Polpharma European CDMO Partner & API Manufacturer since 1951

Find Halofuginone manufacturers, exporters & distributors on PharmaCompass

Halofuginone

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

1 NDC API

1 NDC API

PRICE INFORMATION

API Reference Price, API Exports, API Imports

INTERMEDIATES

1 Suppliers

1 Suppliers

API SUPPLIERS

API Suppliers

US DMFs Filed

CEP/COS Certifications

JDMFs Filed

EU WC

Listed Suppliers

API REF. PRICE (USD / KG)

API Market Place

INTERMEDIATES

DOSSIERS // FDF

USA (Orange Book)

Europe

Canada

Australia

South Africa

Uploaded Dossiers

GLOBAL SALES (USD Million)

U.S. Medicaid

Annual Reports

FDF Market Place

EXCIPIENTS

PATENTS & EXCLUSIVITIES

USFDA Orange Book Patents

USFDA Exclusivities

DIGITAL CONTENT

Blog #PharmaFlow

News

REF STANDARD

EDQM

USP

Other Listed Suppliers

SERVICES

Also known as: (+)-halofuginone, Halocur, Halofuginone, (+)-, 6-chloro-7-bromo-(+)-febrifugine, 55837-20-2, Halofuginon

Molecular Formula

C₁₆H₁₇BrClN₃O₃

Molecular Weight

414.7 g/mol

InChI Key

LVASCWIMLIKXLA-CABCVRRESA-N

FDA UNII

H84E4Y7HC9

halofuginone is a natural product found in Hydrangea febrifuga with data available.

1 2D Structure

Halofuginone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-bromo-6-chloro-3-[3-[(2R,3S)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one

2.1.2 InChI

InChI=1S/C16H17BrClN3O3/c17-11-6-13-10(5-12(11)18)16(24)21(8-20-13)7-9(22)4-14-15(23)2-1-3-19-14/h5-6,8,14-15,19,23H,1-4,7H2/t14-,15+/m1/s1

2.1.3 InChI Key

LVASCWIMLIKXLA-CABCVRRESA-N

2.1.4 Canonical SMILES

C1CC(C(NC1)CC(=O)CN2C=NC3=CC(=C(C=C3C2=O)Cl)Br)O

2.1.5 Isomeric SMILES

C1C[C@@H]([C@H](NC1)CC(=O)CN2C=NC3=CC(=C(C=C3C2=O)Cl)Br)O

2.2 Other Identifiers

2.2.1 UNII

H84E4Y7HC9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (+)-halofuginone

2. (+-)-trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3h)-quinazolinone

3. (+-)-trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3h)-quinazolinone Monohydrobromide

4. (-)-halofuginone

5. (-)-halofuginone Hydrobromide

6. 4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-((2r,3s)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-, Hydrochloride (1:1), Rel-

7. 4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-((2s,3r)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-, Hydrobromide (1:1)

8. 4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, Hydrobromide, Trans-(+-)-

9. 4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, Trans-, Mono(2-hydroxypropanoate)(salt)

10. 6-chloro-7-bromo-(+)-febrifugine

11. 6-chloro-7-bromofebrifugine

12. 7-bromo-6-chloro-3,3-(3-hydroxy-2-piperidyl)acetonyl-4(3h)-quinazolinone-hydrolactate

13. 7-bromo-6-chloro-3-(3-((2r,3s)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3h)-quinazolinone

14. 7-bromo-6-chloro-3-(3-((2s,3r)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3h)-quinazolinone

15. 7-bromo-6-chloro-3-(3-((2s,3r)-3-hydroxy-2-piperidyl)-2-oxo-propyl)quinazolin-4-one Hydrobromide

16. 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3h)-quinazolinone

17. 7-bromo-6-chlorofebrifugine

18. Cebegine

19. Chloro-bromofebrifugine

20. Chlorobromofebrifugine

21. Halagon

22. Halocur

23. Halofuginon

24. Halofuginone Hbr

25. Halofuginone Hcl

26. Halofuginone Hydrobromide

27. Halofuginone Hydrobromide, (-)-

28. Halofuginone Hydrochloride

29. Halofuginone Lactate

30. Halofuginone Monohydrobromide

31. Halofuginone Monohydrochloride

32. Halofuginone, (+)-

33. Halofuginone, (-)-

34. Halofunginone

35. Ru 19110

36. Ru-19110

37. Ru19110

38. Stenorol

39. Trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3h)-quinazolinone

2.3.2 Depositor-Supplied Synonyms

1. (+)-halofuginone

2. Halocur

3. Halofuginone, (+)-

4. 6-chloro-7-bromo-(+)-febrifugine

5. 55837-20-2

6. Halofuginon

7. Halofuginona

8. Halofuginonum

9. H84e4y7hc9

10. L31mm1385e

11. (+/-)-trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)-acetonyl)-4(3h)-quinazolinone

