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239 RELATED EXCIPIENT COMPANIES

425EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: (-)-rapamycin, 53123-88-9, Ay 22989, Ay-22989, I 2190a, I-2190a
Molecular Formula
C51H79NO13
Molecular Weight
914.2  g/mol
InChI Key
QFJCIRLUMZQUOT-HPLJOQBZSA-N
FDA UNII
W36ZG6FT64

Sirolimus
A macrolide compound obtained from Streptomyces hygroscopicus that acts by selectively blocking the transcriptional activation of cytokines thereby inhibiting cytokine production. It is bioactive only when bound to IMMUNOPHILINS. Sirolimus is a potent immunosuppressant and possesses both antifungal and antineoplastic properties.
Sirolimus is a mTOR Inhibitor Immunosuppressant and Kinase Inhibitor. The mechanism of action of sirolimus is as a mTOR Inhibitor and Protein Kinase Inhibitor. The physiologic effect of sirolimus is by means of Decreased Immunologic Activity.
1 2D Structure

Sirolimus

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-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
2.1.2 InChI
InChI=1S/C51H79NO13/c1-30-16-12-11-13-17-31(2)42(61-8)28-38-21-19-36(7)51(60,65-38)48(57)49(58)52-23-15-14-18-39(52)50(59)64-43(33(4)26-37-20-22-40(53)44(27-37)62-9)29-41(54)32(3)25-35(6)46(56)47(63-10)45(55)34(5)24-30/h11-13,16-17,25,30,32-34,36-40,42-44,46-47,53,56,60H,14-15,18-24,26-29H2,1-10H3/b13-11+,16-12+,31-17+,35-25+/t30-,32-,33-,34-,36-,37+,38+,39+,40-,42+,43+,44-,46-,47+,51-/m1/s1
2.1.3 InChI Key
QFJCIRLUMZQUOT-HPLJOQBZSA-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)O)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)O)C)/C)O)OC)C)C)/C)OC
2.2 Other Identifiers
2.2.1 UNII
W36ZG6FT64
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Ay 22 989

2. Ay 22-989

3. Ay 22989

4. I 2190a

5. I-2190a

6. I2190a

7. Rapamune

8. Rapamycin

2.3.2 Depositor-Supplied Synonyms

1. (-)-rapamycin

2. 53123-88-9

3. Ay 22989

4. Ay-22989

5. I 2190a

6. I-2190a

7. I2190a

8. Nsc 226080

9. Rapa

10. Rapammune

11. Rapamune

12. Rapamycin

13. Siia 9268a

14. Wy 090217

15. Rapamycin (sirolimus)

16. Rapalimus

17. Wy-090217

18. L04aa10

19. Npc-12g

20. Antibiotic Ay 22989

21. Chebi:9168

22. W36zg6ft64

23. Sm-88 Component Sirolimus

24. De-109

25. Mfcd00867594

26. Nsc-226080

27. Ncgc00021305-05

28. Dsstox_cid_3582

29. Sirolimusum

30. Dsstox_rid_77091

31. Dsstox_gsid_23582

32. (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-hydroxy-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

33. Sila 9268a

34. Supralimus

35. Rapamycin/sirolimus

36. (1r,9s,12s,15r,16e,18r,19r,21r,23s,24e,26e,28e,30s,32s,35r)-1,18-dihydroxy-12-{(2s)-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[30.3.1.0(4,9)]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone

37. Cas-53123-88-9

38. Perceiva

39. Cypher

40. Ccris 9024

41. Nsc226080

42. Hsdb 7284

43. 1fkb

44. 1pbk

45. Ncgc00181146-01

46. Lcp-siro

47. (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-hydroxy-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

48. (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-hydroxy-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

49. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{(1r)-2-[(1s,3r,4r)-4-hydroxy-3-(methyloxy)cyclohexyl]-1-methylethyl}-6,8,12,14,20,26-hexamethyl-10,21-bis(methyloxy)-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(6h,31h)-pentone

