TRIMEPRAZINE

US Previously Marketed

First approved in 1959

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H22N2S
Molecular Weight	298.446
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(CN(C)C)CN1C2=CC=CC=C2SC3=C1C=CC=C3

InChI

InChIKey=ZZHLYYDVIOPZBE-UHFFFAOYSA-N

InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C18H22N2S
Molecular Weight	298.446
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://rupharma.com/teraligen | https://www.ncbi.nlm.nih.gov/pubmed/7713167

Trimeprazine (also known as Alimemazine), a phenothiazine used as antipsychotic drug. This drug is used in Russia under brand name TERALIGEN and has anti-histamine, sedative, and anti-emetic (anti-nausea) effects. Teraligen is used to treat neurosis, depression and anxiety of different origins. It prevents and relieves allergic conditions, which cause pruritus and urticaria by blocking histamine produced by the body during an allergic reaction. Trimeprazine competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. Trimeprazine is not approved for use in humans in the United States. Nevertheless, combination of alimemazine and prednisolone (commonly sold under the brand name Temaril-P) is licensed as an antipruritic and antitussive in dogs.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7713167	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Neurosis 4 Sources: http://rupharma.com/teraligen/	Primary	Approved 8429	TERALIGEN Approved Use is a drug combining tranquilizing, vegetostabilizing, timoanaleptic, antihistamine and antispasmodic properties. Due to these properties Teraligen has a wide range of use. It is highly effective in treating mental, neurologic and somatic diseases such as neuroses of different origin, allergies, pruritus (itching) and urticaria. Teraligen is used to prevent and relieve allergic conditions as well as to treat sleep disorders.
Allergy 44 Sources: http://rupharma.com/teraligen/	Primary	Approved 8429	TERALIGEN Approved Use is a drug combining tranquilizing, vegetostabilizing, timoanaleptic, antihistamine and antispasmodic properties. Due to these properties Teraligen has a wide range of use. It is highly effective in treating mental, neurologic and somatic diseases such as neuroses of different origin, allergies, pruritus (itching) and urticaria. Teraligen is used to prevent and relieve allergic conditions as well as to treat sleep disorders.
Pruritus 29 Sources: http://rupharma.com/teraligen/	Primary	Approved 8429	TERALIGEN Approved Use is a drug combining tranquilizing, vegetostabilizing, timoanaleptic, antihistamine and antispasmodic properties. Due to these properties Teraligen has a wide range of use. It is highly effective in treating mental, neurologic and somatic diseases such as neuroses of different origin, allergies, pruritus (itching) and urticaria. Teraligen is used to prevent and relieve allergic conditions as well as to treat sleep disorders.
Urticaria 39 Sources: http://rupharma.com/teraligen/	Primary	Approved 8429	TERALIGEN Approved Use is a drug combining tranquilizing, vegetostabilizing, timoanaleptic, antihistamine and antispasmodic properties. Due to these properties Teraligen has a wide range of use. It is highly effective in treating mental, neurologic and somatic diseases such as neuroses of different origin, allergies, pruritus (itching) and urticaria. Teraligen is used to prevent and relieve allergic conditions as well as to treat sleep disorders.

C_max

Value	Dose	Co-administered	Analyte	Population
0.357 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2255680/	3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		TRIMEPRAZINE plasma	Homo sapiens population: UNKNOWN age: CHILD sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
2758 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2255680/	3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		TRIMEPRAZINE plasma	Homo sapiens population: UNKNOWN age: CHILD sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2255680/	3 mg/kg single, oral dose: 3 mg/kg route of administration: Oral experiment type: SINGLE co-administered:		TRIMEPRAZINE plasma	Homo sapiens population: UNKNOWN age: CHILD sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13662943/	unhealthy, adult n = 62 Health Status: unhealthy Condition: pruritic dermatoses Age Group: adult Sex: M+F Population Size: 62 Sources: https://pubmed.ncbi.nlm.nih.gov/13662943/	Disc. AE: Insomnia... AEs leading to discontinuation/dose reduction: Insomnia Sources: https://pubmed.ncbi.nlm.nih.gov/13662943/

AEs

AE	Significance	Dose	Population
Insomnia	Disc. AE	80 mg 1 times / day multiple, oral Highest studied dose Dose: 80 mg, 1 times / day Route: oral Route: multiple Dose: 80 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13662943/	unhealthy, adult n = 62 Health Status: unhealthy Condition: pruritic dermatoses Age Group: adult Sex: M+F Population Size: 62 Sources: https://pubmed.ncbi.nlm.nih.gov/13662943/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1461

