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Chemistry

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Also known as: Zoledronate, 118072-93-8, Zometa, Reclast, Aclasta, (1-hydroxy-2-(1h-imidazol-1-yl)ethane-1,1-diyl)diphosphonic acid
Molecular Formula
C5H10N2O7P2
Molecular Weight
272.09  g/mol
InChI Key
XRASPMIURGNCCH-UHFFFAOYSA-N
FDA UNII
70HZ18PH24

Zoledronic Acid
An imidobisphosphonate inhibitor of BONE RESORPTION that is used for the treatment of malignancy-related HYPERCALCEMIA; OSTEITIS DEFORMANS; and OSTEOPOROSIS.
Zoledronic acid anhydrous is a Bisphosphonate.
1 2D Structure

Zoledronic Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1-hydroxy-2-imidazol-1-yl-1-phosphonoethyl)phosphonic acid
2.1.2 InChI
InChI=1S/C5H10N2O7P2/c8-5(15(9,10)11,16(12,13)14)3-7-2-1-6-4-7/h1-2,4,8H,3H2,(H2,9,10,11)(H2,12,13,14)
2.1.3 InChI Key
XRASPMIURGNCCH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CN(C=N1)CC(O)(P(=O)(O)O)P(=O)(O)O
2.2 Other Identifiers
2.2.1 UNII
70HZ18PH24
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(imidazol-1-yl)-1-hydroxyethylidene-1,1-bisphosphonic Acid

2. Cgp 42'446

3. Cgp 42446

4. Cgp 42446a

5. Cgp-42'446

6. Cgp-42446

7. Cgp42'446

8. Cgp42446

9. Zoledronate

10. Zoledronic Acid Anhydrous

11. Zometa

2.3.2 Depositor-Supplied Synonyms

1. Zoledronate

2. 118072-93-8

3. Zometa

4. Reclast

5. Aclasta

6. (1-hydroxy-2-(1h-imidazol-1-yl)ethane-1,1-diyl)diphosphonic Acid

7. Cgp 42446

8. (1-hydroxy-2-imidazol-1-ylethylidene)diphosphonic Acid

9. Zoledronic Acid Anhydrous

10. Anhydrous Zoledronic Acid

11. (1-hydroxy-2-imidazol-1-yl-1-phosphonoethyl)phosphonic Acid

12. Phosphonic Acid, [1-hydroxy-2-(1h-imidazol-1-yl)ethylidene]bis-

13. Zol

14. [1-hydroxy-2-(1h-imidazol-1-yl)ethane-1,1-diyl]bis(phosphonic Acid)