50. Rap

51. Fyarro

52. Hyftor

53. S1039

54. Sirolimus [inn]

55. Sirolimus [jan]

56. Rapamycin [mi]

57. Sirolimus [hsdb]

58. Sirolimus [usan]

59. Sirolimus [vandf]

60. Biomolki2_000084

61. Sirolimus [mart.]

62. Rapamycin C-7, Analog 4

63. Schembl3463

64. Sirolimus [usp-rs]

65. Sirolimus [who-dd]

66. Rapamycin,sirolimus,rapamune

67. Unii-w36zg6ft64

68. Bidd:pxr0165

69. Sirolimus [ema Epar]

70. Mls006010168

71. Sirolimus [usan:inn:ban]

72. Gtpl6031

73. Sirolimus [orange Book]

74. Dtxsid5023582

75. Bdbm36609

76. Ms-r001

77. Rapa, Rapamune, Sirolimus, Rpm

78. Hms2089a21

79. Hms3403f11

80. Hms3884c03

81. Ex-a1044

82. Rpm

83. Tox21_110870

84. Tox21_112750

85. Ac-722

86. Bdbm50064359

87. Stl570275

88. Akos015850976

89. Akos015961618

90. Zinc169289388

91. Ccg-100684

92. Cs-0063

93. Db00877

94. Nab-rapamycin Component Rapamycin

95. Nsc-2260804

96. Ncgc00021305-06

97. Ncgc00021305-07

98. Rapamycin From Streptomyces Hygroscopicus

99. As-11687

100. Hy-10219

101. Smr004701276

102. Fyarro (sirolimus Albumin-bound Particles)

103. Everolimus Impurity A [ep Impurity]

104. Unm-0000358684

105. A-275

106. R0097

107. Rapamycin, Vetranal(tm), Analytical Standard

108. Ec 610-965-5

109. M02444

110. Q32089

111. 123r889

112. Q-201659

113. Brd-k84937637-001-04-0

114. Brd-k84937637-001-06-5

115. Brd-k89626439-001-01-0

116. 24,25,26,27,32,33,34,34a-hexadecahydro-3h-23,27-epoxypy

117. Rapamycin From Streptomyces Hygroscopicus, >=95% (hplc), Powder

118. Rapamycin From Streptomyces Hygroscopicus, Vetec(tm) Reagent Grade, >=95%

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

120. (1r,9s,12s,15r,16e,18r,19r,21r,23s,24e,26e,28e,30s,32s,35r)-1,18-dihydroxy-12-{(2s)-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

121. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34 As)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hex Adecahydro-9,27-dihydroxy-3-[(1r)-2-[(1s,3r,4r)-4-hydro Xy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy- 6,8,12,14,20,26-hexamethyl-23,27-ep

122. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-4,9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-heptadecahydro-9,27-dihydroxy-3-[(1r)-2-[(1s,3,4r)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl]-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-223,27-epoxy-3h-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29(6h,31h)-pentone

123. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{(1r)-2-[(1s,3r,4r)-4-hydroxy-3-(methyloxy)cyclohexyl]-1-methylethyl}-6,8,12,14,20,26-hexamethyl-10,21-bis(methyloxy)-9,10,12,13,14,21,22,23,24,25,26,27,32,33,34,34a-hexadecahydro

124. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{(1r)-2-[(1s,3r,4r)-4-hydroxy-3-methoxycyclohexyl]-1-methylethyl}-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

125. (3s,6r,7e,9r,10r,12r,14s,15e,17e,19e,21s,23s,26r,27r,34as)-9,27-dihydroxy-3-{1-[(1s,3r,4r)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl}-10,21-dimethoxy-6,8,12,14,20,26-hexamethyl-9,10,12,13,14,21,22,23,

126. 1,18-dihydroxy-12-[2-(4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-ethyl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-aza-tricyclo[30.3.1.0*4,9*]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentaone (rapamycin)

