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Chemistry

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Also known as: 112809-51-5, Femara, 4,4'-((1h-1,2,4-triazol-1-yl)methylene)dibenzonitrile, Letrozol, Cgs 20267, Cgs-20267
Molecular Formula
C17H11N5
Molecular Weight
285.30  g/mol
InChI Key
HPJKCIUCZWXJDR-UHFFFAOYSA-N
FDA UNII
7LKK855W8I

Letrozole
A triazole and benzonitrile derivative that is a selective non-steroidal aromatase inhibitor, similar to ANASTROZOLE. It is used in the treatment of metastatic or locally advanced breast cancer in postmenopausal women.
Letrozole is an Aromatase Inhibitor. The mechanism of action of letrozole is as an Aromatase Inhibitor.
1 2D Structure

Letrozole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-[(4-cyanophenyl)-(1,2,4-triazol-1-yl)methyl]benzonitrile
2.1.2 InChI
InChI=1S/C17H11N5/c18-9-13-1-5-15(6-2-13)17(22-12-20-11-21-22)16-7-3-14(10-19)4-8-16/h1-8,11-12,17H
2.1.3 InChI Key
HPJKCIUCZWXJDR-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=CC=C1C#N)C(C2=CC=C(C=C2)C#N)N3C=NC=N3
2.2 Other Identifiers
2.2.1 UNII
7LKK855W8I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4,4'-(1h-1,2,4-triazol-1-yl-methylene)-bis(benzonitrile)

