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ACTIVE PHARMA INGREDIENTS

44 API Suppliers, 20 USDMF, 11 CEP/COS, 2 JDMF, 3 EU WC, 10 KDMF, 19 NDC API, 30 Listed Suppliers, $ API Reference Price

44 API Suppliers
20 USDMF
11 CEP/COS
2 JDMF
3 EU WC
10 KDMF
19 NDC API
30 Listed Suppliers
$ API Reference Price

DEVELOPMENTS

12 Drugs in Development

12 Drugs in Development

FINISHED DOSAGE FORMULATIONS

345 FDF Dossiers, 53 FDA Orange Book, 16 Europe, 18 Canada, 48 Australia, 191 South Africa, 19 Listed Dossiers

345 FDF Dossiers
53 FDA Orange Book
16 Europe
18 Canada
48 Australia
191 South Africa
19 Listed Dossiers

DRUG PRODUCT COMPOSITIONS

TABLET, FOR SUSPENSION;ORAL - 2MG, TABLET, FOR SUSPENSION;ORAL - 3MG, TABLET, FOR SUSPENSION;ORAL - 5MG, TABLET;ORAL - 10MG, TABLET;ORAL - 2.5MG, TABLET;ORAL - 5MG, TABLET;ORAL - 7.5MG

drugProductComposition
TABLET, FOR SUSPENSION;ORAL - 2MG
TABLET, FOR SUSPENSION;ORAL - 3MG
TABLET, FOR SUSPENSION;ORAL - 5MG
TABLET;ORAL - 10MG
TABLET;ORAL - 2.5MG
TABLET;ORAL - 5MG
TABLET;ORAL - 7.5MG

RELATED EXCIPIENT COMPANIES

1 Rochem International Inc, 13 SPI Pharma, 1 DKSH, 3 Faran Shimi Pharmaceutical, 4 Boai NKY Pharmaceuticals Ltd, 8 Gangwal Healthcare, 1 Nanjing Well Pharmaceutical, 1 Pfanstiehl, 1 ACG Worldwide, 1 Alcedo Pharmachem, 5 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 6 BASF, 10 Corel Pharma Chem, 5 DFE Pharma, 8 Gangwal Chemicals, 5 Ideal Cures Pvt Ltd, 1 Ingredion Pharma Solutions, 37 Kerry, 3 Kima Chemical, 6 Lonza Capsugel, 14 Microlex e.U, 2 Novo Excipients, 2 Pharmatrans-Sanaq, 3 Pluviaendo, 2 Prachin Chemical, 1 Qianhao Chemical (Hebei) Co., Ltd, 1 Qualicaps, 10 Roquette, 6 Seppic, 4 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 1 Shijiazhuang Huaxu Pharmaceutical, 9 Sigachi Industries, 2 The Dow Chemical Company, 1 Ulanqab Kema New Material, 2 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

66 Fillers, Diluents & Binders, 40 Coating Systems & Additives, 35 Direct Compression, 20 Controlled & Modified Release, 18 Granulation, 17 Disintegrants & Superdisintegrants, 16 Co-Processed Excipients, 16 Thickeners and Stabilizers, 14 Chewable & Orodispersible Aids, 12 Taste Masking, 11 Lubricants & Glidants, 6 Film Formers & Plasticizers, 5 Empty Capsules, 5 API Stability Enhancers, 5 Parenteral, 4 Vegetarian Capsules, 4 Solubilizers, 4 Emulsifying Agents, 2 Coloring Agents, 2 Rheology Modifiers

DIGITAL CONTENT

2 DATA COMPILATION #PharmaFlow, 73 NEWS #PharmaBuzz

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2 DATA COMPILATION #PharmaFlow
73 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

4 US Medicaid Prescriptions, 13 Finished Drug Prices, 22 Annual Reports

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4 US Medicaid Prescriptions
13 Finished Drug Prices
22 Annual Reports