15. Orazol

16. Zol 446

17. Zoledronic Acid (inn)

18. Cgp-42446

19. Reclast (tn)

20. Zometa (tn)

21. Chembl924

22. Zoledronic Acid Teva

23. Zoledronic Acid, Anhydrous

24. Nsc-721517

25. Zoledronic Acid Medac

26. Chebi:46557

27. [1-hydroxy-2-(1h-imidazol-1-yl)-1-phosphonoethyl]phosphonic Acid

28. 70hz18ph24

29. Ncgc00159521-02

30. (1-hydroxy-2-(1h-imidazol-1-yl)ethylidene)bisphosphonic Acid

31. Cgp-42446a

32. Zoledronate Hydrate

33. Zoledronic Acid [usan:inn:ban]

34. Phosphonic Acid, (1-hydroxy-2-(1h-imidazol-1-yl)ethylidene)bis-

35. Zoladrona Acid Mylan

36. Zoledronic

37. Zoledronic Acid Accord

38. Zoledronic Acid [inn]

39. Zomera

40. 1-hydroxy-2-(1h-imidazol-1-yl)ethane-1,1-diyldiphosphonic Acid

41. Bisphosphonate 3

42. Zometa (novartis)

43. Aclasta And Reclast

44. C5h10n2o7p2

45. [1-hydroxy-2-(1h-imidazol-1-yl)ethylidene]bisphosphonic Acid

46. Zoledronic-acid

47. Unii-70hz18ph24

48. Bph 91

49. [1-hydroxy-2-(1h-imidazol-1-yl)-ethylidene]bisphosphonic Acid

50. Dsstox_cid_22668

51. Dsstox_rid_80065

52. Zoledronic Acid, Zoledronate

53. Bidd:pxr0134

54. Dsstox_gsid_42668

55. Schembl19054

56. Zoledronic Acid [mi]

57. Bidd:gt0292

58. Zoledronic Acid (zoledronate)

59. Gtpl3177

60. Jmc515594 Compound 55

61. Dtxsid0042668

62. Bdbm12578

63. Cgp42446a

64. Zoledronic Acid [who-dd]

65. Hms2089o09

66. Bcp22750

67. Cgp-4244

68. Zinc3803652

69. Tox21_111739

70. Mfcd00867791

71. Nsc721517

72. S1314

73. Stl452893

74. Akos005145739

75. Ab07564

76. Ac-1092

77. Cs-1829

78. Db00399

79. Hs-0091

80. Nsc 721517

81. Ncgc00159521-03

82. Ncgc00159521-04

83. Ncgc00159521-05

84. Ncgc00159521-09

85. Ncgc00159521-18

86. Hy-13777

87. Cas-118072-93-8

88. Ft-0601384

89. Z0031

90. D08689

91. H11422

92. S00092

93. Ab01273947-01

94. Ab01273947-02

95. Ab01273947-03

96. Ab01273947_04

97. 072z938

98. A803876

99. Q218507

100. Sr-05000001436

101. Q-201946

102. Sr-05000001436-1

103. 1-hydroxy-2-(1-imidazolyl)ethane-1,1-diphosphonic Acid

104. Z1691545083

105. (1-hydroxy-2-(1h-imidazol-1-yl)ethane-1,1-diyl)diphosphonicacid

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 272.09 g/mol
Molecular Formula C5H10N2O7P2
XLogP3-4.3
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count4
Exact Mass271.99632466 g/mol
Monoisotopic Mass271.99632466 g/mol
Topological Polar Surface Area153 Ų
Heavy Atom Count16
Formal Charge0
Complexity327
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameReclast
Drug LabelReclast contains zoledronic acid, a bisphosphonic acid which is an inhibitor of osteoclastic bone resorption. Zoledronic acid is designated chemically as (1-Hydroxy-2-imidazol-1-yl-phosphonoethyl) phosphonic acid monohydrate and its structural formul...
Active IngredientZoledronic acid
Dosage FormInjectable
Routeinjection; Iv (infusion)
Strengtheq 5mg base/100ml; 5mg/100ml
Market StatusPrescription
CompanyNovartis Pharms; Novartis

2 of 6  
Drug NameZoledronic acid
PubMed HealthZoledronic Acid (Injection)
Drug ClassesCalcium Regulator
Drug LabelZoledronic Acid Injection contains zoledronic acid, a bisphosphonic acid which is an inhibitor of osteoclastic bone resorption. Zoledronic acid is designated chemically as (1-Hydroxy-2-imidazol-1-yl-phosphonoethyl) phosphonic acid monohydrate and its...
Active IngredientZoledronic acid
Dosage FormInjectable
Routeinjection; Iv (infusion); Injection; iv (infusion)
Strengtheq 5mg base/100ml; 5mg/100ml; 4mmg; eq 4mg base/100ml; eq 4mg base/5ml; 4mg/100ml; 4mg/5ml(0.8mg/ml); eq 4mg base/vial
Market StatusTentative Approval; Prescription
CompanyPharmaceutics; Hospira; Gland Pharma; Teva Parenteral; Apotex; Hikma Farmaceutica; Usv North America; Acs Dobfar Info Sa; Pharmaforce; Cipla; Sun Pharma Global; Emcure Pharms; Pharms; Dr Reddys Labs; Agila Speclts; Actavis; Akorn

3 of 6  
Drug NameZometa
PubMed HealthZoledronic Acid (Injection)
Drug ClassesCalcium Regulator
Drug LabelZometa contains zoledronicacid, a bisphosphonic acid which is an inhibitor of osteoclastic bone resorption. Zoledronicacid is designated chemically as (1-Hydroxy-2-imidazol-1-yl-phosphonoethyl) phosphonic acid monohydrate and its structural formu...
Active IngredientZoledronic acid
Dosage FormInjectable
RouteIv (infusion); iv (infusion)
Strengtheq 4mg base/100ml; eq 4mg base/5ml; eq 4mg base/vial
Market StatusPrescription
CompanyNovartis

4 of 6  
Drug NameReclast
Drug LabelReclast contains zoledronic acid, a bisphosphonic acid which is an inhibitor of osteoclastic bone resorption. Zoledronic acid is designated chemically as (1-Hydroxy-2-imidazol-1-yl-phosphonoethyl) phosphonic acid monohydrate and its structural formul...
Active IngredientZoledronic acid
Dosage FormInjectable
Routeinjection; Iv (infusion)
Strengtheq 5mg base/100ml; 5mg/100ml
Market StatusPrescription
CompanyNovartis Pharms; Novartis