2.3.3 Other Synonyms

1. (rs)-rapamycin

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 914.2 g/mol
Molecular Formula C51H79NO13
XLogP36
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count13
Rotatable Bond Count6
Exact Mass913.55514157 g/mol
Monoisotopic Mass913.55514157 g/mol
Topological Polar Surface Area195 Ų
Heavy Atom Count65
Formal Charge0
Complexity1760
Isotope Atom Count0
Defined Atom Stereocenter Count15
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameRapamune
PubMed HealthSirolimus (By mouth)
Drug ClassesImmune Suppressant
Drug LabelRapamune (sirolimus) is an immunosuppressive agent. Sirolimus is a macrocyclic lactone produced by Streptomyces hygroscopicus. The chemical name of sirolimus (also known as rapamycin) is (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10...
Active IngredientSirolimus
Dosage FormTablet; Solution
RouteOral
Strength1mg/ml; 0.5mg; 1mg; 2mg
Market StatusPrescription
CompanyPf Prism Cv

2 of 4  
Drug NameSirolimus
PubMed HealthSirolimus (By mouth)
Drug ClassesImmune Suppressant
Drug LabelRapamune (sirolimus) is an immunosuppressive agent. Sirolimus is a macrocyclic lactone produced by Streptomyces hygroscopicus. The chemical name of sirolimus (also known as rapamycin) is (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10...
Active IngredientSirolimus
Dosage FormTablet
Routeoral; Oral
Strength0.5mg; 1mg; 2mg
Market StatusTentative Approval; Prescription
CompanyZydus Pharms Usa; Dr Reddys Labs

3 of 4  
Drug NameRapamune
PubMed HealthSirolimus (By mouth)
Drug ClassesImmune Suppressant
Drug LabelRapamune (sirolimus) is an immunosuppressive agent. Sirolimus is a macrocyclic lactone produced by Streptomyces hygroscopicus. The chemical name of sirolimus (also known as rapamycin) is (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10...
Active IngredientSirolimus
Dosage FormTablet; Solution
RouteOral
Strength1mg/ml; 0.5mg; 1mg; 2mg
Market StatusPrescription
CompanyPf Prism Cv

4 of 4  
Drug NameSirolimus
PubMed HealthSirolimus (By mouth)
Drug ClassesImmune Suppressant
Drug LabelRapamune (sirolimus) is an immunosuppressive agent. Sirolimus is a macrocyclic lactone produced by Streptomyces hygroscopicus. The chemical name of sirolimus (also known as rapamycin) is (3S,6R,7E,9R,10R,12R,14S,15E,17E,19E,21S,23S,26R,27R,34aS)-9,10...
Active IngredientSirolimus
Dosage FormTablet
Routeoral; Oral
Strength0.5mg; 1mg; 2mg
Market StatusTentative Approval; Prescription
CompanyZydus Pharms Usa; Dr Reddys Labs

4.2 Therapeutic Uses

Sirolimus is indicated for the prevention of rejection of transplanted kidney allografts. It is recommended that sirolimus be used in a regimen with cyclosporine and corticosteroids. /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2546


Long-term results after percutaneous coronary intervention in the treatment of chronic total coronary occlusions is hindered by a significant rate of restenosis and reocclusion. In the treatment of relatively simple nonocclusive lesions, sirolimus-eluting stents have shown dramatically reduced restenosis rates compared with bare metal stents, but whether these results are more widely applicable is unknown. ... The use of sirolimus-eluting stents in the treatment of chronic total coronary occlusions is associated with a reduction in the rate of major adverse cardiac events and restenosis compared with bare metal stents.