2. Cgs 20267

3. Cgs-20267

4. Cgs20267

5. Fmara

6. Femara

2.3.2 Depositor-Supplied Synonyms

1. 112809-51-5

2. Femara

3. 4,4'-((1h-1,2,4-triazol-1-yl)methylene)dibenzonitrile

4. Letrozol

5. Cgs 20267

6. Cgs-20267

7. 4-[(4-cyanophenyl)-(1,2,4-triazol-1-yl)methyl]benzonitrile

8. 4,4'-(1h-1,2,4-triazol-1-ylmethylene)dibenzonitrile

9. Letrazole

10. Benzonitrile, 4,4'-(1h-1,2,4-triazol-1-ylmethylene)bis-

11. Femera

12. 4,4'-(1h-1,2,4-triazol-1-ylmethanediyl)dibenzonitrile

13. 4,4'-(1h-1,2,4-triazol-1-ylmethylene)bisbenzonitrile

14. Nsc-759652

15. Chembl1444

16. 4-[(4-cyanophenyl)(1h-1,2,4-triazol-1-yl)methyl]benzonitrile

17. 4,4'-(1h-1,2,4-triazol-1-ylmethylene)bis-benzonitrile

18. 7lkk855w8i

19. Chebi:6413

20. 4,4'-(1h-1,2,4-triazol-1-ylmethylene) Bis-benzonitrile

21. Ncgc00016973-01

22. Letoval

23. Cas-112809-51-5

24. Dsstox_cid_3202

25. Dsstox_rid_76924

26. Dsstox_gsid_23202

27. Smr000466343

28. Femara (tn)

29. Hsdb 7461

30. Sr-01000759382

31. Letrozole (jan/usp/inn)

32. Unii-7lkk855w8i

33. Ccris 8822

34. 1-[bis(4-cyanophenyl)methyl]-1,2,4-triazole

35. Fem-345

36. Femara, Letrozole

37. Letrozole [usan:usp:inn:ban]

38. Letrozole- Bio-x

39. Cgs20267

40. Mfcd00866241

41. Letrozole [inn]

42. Letrozole [jan]

43. Letrozole [mi]

44. Letrozole [hsdb]

45. Letrozole [usan]

46. Prestwick0_001025

47. Prestwick1_001025

48. Prestwick2_001025

49. Prestwick3_001025

50. Femara (tn) (novartis)

51. Letrozole [mart.]

52. Letrozole [usp-rs]

53. Letrozole [who-dd]

54. Schembl4331

55. 1-[bis-(4-cyanophenyl)methyl]-1,2,4-triazole

56. Bidd:pxr0130

57. Bspbio_001209

58. Mls000759455

59. Mls001424038

60. Mls002584991

61. Mls006010040

62. Bidd:gt0015

63. Spbio_003070

64. Bpbio1_001331

65. Gtpl5209

66. Letrozole [ep Impurity]

67. Letrozole [orange Book]

68. Dtxsid4023202

69. Letrozole [ep Monograph]

70. Letrozole, >=98% (hplc)

71. Bdbm13061

72. Ex-a965

73. Letrozole [usp Monograph]

74. Hms1571m11

75. Hms2051e08

76. Hms2089l22

77. Hms2098m11

78. Hms2233c23

79. Hms3369e11

80. Hms3393e08

81. Hms3651k05

82. Hms3715m11

83. Pharmakon1600-01502354

84. Amy32541

85. Bcp23354

86. Zinc3778874

87. Tox21_110719

88. Tox21_303572

89. Nsc719345

90. Nsc759652

91. S1235

92. Stl451047

93. Akos005145822

94. Ab07525

95. Ac-1193

96. Bcp9000848

97. Ccg-100849

98. Cs-1776

99. Db01006

100. Ks-1269

101. Nc00099

102. Nsc 759652

103. Nsc-719345

104. Ncgc00016973-02

105. Ncgc00016973-03

106. Ncgc00016973-06

107. Ncgc00257460-01

108. Bl164620

109. Hy-14248

110. Bcp0726000213

111. 1-bis(4-cyanophenyl)methyl-1,2,4-triazole

112. 4,2,4-triazol-1-ylmethylene)dibenzonitrile

113. Ab00514009

114. L0248

115. Sw197294-4

116. A25380

117. C08163

118. D00964

119. Ab00514009-05

120. Ab00514009-07

121. Ab00514009-08

122. Ab00514009-09

123. Ab00514009_10

124. Ab00514009_11

125. 809l515

126. Kisqali Femara Co-pack Component Letrozole

127. Q194974

128. W-60273

129. 4,4'-(1,2,4-triazol-1-ylmethylene)dibenzonitrile

130. Letrozole Component Of Kisqali Femara Co-pack

131. Q-201291

132. Sr-01000759382-4

133. Sr-01000759382-5

134. Brd-k88789588-001-03-2

135. 4,4 -(1h-1,2,4-triazol-1-ylmethanediyl)dibenzonitrile

136. 4,4'-(1h-1,2,4-triazol-1-ylmethylene)-bisbenzonitrile

137. F2173-0288

138. Z1741968261

139. 4,4'-((1h-1,2,4-triazol-1-yl)-methylene)dibenzonitrile

140. Letrozole, European Pharmacopoeia (ep) Reference Standard

141. Letrozole, United States Pharmacopeia (usp) Reference Standard

142. 4-[1-(4-cyanophenyl)-1-(1,2,4-triazol-1-yl)methyl]benzonitrile

143. Letrozole, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 285.30 g/mol
Molecular Formula C17H11N5
XLogP32.7
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count3
Exact Mass285.10144537 g/mol
Monoisotopic Mass285.10144537 g/mol
Topological Polar Surface Area78.3 Ų
Heavy Atom Count22
Formal Charge0
Complexity420
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 4  
Drug NameFemara
PubMed HealthLetrozole (By mouth)
Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
Drug LabelFemara tablets for oral administration contains 2.5 mg of letrozole, a nonsteroidal aromatase inhibitor (inhibitor of estrogen synthesis). It is chemically described as 4,4'-(1H-1,2,4-Triazol-1-ylmethylene)dibenzonitrile, and its structural formula i
Active IngredientLetrozole
Dosage FormTablet
RouteOral
Strength2.5mg
Market StatusPrescription
CompanyNovartis Pharms

2 of 4  
Drug NameLetrozole
PubMed HealthLetrozole (By mouth)
Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
Drug LabelLetrozole tablets USP for oral administration contain 2.5 mg of letrozole, a nonsteroidal aromatase inhibitor (inhibitor of estrogen synthesis). It is chemically described as 4,4'-(1H-1,2,4-triazol-1-ylmethylene)dibenzonitrile, and its structural for
Active IngredientLetrozole
Dosage FormTablet
Routeoral; Oral
Strength2.5mg
Market StatusTentative Approval; Prescription
CompanyVintage Pharms; Fresenius Kabi Oncol; Apotex; Accord Hlthcare; Jiangsu Hengrui Med; Indicus Pharma; Natco Pharma; Sun Pharm Inds; Roxane; Teva Pharms; Kudco Ireland; Zydus Pharms Usa; Dr Reddys Labs; Mylan; Impax Labs

3 of 4  
Drug NameFemara
PubMed HealthLetrozole (By mouth)
Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
Drug LabelFemara tablets for oral administration contains 2.5 mg of letrozole, a nonsteroidal aromatase inhibitor (inhibitor of estrogen synthesis). It is chemically described as 4,4'-(1H-1,2,4-Triazol-1-ylmethylene)dibenzonitrile, and its structural formula i
Active IngredientLetrozole
Dosage FormTablet
RouteOral
Strength2.5mg
Market StatusPrescription
CompanyNovartis Pharms