5 of 6  
Drug NameZoledronic acid
PubMed HealthZoledronic Acid (Injection)
Drug ClassesCalcium Regulator
Drug LabelZoledronic Acid Injection contains zoledronic acid, a bisphosphonic acid which is an inhibitor of osteoclastic bone resorption. Zoledronic acid is designated chemically as (1-Hydroxy-2-imidazol-1-yl-phosphonoethyl) phosphonic acid monohydrate and its...
Active IngredientZoledronic acid
Dosage FormInjectable
Routeinjection; Iv (infusion); Injection; iv (infusion)
Strengtheq 5mg base/100ml; 5mg/100ml; 4mmg; eq 4mg base/100ml; eq 4mg base/5ml; 4mg/100ml; 4mg/5ml(0.8mg/ml); eq 4mg base/vial
Market StatusTentative Approval; Prescription
CompanyPharmaceutics; Hospira; Gland Pharma; Teva Parenteral; Apotex; Hikma Farmaceutica; Usv North America; Acs Dobfar Info Sa; Pharmaforce; Cipla; Sun Pharma Global; Emcure Pharms; Pharms; Dr Reddys Labs; Agila Speclts; Actavis; Akorn

6 of 6  
Drug NameZometa
PubMed HealthZoledronic Acid (Injection)
Drug ClassesCalcium Regulator
Drug LabelZometa contains zoledronicacid, a bisphosphonic acid which is an inhibitor of osteoclastic bone resorption. Zoledronicacid is designated chemically as (1-Hydroxy-2-imidazol-1-yl-phosphonoethyl) phosphonic acid monohydrate and its structural formu...
Active IngredientZoledronic acid
Dosage FormInjectable
RouteIv (infusion); iv (infusion)
Strengtheq 4mg base/100ml; eq 4mg base/5ml; eq 4mg base/vial
Market StatusPrescription
CompanyNovartis

4.2 Drug Indication

Zoledronic acid is indicated to treat hypercalcemia of malignancy, multiple myeloma, bone metastases from solid tumors, osteoporosis in men and postmenopausal women, glucocorticoid induced osteoporosis, and Paget's disease of bone in men and women. Zoledronic acid is also indicated for the prevention of osteoporosis in post menopausal women and glucocorticoid induced osteoporosis.


Prevention of skeletal-related events and treatment of tumour-induced hypercalcaemia.


Prevention of skeletal-related events (pathological fractures, spinal compression, radiation or surgery to bone, or tumour-induced hypercalcaemia) in adult patients with advanced malignancies involving bone.

Treatment of adult patients with tumour-induced hypercalcaemia.


* 4 mg / 5 ml and 4 mg / 100 ml: :

- Prevention of skeletal-related events (pathological fractures, spinal compression, radiation or surgery to bone, or tumour-induced hypercalcaemia) in adult patients with advanced malignancies involving bone.

- Treatment of adult patients with tumour-induced hypercalcaemia (TIH).

* 5 mg / 100 ml: :

Treatment of osteoporosis:

- in post-menopausal women;

- in men;

at increased risk of fracture, including those with a recent low-trauma hip fracture.

Treatment of osteoporosis associated with long-term systemic glucocorticoid therapy:

- in post-menopausal women;

- in men;

at increased risk of fracture.

Treatment of Paget's disease of the bone in adults.


Prevention of skeletal related events (pathological fractures, spinal compression, radiation or surgery to bone, or tumour-induced hypercalcaemia) in adult patients with advanced malignancies involving bone.

Treatment of adult patients with tumour-induced hypercalcaemia (TIH).


- Prevention of skeletal related events (pathological fractures, spinal compression, radiation or surgery to bone, or tumour-induced hypercalcaemia) in adult patients with advanced malignancies involving bone;

- treatment of adult patients with tumour-induced hypercalcaemia (TIH).


Treatment of osteoporosis:

- in post-menopausal women;

- in men;

at increased risk of fracture, including those with a recent low-trauma hip fracture.

Treatment of osteoporosis associated with long-term systemic glucocorticoid therapy in post-menopausal women and in men at increased risk of fracture.

Treatment of Paget's disease of the bone.


Prevention of skeletal related events (pathological fractures, spinal compression, radiation or surgery to bone, or tumour-induced hypercalcaemia) in adult patients with advanced malignancies involving bone.

Treatment of adult patients with tumour-induced hypercalcaemia (TIH).


Treatment of osteoporosis:

- in post-menopausal women;

- in men;

at increased risk of fracture including those with a recent low-trauma hip fracture.

Treatment of osteoporosis associated with long-term systemic glucocorticoid therapy:

- in post-menopausal women;

- in men;

at increased risk of fracture.

