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2D Structure
Also known as: 1257-78-9, Prochlorperazine edisylate, usp, Prochlorperazine ethanedisulfonate, Pg20w5vqzs, Nsc-757299, Prochlorperazine edisylate salt
Molecular Formula
C22H30ClN3O6S3
Molecular Weight
564.1  g/mol
InChI Key
SWOUGRBFXFILIB-UHFFFAOYSA-N
FDA UNII
PG20W5VQZS

A phenothiazine antipsychotic used principally in the treatment of NAUSEA; VOMITING; and VERTIGO. It is more likely than CHLORPROMAZINE to cause EXTRAPYRAMIDAL DISORDERS. (From Martindale, The Extra Pharmacopoeia, 30th ed, p612)
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine;ethane-1,2-disulfonic acid
2.1.2 InChI
InChI=1S/C20H24ClN3S.C2H6O6S2/c1-22-11-13-23(14-12-22)9-4-10-24-17-5-2-3-6-19(17)25-20-8-7-16(21)15-18(20)24;3-9(4,5)1-2-10(6,7)8/h2-3,5-8,15H,4,9-14H2,1H3;1-2H2,(H,3,4,5)(H,6,7,8)
2.1.3 InChI Key
SWOUGRBFXFILIB-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1CCN(CC1)CCCN2C3=CC=CC=C3SC4=C2C=C(C=C4)Cl.C(CS(=O)(=O)O)S(=O)(=O)O
2.2 Other Identifiers
2.2.1 UNII
PG20W5VQZS
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Compazine

2. Edisylate Salt, Prochlorperazine

3. Edisylate, Prochlorperazine

4. Maleate, Prochlorperazine

5. Prochlorperazine

6. Prochlorperazine Edisylate Salt

7. Prochlorperazine Maleate

8. Salt, Prochlorperazine Edisylate

2.3.2 Depositor-Supplied Synonyms

1. 1257-78-9

2. Prochlorperazine Edisylate, Usp

3. Prochlorperazine Ethanedisulfonate

4. Pg20w5vqzs

5. Nsc-757299

6. Prochlorperazine Edisylate Salt

7. Prochlorperazine Edisylate [usp]

8. 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine 1,2-ethanedisulfonate (1:1)

9. Compazine Syrup

10. 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine;ethane-1,2-disulfonic Acid

11. Phenothiazine, 2-chloro-10-(3-(1-methyl-4-piperazinyl)propyl)-, Ethanedisulfonate

12. Compazine Injection

13. 10h-phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-, 1,2-ethanedisulfonate (1:1)

14. Prochlorperazine Edisylate (usp)

15. Mls001148133

16. Prochlorperazine Ethane Disulfonate

17. Smr000653454

18. Einecs 215-019-1

19. Unii-pg20w5vqzs

20. 2-chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine 1,2-ethanedisulfonate (1:1)

21. Compazine Syrup (tn)

22. Prochlorperazine Edisilate

23. 2-chloro-10-(3-(1-methyl-4-piperazinyl)propyl)phenothiazine Edisylate

24. Prochlorperazineedisylate,usp

25. Schembl40855

26. Spectrum1500505

27. Chembl1201154

28. Dtxsid4074483

29. Hms501e15

30. Hms1920l08

31. Hms2092c09

32. Hms2234e05

33. Hms3372m12

34. Pharmakon1600-01500505

35. Bcp15822

36. Ccg-39235

37. Mfcd00801002

38. Nsc665801

39. Nsc757299

40. Akos030228220

41. Nsc 757299

42. Nsc-665801

43. Ncgc00094768-01

44. Ncgc00094768-02

45. Ncgc00094768-03

46. Prochlorperazine Ethanedisulphonate

47. 1,2-ethanedisulfonic Acid, Compd. With 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-10h-phenothiazine (1:1)

48. As-60444

49. Ethane-1,2-disulphonic Acid, Compound With 2-chloro-10-(3-(4-methylpiperazin-1-yl)propyl)-10h-phenothiazine (1:1)

50. Prochlorperazine Edisilate [mart.]

51. Prochlorperazine Edisylate [vandf]

52. Prochlorperazine Edisylate [who-dd]

53. D02609

54. Prochlorperazine Edisylate [green Book]

55. Prochlorperazine Edisylate [orange Book]

56. Prochlorperazine Edisylate [usp Monograph]

57. Sr-05000001704

58. Sr-05000001704-1

59. Q27286529

60. Phenothiazine, 2-chloro-10-(3-(1-methyl-4-piperazinyl)propyl)-, Ethanedisulphonate

61. 10h-phenothiazine, 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)-, 1,2-ethanedisulphonate (1:1)

62. 2-chloro-10-(3-(4-methyl-1-piperazinyl)propyl)phenothiazine 1,2-ethanedisulphonate (1:1)

63. 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]-10h-phenothiazine; Ethane-1,2-disulfonic Acid

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 564.1 g/mol
Molecular Formula C22H30ClN3O6S3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count7
Exact Mass563.0985269 g/mol
Monoisotopic Mass563.0985269 g/mol
Topological Polar Surface Area161 Ų
Heavy Atom Count35
Formal Charge0
Complexity668
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameProchlorperazine edisylate
Drug LabelProchlorperazine edisylate, 2-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine 1,2-ethanedisulfonate (1:1), has the following structural formula:C20H24ClN3SC2H6O6S2 MW 564.14Prochlorperazine Edis...
Active IngredientProchlorperazine edisylate
Dosage FormInjectable
RouteInjection
Strengtheq 5mg base/ml
Market StatusPrescription
CompanyBedford; Emcure Pharms; Hikma Maple

2 of 2  
Drug NameProchlorperazine edisylate
Drug LabelProchlorperazine edisylate, 2-Chloro-10-[3-(4-methyl-1-piperazinyl)propyl]phenothiazine 1,2-ethanedisulfonate (1:1), has the following structural formula:C20H24ClN3SC2H6O6S2 MW 564.14Prochlorperazine Edis...
Active IngredientProchlorperazine edisylate
Dosage FormInjectable
RouteInjection
Strengtheq 5mg base/ml
Market StatusPrescription
CompanyBedford; Emcure Pharms; Hikma Maple

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antiemetics

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


Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)


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.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Phenothiazines [CS]; Phenothiazine [EPC]