MARKET PLACE

18 APIs, 12 FDF Dossiers

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18 APIs
12 FDF Dossiers

PATENTS & EXCLUSIVITIES

12 US Patents, 3 US Exclusivities, 43 Health Canada Patents

patents
12 US Patents
3 US Exclusivities
43 Health Canada Patents

REF. STANDARDS & IMPURITIES

4 Others

otherSolutions
4 Others

ANALYTICAL

1 BioAnalytical Methods

otherMethods
1 BioAnalytical Methods

Farmhispania Everolimus

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 263,673

MARKET PLACE

API

FDF

0INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

345

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

191

South Africa

Listed Dossiers

12DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

335,271,220

Annual Reports (USD Million)

14,328

Finished Drug Prices

180 RELATED EXCIPIENT COMPANIES

302EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 001, rad, 40-o-(2-hydroxyethyl)-rapamycin, 40-o-(2-hydroxyethyl)rapamycin, Afinitor, Certican, Rad

Molecular Formula

C₅₃H₈₃NO₁₄

Molecular Weight

958.2 g/mol

InChI Key

HKVAMNSJSFKALM-GKUWKFKPSA-N

FDA UNII

9HW64Q8G6G

A derivative of sirolimus and an inhibitor of TOR SERINE-THREONINE KINASES. It is used to prevent GRAFT REJECTION in heart and kidney transplant patients by blocking cell proliferation signals. It is also an ANTINEOPLASTIC AGENT.

Everolimus is a Kinase Inhibitor and mTOR Inhibitor Immunosuppressant. The mechanism of action of everolimus is as a Protein Kinase Inhibitor and Cytochrome P450 3A4 Inhibitor and Cytochrome P450 2D6 Inhibitor and mTOR Inhibitor. The physiologic effect of everolimus is by means of Decreased Immunologic Activity.

1 2D Structure

Everolimus

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-(2-hydroxyethoxy)-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

2.1.2 InChI

InChI=1S/C53H83NO14/c1-32-16-12-11-13-17-33(2)44(63-8)30-40-21-19-38(7)53(62,68-40)50(59)51(60)54-23-15-14-18-41(54)52(61)67-45(35(4)28-39-20-22-43(66-25-24-55)46(29-39)64-9)31-42(56)34(3)27-37(6)48(58)49(65-10)47(57)36(5)26-32/h11-13,16-17,27,32,34-36,38-41,43-46,48-49,55,58,62H,14-15,18-26,28-31H2,1-10H3/b13-11+,16-12+,33-17+,37-27+/t32-,34-,35-,36-,38-,39+,40+,41+,43-,44+,45+,46-,48-,49+,53-/m1/s1

2.1.3 InChI Key

HKVAMNSJSFKALM-GKUWKFKPSA-N

2.1.4 Canonical SMILES

CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)OCCO)C)C)O)OC)C)C)C)OC

2.1.5 Isomeric SMILES

C[C@@H]1CC[C@H]2C[C@@H](/C(=C/C=C/C=C/[C@H](C[C@H](C(=O)[C@@H]([C@@H](/C(=C/[C@H](C(=O)C[C@H](OC(=O)[C@@H]3CCCCN3C(=O)C(=O)[C@@]1(O2)O)[C@H](C)C[C@@H]4CC[C@H]([C@@H](C4)OC)OCCO)C)/C)O)OC)C)C)/C)OC

2.2 Other Identifiers

2.2.1 UNII

9HW64Q8G6G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 001, Rad

2. 40-o-(2-hydroxyethyl)-rapamycin

3. Afinitor

4. Certican

5. Rad 001

6. Rad, Sdz

7. Rad001

8. Sdz Rad

9. Sdz-rad

10. Zortress

2.3.2 Depositor-Supplied Synonyms

1. 001, Rad

2. 40-o-(2-hydroxyethyl)-rapamycin

3. 40-o-(2-hydroxyethyl)rapamycin

4. Afinitor

5. Certican

6. Rad

7. Rad 001

8. Rad, Sdz

9. Rad001

10. Sdz Rad

11. Sdz-rad

12. Zortress

13. 159351-69-6

14. Votubia

15. 42-o-(2-hydroxyethyl)rapamycin

16. Rad-001

17. Afinitor Disperz

18. Chebi:68478

19. Rapamycin, 42-o-(2-hydroxyethyl)-

20. 9hw64q8g6g

21. Rad 666

22. Rad-666

23. Everolimus (inn)

24. Ncgc00167512-01

25. Everolimus (rad001)

26. Everolimus [inn]

27. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{(2r)-1-[(1s,3r,4r)-4-(2-hydroxyethoxy)-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-3h-23,27-epoxypyrido[2,1-c][1,4]oxazacyclohentriacontine-1,5,11,28,29(4h,6h,31h)-pentone

