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Details

Stereochemistry EPIMERIC
Molecular Formula 2C18H22N2S.C4H6O6
Molecular Weight 746.978
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIMEPRAZINE TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.CC(CN(C)C)CN1C2=CC=CC=C2SC3=C1C=CC=C3.CC(CN(C)C)CN4C5=CC=CC=C5SC6=C4C=CC=C6

InChI

InChIKey=AJZJIYUOOJLBAU-CEAXSRTFSA-N
InChI=1S/2C18H22N2S.C4H6O6/c2*1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20;5-1(3(7)8)2(6)4(9)10/h2*4-11,14H,12-13H2,1-3H3;1-2,5-6H,(H,7,8)(H,9,10)/t;;1-,2-/m..1/s1

HIDE SMILES / InChI
Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
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

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

CNS Non-penetrant
1014
Curator's Comment: Trimeprazine concentrations in cerebrospinal fluid (CSF) and in venous blood were compared in three other children, measured by gas chromatography. No trimeprazine was detected in the cerebrospinal fluid

Approval Year

1959
138
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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.
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.
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.
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.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1461
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
P-gp
1650
 weak
CYP2D6
1891
 yes
yes (co-administration study)
Comment: A similar effect as for the CYP2D6 inhibitors was observed when aripiprazole was coadministered with alimemazine (TRIMEPRAZINE)
Sourcing

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
Possible role of phenothiazines in sudden infant death.
1979 Aug 18
Adverse cardiovascular response to oral trimeprazine in children.
1985 May 25
Patents

Patents

JP2003012514A
7

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 14:58:33 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:33 UTC 2023
Record UNII
362NW1LD6Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIMEPRAZINE TARTRATE
GREEN BOOK   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
NSC-757358
Code English
10-[3-(Dimethylamino)-2-methylpropyl]phenothiazine tartrate (2:1)
Systematic Name English
10H-PHENOTHIAZINE-10-PROPANAMINE N,N,.BETA.-TRIMETHYL-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE (2:1)
Common Name English
VALLERGAN
Brand Name English
NSC-17475
Code English
TRIMEPRAZINE HEMITARTRATE
Common Name English
TRIMEPRAZINE TARTRATE [USP MONOGRAPH]
Common Name English
THERALENE
Brand Name English
Alimemazine tartrate [WHO-DD]
Common Name English
REPELTIN
Brand Name English
ALIMEMAZINE HEMITARTRATE
Common Name English
ALIMEMAZINE HEMITARTRATE [EP MONOGRAPH]
Common Name English
METHYLPROMAZINE TARTRATE
Common Name English
TEMARIL
Brand Name English
TRIMEPRAZINE TARTRATE [USP IMPURITY]
Common Name English
ALIMEMAZINE TARTRATE
MART.   WHO-DD  
Common Name English
TRIMEPRAZINE TARTRATE [VANDF]
Common Name English
TRIMEPRAZINE TARTRATE [MI]
Common Name English
PANECTYL
Brand Name English
ALIMEMAZINE TARTRATE [MART.]
Common Name English
TRIMEPRAZINE TARTRATE [ORANGE BOOK]
Common Name English
ALIMEMAZINE TARTRATE [JAN]
Common Name English
TRIMEPRAZINE TARTRATE [GREEN BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
NCI_THESAURUS C267
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
Code System Code Type Description
PUBCHEM
441236
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
FDA UNII
362NW1LD6Z
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL829
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
DAILYMED
362NW1LD6Z
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
CAS
2015-31-8
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
NON-SPECIFIC STOICHIOMETRY
EPA CompTox
DTXSID3045560
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
MERCK INDEX
m11143
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY Merck Index
CAS
4330-99-8
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
ECHA (EC/EINECS)
224-368-9
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
NSC
17475
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
EVMPD
SUB00343MIG
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
NSC
757358
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
RXCUI
164308
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY RxNorm
RS_ITEM_NUM
1689001
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
CAS
41375-66-0
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
ALTERNATIVE
NCI_THESAURUS
C66638
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
SMS_ID
100000085662
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
DRUG BANK
DBSALT000183
Created by admin on Fri Dec 15 14:58:33 UTC 2023 , Edited by admin on Fri Dec 15 14:58:33 UTC 2023
PRIMARY
Related Record Type Details
Structure of TRIMEPRAZINE TARTRATE, (R)-
ENANTIOMER -> RACEMATE
Structure of TRIMEPRAZINE
PARENT -> SALT/SOLVATE
Structure of TRIMEPRAZINE TARTRATE, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of TRIMEPRAZINE SULFOXIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N-DESMETHYLTRIMEPRAZINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of PHENOTHIAZINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of TRIMEPRAZINE
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