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16277030/	weak
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19142178/	yes		yes (co-administration study) Comment: A similar effect as for the CYP2D6 inhibitors was observed when aripiprazole was coadministered with alimemazine (TRIMEPRAZINE) Sources: https://pubmed.ncbi.nlm.nih.gov/19142178/

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY573838	https://www.001chemical.com/chem/84-96-8
AbMole Bioscience	M3873	http://www.abmole.com/products/alimemazine-d6.html
Alsachim	3901	http://www.alsachim.com/product-C5206-glo.bal-view.html
BLD Pharm	BD155400	http://www.bldpharm.com/products/84-96-8.html
BOC Sciences	1346603-88-0	https://www.bocsci.com/alimemazine-d6-cas-1346603-88-0-item-482240.html
Chem Scene	CS-0012341	http://www.chemscene.com/84-96-8.html
ChemMol	30107593	http://www.chemmol.com/chemmol/30107593.html
ChemMol	49426092	http://www.chemmol.com/chemmol/49426092.html
ChemMol	99164394	http://www.chemmol.com/chemmol/99164394.html
Clearsynth	CS-CX-00070	https://www.clearsynth.com/en/CSCX00070.html
Clearsynth	CS-O-03235	https://www.clearsynth.com/en/CSO03235.html
Lab Network	LN01305673	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01305673
MedChem Express	HY-12752	https://www.medchemexpress.com/alimemazine.html
Molcore	MC573838	https://www.molcore.com/product/84-96-8
OChem	11988	http://www.ocheminc.com/index.php?act=psearch&pid=084T968
Smolecule	S545878	http://www.smolecule.com/products/s545878
Smolecule	S748715	https://www.smolecule.com/products/s748715
THE BioTek	bt-286870	https://www.thebiotek.com/product/inhibitors/bt-286870
THE BioTek	bt-295547	https://www.thebiotek.com/product/others/bt-295547
eNovation Chemicals	D674825	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674825

PubMed

Title	Date	PubMed
Possible role of phenothiazines in sudden infant death.	1979 Aug 18	89428
Adverse cardiovascular response to oral trimeprazine in children.	1985 May 25	3924159
[Antimycobacterial properties of phenothiazine type compounds].	1989 Mar	2502103
Trimeprazine tartrate and convulsions.	1995 Jan	7702180

Patents

Sample Use Guides

In Vivo Use Guide

Teraligen is administrated orally 3-4 times a day. Hypnotic effect for adults: initial dose is 5-10 mg/day. Anxiolytic effect: initial dose is 60-80 mg/day. Antipsychotic effect: initial dose 200-400 mg/day. Sedative effect for chidren: initial dose 2.5-5 mg/day Symptomatic treatment of allergic reactions: initial dose 5-20 mg/day Anxiolytic effect: initial dose 20-40 mg/day

Route of Administration: Oral

In Vitro Use Guide

Trimeprazine (TMP), a phenothiazine used as antipsychotic drug, was previously shown to induce a decrease in thyroid hormone serum levels in rats. Different mechanisms might be involved, mainly (i) a central mechanism, involving a reduction of thyroid-stimulating hormone (TSH) secretion; (ii) a peripheral mechanism, acting upon the synthesis of thyroid hormones, by inhibition of thyroperoxidase (TPO) or trapping of molecular iodine present in the thyroid gland. In vitro studies concerned TMP, and its three main metabolites: trimeprazine sulphoxide (TSO), N-desmethyl trimeprazine (NDT), and 3-hydroxy-trimeprazine (3-OHT). TMP and TSO expressed a high affinity for iodine in vitro, contrary to NDT, which did not complex iodine. Only 3-OHT inhibited TPO in vitro.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:34:46 UTC 2023` Edited by `admin` on `Fri Dec 15 17:34:46 UTC 2023`
Record UNII	76H78MJJ52
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TRIMEPRAZINE

Common Name

English

(±)-TRIMEPRAZINE

Common Name

English

TRIMEPRAZINE [VANDF]

Common Name

English

BAYER-1219

Code

English

ALIMEMAZINE [HSDB]

Common Name

English

alimemazine [INN]

Common Name

English

RP-6549

Code

English

Alimemazine [WHO-DD]

Common Name

English

10-(3-(DIMETHYLAMINO)-2-METHYLPROPYL)PHENOTHIAZINE

Systematic Name

English

(±)-ALIMEMAZINE

Common Name

English

10H-PHENOTHIAZINE-10-PROPANAMINE N,N,.BETA.-TRIMETHYL-

Common Name

English

ALIMEMAZINE

Official Name

English

DL-TRIMEPRAZINE

Common Name

English

METHYLPROMAZINE

Common Name

English

TRIMEPRAZINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29756