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Chemistry

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Also known as: 107868-30-4, Aromasin, 6-methyleneandrosta-1,4-diene-3,17-dione, Fce 24304, Fce-24304, Exemestano

Molecular Formula

C₂₀H₂₄O₂

Molecular Weight

296.4 g/mol

InChI Key

BFYIZQONLCFLEV-DAELLWKTSA-N

FDA UNII

NY22HMQ4BX

Exemestane is an irreversible steroidal aromatase inhibitor, with antiestrogen and antineoplastic activities. Upon oral administration, exemestane binds irreversibly to and inhibits the enzyme aromatase, thereby blocking the peripheral aromatization of androgens, including androstenedione and testosterone, to estrogens. This lowers estrogen levels in the blood circulation.

Exemestane is an Aromatase Inhibitor. The mechanism of action of exemestane is as an Aromatase Inhibitor.

1 2D Structure

Exemestane

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8R,9S,10R,13S,14S)-10,13-dimethyl-6-methylidene-7,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,17-dione

2.1.2 InChI

InChI=1S/C20H24O2/c1-12-10-14-15-4-5-18(22)20(15,3)9-7-16(14)19(2)8-6-13(21)11-17(12)19/h6,8,11,14-16H,1,4-5,7,9-10H2,2-3H3/t14-,15-,16-,19+,20-/m0/s1

2.1.3 InChI Key

BFYIZQONLCFLEV-DAELLWKTSA-N

2.1.4 Canonical SMILES

CC12CCC3C(C1CCC2=O)CC(=C)C4=CC(=O)C=CC34C

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CC(=C)C4=CC(=O)C=C[C@]34C

2.2 Other Identifiers

2.2.1 UNII

NY22HMQ4BX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6-methyleneandrosta-1,4-diene-3,17-dione

2. Aromasil

3. Aromasin

4. Aromasine

5. Examestane

6. Fce 24304

7. Fce-24304

2.3.2 Depositor-Supplied Synonyms

1. 107868-30-4

2. Aromasin

3. 6-methyleneandrosta-1,4-diene-3,17-dione

4. Fce 24304

5. Fce-24304

6. Exemestano

7. Exemestanum

8. Exemestanum [inn-latin]

9. Exemestano [inn-spanish]

10. 6-methylene-androsta-1,4-diene-3,17-dione

11. Androsta-1,4-diene-3,17-dione, 6-methylene-

12. Fce24304

13. Pnu-155971

14. Aromasine

15. Ny22hmq4bx

16. Chebi:4953

17. (8r,9s,10r,13s,14s)-10,13-dimethyl-6-methylene-7,8,9,10,11,12,13,14,15,16-decahydro-3h-cyclopenta[a]phenanthrene-3,17(6h)-dione

18. (8r,9s,10r,13s,14s)-10,13-dimethyl-6-methylene-7,8,9,11,12,13,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17(10h,14h)-dione

19. (8r,9s,10r,13s,14s)-10,13-dimethyl-6-methylidene-7,8,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,17-dione

