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Synopsis

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