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ACTIVE PHARMA INGREDIENTS

4 VMF, $ API Reference Price

4 VMF
$ API Reference Price

Synopsis

ACTIVE PHARMA INGREDIENTS

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$ 52

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Also known as: Piperazine hydrochloride, 7542-23-6, Piperazine, monohydrochloride, Piperazine hcl, 6094-40-2, Piperazine;hydrochloride

Molecular Formula

C₄H₁₁ClN₂

Molecular Weight

122.60 g/mol

InChI Key

MSQACBWWAIBWIC-UHFFFAOYSA-N

FDA UNII

7N36JHA4P6

An anti-nematodal agent effective against the intestinal nematodes ASCARIS LUMBRICOIDES (roundworm) and ENTEROBIUS VERMICULARIS (pinworm, threadworm). It produces a neuromuscular block leading to flaccid muscle paralysis in susceptible worms, which are then dislodged from the gut and expelled in feces.

1 2D Structure

Piperazine Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

piperazine;hydrochloride

2.1.2 InChI

InChI=1S/C4H10N2.ClH/c1-2-6-4-3-5-1;/h5-6H,1-4H2;1H

2.1.3 InChI Key

MSQACBWWAIBWIC-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CNCCN1.Cl

2.2 Other Identifiers

2.2.1 UNII

7N36JHA4P6

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1,4 Diazacyclohexane

2. 1,4 Piperazine

3. 1,4-diazacyclohexane

4. 1,4-piperazine

5. Piperazine

6. Piperazine Diacetate

7. Piperazine Dihydrochloride

8. Piperazine Hexahydrate

9. Piperazine Hydrate

10. Piperazine Hydrobromide

11. Piperazine Hydrochloride

12. Piperazine Phosphate

13. Piperazine Phosphate (1:1)

14. Piperazine Phosphate Anhydrous

15. Piperazine Salt

16. Piperazine Sulfate

17. Piperazine Tartrate

18. Piperazine Tartrate (1:1), (r-(r*,r*))-isomer

19. Piperazine Tartrate, (r-(r*,r*))-isomer

20. Piperazinium Oleate

21. Pripsen

2.3.2 Depositor-Supplied Synonyms

1. Piperazine Hydrochloride

2. 7542-23-6

3. Piperazine, Monohydrochloride

4. Piperazine Hcl

5. 6094-40-2

6. Piperazine;hydrochloride

7. Unii-7n36jha4p6

8. 7n36jha4p6

9. Piperazine Hydrochloride Hydrate

10. Einecs 231-422-5

11. Dtxsid2064739

12. Piperazine, Hydrochloride (1:1)

13. Einecs 228-042-7

14. Purina Liquid Dog Wormer

15. Schembl7690

16. Piperazine Hydrochloride Salt

17. Dtxcid1047782

18. Piperazine Hydrochloric Acid Salt

19. 8006-71-1

20. Db-309178

21. Ns00081249

22. Ns00082816

23. Piperazine Monohydrochloride [green Book]

24. A845331

25. Q27268592

2.3.3 Other Synonyms

1. Piperazine Hydrochloride

2. Piperazine Dihydrochloride

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₄H₁₁ClN₂
Molecular Weight	122.60 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	24.1
Heavy Atom Count	7
Formal Charge	0
Complexity	26.5
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Therapeutic Uses

Antinematodal Agents

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

MEDICATION (VET): HIGHLY EFFECTIVE AS ANTHELMINTIC FOR REMOVAL OF LARGE ROUNDWORMS, ASCARIDS, FROM POULTRY AND SWINE NODULAR WORMS (OESOPHAGOSTOMUM SPP) FROM SWINE, SHEEP AND CATTLE; AND PINWORMS AND SMALL STRONGYLES IN HORSES.

Spencer, E.Y. Guide to the Chemicals Used in Crop Protection. 6th ed. Publication 1093, Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1973., p. 416

CLINICALLY, THE DRUG IS HIGHLY EFFECTIVE AGAINST BOTH ASCARIS LUMBRICOIDES & ENTEROBIUS (OXYURIS) VERMICULARIS. A LARGE NUMBER OF SUBSTITUTED PIPERAZINE DERIVATIVES EXHIBIT ANTIHELMINTIC ACTIVITY, BUT APART FROM DIETHYLCARBAMAZINE NONE HAS FOUND A PLACE IN HUMAN THERAPEUTICS.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 966

PIPERAZINE PREPN ARE ALWAYS GIVEN ORALLY. PRIOR FASTING OR SUMPPLEMENTARY TREATMENT WITH CATHARTICS OR ENEMAS IS UNECESSARY.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 967

For more Therapeutic Uses (Complete) data for PIPERAZINE HYDROCHLORIDE (9 total), please visit the HSDB record page.

4.2 Drug Warning

VET: VAPORS & SKIN OR EYE CONTACT WITH CONCN MATERIAL MUST BE AVOIDED.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 460

Adequate and well-controlled studies in humans have not been done. Piperazine has been used without apparent adverse effects during pregnancy. In three cases of first trimester exposures to piperazine by pregnant women, no malformations were seen in the fetuses. However, because a study showed that orally administered piperazine undergoes partial conversion to a potentially carcinogenic nitrosamine derivative, it is recommended that piperazine be given to pregnant women only if clearly indicated and then only if alternative drugs are not available.

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 2960

PIPERAZINE IS CONTRAINDICATED IN PATIENTS A WITH HISTORY OF EPILEPSY. NEUROTOXIC EFFECTS HAVE OCCURRED IN INDIVIDUALS WITH RENAL DYSFUNCTION BECAUSE URINARY EXCRETION IS MAIN ROUTE OF ELIMINATION OF THE DRUG.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 967

There has been a report of cross-reactivity between piperazine and ethylenediamine, a substance used as a stabilizer in topical creams. Piperazine can cause a contact allergy that could be life-threatening in a person who has been sensitized to ethylenediamine either by topical application or by occupational exposure. Although rare, adverse dermatologic problems also may occur due to the cross-sensitivity of these two medications.

USP Convention. USPDI-Drug Information for the Health Care Professional. 14th ed. Volume I. Rockville, MD: United States Pharmacopeial Convention, Inc., 1994. (Plus Updates)., p. 2960

It is contraindicated in patients with renal or hepatic insufficiency or epilepsy. /Piperazine citrate/

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1754

4.3 Minimum/Potential Fatal Human Dose

2= SLIGHTLY TOXIC; PROBABLE ORAL LETHAL DOSE (HUMAN) 5-15 G/KG, BETWEEN 1 PINT & 1 QT FOR 70 KG PERSON (150 LB).

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-390

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antinematodal Agents

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)

5.2 Absorption, Distribution and Excretion

NOT ABSORBED THROUGH SKIN IN ACUTE TOXIC AMT.

Spencer, E.Y. Guide to the Chemicals Used in Crop Protection. 6th ed. Publication 1093, Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1973., p. 416

5.3 Metabolism/Metabolites

PIPERAZINE IS PARTLY METABOLIZED IN AN UNKNOWN MANNER IN MAN, SINCE ONLY 15% OF 2 G DOSES ARE EXCRETED UNCHANGED. /PIPERAZINE/

WILLIAMS RT; 2ND ED, CHAPMAN AND HALL, 614 (1959)

5.4 Mechanism of Action

ANTHELMINTIC ACTION IS BY NARCOTIZING AND IMMOBILIZING INTERNAL PARASITES.

Spencer, E.Y. Guide to the Chemicals Used in Crop Protection. 6th ed. Publication 1093, Research Institute, Agriculture Canada, Ottawa, Canada: Information Canada, 1973., p. 416

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