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NCGC00024846-08

NCGC00024846-08

Synopsis, Chemistry

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Also known as: Guanabenz, 5051-62-7, Hydrazinecarboximidamide, 2-[(2,6-dichlorophenyl)methylene]-, (e)-, Dsstox_cid_25666, Dsstox_rid_81042, Dsstox_gsid_45666

Molecular Formula

C₈H₈Cl₂N₄

Molecular Weight

231.08 g/mol

InChI Key

WDZVGELJXXEGPV-UHFFFAOYSA-N

An alpha-2 selective adrenergic agonist used as an antihypertensive agent.

1 2D Structure

NCGC00024846-08

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[(2,6-dichlorophenyl)methylideneamino]guanidine

2.1.2 InChI

InChI=1S/C8H8Cl2N4/c9-6-2-1-3-7(10)5(6)4-13-14-8(11)12/h1-4H,(H4,11,12,14)

2.1.3 InChI Key

WDZVGELJXXEGPV-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C(=C1)Cl)C=NN=C(N)N)Cl

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 2,6 Dichlorobenzylideneaminoguanidine

2. 2,6-dichlorobenzylideneaminoguanidine

3. Acetate Wyeth-ayerst, Guanabenz

4. Acetate, Guanabenz

5. Br 750

6. Br-750

7. Br750

8. Guanabenz

9. Guanabenz Acetate

10. Guanabenz Acetate Wyeth-ayerst

11. Guanabenz Monoacetate

12. Monoacetate, Guanabenz

13. Wy 8678

14. Wy-8678

15. Wy8678

16. Wyeth Ayerst Of Guanabenz Acetate

17. Wyeth-ayerst Of Guanabenz Acetate

18. Wytensin

2.2.2 Depositor-Supplied Synonyms

1. Guanabenz

2. 5051-62-7

3. Hydrazinecarboximidamide, 2-[(2,6-dichlorophenyl)methylene]-, (e)-

4. Dsstox_cid_25666

5. Dsstox_rid_81042

6. Dsstox_gsid_45666

7. Cas-5051-62-7

8. Ncgc00024846-03

9. Spectrum_000843

10. Prestwick0_000096

11. Prestwick1_000096

12. Spectrum2_001114

13. Spectrum3_000445

14. Spectrum4_000567

15. Kbiogr_000974

16. Kbioss_001323

17. Divk1c_000010

18. Spbio_001248

19. Spbio_001991

20. Chembl1313657

21. Dtxsid6045666

22. Kbio1_000010

23. Kbio2_001323

24. Kbio2_003891

25. Kbio2_006459

26. Kbio3_001310

27. Ninds_000010

28. Hms2233d12

29. Hms3370a17

30. Bcp30851

31. Tox21_110932

32. Akos017264577

33. Tox21_110932_1

34. Zinc242701441

35. Db00629

36. 2,6-dichlorobenzaldehyde Guanylhydrazone

37. Mrf-0000008

38. Ncgc00024846-08

39. Db-051784

40. Ft-0635524

41. Guanabenzum;wy-8678; Wy 8678; Wy8678

42. N-(2,6-dichlorobenzylidene)-n'-amidino Hydrazine

43. Sr-01000721838

44. Sr-01000721838-5

45. Q27164730

2.3 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₈H₈Cl₂N₄
Molecular Weight	231.08 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	230.0126017 g/mol
Monoisotopic Mass	230.0126017 g/mol
Topological Polar Surface Area	76.8 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	228
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	1
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For management of High blood pressure

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Guanabenz, a centrally acting α-2 adrenergic agonist, is indicated for treatment of hypertension.

5.2 MeSH Pharmacological Classification

Adrenergic alpha-2 Receptor Agonists

Compounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Agonists.)

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

5.3 Absorption, Distribution and Excretion

Absorption

Approximately 75% absorbed from gastrointestinal tract

5.4 Metabolism/Metabolites

Hepatic

5.5 Biological Half-Life

6 hours.

5.6 Mechanism of Action

Guanabenz's antihypertensive effect is thought to be due to central alpha-adrenergic stimulation, which results in a decreased sympathetic outflow to the heart, kidneys, and peripheral vasculature in addition to a decreased systolic and diastolic blood pressure and a slight slowing of pulse rate. Chronic administration of guanabenz also causes a decrease in peripheral vascular resistance.