TRIMEPRAZINE

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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	Antagonist 2,778

Conditions

Condition	Modality	Highest Phase	Product
Neurosis 4	Primary	Approved 8,429	TERALIGEN
Allergy 44	Primary	Approved 8,429	TERALIGEN
Pruritus 29	Primary	Approved 8,429	TERALIGEN
Urticaria 39	Primary	Approved 8,429	TERALIGEN

C_max

Value	Dose	Co-administered	Analyte	Population
0.357 μM	3 mg/kg single, oral		TRIMEPRAZINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
2758 μM × h	3 mg/kg single, oral		TRIMEPRAZINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.8 h	3 mg/kg single, oral		TRIMEPRAZINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
80 mg 1 times / day multiple, oral Highest studied dose	unhealthy, adult	Disc. AE: Insomnia...

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AEs

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AE	Significance	Dose	Population
Insomnia	Disc. AE	80 mg 1 times / day multiple, oral Highest studied dose	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1,461

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1,650	inhibitor 3,277	weak
CYP2D6 1,891	inhibitor 3,277	yes		yes (co-administration study)

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Possible role of phenothiazines in sudden infant death.	1979 Aug 18	89428
Trimeprazine tartrate and convulsions.	1995 Jan	7702180

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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.