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Halofuginone Lactate

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Chemistry

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Also known as: 82186-71-8, Schembl2562822, Chembl1162014, Ac-30636, 7-bromo-6-chloro-3-(3-((2s,3r)-3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3h)-one 2-hydroxypropanoate, 7-bromo-6-chloro-3-[3-[(2s,3r)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one;2-hydroxypropanoic acid

Molecular Formula

C₁₉H₂₃BrClN₃O₆

Molecular Weight

504.8 g/mol

InChI Key

GATQERNJKZPJNX-LDXVYITESA-N

1 2D Structure

Halofuginone Lactate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C16H17BrClN3O3.C3H6O3/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;1-2(4)3(5)6/h5-6,8,14-15,19,23H,1-4,7H2;2,4H,1H3,(H,5,6)/t14-,15+;/m0./s1

2.1.3 InChI Key

GATQERNJKZPJNX-LDXVYITESA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

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

2.2 Synonyms

2.2.1 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

25. Halofuginone Hbr

26. Halofuginone Hcl

27. Halofuginone Hydrobromide

28. Halofuginone Hydrobromide, (-)-

29. Halofuginone Hydrochloride

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

2.2.2 Depositor-Supplied Synonyms

1. 82186-71-8

2. Schembl2562822

3. Chembl1162014

4. Ac-30636

5. 7-bromo-6-chloro-3-(3-((2s,3r)-3-hydroxypiperidin-2-yl)-2-oxopropyl)quinazolin-4(3h)-one 2-hydroxypropanoate

6. 7-bromo-6-chloro-3-[3-[(2s,3r)-3-hydroxypiperidin-2-yl]-2-oxopropyl]quinazolin-4-one;2-hydroxypropanoic Acid

2.3 Create Date

2007-12-12

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₃BrClN₃O₆
Molecular Weight	504.8 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	503.04588 g/mol
Monoisotopic Mass	503.04588 g/mol
Topological Polar Surface Area	140 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	592
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

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.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

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.)

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.)

5.2 ATC Code

QP51AX08

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