20. Aromasil

21. Nsc713563

22. Nsc-758907

23. Exe

24. Dsstox_cid_3037

25. Dsstox_rid_76844

26. Dsstox_gsid_23037

27. 6-methylideneandrosta-1,4-diene-3,17-dione

28. Exemestane [usan:inn:ban]

29. Nikidess

30. (8alpha,10alpha,13alpha)-6-methylideneandrosta-1,4-diene-3,17-dione

31. Aromasin (tn)

32. Smr000466314

33. Cas-107868-30-4

34. Hsdb 7463

35. Curator_000009

36. Unii-ny22hmq4bx

37. Exemestane (jan/usp/inn)

38. Ccris 9351

39. Ncgc00095289-01

40. Exemestane [inn]

41. Exemestane; Aromasin

42. Exemestane, Aromasin

43. Pnu 155971

44. Exemestane [mi]

45. Exemestane [jan]

46. Exemestane [hsdb]

47. Exemestane [usan]

48. Exemestane [vandf]

49. Exemestane [mart.]

50. Schembl6215

51. Aromasin (pharmacia Upjohn)

52. Exemestane [usp-rs]

53. Exemestane [who-dd]

54. Exemestane(fce 24304)

55. Mls000759419

56. Mls001424062

57. Gtpl7073

58. 6-methylenandrosta-1,17-dione

59. Chembl1200374

60. Dtxsid5023037

61. Exemestane [orange Book]

62. Exemestane, >=98% (hplc)

63. Exemestane [ep Monograph]

64. Bcpp000235

65. Exemestane [usp Monograph]

66. Hms2051j04

67. Hms3713h12

68. Bcp23353

69. Zinc3973334

70. Tox21_111499

71. Bdbm50398447

72. Pnu155971

73. S1196

74. Akos015840113

75. Akos015895161

76. Tox21_111499_1

77. Ac-2171

78. Bcp9000676

79. Ccg-100995

80. Cs-1766

81. Db00990

82. Ks-5136

83. Nc00245

84. Nsc 758907

85. Nsc-713563

86. Ncgc00271596-03

87. 6-methylenandrost-1,4-dien-3,17-dione

88. As-31053

89. Cpd000466314

90. Hy-13632

91. Bcp0726000226

92. 6-methylen-androst-1,4-diene-3,17-dione

93. E0941

94. C08162

95. D00963

96. Ab00639936-06

97. Ab00639936-08

98. Ab00639936-09

99. Ab00639936-10

100. Ab00639936_11

101. 868e304

102. A801772

103. Q418819

104. Sr-01000759393

105. Sr-01000759393-4

106. Brd-k33425534-001-12-5

107. Exemestane, European Pharmacopoeia (ep) Reference Standard

108. Exemestane, United States Pharmacopeia (usp) Reference Standard

109. Exemestane, Pharmaceutical Secondary Standard; Certified Reference Material

110. Exemestane For System Suitability, European Pharmacopoeia (ep) Reference Standard

111. (1s,2r,10r,11s,15s)-2,15-dimethyl-8-methylidenetetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-5,14-dione

112. Exm

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₄O₂
Molecular Weight	296.4 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	0
Exact Mass	296.177630004 g/mol
Monoisotopic Mass	296.177630004 g/mol
Topological Polar Surface Area	34.1 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	653
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Aromasin
PubMed Health	Exemestane (By mouth)
Drug Classes	Antineoplastic Agent, Endocrine-Metabolic Agent
Drug Label	AROMASIN Tablets for oral administration contain 25 mg of exemestane, an irreversible, steroidal aromatase inactivator. Exemestane is chemically described as 6-methylenandrosta-1,4-diene-3,17-dione. Its molecular formula is C20H24O2 and its structu...
Active Ingredient	Exemestane
Dosage Form	Tablet
Route	Oral
Strength	25mg
Market Status	Prescription
Company	Pharmacia And Upjohn

2 of 4
Drug Name	Exemestane
PubMed Health	Exemestane (By mouth)
Drug Classes	Antineoplastic Agent, Endocrine-Metabolic Agent
Drug Label	EXEMESTANE tablets for oral administration contain 25 mg of EXEMESTANE, an irreversible, steroidal aromatase inactivator. EXEMESTANE is chemically described as 6-methylenandrosta-1,4-diene-3,17-dione. Its molecular formula is C20H24O2 and its structu...
Active Ingredient	Exemestane
Dosage Form	Tablet
Route	Oral
Strength	25mg
Market Status	Prescription
Company	Alvogen; Roxane

3 of 4
Drug Name	Aromasin
PubMed Health	Exemestane (By mouth)
Drug Classes	Antineoplastic Agent, Endocrine-Metabolic Agent
Drug Label	AROMASIN Tablets for oral administration contain 25 mg of exemestane, an irreversible, steroidal aromatase inactivator. Exemestane is chemically described as 6-methylenandrosta-1,4-diene-3,17-dione. Its molecular formula is C20H24O2 and its structu...
Active Ingredient	Exemestane
Dosage Form	Tablet
Route	Oral
Strength	25mg
Market Status	Prescription
Company	Pharmacia And Upjohn

4 of 4
Drug Name	Exemestane
PubMed Health	Exemestane (By mouth)
Drug Classes	Antineoplastic Agent, Endocrine-Metabolic Agent
Drug Label	EXEMESTANE tablets for oral administration contain 25 mg of EXEMESTANE, an irreversible, steroidal aromatase inactivator. EXEMESTANE is chemically described as 6-methylenandrosta-1,4-diene-3,17-dione. Its molecular formula is C20H24O2 and its structu...
Active Ingredient	Exemestane
Dosage Form	Tablet
Route	Oral
Strength	25mg
Market Status	Prescription
Company	Alvogen; Roxane

4.2 Therapeutic Uses

Antineoplastic (hormonal).