12. Halofuginone [inn:ban]

13. 7-bromo-6-chloro-3-(3-((2r,3s)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3h)-quinazolinone

14. Halofuginone ((2r,3s) And (2s,3r) Mixture)

15. Halofunginone

16. 7-bromo-6-chloro-3-{3-[(2r,3s)-3-hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3h)-one

17. 4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-((2r,3s)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-

18. 868851-54-1

19. Rel-7-bromo-6-chloro-3-(3-((2r,3s)-3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3h)-one

20. Halofuginone [inn]

21. Halofuginonum [inn-latin]

22. Halofuginona [inn-spanish]

23. Unii-l31mm1385e

24. Halocurtm

25. Ht-100

26. 7-bromo-6-chloro-3-[3-[(2r,3s)-3-hydroxy-2-piperidyl]-2-oxo-propyl]quinazolin-4-one

27. Hfg

28. Nsc713205

29. Halofuginone [mi]

30. Unii-h84e4y7hc9

31. Schembl9541147

32. Chembl1199540

33. Dtxsid301339439

34. Zinc5784191

35. S8144

36. Akos022185424

37. Ccg-268823

38. Db04866

39. (+-)-trans-7-brom-6-chlor-3-(3-(3-hydroxy-2-piperidyl)acetonyl-4(3h)-chinazolinon

40. (+-)-trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidyl)acetonyl-4(3h)-quinazolinone

41. Trans-7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-4(3h)-quinazolinone

42. 4(3h4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, Trans-(+/-)-

43. Halofuginone [ema Epar Veterinary]

44. Rel-7-bromo-6-chloro-3-[3-[(2r,3s)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-4(3h)-quinazolinone

45. Q4132745

46. (+/-)-trans-7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3h)-quinazolinone Hydrobromide

47. 4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-((2r,3s)-3-hydroxy-2-piperidinyl)-2-oxopropyl)-, Rel-

48. 4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, Trans-

49. 4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, Trans-(+-)-

50. 4(3h)-quinazolinone, 7-bromo-6-chloro-3-(3-(3-hydroxy-2-piperidinyl)-2-oxopropyl)-, Trans-(+/-)-

51. 7-bromo-6-chloro-3-{3-[(2r,3s)-3-hydroxypiperidin-2-yl]-2-oxopropyl}-3,4-dihydroquinazolin-4-one

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₁₇BrClN₃O₃
Molecular Weight	414.7 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	413.01418 g/mol
Monoisotopic Mass	413.01418 g/mol
Topological Polar Surface Area	82 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	533
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

For the treatment of scleroderma, cancer, and restenosis.

In newborn calves:

- Prevention of diarrhoea due to diagnosed Cryptosporidium parvum infection, in farms with history of cryptosporidiosis. Administration should start in the first 24 to 48 hours of age.

- Reduction of diarrhoea due to diagnosed Cryptosporidium parvum infection. Administration should start within 24 hours after the onset of diarrhoea. In both cases, the reduction of oocysts excretion has been demonstrated.

* In newborn calves:

Prevention of diarrhoea due to diagnosed Cryptosporidium parvum in farms with history of cryptosporidiosis.

Administration should start in the first 24 to 48 hours of age.

Reduction of diarrhoea due to diagnosed Cryptosporidium parvum.

Administration should start within 24 hours after the onset of diarrhoea.

In both cases, the reduction of oocyst excretion has been demonstrated.

In new born calves:

- Prevention of diarrhoea due to diagnosed Cryptosporidium parvum, in farms with history of cryptosporidiosis,

Administration should start in the first 24 to 48 hours of age

- Reduction of diarrhoea due to diagnosed Cryptosporidium parvum.

Administration should start within 24 hours after the onset of diarrhoea.

In both cases, the reduction of oocysts excretion has been demonstrated.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Halofuginone, a fully synthetic small molecule, is a potent and selective regulator of stromal cell activation, cell migration and Collagen type I synthesis, a process that has been identified as a 'master switch' in the body's tissue repair process.

5.2 MeSH Pharmacological Classification

Coccidiostats

Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals. (See all compounds classified as Coccidiostats.)

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

Angiogenesis Inhibitors

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels. (See all compounds classified as Angiogenesis Inhibitors.)

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

5.3 ATC Code

QP51AX08

5.4 Absorption, Distribution and Excretion

Absorption

Readily bioavailable and rapidly absorbed following oral administration.

5.5 Biological Half-Life

23.8 to 72.1 hours

5.6 Mechanism of Action

Halofuginone is a potent inhibitor of collagen a1(I) and matrix metalloproteinase 2 (MMP-2) gene expression. Halofuginone also suppresses extracellular matrix deposition and cell proliferation. The profound antitumoral effect of halofuginone is attributed to its combined inhibition of the tumor stromal support, vascularization, invasiveness, and cell proliferation.