28. (1r,9s,12s,15r,16e,18r,19r,21r,23s,24e,26e,28e,30s,35r)-1,18-dihydroxy-12-{(2r)-1-[(1s,3r,4r)-4-(2-hydroxyethoxy)-3-methoxycyclohexyl]propan-2-yl}-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0(4,9)]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

29. Everolimus [usan]

30. Everolimusum

31. Nsc733504

32. Everolimus Solution

33. Sdzrad

34. Everolimus Solution, 1.0 Mg/ml In Acetonitrile

35. Xience V

36. Everolimus [mi]

37. Everolimus - Rad001

38. Everolimus [jan]

39. Everolimus [vandf]

40. Everolimus [mart.]

41. Schembl4378

42. Dsstox_cid_20599

43. Dsstox_rid_79508

44. Everolimus [usp-rs]

45. Everolimus [who-dd]

46. Nvp-rad001

47. Unii-9hw64q8g6g

48. Dsstox_gsid_40599

49. Everolimus [ema Epar]

50. Everolimus [usan:inn:ban]

51. Nvp-rad-001

52. Everolimus, Analytical Standard

53. Gtpl5889

54. Rad-001c

55. Chembl1908360

56. Dtxsid0040599

57. Everolimus [orange Book]

58. Hsdb 8255

59. Everolimus [ep Monograph]

60. Everolimus; Rad001; Sdz-rad

61. 42-o-(2-hydroxyethyl)-rapamycin

62. Ex-a2057

63. Tox21_112510

64. Bdbm50088378

65. Akos015850977

66. Zinc169677008

67. Cs-0064

68. Db01590

69. (1r,9s,12s,15r,16e,18r,19r,21r,23s,24e,26e,28e,30s,32s,35r)-1,18-dihydroxy-12-((1r)-2-((1s,3r,4r)-4-(2-hydroxyethoxy)-3-methoxycyclohexyl)-1-methylethyl)-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo(30.3.1.0(sup 4,9))hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentaone

70. (1r,9s,12s,15r,16e,18r,19r,21r,23s,24e,26e,28e,30s,32s,35r)-1,18-dihydroxy-12-((1r)-2-((1s,3r,4r)-4-(2-hydroxyethoxy)-3-methoxycyclohexyl)-1-methylethyl)-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo(30.3.1.04,9)hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentaone

71. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro-9,27-dihydroxy-3-((1r)-2-((1s,3r,4r)-4-(2-hydroxyethoxy)-3-methoxycyclohexyl)-1-methylethyl)-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-23,27-epoxy-3h-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4h,6h,31h)-pentone

72. As-16971

73. Hy-10218

74. Cas-159351-69-6

75. 351e696

76. Q421052

77. Q-101413

78. Brd-k13514097-001-01-2

79. Brd-k13514097-001-05-3

80. Dihydroxy-[(1r)-2-[(1s,3r,4r)-4-(2-hydroxyethoxy)-3-methoxy-cyclohexyl]-1-methyl-ethyl]-dimethoxy-hexamethyl-[?]pentone

81. Everolimus Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2006-04-28

3 Chemical and Physical Properties

Molecular Formula	C₅₃H₈₃NO₁₄
Molecular Weight	958.2 g/mol
XLogP3	5.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	9
Exact Mass	957.58135632 g/mol
Monoisotopic Mass	957.58135632 g/mol
Topological Polar Surface Area	205 Å²
Heavy Atom Count	68
Formal Charge	0
Complexity	1810
Isotope Atom Count	0
Defined Atom Stereocenter Count	15
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	4
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Afinitor
PubMed Health	Everolimus (By mouth)
Drug Classes	Antineoplastic Agent, Immune Suppressant
Drug Label	AFINITOR (everolimus), an inhibitor of mammalian target of rapamycin (mTOR), is an antineoplastic agent.The chemical name of everolimus is (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18- dihydroxy-12-{(1R)-2-[(1S,3R,4R)-4-(2-hydroxy...
Active Ingredient	Everolimus
Dosage Form	Tablet
Route	Oral
Strength	2.5mg; 5mg; 7.5mg; 10mg
Market Status	Prescription
Company	Novartis