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. 692

Exemestane is indicated for the treatment of advanced breast cancer in postmenopausal women whose disease has progressed following tamoxifen therapy. /Included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1434

Use of exemestane in premenopausal women is not accepted. /Included in US product label/

Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2006., p. 1434

4.3 Drug Warning

Adverse events of any cause observed in the overall clinical trials program (N=1058) in 5% or greater of patients treated with exemestane 25 mg once daily but not in the comparative study included pain at tumor sites (8%), asthenia (6%) and fever (5%). Adverse events of any cause reported in 2% to 5% of all patients treated with exemestane 25 mg in the overall clinical trials program but not in the comparative study included chest pain, hypoesthesia, confusion, dyspepsia, arthralgia, back pain, skeletal pain, infection, upper respiratory tract infection, pharyngitis, rhinitis, and alopecia.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2602

Less frequent adverse events of any cause (from 2% to 5%) reported in the comparative study for patients receiving /exemestane/ 25 mg once daily were fever, generalized weakness, paresthesia, pathological fracture, bronchitis, sinusitis, rash, itching, urinary tract infection, and lymphedema.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2601

Other adverse effects occurring in at least 5%, regardless of causality, include mental depression, pain, insomnia, anxiety, dyspnea, dizziness, headache, edema, vomiting, abdominal pain, anorexia, cough, flu-like symptoms, hypertension, and constipation.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1044

Lymphocytopenia grade 3 or 4 was also reported in 20% of patients; however, 89% of these patients had a preexisting lower-grade lymphopenia, and 40% either recovered or improved to a lesser severity lymphopenia during exemestane. Patients did not experience a significant increase in viral infections, and no opportunistic infections were observed.

McEvoy, G.K. (ed.). American Hospital Formulary Service. AHFS Drug Information. American Society of Health-System Pharmacists, Bethesda, MD. 2006., p. 1044

For more Drug Warnings (Complete) data for EXEMESTANE (11 total), please visit the HSDB record page.

4.4 Drug Indication

For the treatment of advanced breast cancer in postmenopausal women whose disease has progressed following tamoxifen therapy.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Aromatase is an enzyme that converts hormones to estrogen in the body's adrenal glands. The aromatase inhibitors (AIs) are drugs that reduce estrogen levels by blocking the action of aromatase in the adrenal glands. The selective AIs (SAIs) selectively reduce levels of estrogen without interfering with levels of other steroid hormones that are produced by the adrenal gland. Drugs in this class include anastrozole (Arimidex ™), letrozole (Femara ™) and exemestane (Aromasin ™).

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

EXEMESTANE

5.3.2 FDA UNII

NY22HMQ4BX

5.3.3 Pharmacological Classes

Aromatase Inhibitors [MoA]; Aromatase Inhibitor [EPC]

5.4 ATC Code

L - Antineoplastic and immunomodulating agents

L02 - Endocrine therapy

L02B - Hormone antagonists and related agents

L02BG - Aromatase inhibitors

L02BG06 - Exemestane

5.5 Absorption, Distribution and Excretion

Absorption

42%

Following oral administration of radiolabeled exemestane, at least 42% of radioactivity was absorbed from the gastrointestinal tract. Exemestane plasma levels increased by approximately 40% after a high-fat breakfast.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2600

The pharmacokinetics of exemestane are dose proportional after single (10 to 200 mg) or repeated oral doses (0.5 to 50 mg). Following repeated daily doses of exemestane 25 mg, plasma concentrations of unchanged drug are similar to levels measured after a single dose.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2600

Pharmacokinetic parameters in postmenopausal women with advanced breast cancer following single or repeated doses have been compared with those in healthy, postmenopausal women. Exemestane appeared to be more rapidly absorbed in the women with breast cancer than in the healthy women, with a mean tmax of 1.2 hours in the women with breast cancer and 2.9 hours in the healthy women. After repeated dosing, the average oral clearance in women with advanced breast cancer was 45% lower than the oral clearance in healthy postmenopausal women, with corresponding higher systemic exposure. Mean AUC values following repeated doses in women with breast cancer (75.4 nghr/mL) were about twice those in healthy women (41.4 nghr/mL).

