PIPAMAZINE

First approved in 1959

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H24ClN3OS
Molecular Weight	401.953
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1CCN(CCCN2C3=CC(Cl)=CC=C3SC4=C2C=CC=C4)CC1

InChI

InChIKey=OSJJYEUEJRVVOD-UHFFFAOYSA-N

InChI=1S/C21H24ClN3OS/c22-16-6-7-20-18(14-16)25(17-4-1-2-5-19(17)27-20)11-3-10-24-12-8-15(9-13-24)21(23)26/h1-2,4-7,14-15H,3,8-13H2,(H2,23,26)

HIDE SMILES / InChI

Molecular Formula	C21H24ClN3OS
Molecular Weight	401.953
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15983284 | https://pubchem.ncbi.nlm.nih.gov/compound/6761

PIPAMAZINE is a drug of the phenothiazine class formerly used as an antiemetic. It was eventually withdrawn from the US market in 1969, after reports of hepatotoxicity (liver injury).

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vomiting and nausea 2

Doses

Dose	Population	Adverse events
100 mg single, oral Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	unhealthy, 2 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 2 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	Other AEs: Stupor, Cyanosis... Other AEs: Stupor Cyanosis (slight) Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164
100 mg single, oral Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	unhealthy, 2.5 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 2.5 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	Other AEs: Coma... Other AEs: Coma Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165
125 mg single, oral Overdose Dose: 125 mg Route: oral Route: single Dose: 125 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	unhealthy, 2.5 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 2.5 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	Other AEs: Coma... Other AEs: Coma Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165
100 mg single, oral (max) Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	unhealthy, 3 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 3 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	Other AEs: Comatose, Constricted pupils... Other AEs: Comatose Constricted pupils Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164
20 mg single, oral (max) Overdose Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	unhealthy, 3 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 3 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	Other AEs: Depression central nervous system... Other AEs: Depression central nervous system (mild) Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164
25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	unhealthy, 3 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 3 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	Other AEs: Ataxia, Vision loss... Other AEs: Ataxia Vision loss Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165
5 mg 4 times / day multiple, oral Recommended Dose: 5 mg, 4 times / day Route: oral Route: multiple Dose: 5 mg, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	unhealthy Health Status: unhealthy Condition: Morning sickness Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164

AEs

AE	Significance	Dose	Population
Stupor		100 mg single, oral Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	unhealthy, 2 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 2 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164
Cyanosis	slight	100 mg single, oral Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	unhealthy, 2 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 2 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164
Coma		100 mg single, oral Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	unhealthy, 2.5 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 2.5 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165
Coma		125 mg single, oral Overdose Dose: 125 mg Route: oral Route: single Dose: 125 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	unhealthy, 2.5 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 2.5 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165
Comatose		100 mg single, oral (max) Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	unhealthy, 3 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 3 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164
Constricted pupils		100 mg single, oral (max) Overdose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	unhealthy, 3 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 3 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164
Depression central nervous system	mild	20 mg single, oral (max) Overdose Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164	unhealthy, 3 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 3 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.164
Ataxia		25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	unhealthy, 3 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 3 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165
Vision loss		25 mg single, oral Overdose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165	unhealthy, 3 n = 1 Health Status: unhealthy Condition: Morning sickness Age Group: 3 Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13807442 Page: p.165

Sourcing

Vendor/Aggregator	ID	URL
AAA Chemistry	AR-1B9111
ABI Chem	AC1L1N8V
ABI Chem	AC1Q5J13
BOC Sciences	84-04-8	https://www.bocsci.com/pipamazine-cas-84-04-8-item-181652.html
ChemTik	CTK8D7913
Compound Cloud	6761
Kingston Chemistry	KST-1A9294
LGC Standards	LGCFOR1603.00	https://www.lgcstandards.com/US/en/p/LGCFOR1603.00
MuseChem	R015295
NovoSeek	6761
Smolecule	S579699	https://www.smolecule.com/products/s579699
THE BioTek	bt-365044	https://www.thebiotek.com/product/others/bt-365044
ZINC	ZINC000000538183	http://zinc15.docking.org/substances/ZINC000000538183
eMolecules	110048163

PubMed

Title	Date	PubMed
The antisialogogue effect of phenothiazine derivatives: comparison of pecazine, perphenazine, fluphenazine, thiopropazate, pipamazine and triflupromazine.	1960 Feb	13817061
Potentiation of thiopentone anaesthesia. Comparison of promethazine, chlorpromazine, perphenazine, fluphenazine, thiopropazate, pipamazine and triflupromazine.	1960 Sep	13723253
Pipamazine, a new antiemetic.	1960 Sep	13838459

Sample Use Guides

In Vivo Use Guide

The usual adult dose is 5 mg (1 cc) intramuscularly or orally every 4 to 6 hours as needed.

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:05:51 GMT 2023` Edited by `admin` on `Fri Dec 15 15:05:51 GMT 2023`
Record UNII	653552FH1N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIPAMAZINE

Official Name

English

PIPAMAZINE [MI]

Common Name

English

10-(3-(4-CARBAMOYLPIPERIDINO)PROPYL)-2-CHLOROPHENOTHIAZINE

Systematic Name

English

Pipamazine [WHO-DD]

Common Name

English

pipamazine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C267