2 of 4
Drug Name	Zortress
PubMed Health	Everolimus (By mouth)
Drug Classes	Antineoplastic Agent, Immune Suppressant
Drug Label	Zortress (everolimus) is a macrolide immunosuppressant.The chemical name of everolimus is(1R, 9S, 12S, 15R, 16E, 18R, 19R, 21R, 23S, 24E, 26E, 28E, 30S, 32S, 35R)-1, 18-dihydroxy-12-{(1R)-2-[(1S,3R,4R)-4-(2-hydroxyethoxy)-3-methoxycyclohexyl]-1-m...
Active Ingredient	Everolimus
Dosage Form	Tablet
Route	Oral
Strength	0.5mg; 0.25mg; 0.75mg
Market Status	Prescription
Company	Novartis

3 of 4
Drug Name	Afinitor
PubMed Health	Everolimus (By mouth)
Drug Classes	Antineoplastic Agent, Immune Suppressant
Drug Label	AFINITOR (everolimus), an inhibitor of mammalian target of rapamycin (mTOR), is an antineoplastic agent.The chemical name of everolimus is (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18- dihydroxy-12-{(1R)-2-[(1S,3R,4R)-4-(2-hydroxy...
Active Ingredient	Everolimus
Dosage Form	Tablet
Route	Oral
Strength	2.5mg; 5mg; 7.5mg; 10mg
Market Status	Prescription
Company	Novartis

4 of 4
Drug Name	Zortress
PubMed Health	Everolimus (By mouth)
Drug Classes	Antineoplastic Agent, Immune Suppressant
Drug Label	Zortress (everolimus) is a macrolide immunosuppressant.The chemical name of everolimus is(1R, 9S, 12S, 15R, 16E, 18R, 19R, 21R, 23S, 24E, 26E, 28E, 30S, 32S, 35R)-1, 18-dihydroxy-12-{(1R)-2-[(1S,3R,4R)-4-(2-hydroxyethoxy)-3-methoxycyclohexyl]-1-m...
Active Ingredient	Everolimus
Dosage Form	Tablet
Route	Oral
Strength	0.5mg; 0.25mg; 0.75mg
Market Status	Prescription
Company	Novartis

4.2 Therapeutic Uses

Immunosuppressive Agents

National Library of Medicine's Medical Subject Headings. Everolimus. Online file (MeSH, 2015). Available from, as of May 1, 2015: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html

/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health(NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. Everolimus is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of July 18, 2015: https://clinicaltrials.gov/search/intervention=Everolimus

Afinitor is indicated for the treatment of postmenopausal women with advanced hormone receptor-positive, HER2-negative breast cancer (advanced HR+ BC) in combination with exemestane, after failure of treatment with letrozole or anastrozole. /Included in US product label/

NIH; DailyMed. Current Medication Information for Afinitor (Everolimus) Tablet; Afinitor Disperz (Everolimus) Tablet, For Suspension (Updated: January 2015). Available from, as of May 4, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2150f73a-179b-4afc-b8ce-67c85cc72f04

Afinitor Tablets and Afinitor Disperz are indicated in pediatric and adult patients with tuberous sclerosis complex (TSC) for the treatment of subependymal giant cell astrocytoma (SEGA) that requires therapeutic intervention but cannot be curatively resected. /Included in US product label/c

For more Therapeutic Uses (Complete) data for EVEROLIMUS (9 total), please visit the HSDB record page.

4.3 Drug Warning

/BOXED WARNING/ WARNING: MALIGNANCIES AND SERIOUS INFECTIONS. Only physicians experienced in immunosuppressive therapy and management of transplant patients should prescribe Zortress. Patients receiving the drug should be managed in facilities equipped and staffed with adequate laboratory and supportive medical resources. The physician responsible for maintenance therapy should have complete information requisite for the follow-up of the patient. Increased susceptibility to infection and the possible development of malignancies such as lymphoma and skin cancer may result from immunosuppression.