PMID:15172397 Hoye A et al; J Am Coll Cardiol 43 (11): 1954-8 (2004)


Chronic renal failure triggered by calcineurin inhibitor (CNI)-based immunosuppression is a common complication after cardiac transplantation. Sirolimus and mycophenolate mofetil (MMF) are 2 newer immunosuppressive agents with no documented nephrotoxic side effects. This case report describes a patient with ongoing chronic renal failure 10 months after cardiac transplantation on cyclosporine-based immunosuppressive therapy. Conversion of the immunosuppressive regimen from cyclosporine to sirolimus and MMF resulted in freedom from acute rejection, excellent cardiac graft function and consistently improved renal function. This case illustrates the beneficial potential of sirolimus and MMF as CNI-free and safe long-term immunosuppression in a patient with chronic renal failure after heart transplantation.

PMID:15366440 Groetzner J et al; J Heart Lung Transplant 23 (6): 770-3 (2004)


4.3 Drug Warning

/BOXED WARNING/ IMMUNOSUPPRESSION, USE IS NOT RECOMMENDED IN LIVER OR LUNG TRANSPLANT PATIENTS. Increased susceptibility to infection and the possible development of lymphoma and other malignancies may result from immunosuppression Increased susceptibility to infection and the possible development of lymphoma may result from immunosuppression. Only physicians experienced in immunosuppressive therapy and management of renal transplant patients should use Rapamune. 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. The safety and efficacy of Rapamune (sirolimus) as immunosuppressive therapy have not been established in liver or lung transplant patients, and therefore, such use is not recommended. Liver Transplantation - Excess Mortality, Graft Loss, and Hepatic Artery Thrombosis (HAT): The use of Rapamune in combination with tacrolimus was associated with excess mortality and graft loss in a study in de novo liver transplant patients. Many of these patients had evidence of infection at or near the time of death. In this and another study in de novo liver transplant patients, the use of Rapamune in combination with cyclosporine or tacrolimus was associated with an increase in HAT; most cases of HAT occurred within 30 days post-transplantation and most led to graft loss or death. Lung Transplantation - Bronchial Anastomotic Dehiscence: Cases of bronchial anastomotic dehiscence, most fatal, have been reported in de novo lung transplant patients when Rapamune has been used as part of an immunosuppressive regimen.

US Natl Inst Health; DailyMed. Current Medication Information for Rapamune (sirolimus) solution; Rapamune (sirolimus) tablet, sugar coated (Updated: March 2015). Available from, as of April 23, 2015: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=3275b824-3f82-4151-2ab2-0036a9ba0acc


Grapefruit juice may inhibit CYP 3A4 enzymes, leading to decreased metabolism of sirolimus; must not be taken with or used to dilute sirolimus.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2547


Cases of bronchial anastomotic dehiscence, most of which were fatal, have been reported in de novo lung transplant patients who received sirolimus in combination with other immunosuppressants. Because safety and efficacy of sirolimus as immunosuppressive therapy in lung transplant patients have not been established, such use in not recommended by the manufacturer.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3645


Use of sirolimus in combination with other immunosuppressants (i.e., cyclosporine, tacrolimus) has been associated with an increased risk on hepatic artery thrombosis, graft loss, and death in de novo liver transplant recipients. Because safety and efficacy of sirolimus as immunosuppressive therapy in liver transplant patients have not been established, such use is not recommended by the manufacturer.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3646


For more Drug Warnings (Complete) data for SIROLIMUS (27 total), please visit the HSDB record page.


4.4 Drug Indication

Sirolimus is indicated for the prophylaxis of organ rejection in patients aged 13 years or older receiving renal transplants. In patients at low-to moderate-immunologic risk, it is recommended that sirolimus be used initially in a regimen with [cyclosporine] and corticosteroids; cyclosporine should be withdrawn two to four months after transplantation. In patients at high-immunologic risk (defined as Black recipients and/or repeat renal transplant recipients who lost a previous allograft for immunologic reason and/or patients with high panel-reactive antibodies [PRA; peak PRA level > 80%]), it is recommended that sirolimus be used in combination with cyclosporine and corticosteroids for the first year following transplantation. It is also used to treat lymphangioleiomyomatosis. In the US, albumin-bound sirolimus for intravenous injection is indicated for the treatment of adult patients with locally advanced unresectable or metastatic malignant perivascular epithelioid cell tumour (PEComa). In Europe, it is recommended that sirolimus for the prophylaxis of organ rejection in renal transplants is used in combination with cyclosporin microemulsion and corticosteroids for two to three months. Sirolimus may be continued as maintenance therapy with corticosteroids only if cyclosporin microemulsion can be progressively discontinued.


