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Chemistry

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Also known as: Thiethylperazine dimalate, 52239-63-1, Torecan, Thietylperazine malate, Hp46xk89xb, 2-(ethylthio)-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine malate (1:2)

Molecular Formula

C₃₀H₄₁N₃O₁₀S₂

Molecular Weight

667.8 g/mol

InChI Key

GTHHLZDYRHLACN-UHFFFAOYSA-N

FDA UNII

HP46XK89XB

A dopamine antagonist that is particularly useful in treating the nausea and vomiting associated with anesthesia, mildly emetic cancer chemotherapy agents, radiation therapy, and toxins. This piperazine phenothiazine does not prevent vertigo or motion sickness. (From AMA Drug Evaluations Annual, 1994, p457)

1 2D Structure

Thiethylperazine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-ethylsulfanyl-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine;2-hydroxybutanedioic acid

2.1.2 InChI

InChI=1S/C22H29N3S2.2C4H6O5/c1-3-26-18-9-10-22-20(17-18)25(19-7-4-5-8-21(19)27-22)12-6-11-24-15-13-23(2)14-16-24;2*5-2(4(8)9)1-3(6)7/h4-5,7-10,17H,3,6,11-16H2,1-2H3;2*2,5H,1H2,(H,6,7)(H,8,9)

2.1.3 InChI Key

GTHHLZDYRHLACN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CCSC1=CC2=C(C=C1)SC3=CC=CC=C3N2CCCN4CCN(CC4)C.C(C(C(=O)O)O)C(=O)O.C(C(C(=O)O)O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

HP46XK89XB

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Norzine

2. Thiethylperazine

3. Thiethylperazine Maleate (2:1)

4. Torecan

2.3.2 Depositor-Supplied Synonyms

1. Thiethylperazine Dimalate

2. 52239-63-1

3. Torecan

4. Thietylperazine Malate

5. Hp46xk89xb

6. 2-(ethylthio)-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine Malate (1:2)

7. 2-ethylsulfanyl-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine;2-hydroxybutanedioic Acid

8. Thiethylperazine Malate (jan)

9. Norzine Ampuls

10. Thiethylperazine Malate [jan]

11. 10h-phenothiazine, 2-(ethylthio)-10-(3-(4-methyl-1-piperazinyl)propyl)-, 2-hydroxy-1,4-butanedioate (1:2)

12. Malic Acid, Compound With 2-(ethylthio)-10-[3-(4-methylpiperazin-1-yl)propyl]-10h-phenothiazine (2:1)

13. Ncgc00017115-01

14. Cas-52239-63-1

15. Unii-hp46xk89xb

16. Thiethylperazine Malate [usp]

17. Malic Acid, Compound With 2-(ethylthio)-10-(3-(4-methylpiperazin-1-yl)propyl)-10h-phenothiazine (2:1)

18. Einecs 257-780-2

19. Torecan (tn)

20. Dsstox_cid_25586

21. Dsstox_rid_80982

22. Dsstox_gsid_45586

23. Schembl466913

24. Chembl2359670

25. Dtxsid1045586

26. Hms1571e18

27. Hms2098e18

28. Hms3715e18

29. Tox21_110784

30. Thiethylperazine Dimalate [mi]

31. Ccg-221068

32. Thiethylperazine Malate [mart.]

33. Thiethylperazine Malate [orange Book]

34. D02610

35. Sr-01000841243

36. Sr-01000841243-2

37. Q27280042

38. 2-(ethylthio)-10-[3-(4-methyl-1-piperazinyl)propyl]-10h-phenothiazine Hydroxybutanedioate (1:2)

39. Butanedioic Acid, Hydroxy-, Compd. With 2-(ethylthio)-10-(3-(4-methyl-1-piperazinyl)propyl)-10h-phenothiazine (2:1)

40. Hydroxybutanedioic Acid Compd. With 2-(ethylthio)-10-[3-(4-methyl-1-piperazinyl)propyl]-10h-phenothiazine (2:1)

2.4 Create Date

2006-11-22

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₄₁N₃O₁₀S₂
Molecular Weight	667.8 g/mol
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	12
Exact Mass	667.22333686 g/mol
Monoisotopic Mass	667.22333686 g/mol
Topological Polar Surface Area	250 Å²
Heavy Atom Count	45
Formal Charge	0
Complexity	584
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

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