NIH; DailyMed. Current Medication Information for Zortress (Everolimus) Tablet (Updated: January 2015). Available from, as of May 19, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e082a024-7850-400b-a5c2-2a140612562a

/BOXED WARNING/ WARNING: KIDNEY GRAFT THROMBOSIS. An increased risk of kidney arterial and venous thrombosis, resulting in graft loss, was reported, mostly within the first 30 days post-transplantation.

/BOXED WARNING/ WARNING: NEPHROTOXICITY. Increased nephrotoxicity can occur with use of standard doses of cyclosporine in combination with Zortress. Therefore reduced doses of cyclosporine should be used in combination with Zortress in order to reduce renal dysfunction. It is important to monitor the cyclosporine and everolimus whole blood trough concentrations.

/BOXED WARNING/ WARNING: MORTALITY IN HEART TRANSPLANTATION. Increased mortality, often associated with serious infections, within the first three months post-transplantation was observed in a clinical trial of de novo heart transplant patients receiving immunosuppressive regimens with or without induction therapy. Use in heart transplantation is not recommended.

For more Drug Warnings (Complete) data for EVEROLIMUS (32 total), please visit the HSDB record page.

4.4 Drug Indication

Everolimus is indicated for the treatment of postmenopausal women with advanced hormone receptor-positive, HER2-negative breast cancer (advanced HR+ BC) in combination with exemestane, after failure of treatment with letrozole or anastrozole. Indicated for the treatment of adult patients with progressive neuroendocrine tumors of pancreatic origin (PNET) with unresectable, locally advanced or metastatic disease. Indicated for the treatment of adult patients with advanced renal cell carcinoma (RCC) after failure of treatment with sunitinib or sorafenib. Indicated for the treatment of adult patients with renal angiomyolipoma and tuberous sclerosis complex (TSC), not requiring immediate surgery. Indicated in pediatric and adult patients with tuberous sclerosis complex (TSC) for the treatment of subependymal giant cell astrocytoma (SEGA) that requires therapeutic intervention but cannot be curatively resected.

FDA Label

* Hormone-receptor-positive advanced breast:

* cancer :

Afinitor is indicated for the treatment of hormone-receptor-positive, HER2/neu-negative advanced breast cancer , in combination with exemestane, in post-menopausal women without symptomatic visceral disease after recurrence or progression following a non-steroidal aromatase inhibitor.

* Neuroendocrine tumours of pancreatic origin:

Afinitor is indicated for the treatment of unresectable or metastatic, well or moderately differentiated neuroendocrine tumours of pancreatic origin in adults with progressive disease.

* Neuroendocrine tumours of gastrointestinal or lung origin:

Afinitor is indicated for the treatment of unresectable or metastatic, well-differentiated (Grade 1 or Grade 2) non-functional neuroendocrine tumours of gastrointestinal or lung origin in adults with progressive disease.

* Renal-cell carcinoma:

Afinitor is indicated for the treatment of patients with advanced renal-cell carcinoma, whose disease has progressed on or after treatment with VEGF-targeted therapy.

* Renal angiomyolipoma associated with tuberous sclerosis complex (TSC):

Votubia is indicated for the treatment of adult patients with renal angiomyolipoma associated with tuberous sclerosis complex (TSC) who are at risk of complications (based on factors such as tumour size or presence of aneurysm, or presence of multiple or bilateral tumours) but who do not require immediate surgery.

The evidence is based on analysis of change in sum of angiomyolipoma volume.

* Subependymal giant cell astrocytoma (SEGA) associated with tuberous sclerosis complex (TSC):

Votubia is indicated for the treatment of patients with subependymal giant cell astrocytoma (SEGA) associated with tuberous sclerosis complex (TSC) who require therapeutic intervention but are not amenable to surgery.

The evidence is based on analysis of change in SEGA volume. Further clinical benefit, such as improvement in diseaserelated symptoms, has not been demonstrated.

Treatment of tuberous sclerosis complex

Treatment of thoracic neuroendocrine tumour

Carcinoid tumours

Prevention of rejection of transplanted liver, Prevention of rejection of transplanted heart, Prevention of rejection of transplanted kidney

Treatment of angiomyolipoma, Treatment of subependymal giant-cell astrocytoma

Renal cell carcinoma and pancreatic neuroendocrine tumour

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Immunosuppressive Agents

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

MTOR Inhibitors

Agents that inhibit the activity of TOR SERINE-THREONINE KINASES. (See all compounds classified as MTOR Inhibitors.)