FDA Label


Rapamune is indicated for the prophylaxis of organ rejection in adult patients at low to moderate immunological risk receiving a renal transplant. It is recommended that Rapamune be used initially in combination with ciclosporin microemulsion and corticosteroids for 2 to 3 months. Rapamune may be continued as maintenance therapy with corticosteroids only if ciclosporin microemulsion can be progressively discontinued.

Rapamune is indicated for the treatment of patients with sporadic lymphangioleiomyomatosis with moderate lung disease or declining lung function.


Prevention of arteriovenous access dysfunction


Treatment of chronic non-infectious uveitis


5 Pharmacology and Biochemistry
5.1 Pharmacology

Sirolimus is an immunosuppressant drug with antifungal and antitumour effects. In animal models, sirolimus prolonged allograft survival following various organ transplants and reversed an acute rejection of heart and kidney allografts in rats. Upon oral administration of 2 mg/day and 5 mg/day, sirolimus significantly reduced the incidence of organ rejection in low- to moderate-immunologic risk renal transplant patients at six months following transplantation compared with either azathioprine or placebo. In some studies, the immunosuppressive effect of sirolimus lasted up to six months after discontinuation of therapy: this tolerization effect is alloantigen-specific. Sirolimus potently inhibits antigen-induced proliferation of T cells, B cells, and antibody production. In rodent models of autoimmune disease, sirolimus suppressed immune-mediated events associated with systemic lupus erythematosus, collagen-induced arthritis, autoimmune type I diabetes, autoimmune myocarditis, experimental allergic encephalomyelitis, graft-versus-host disease, and autoimmune uveoretinitis.


5.2 MeSH Pharmacological Classification

Antibiotics, Antineoplastic

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)


Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)


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.)


Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
SIROLIMUS
5.3.2 FDA UNII
W36ZG6FT64
5.3.3 Pharmacological Classes
Kinase Inhibitor [EPC]; Protein Kinase Inhibitors [MoA]; mTOR Inhibitor Immunosuppressant [EPC]; mTOR Inhibitors [MoA]; Decreased Immunologic Activity [PE]
5.4 ATC Code

L04AA10


L04AA10

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

L04 - Immunosuppressants

L04A - Immunosuppressants

L04AA - Selective immunosuppressants

L04AA10 - Sirolimus


S - Sensory organs

S01 - Ophthalmologicals

S01X - Other ophthalmologicals

S01XA - Other ophthalmologicals

S01XA23 - Sirolimus


5.5 Absorption, Distribution and Excretion

Absorption

In adult renal transplant patients with low- to moderate-immunologic risk, oral administration of 2 mg sirolimus led to a Cmax of 14.4 5.3 ng/mL for oral solution and 15.0 4.9 ng/mL for oral tablets. The tmax was 2.1 0.8 hours for oral solution and 3.5 2.4 hours for oral tablets. In healthy subjects, the tmax is one hour. In a multi-dose study, steady-state was reached six days following repeated twice-daily administration without an initial loading dose, with the average trough concentration of sirolimus increased approximately 2- to 3-fold. It is suspected that a loading dose of three times the maintenance dose will provide near steady-state concentrations within one day in most patients. The systemic availability of sirolimus is approximately 14%. In healthy subjects, the mean bioavailability of sirolimus after administration of the tablet is approximately 27% higher relative to the solution. Sirolimus tablets are not bioequivalent to the solution; however, clinical equivalence has been demonstrated at the 2 mg dose level. Sirolimus concentrations, following the administration of Rapamune Oral Solution to stable renal transplant patients, are dose-proportional between 3 and 12 mg/m2.


