDE SMILES / InChI

Molecular Formula C22H27N3O3S2
Molecular Weight 445.598
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Metopimazine, a phenothiazine derivative, is a dopamine D2 receptor antagonist. It exerts its antiemetic effects via the chemoreceptor trigger zone. Metopimazine showed potent alpha-adrenergic blocking activity, showed histamine H1 antagonism, and induced palpebral ptosis. Metopimazine can occasionally be associated with orthostatic hypotension, which probably relates to its affinity for the α1-adrenoceptor. Therapeutic doses of metopimazine are likely to produce sedation and side-effects related to autonomic blockade. Metopimazine (Vogalene®) is indicated for the prevention and treatment of nausea and vomiting.

Approval Year

PubMed

PubMed

TitleDatePubMed
Ondansetron plus metopimazine compared with ondansetron plus metopimazine plus prednisolone as antiemetic prophylaxis in patients receiving multiple cycles of moderately emetogenic chemotherapy.
2001 Apr 1
Differential pulse cathodic voltammetric determination of floctafenine and metopimazine.
2007 Mar 12
Aprepitant: the evidence for its place in the prevention of chemotherapy-induced nausea and vomiting.
2007 Mar 31
Effect of iontophoresis and penetration enhancers on transdermal absorption of metopimazine.
2008 Dec
Development and validation of stability indicating HPLC and HPTLC methods for determination of sulpiride and mebeverine hydrochloride in combination.
2010 Sep

Sample Use Guides

Adults:Take 1 orodispersible tablet at the onset of symptoms. If symptoms persist or return, treatment may be continued to a maximum of 4 tablets (= 30 mg of metopimazine) per day. Children over 6 years:Take 1 orodispersible tablet at the onset of symptoms. If symptoms persist or return, treatment may be continued to a maximum of 2 tablets (= 15 mg of metopimazine) per day.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:53:37 UTC 2023
Edited
by admin
on Wed Jul 05 22:53:37 UTC 2023
Record UNII
238S75V9AV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METOPIMAZINE
INN   MART.   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
METOPIMAZINE [MI]
Common Name English
Metopimazine [WHO-DD]
Common Name English
1-[3-[2-(Methylsulfonyl)phenothiazin-10-yl]propyl]isonipecotamide
Systematic Name English
4-PIPERIDINECARBOXAMIDE, 1-(3-(2-(METHYLSULFONYL)-10H-PHENOTHIAZIN-10-YL)PROPYL)-
Systematic Name English
EXP 999
Code English
metopimazine [INN]
Common Name English
METOPIMAZINE [MART.]
Common Name English
METOPIMAZINE [USAN]
Common Name English
EXP-999
Code English
Classification Tree Code System Code
WHO-VATC QA04AD05
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
WHO-ATC A04AD05
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
NCI_THESAURUS C267
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
Code System Code Type Description
MERCK INDEX
M7496
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY Merck Index
MESH
C005260
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
RXCUI
29954
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY RxNorm
FDA UNII
238S75V9AV
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
WIKIPEDIA
METOPIMAZINE
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
NCI_THESAURUS
C81497
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
PUBCHEM
26388
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
CAS
14008-44-7
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
DRUG CENTRAL
1784
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID80161224
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
INN
2178
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
SMS_ID
100000092507
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
EVMPD
SUB08908MIG
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
237-818-4
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL398615
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
DRUG BANK
DB13591
Created by admin on Wed Jul 05 22:53:37 UTC 2023 , Edited by admin on Wed Jul 05 22:53:37 UTC 2023
PRIMARY
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TARGET -> INHIBITOR
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ACTIVE MOIETY