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

EVEROLIMUS

5.2.2 FDA UNII

9HW64Q8G6G

5.2.3 Pharmacological Classes

Cytochrome P450 3A4 Inhibitors [MoA]; Decreased Immunologic Activity [PE]; Kinase Inhibitor [EPC]; P-Glycoprotein Inhibitors [MoA]; Protein Kinase Inhibitors [MoA]; mTOR Inhibitor Immunosuppressant [EPC]; mTOR Inhibitors [MoA]; Cytochrome P450 2D6 Inhibitors [MoA]

5.3 ATC Code

L01XE10

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01E - Protein kinase inhibitors

L01EG - Mammalian target of rapamycin (mtor) kinase inhibitors

L01EG02 - Everolimus

L - Antineoplastic and immunomodulating agents

L04 - Immunosuppressants

L04A - Immunosuppressants

L04AA - Selective immunosuppressants

L04AA18 - Everolimus

5.4 Absorption, Distribution and Excretion

Absorption

In patients with advanced solid tumors, peak everolimus concentrations are reached 1 to 2 hours after administration of oral doses ranging from 5 mg to 70 mg. Following single doses, Cmax is dose-proportional between 5 mg and 10 mg. At doses of 20 mg and higher, the increase in Cmax is less than dose-proportional, however AUC shows dose-proportionality over the 5 mg to 70 mg dose range. Steady-state was achieved within 2 weeks following once-daily dosing. Dose Proportionality in Patients with SEGA (subependymal giant-cell astrocytomas) and TSC (tuberous sclerosis complex): In patients with SEGA and TSC, everolimus Cmin was approximately dose-proportional within the dose range from 1.35 mg/m2 to 14.4 mg/m2.

Route of Elimination

After a single dose of radiolabeled everolimus was given to transplant patients receiving cyclosporine, the majority (80%) of radioactivity was recovered from the feces and only a minor amount (5%) was excreted in urine.

Volume of Distribution

The blood-to-plasma ratio of everolimus is 17% to 73%.

Clearance

Following a 3 mg radiolabeled dose of everolimus, 80% of the radioactivity was recovered from the feces, while 5% was excreted in the urine.

The blood-to-plasma ratio of everolimus is concentration dependent ranging from 17% to 73% over the range of 5 ng/mL to 5000 ng/mL. Plasma protein binding is approximately 74% in healthy subjects and in patients with moderate hepatic impairment. The apparent distribution volume associated with the terminal phase (Vz/F) from a single-dose pharmacokinetic study in maintenance kidney transplant patients is 342 to 107 L (range 128 to 589 L).

NIH; DailyMed. Current Medication Information for Zortress (Everolimus) Tablet (Updated: January 2015). Available from, as of May 4, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=e082a024-7850-400b-a5c2-2a140612562a

The blood-to-plasma ratio of everolimus, which is concentration-dependent over the range of 5 to 5000 ng/mL, is 17% to 73%. The amount of everolimus confined to the plasma is approximately 20% at blood concentrations observed in cancer patients given Afinitor 10 mg/day. Plasma protein binding is approximately 74% both in healthy subjects and in patients with moderate hepatic impairment.

After administration of Afinitor tablets in patients with advanced solid tumors, peak everolimus concentrations are reached 1 to 2 hours after administration of oral doses ranging from 5 mg to 70 mg. Following single doses, Cmax is dose-proportional with daily dosing between 5 mg and 10 mg. With single doses of 20 mg and higher, the increase in Cmax is less than dose-proportional, however AUC shows dose-proportionality over the 5 mg to 70 mg dose range. Steady-state was achieved within 2 weeks following once-daily dosing.

No specific elimination studies have been undertaken in cancer patients. Following the administration of a 3 mg single dose of radiolabeled everolimus in patients who were receiving cyclosporine, 80% of the radioactivity was recovered from the feces, while 5% was excreted in the urine. The parent substance was not detected in urine or feces. The mean elimination half-life of everolimus is approximately 30 hours.

For more Absorption, Distribution and Excretion (Complete) data for EVEROLIMUS (7 total), please visit the HSDB record page.