Treatment of Pagets disease of the bone in adults.


- Prevention of skeletal related events (pathological fractures, spinal compression, radiation or surgery to bone, or tumour-induced hypercalcaemia) in patients with advanced malignancies involving bone;

- treatment of tumour-induced hypercalcaemia (TIH);

- prevention of skeletal related events (pathological fractures, spinal compression, radiation or surgery to bone, or tumour-induced hypercalcaemia) in patients with advanced malignancies involving bone;

- treatment of tumour-induced hypercalcaemia (TIH);

- prevention of skeletal related events (pathological fractures, spinal compression, radiation or surgery to bone, or tumour-induced hypercalcaemia) in adult patients with advanced malignancies involving bone;

- treatment of adult patients with tumour-induced hypercalcaemia (TIH).


Treatment of osteoporosis

- in post-menopausal women

- in adult men

at increased risk of fracture, including those with recent low-trauma hip fracture.

Treatment of osteoporosis associated with long-term systemic glucocorticoid therapy

- in post-menopausal women

- in adult men

at increased risk of fracture.

Treatment of Paget's disease of the bone in adults.


Osteogenesis imperfecta, Prevention of fracture and bone loss in postmenopausal women with early-stage breast cancer treated with aromatase inhibitors, Prevention of skeletal related events in patients with advanced malignancies involving bone, Tumour-induced hypercalcaemia


Treatment of osteoporosis, Treatment of Pagets disease of the bone


5 Pharmacology and Biochemistry
5.1 Pharmacology

Zoledronic acid is a third generation, nitrogen containing bisphosphonate that inhibits osteoclast function and prevents bone resorption. The therapeutic window is wide as patients are unlikely to suffer severe effects from overdoses and the duration of action is long. Patients should be counselled regarding the risk of electrolyte deficiencies, renal impairment, osteonecrosis of the jaw, atypical femoral fractures, bronchoconstriction, hepatic impairment, hypocalcemia, and embryo-fetal toxicity.


5.2 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
ZOLEDRONIC ACID ANHYDROUS
5.3.2 FDA UNII
70HZ18PH24
5.3.3 Pharmacological Classes
Diphosphonates [CS]; Bisphosphonate [EPC]
5.4 ATC Code

M05BA08


M05BA08


M05BA08


M05BA08


M05BA08


M05BA08


M05BA08


M05BA08


M05BA08


M05BA08


M05BA08

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


M - Musculo-skeletal system

M05 - Drugs for treatment of bone diseases

M05B - Drugs affecting bone structure and mineralization

M05BA - Bisphosphonates

M05BA08 - Zoledronic acid


5.5 Absorption, Distribution and Excretion

Absorption

A 4mg intravenous dose reaches a Cmax of 37078.5ng/mL, with a Tmax of 0.3170.014h, and an AUC of 788181ng\*h/mL. A 5mg intravenous dose reaches a Cmax of 47176.1ng/mL, with a Tmax of 0.3680.005h, and an AUC of 917226ng\*h/mL.


Route of Elimination

Zoledronic acid is 39 16% eliminated in the urine as the unmetabolized parent drug.


Clearance

Zoledronic acid has a renal clearance of 3.7 2.0 L/h.


5.6 Metabolism/Metabolites

Zoledronic acid is not metabolized _in vivio_.


5.7 Biological Half-Life

Zoledronic acid has a terminal elimination half life of 146 hours.


5.8 Mechanism of Action

Bisphosphonates are taken into the bone where they bind to hydroxyapatite. Bone resorption by osteoclasts causes local acidification, releasing the bisphosphonate, which is taken into the osteoclast by fluid-phase endocytosis. Endocytic vesicles become acidified, releasing bisphosphonates into the cytosol of osteoclasts where they act. Osteoclasts mediate resorption of bone. When osteoclasts bind to bone they form podosomes, ring structures of F-actin. Etidronic acid also inhibits V-ATPases in the osteoclast, though the exact subunits are unknown, preventing F-actin from forming podosomes. Disruption of the podosomes causes osteoclasts to detach from bones, preventing bone resorption. Nitrogen containing bisphosphonates such as zoledronate are known to induce apoptosis of hematopoietic tumor cells by inhibiting the components of the mevalonate pathway farnesyl diphosphate synthase, farnesyl diphosphate, and geranylgeranyl diphosphate. These components are essential for post-translational prenylation of GTP-binding proteins like Rap1. The lack of prenylation of these proteins interferes with their function, and in the case of Rap1, leads to apoptosis. zoledronate also activated caspases which further contribute to apoptosis.