Route of Elimination

Following oral administration of [14C] sirolimus in healthy subjects, about 91% of the radioactivity was recovered from feces and only 2.2% of the radioactivity was detected in urine. Some of the metabolites of sirolimus are also detectable in feces and urine.


Volume of Distribution

The mean ( SD) blood-to-plasma ratio of sirolimus was 36 18 L in stable renal allograft patients, indicating that sirolimus is extensively partitioned into formed blood elements. The mean volume of distribution (Vss/F) of sirolimus is 12 8 L/kg.


Clearance

In adult renal transplant patients with low- to moderate-immunologic risk, oral administration of 2 mg sirolimus led to oral clearance of 173 50 mL/h/kg for oral solution and 139 63 mL/h/kg for oral tablets.


Following administration of /Sirolimus/ Oral Solution, sirolimus is rapidly absorbed, with a mean time-to-peak concentration (t max ) of approximately 1 hour after a single dose in healthy subjects and approximately 2 hours after multiple oral doses in renal transplant recipients. The systemic availability of sirolimus was estimated to be approximately 14% after the administration of /Sirolimus/ Oral Solution. The mean bioavailability of sirolimus after administration of the tablet is about 27% higher relative to the oral solution.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3483


In 22 healthy volunteers receiving Rapamune Oral Solution, a high-fat meal altered the bioavailability characteristics of sirolimus. Compared with fasting, a 34% decrease in the peak blood sirolimus concentration (C max ), a 3.5-fold increase in the time-to-peak concentration (t max ), and a 35% increase in total exposure (AUC) was observed. After administration of Rapamune Tablets and a high-fat meal in 24 healthy volunteers, C max , t max , and AUC showed increases of 65%, 32%, and 23%, respectively.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3483


Absorption: Rapid, from the gastrointestinal tract. Bioavailability is approximately 14%. Rate of absorption is decreased in the presence of a high-fat diet. The rate and extent of absorption is reduced in black patients.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2546


The mean (+/- SD) blood-to-plasma ratio of sirolimus was 36 +/- 17.9 in stable renal allograft recipients, indicating that sirolimus is extensively partitioned into formed blood elements. The mean volume of distribution of sirolimus is 12 +/- 7.52 L/kg. Sirolimus is extensively bound (approximately 92%) to human plasma proteins. In man, the binding of sirolimus was shown mainly to be associated with serum albumin (97%), (alpha) 1 -acid glycoprotein, and lipoproteins.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3483


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


5.6 Metabolism/Metabolites

Sirolimus undergoes extensive metabolism in the intestinal wall and liver. Sirolimus is primarily metabolized by O-demethylation and/or hydroxylation via CYP3A4 to form seven major metabolites, including hydroxy, demethyl, and hydroxydemethyl metabolites, which are pharmacologically inactive. Sirolimus also undergoes counter-transport from enterocytes of the small intestine into the gut lumen.


Sirolimus is a substrate for both cytochrome P450 IIIA4 (CYP3A4) and P-glycoprotein. Sirolimus is extensively metabolized by O-demethylation and/or hydroxylation. Seven major metabolites, including hydroxy, demethyl, and hydroxydemethyl, are identifiable in whole blood. Some of these metabolites are also detectable in plasma, fecal, and urine samples. Glucuronide and sulfate conjugates are not present in any of the biologic matrices.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 3484


Biotransformation: Hepatic, extensive, by cytochrome p450 3A enzymes. Major metabolites include hydroxysirolimus, demethylsirolimus, and hydroxydemethyl-sirolimus.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2546


... After incubation of sirolimus with human and pig small intestinal microsomes, five metabolites were detected using high performance liquid chromatography/electrospray-mass spectrometry: hydroxy, dihydroxy, trihydroxy, desmethyl and didesmethyl sirolimus. The same metabolites were generated by human liver microsomes and pig small intestinal mucosa in the Ussing chamber. Anti-CYP3A antibodies, as well as the specific CYP3A inhibitors troleandomycin and erythromycin, inhibited small intestinal metabolism of sirolimus, confirming that, as in the liver, CYP3A enzymes are responsible for sirolimus metabolism in the small intestine. ...