5.5 Metabolism/Metabolites

Everolimus is a substrate of CYP3A4 and PgP (phosphoglycolate phosphatase). Three monohydroxylated metabolites, two hydrolytic ring-opened products, and a phosphatidylcholine conjugate of everolimus were the 6 primary metabolites detected in human blood. In vitro, everolimus competitively inhibited the metabolism of CYP3A4 and was a mixed inhibitor of the CYP2D6 substrate dextromethorphan.

Everolimus is a substrate of CYP3A4 and PgP. Following oral administration, everolimus is the main circulating component in human blood. Six main metabolites of everolimus have been detected in human blood, including three monohydroxylated metabolites, two hydrolytic ring-opened products, and a phosphatidylcholine conjugate of everolimus. These metabolites were also identified in animal species used in toxicity studies, and showed approximately 100-times less activity than everolimus itself.

Everolimus has known human metabolites that include (1R,9S,12S,15R,16Z,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-Dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone and (1R,9S,12S,15R,16Z,18R,19R,21R,23S,24E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-3-hydroxy-4-(2-hydroxyethoxy)cyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.04,9]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.6 Biological Half-Life

~30 hours.

The mean elimination half-life of everolimus is approximately 30 hours.

5.7 Mechanism of Action

Everolimus is a mTOR inhibitor that binds with high affinity to the FK506 binding protein-12 (FKBP-12), thereby forming a drug complex that inhibits the activation of mTOR. This inhibition reduces the activity of effectors downstream, which leads to a blockage in the progression of cells from G1 into S phase, and subsequently inducing cell growth arrest and apoptosis. Everolimus also inhibits the expression of hypoxia-inducible factor, leading to a decrease in the expression of vascular endothelial growth factor. The result of everolimus inhibition of mTOR is a reduction in cell proliferation, angiogenesis, and glucose uptake.

Mechanistic target of rapamycin (mTOR) is a serine-threonine kinase that functions via two multiprotein complexes, namely mTORC1 and mTORC2, each characterized by different binding partners that confer separate functions. mTORC1 function is tightly regulated by PI3-K/Akt and is sensitive to rapamycin. mTORC2 is sensitive to growth factors, not nutrients, and is associated with rapamycin-insensitivity. mTORC1 regulates protein synthesis and cell growth through downstream molecules: 4E-BP1 (also called EIF4E-BP1) and S6K. Also, mTORC2 is thought to modulate growth factor signaling by phosphorylating the C-terminal hydrophobic motif of some AGC kinases such as Akt and SGK. Recent evidence has suggested that mTORC2 may play an important role in maintenance of normal as well as cancer cells by virtue of its association with ribosomes, which may be involved in metabolic regulation of the cell. Rapamycin (sirolimus) and its analogs known as rapalogues, such as RAD001 (everolimus) and CCI-779 (temsirolimus), suppress mTOR activity through an allosteric mechanism that acts at a distance from the ATP-catalytic binding site, and are considered incomplete inhibitors. Moreover, these compounds suppress mTORC1-mediated S6K activation, thereby blocking a negative feedback loop, leading to activation of mitogenic pathways promoting cell survival and growth. Consequently, mTOR is a suitable target of therapy in cancer treatments. However, neither of these complexes is fully inhibited by the allosteric inhibitor rapamycin or its analogs. In recent years, new pharmacologic agents have been developed which can inhibit these complexes via ATP-binding mechanism, or dual inhibition of the canonical PI3-K/Akt/mTOR signaling pathway. These compounds include WYE-354, KU-003679, PI-103, Torin1, and Torin2, which can target both complexes or serve as a dual inhibitor for PI3-K/mTOR. This investigation describes the mechanism of action of pharmacological agents that effectively target mTORC1 and mTORC2 resulting in suppression of growth, proliferation, and migration of tumor and cancer stem cells.