4 of 4  
Drug NameLetrozole
PubMed HealthLetrozole (By mouth)
Drug ClassesAntineoplastic Agent, Endocrine-Metabolic Agent
Drug LabelLetrozole tablets USP for oral administration contain 2.5 mg of letrozole, a nonsteroidal aromatase inhibitor (inhibitor of estrogen synthesis). It is chemically described as 4,4'-(1H-1,2,4-triazol-1-ylmethylene)dibenzonitrile, and its structural for
Active IngredientLetrozole
Dosage FormTablet
Routeoral; Oral
Strength2.5mg
Market StatusTentative Approval; Prescription
CompanyVintage Pharms; Fresenius Kabi Oncol; Apotex; Accord Hlthcare; Jiangsu Hengrui Med; Indicus Pharma; Natco Pharma; Sun Pharm Inds; Roxane; Teva Pharms; Kudco Ireland; Zydus Pharms Usa; Dr Reddys Labs; Mylan; Impax Labs

4.2 Therapeutic Uses

Antineoplastic

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 974


Letrozole is indicated for first-line treatment of postmenopausal women with hormone receptor positive or hormone receptor unknown locally advanced or metastatic breast cancer. Letrozole is also indicated for treatment of advanced breast cancer in postmenopausal women with disease progression following antiestrogen therapy. /Included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1902


4.3 Drug Warning

A 37-year-old premenopausal woman with relapsed breast cancer (BC) in the right supraclavicular nodes, after failed treatment with the combination luteinizing hormone releasing hormone-a (LHRHa; triptorelin) plus tamoxifen, was started on triptorelin 3.75 mg every 28 days plus letrozole 2.5 mg daily. Approximately 6 months after starting this therapy, she complained of a daily scalp hair loss while combing and progressively developed a diffuse non-scarring alopecia on her crown. There were no signs of virilization ... She was not taking any other drug. Hematological parameters were normal. Blood examination ruled out pituitary or thyroid problems. There were no other possible causes that could induce alopecia, such as lupus erythematosus, HIV infection, secondary syphilis, or deficiencies of protein, iron, biotin or zinc.

PMID:14581280 Carlini P et al; Ann Oncol 14 (11): 1689-90 (2003)


In patients receiving letrozole as first-line therapy, bone pain, back pain, and limb pain occurred in 22, 18, and 10% of patients, respectively. In patients receiving letrozole as second-line therapy, adverse musculoskeletal effects (including musculoskeletal pain, skeletal pain, back pain, arm pain, and leg pain) were reported in 21% and fracture was reported in less than 5% of patients. Arthralgia was reported in 16% of patients receiving letrozole as first-line therapy and in 8% of patients receiving the drug as second-line therapy. Hypercalcemia occurred in less than 5% of patients receiving letrozole as second-line therapy.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1114


Adverse musculoskeletal effects have been reported in patients receiving letrozole as adjuvant therapy for early-stage breast cancer in clinical trials. In a double-blind, randomized trial in postmenopausal women with hormone receptor-positive breast cancer who had received approximately 5 years of tamoxifen adjuvant therapy following primary treatment for early breast cancer, extended adjuvant therapy with letrozole was associated with an increased incidence of arthritis, arthralgia, and myalgia, and a trend toward higher rates of newly diagnosed osteoporosis and bone fracture compared with placebo therapy.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1114


All women receiving adjuvant therapy with letrozole should be advised to adopt lifestyle changes (eg, weight-bearing exercise, abstinence from smoking, moderation in alcohol consumption) and dietary supplementation with calcium and vitamin D to reduce the risk of osteoporosis.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1114


For more Drug Warnings (Complete) data for LETROZOLE (26 total), please visit the HSDB record page.


4.4 Drug Indication

Letrozole is indicated to treat postmenopausal women with hormone receptor (HR) positive early breast cancer, postmenopausal women with early breast cancer who have periviously been treated with tamoxifen, and postmenopausal women with HR+ or unknown advanced breast cancer. Letrozole, given with ribociclib, is indicated to treat pre, peri, and postmenopausal women with HR+ and human epidermal growth factor 2 (HER2) negative advanced or metastatic breast cancer.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Letrozole is an aromatase inhibitor used in the treatment of breast cancer. Aromatase inhibitors work by inhibiting the action of the enzyme aromatase, which converts androgens into estrogens by a process called aromatization. As breast tissue is stimulated by estrogens, decreasing their production is a way of suppressing recurrence of the breast tumor tissue. Letrozole is a third generation type II aromatase inhibitor used to treat estrogen dependant breast cancers. It has a long duration of action as it has a half life of over 42 hours in breast cancer patients. Patients should be counselled regarding the risk of interstitial lung disease, pneumonitis, QT prolongation, elevated transaminase levels, neutropenia, and embryo-fetal toxicity.