PMID:9618413 Lampen A et al; J Pharmacol Exp Ther 285 (3): 1104-12 (1998)


Sirolimus has known human metabolites that include 11-Hydroxy-sirolimus, 12-Hydroxy-sirolimus, 16-O-Desmethylsirolimus, 24-Hydroxy-sirolimus, 25-Hydroxy-sirolimus, 39-O-Desmethylsirolimus, and 46-Hydroxy-sirolimus.

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


5.7 Biological Half-Life

The mean SD terminal elimination half-life (t) of sirolimus after multiple dosing in stable renal transplant patients was estimated to be about 62 16 hours.


The drug has an elimination half life of 57-63 hours in kidney transplant recipients.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 3647


5.8 Mechanism of Action

Sirolimus works by inhibiting T-lymphocyte activation and proliferation stimulated by antigens and cytokines such as interleukin (IL)-2, IL-4, and IL-15. In target cells, sirolimus binds to the cytoplasmic receptor FK506-binding protein-12 (FKBP12), an immunophilin, to form an immunosuppressive complex. FKBP12-sirolimus complex binds to and inhibits the activation of the mammalian target of rapamycin (mTOR), which is a serine/threonine-specific protein kinase that regulates cell growth, proliferation, survival, mobility, and angiogenesis. mTOR regulates the downstream signalling pathways involved in cell survival, such as the phosphatidylinositol-3 kinase (PI3K)/Akt signalling pathway. Inhibition of mTOR leads to the suppression of cytokine-driven T-cell proliferation, thus the progression from the G1 to the S phase of the cell cycle is inhibited. Sirolimus also inhibits antibody production. _In vitro_, sirolimus and other mTOR inhibitors inhibit the production of certain growth factors that may affect angiogenesis, fibroblast proliferation, and vascular permeability. Lymphangioleiomyomatosis is a disorder that primarily affects the lungs. It is characterized by lung tissue infiltration, unregulated alveolar smooth muscle proliferation, and cystic destruction of parenchyma. Although infrequent, it occurs as a symptomatic pulmonary complication in tuberous sclerosis complex (TSC), which is an inherited disorder caused by mutations in TSC genes. Loss of functional TSC gene leads to the aberrant activation of the mTOR signalling pathway, resulting in cellular proliferation and release of lymphangiogenic growth factors. Sirolimus inhibits the activated mTOR pathway and proliferation of alveolar smooth muscle cell proliferation.


Sirolimus inhibits cytokine (Interleukin (IL)-2, IL-4, and IL-15) -- stimulated T lymphocyte activation and proliferation; it also inhibits antibody production. This may occur through formation of an immunosuppressive complex with FK Binding Protein-12 (FKBP-12). Although the sirolimus-(FKBP-12) complex is inactive against calcineurin activity, the complex binds to and inhibits activation of a key regulatory kinase, mammalian Target of Rapamycin (mTOR). This is believed to suppress cytokine-driven T-cell proliferation, inhibiting cell cycle progression from the G, to S phase.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2546


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05-Jan-2021
31-Aug-2024
KGS
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DOSAGE - TABLET;ORAL - 0.5MG

USFDA APPLICATION NUMBER - 21110

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DOSAGE - TABLET;ORAL - 1MG

USFDA APPLICATION NUMBER - 21110

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DOSAGE - TABLET;ORAL - 2MG

USFDA APPLICATION NUMBER - 21110

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DOSAGE - TABLET;ORAL - 5MG **Federal Register...DOSAGE - TABLET;ORAL - 5MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 21110

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