PMID:25442674 Jhanwar-Uniyal M et al; Adv Biol Regul 57: 64-74 (2015)

Mammalian target of rapamycin (mTOR) inhibitors have anti-tumor effects against renal cell carcinoma, pancreatic neuroendocrine cancer and breast cancer. In this study, we analyzed the antitumor effects of mTOR inhibitors in small cell lung cancer (SCLC) cells and sought to clarify the mechanism of resistance to mTOR inhibitors. We analyzed the antitumor effects of three mTOR inhibitors including everolimus in 7 SCLC cell lines by MTS assay. Gene-chip analysis, receptor tyrosine kinases (RTK) array and Western blotting analysis were performed to identify molecules associated with resistance to everolimus. Only SBC5 cells showed sensitivity to everolimus by MTS assay. We established two everolimus resistant-SBC5 cell lines (SBC5 R1 and SBC5 R10) by continuous exposure to increasing concentrations of everolimus stepwise. SPP1 and MYC were overexpressed in both SBC5 R1 and SBC5 R10 by gene-chip analysis. High expression levels of eukaryotic translation initiation factor 4E (eIF4E) were observed in 5 everolimus-resistant SCLC cells and SBC5 R10 cells by Western blotting. MYC siRNA reduced eIF4E phosphorylation in SBC5 cells, suggesting that MYC directly activates eIF4E by an mTOR-independent bypass pathway. Importantly, after reduction of MYC or eIF4E by siRNAs, the SBC5 parent and two SBC5-resistant cells displayed increased sensitivity to everolimus relative to the siRNA controls. These findings suggest that eIF4E has been shown to be an important factor in the resistance to everolimus in SCLC cells. Furthermore, a link between MYC and mTOR-independent eIF4E contribute to the resistance to everolimus in SCLC cells. Control of the MYC-eIF4E axis may be a novel therapeutic strategy for everolimus action in SCLC.

PMID:25884680 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4414307 Matsumoto M et al; BMC Cancer. 2015 Apr 9;15:241. doi: 10.1186/s12885-015-1202-4

Everolimus inhibits antigenic and interleukin (IL-2 and IL-15) stimulated activation and proliferation of T and B lymphocytes. In cells, everolimus binds to a cytoplasmic protein, the FK506 Binding Protein-12 (FKBP-12), to form an immunosuppressive complex (everolimus: FKBP-12) that binds to and inhibits the mammalian Target Of Rapamycin (mTOR), a key regulatory kinase. In the presence of everolimus phosphorylation of p70 S6 ribosomal protein kinase (p70S6K), a substrate of mTOR, is inhibited. Consequently, phosphorylation of the ribosomal S6 protein and subsequent protein synthesis and cell proliferation are inhibited. The everolimus: FKBP-12 complex has no effect on calcineurin activity. In rats and nonhuman primate models, everolimus effectively reduces kidney allograft rejection resulting in prolonged graft survival.

Everolimus is an inhibitor of mammalian target of rapamycin (mTOR), a serine-threonine kinase, downstream of the PI3K/AKT pathway. The mTOR pathway is dysregulated in several human cancers. Everolimus binds to an intracellular protein, FKBP-12, resulting in an inhibitory complex formation with mTOR complex 1 (mTORC1) and thus inhibition of mTOR kinase activity. Everolimus reduced the activity of S6 ribosomal protein kinase (S6K1) and eukaryotic initiation factor 4E-binding protein (4E-BP1), downstream effectors of mTOR, involved in protein synthesis. S6K1 is a substrate of mTORC1 and phosphorylates the activation domain 1 of the estrogen receptor which results in ligand-independent activation of the receptor. In addition, everolimus inhibited the expression of hypoxia-inducible factor (e.g., HIF-1) and reduced the expression of vascular endothelial growth factor (VEGF). Inhibition of mTOR by everolimus has been shown to reduce cell proliferation, angiogenesis, and glucose uptake in in vitro and/or in vivo studies. Constitutive activation of the PI3K/Akt/mTOR pathway can contribute to endocrine resistance in breast cancer. In vitro studies show that estrogen-dependent and HER2+ breast cancer cells are sensitive to the inhibitory effects of everolimus, and that combination treatment with everolimus and Akt, HER2, or aromatase inhibitors enhances the anti-tumor activity of everolimus in a synergistic manner. Two regulators of mTORC1 signaling are the oncogene suppressors tuberin-sclerosis complexes 1 and 2 (TSC1, TSC2). Loss or inactivation of either TSC1 or TSC2 leads to activation of downstream signaling. In TSC, a genetic disorder, inactivating mutations in either the TSC1 or the TSC2 gene lead to hamartoma formation throughout the body.

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