5.2 MeSH Pharmacological Classification

Antineoplastic Agents

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


Aromatase Inhibitors

Compounds that inhibit AROMATASE in order to reduce production of estrogenic steroid hormones. (See all compounds classified as Aromatase Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
LETROZOLE
5.3.2 FDA UNII
7LKK855W8I
5.3.3 Pharmacological Classes
Aromatase Inhibitors [MoA]; Aromatase Inhibitor [EPC]
5.4 ATC Code

L02BG04

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


L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02B - Hormone antagonists and related agents

L02BG - Aromatase inhibitors

L02BG04 - Letrozole


5.5 Absorption, Distribution and Excretion

Absorption

Letrozole is 99.9% orally bioavailable. A 2.5mg oral dose reaches a Cmax of 104nmol/L with a Tmax of 8.10h, and an AUC of 7387nmol\*h/L.


Route of Elimination

Letrozole is 90% eliminated in the urine. 75% of the dose is recovered as a glucuronide metabolite, 9% is in the form of the ketone and carbinol metabolites, and 6% is recovered in urine as unchanged letrozole.


Volume of Distribution

The volume of distribution of letrozole is 1.87L/kg.


Clearance

The average clearance after a single dose of letrozole was 1.52L/h and at steady state was 1.20L/h.


Letrozole is rapidly and completely absorbed from the GI tract following oral administration. Steady-state plasma concentrations of the drug are reached in 2-6 weeks in patients receiving letrozole 2.5 mg daily. Letrozole exhibits slightly nonlinear pharmacokinetics with repeated administration of 2.5 mg daily, with steady-state plasma concentrations 1.5-2 times higher than predicted based on plasma concentrations measured after a single dose. However, continuous accumulation of letrozole does not occur, and steady-state concentrations are maintained over extended periods of daily drug administration. Food does not affect the oral absorption of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1116


Letrozole has a large volume of distribution of approximately 1.9 L/kg. Letrozole is weakly bound to plasma proteins.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1116


Following oral administration of radiolabeled letrozole, 90% of the administered dose was excreted in the urine. Of the radiolabeled drug recovered in urine, at least 75% was the glucuronide of the carbinol metabolite, about 9% consisted of 2 unidentified metabolites, and 6% was unchanged drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1116


It is not known whether letrozole is distributed into human breast milk.

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1902


For more Absorption, Distribution and Excretion (Complete) data for LETROZOLE (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Letrozole is metabolized by CYP2A6 to a ketone analog metabolite, which is further metabolized by CYP3A4 and CYP2A6 to 4,4'-(hydroxymethylene)dibenzonitrile. 4,4'-(hydroxymethylene)dibenzonitrile is glucuronidated by UGT2B7.


The primary elimination pathway of letrozole consists of slow metabolism in the liver to a pharmacologically inactive carbinol metabolite (4,4'-methanol-bisbenzonitrile) followed by renal excretion of the glucuronide conjugate of this metabolite. Formation of the carbinol metabolite is mediated by cytochrome P-450 (CYP) isoenzymes 3A4 and 2A6, and formation of the ketone analog of the carbinol metabolite is mediated by isoenzyme 2A6.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1116


5.7 Biological Half-Life

The terminal elimination half life of letrozole is approximately 42h in healthy volunteers, but longer in breast cancer patients.


Letrozole has a terminal elimination half-life of about 2 days.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1116


5.8 Mechanism of Action

Letrozole is a non-steroidal type II aromatase inhibitor. It blocks the active site, and therefore the electron transfer chain of CYP19A1. This competitive inhibition prevents the conversion of androgens to estrogen. This action leads to a reduction in uterine weight and elevated leuteinizing hormone. In postmenopausal women, the action of aromatase is responsible for the majority of estrogen production. With reduced availability of estrogen, estrogen-dependant tumors regress. Third generation aromatase inhibitors do not significantly affect cortisol, aldosterone, and thyroxine levels.


Letrozole is a nonsteroidal competitive inhibitor of the aromatase enzyme system; it inhibits the conversion of androgens to estrogens. In adult nontumor- and tumor-bearing female animals, letrozole is as effective as ovariectomy in reducing uterine weight, elevating serum LH, and causing the regression of estrogen-dependent tumors. In contrast to ovariectomy, treatment with letrozole does not lead to an increase in serum FSH. Letrozole selectively inhibits gonadal steroidogenesis but has no significant effect on adrenal mineralocorticoid or glucocorticoid synthesis. Letrozole inhibits the aromatase enzyme by competitively binding to the heme of the cytochrome P450 subunit of the enzyme, resulting in a reduction of estrogen biosynthesis in all tissues. Treatment of women with letrozole significantly lowers serum estrone, estradiol and estrone sulfate and has not been shown to significantly affect adrenal corticosteroid synthesis, aldosterone synthesis, or synthesis of thyroid hormones.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2210


API Reference Price

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30-Jan-2021
29-Aug-2024
KGS
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