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2600

Exemestane is distributed extensively into tissues. Exemestane is 90% bound to plasma proteins and the fraction bound is independent of the total concentration. Albumin and (alpha) 1 -acid glycoprotein both contribute to the binding. The distribution of exemestane and its metabolites into blood cells is negligible.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2600

For more Absorption, Distribution and Excretion (Complete) data for EXEMESTANE (11 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Hepatic

Exemestane is extensively metabolized, with levels of the unchanged drug in plasma accounting for less than 10% of the total radioactivity. The initial steps in the metabolism of exemestane are oxidation of the methylene group in position 6 and reduction of the 17-keto group with subsequent formation of many secondary metabolites. Each metabolite accounts only for a limited amount of drug-related material. The metabolites are inactive or inhibit aromatase with decreased potency compared with the parent drug. One metabolite may have androgenic activity. Studies using human liver preparations indicate that cytochrome P-450 3A4 (CYP 3A4) is the principal isoenzyme involved in the oxidation of exemestane.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2600

5.7 Biological Half-Life

24 hours

Following oral administration to healthy postmenopausal women, exemestane is rapidly absorbed. After maximum plasma concentration is reached, levels decline polyexponentially with a mean terminal half-life of about 24 hours.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2600

... The terminal half-life was 8.9 hr. Maximal estradiol suppression of 62 +/- 14% was observed at 12 hr.

PMID:14671195 Mauras N et al; J Clin Endocrinol Metab 88 (12): 5951-6 (2003)

5.8 Mechanism of Action

Breast cancer cell growth may be estrogen-dependent. Aromatase (exemestane) is the principal enzyme that converts androgens to estrogens both in pre- and postmenopausal women. While the main source of estrogen (primarily estradiol) is the ovary in premenopausal women, the principal source of circulating estrogens in postmenopausal women is from conversion of adrenal and ovarian androgens (androstenedione and testosterone) to estrogens (estrone and estradiol) by the aromatase enzyme in peripheral tissues. Estrogen deprivation through aromatase inhibition is an effective and selective treatment for some postmenopausal patients with hormone-dependent breast cancer. Exemestane is an irreversible, steroidal aromatase inactivator, structurally related to the natural substrate androstenedione. It irreversibly binds to the active site causing permanent inhibition necessitating de novo synthesis to restore enzymatic function. Exemestane significantly lowers circulating estrogen concentrations in postmenopausal women, but has no detectable effect on the adrenal biosynthesis of corticosteroids or aldosterone. This reduction in serum and tumor concentrations of estrogen delays tumor growth and disease progression. Exemestane has no effect on other enzymes involved in the steroidogenic pathway up to a concentration at least 600 times higher than that inhibiting the aromatase enzyme.

... exemestane is a potent aromatase inhibitor in men and an alternative to the choice of available inhibitors...

PMID:14671195 Mauras N et al; J Clin Endocrinol Metab 88 (12): 5951-6 (2003)

Estrogen deprivation through aromatase inhibition is an effective and selective treatment for some postmenopausal patients with hormone-dependent breast cancer. Exemestane is an irreversible, steroidal aromatase inactivator, structurally related to the natural substrate androstenedione. It acts as a false substrate for the aromatase enzyme, and is processed to an intermediate that binds irreversibly to the active site of the enzyme causing its inactivation, an effect also known as "suicide inhibition." Exemestane significantly lowers circulating estrogen concentrations in postmenopausal women, but has no detectable effect on adrenal biosynthesis of corticosteroids or aldosterone. Exemestane has no effect on other enzymes involved in the steroidogenic pathway up to a concentration at least 600 times higher than that inhibiting the aromatase enzyme.

