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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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