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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
Options for the prevention and management of acute chemotherapy-induced nausea and vomiting in children.
2003
A pilot study of ondansetron plus metopimazine vs. ondansetron monotherapy in children receiving highly emetogenic chemotherapy: a Bayesian randomized serial N-of-1 trials design.
2006 Mar
Randomized, double-blind trial comparing the antiemetic effect of tropisetron plus metopimazine with tropisetron plus placebo in patients receiving multiple cycles of multiple-day cisplatin-based chemotherapy.
2007 Apr
Percutaneous absorption of metopimazine and effect of cyclodextrins.
2008 May

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 Fri Dec 15 15:23:12 GMT 2023
Edited
by admin
on Fri Dec 15 15:23:12 GMT 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 Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
WHO-ATC A04AD05
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
NCI_THESAURUS C267
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
Code System Code Type Description
MERCK INDEX
m7496
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY Merck Index
MESH
C005260
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
RXCUI
29954
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY RxNorm
FDA UNII
238S75V9AV
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
WIKIPEDIA
METOPIMAZINE
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
NCI_THESAURUS
C81497
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
PUBCHEM
26388
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
CAS
14008-44-7
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
DRUG CENTRAL
1784
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID80161224
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
INN
2178
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
SMS_ID
100000092507
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
EVMPD
SUB08908MIG
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
237-818-4
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL398615
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
DRUG BANK
DB13591
Created by admin on Fri Dec 15 15:23:12 GMT 2023 , Edited by admin on Fri Dec 15 15:23:12 GMT 2023
PRIMARY
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