Physicians Desk Reference 60th ed, Thomson PDR, Montvale, NJ 2006., p. 2600

... Treatment with exemestane suppressed whole body aromatization from a mean pretreatment value of 2.059% to 0.042% (mean suppression of 97.9%). Plasma levels of estrone, estradiol, and estrone sulfate were found to be suppressed by 94.5%, 92.2%, and 93.2%, respectively. This is the first study revealing near total aromatase inhibition in vivo with the use of a steroidal aromatase inhibitor. The observation that exemestane is a highly potent aromatase inhibitor, together with the fact that the drug is administered p.o. and causes limited side effects, suggests that exemestane is a promising new drug for the treatment of hormone sensitive breast cancer.

PMID:9748124 Geisler J et al; Clin Cancer Res 4 (9): 2089-93 (1998)

... Exemestane induces aromatase degradation in a dose-responsive manner (25-200 nmol/L), and the effect can be seen in as early as 2 hours. Metabolic labeling with S(35)-methionine was used to determine the half-life (t(1/2)) of aromatase protein. In the presence of 200 nmol/L exemestane, the t(1/2) of aromatase was reduced to 12.5 hours from 28.2 hours in the untreated cells. ...

PMID:17079446 Wang X et al; Cancer Res 66 (21): 10281-6 (2006)

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YANCHENG XINYI PHARM AND CHEM CO L...

China

USDMF, CEP/COS, JDMF, EU-WC, NDC, KDMF, VMF, Others

Medlab Asia & Asia Health

Not Confirmed

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USDMF

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CEP/COS

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JDMF

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EU WC

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NDC API

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Listed Suppliers

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API Reference Price

[{"dataSource":"API Export","activeIngredients":"","year":"2022","qtr":"Q1","strtotime":1647801000,"product":"EXEMESTANE USP","address":"CIPLA HOUSE, PENINSULA BUSINESS,PA RK,GANPATRAO KADAM MARG,LOWER","city":"PAREL MUMBAI MAHARASHTRA,MAHARASHTR","supplier":"CIPLA","supplierCountry":"INDIA","foreign_port":"DHAKA","customer":"PRIME BANK LTD. 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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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Market Place

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

28 API Suppliers

17 USDMF

10 CEP/COS

1 JDMF

4 EU WC

17 NDC API

16 Listed Suppliers

$ API Reference Price

DEVELOPMENTS

4 Drugs in Development

FINISHED DOSAGE FORMULATIONS

118 FDF Dossiers

12 FDA Orange Book

71 Europe

4 Canada

16 Australia

6 South Africa

9 Listed Dossiers

RELATED EXCIPIENT COMPANIES

1 Rochem International Inc

16 SPI Pharma

2 Seqens

3 DKSH

4 Faran Shimi Pharmaceutical

2 Boai NKY Pharmaceuticals Ltd

9 Gangwal Healthcare

3 Nanjing Well Pharmaceutical

2 Pfanstiehl

1 ACG Worldwide

6 Actylis

1 Alcedo Pharmachem

5 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

19 BASF

10 Corel Pharma Chem

5 DFE Pharma

1 Finar

10 Gangwal Chemicals

1 Huzhou Sunflower Pharmaceutical

7 Ideal Cures Pvt Ltd

2 Ingredion Pharma Solutions

33 Kerry

3 Kima Chemical

6 Lonza Capsugel

13 Microlex e.U

1 Nanjing Bold Chemical

2 Nomisma Healthcare

3 Novo Excipients

2 Pharmatrans-Sanaq

4 Pluviaendo

3 Prachin Chemical

1 Qianhao Chemical (Hebei) Co., Ltd

1 Qualicaps

14 Roquette

12 Seppic

4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

1 Shijiazhuang Huaxu Pharmaceutical

10 Sigachi Industries

2 The Dow Chemical Company

4 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

67 Fillers, Diluents & Binders

53 Coating Systems & Additives

34 Direct Compression

29 Controlled & Modified Release

22 Thickeners and Stabilizers

20 Granulation

18 Co-Processed Excipients

17 Solubilizers

16 Disintegrants & Superdisintegrants

16 Taste Masking

15 Lubricants & Glidants

15 Film Formers & Plasticizers

14 Parenteral

13 Topical