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Tiludronic Acid

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Chemistry

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Also known as: 149845-07-8, Tiludronic acid disodium salt, Skelid, Disodium tiludronate, Sr 41319b, Tiludronate disodium [usan]

Molecular Formula

C₇H₇ClNa₂O₆P₂S

Molecular Weight

362.57 g/mol

InChI Key

SKUHWSDHMJMHIW-UHFFFAOYSA-L

FDA UNII

BH6M93CIA0

Tiludronate Disodium is the disodium salt form of tiludronate, a first-generation, non-nitrogenous bisphosphonate analogue of endogenous pyrophosphate. Tiludronate adsorbs to hydroxyapatite cells, and although the exact mechanism through which this bisphosphonate exerts its effect has yet to be fully elucidated, tiludronate appears to inhibit protein-tyrosine-phosphatase (PTP) in osteoclasts, thereby disrupting the cytoskeletal ring structure and suppressing the bone resorbing activity of osteoclasts. In addition, tiludronate appears to inhibit the vacuolar-type proton ATPase (V-ATPase) in osteoclasts. Altogether, this may reduce the number of osteoclasts, inhibit abnormal bone resorption and reduce bone turnover.

1 2D Structure

Tiludronic Acid

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

disodium;[(4-chlorophenyl)sulfanyl-[hydroxy(oxido)phosphoryl]methyl]-hydroxyphosphinate

2.1.2 InChI

InChI=1S/C7H9ClO6P2S.2Na/c8-5-1-3-6(4-2-5)17-7(15(9,10)11)16(12,13)14;;/h1-4,7H,(H2,9,10,11)(H2,12,13,14);;/q;2*+1/p-2

2.1.3 InChI Key

SKUHWSDHMJMHIW-UHFFFAOYSA-L

2.1.4 Canonical SMILES

C1=CC(=CC=C1SC(P(=O)(O)[O-])P(=O)(O)[O-])Cl.[Na+].[Na+]

2.2 Other Identifiers

2.2.1 UNII

BH6M93CIA0

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (4-chlorophenyl)thiomethylene Bisphosphonic Acid

2. (chloro-4-phenyl)thiomethylene Biphosphonate

3. (chloro-4-phenyl)thiomethylene Bisphosphonate

4. Cl2smbp

5. Skelid

6. Tiludronate

7. Tiludronic Acid

2.3.2 Depositor-Supplied Synonyms

1. 149845-07-8

2. Tiludronic Acid Disodium Salt

3. Skelid

4. Disodium Tiludronate

5. Sr 41319b

6. Tiludronate Disodium [usan]

7. Tiludronate Sodium

8. Tiludronic Acid, Disodium Salt

9. Sr-41319b

10. Tiludronic Acid (disodium)

11. Bh6m93cia0

12. Tiludronate (disodium)

13. Tiludronate Disodium Anhydrous

14. Disodium Dihydrogen (((p-chlorophenyl)thio)methylene)diphosphonate

15. 149845-07-8 (sodium)

16. Phosphonic Acid, (((4-chlorophenyl)thio)methylene)bis-, Disodium Salt

17. Tiludronate Disodium (usan)

18. [(4-chlorophenyl)sulfanyl-[hydroxy(oxido)phosphoryl]methyl]-hydroxyphosphinate Disodium

19. Phosphonic Acid, [[(4-chlorophenyl)thio]methylene]bis-, Sodium Salt (1:2)

20. Ncgc00182026-01

21. Unii-bh6m93cia0

22. Skelid (tn)

23. Cl-tmbp

24. Dsstox_cid_28547

25. Dsstox_rid_82819

26. Dsstox_gsid_48621

27. Schembl41053

28. Chembl1200448

29. Dtxsid1048621

30. Bcp22736

31. Tiludronate Sodium [who-dd]

32. Tiludronate Disodium [vandf]

33. Tox21_112961

34. Disodium [[(4-chlorophenyl)thio]methylene]bis(hydrogenphosphonate)

35. Mfcd04039691

36. Tiludronate Disodium [mart.]

37. Akos015894005

38. Me-3737

39. Disodium;[(4-chlorophenyl)sulfanyl-[hydroxy(oxido)phosphoryl]methyl]-hydroxyphosphinate

40. Tiludronate Disodium [green Book]

41. As-73111

42. Tiludronate Disodium [orange Book]

43. Tiludronic Acid Disodium Salt [mi]

44. Cas-149845-07-8

45. D4167

46. Ft-0675237

47. D02285

48. D90259

49. J-008635

50. Q27274665

51. Disodium Hydrogen {[(4-chlorophenyl)sulfanyl](hydrogen Phosphonato)methyl}phosphonate

52. Disodium [(4-chlorophenyl)sulfanyl-(hydroxy-oxido-phosphoryl)methyl]-hydroxy-oxido-oxo-phosphorane

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₇H₇ClNa₂O₆P₂S
Molecular Weight	362.57 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	361.8922494 g/mol
Monoisotopic Mass	361.8922494 g/mol
Topological Polar Surface Area	146 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	320
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	3

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Bone Density Conservation Agents

Agents that inhibit BONE RESORPTION and/or favor BONE MINERALIZATION and BONE REGENERATION. They are used to heal BONE FRACTURES and to treat METABOLIC BONE DISEASES such as OSTEOPOROSIS. (See all compounds classified as Bone Density Conservation Agents.)

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