Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00627)
Name
Sirolimus
Synonyms    Click to Show/Hide the Synonyms of This API
(-)-Rapamycin; 53123-88-9; AY 22989; AY-22989; I 2190A; I-2190A; I2190A; NSC 226080; Rapammune; Rapamune; Rapamycin; SIIA 9268A; Sirolimus; Wy 090217; Rapamycin (Sirolimus); Antibiotic AY 22989; UNII-W36ZG6FT64; CHEBI:9168; W36ZG6FT64; WY-090217; DE-109; MFCD00867594; NCGC00021305-05; Rapamycin from Streptomyces hygroscopicus; DSSTox_CID_3582; DSSTox_RID_77091; DSSTox_GSID_23582; SILA 9268A; Supralimus; C51H79NO13; CAS-53123-88-9; sirolimusum; Perceiva; Cypher; CCRIS 9024; NSC226080; HSDB 7284; Sirolimus solution; NSC-226080; NCGC00181146-01; LCP-Siro; PubChem16645; BiomolKI2_000084; Rapamycin C-7, analog 4; SCHEMBL3463; Rapamycin,Sirolimus,Rapamune; BIDD:PXR0165; 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine; MLS006010168; Sirolimus [USAN:INN:BAN]; GTPL6031; DTXSID5023582; BDBM36609; L04AA10; MS-R001; SYN1185; SM-88 COMPONENT SIROLIMUS; HMS2089A21; HMS3403F11; HMS3884C03; EX-A1044; Tox21_110870; Tox21_112750; AC-722; BDBM50064359; STL570275; AKOS015850976; AKOS015961618; ZINC169289388; ACN-035837; CCG-100684; CS-0063; DB00877; NCGC00021305-06; NCGC00021305-07; AS-11687; HY-10219; SMR004701276; UNM-0000358684; Rapamycin, RAPA, Rapamune, Sirolimus, RPM; Rapamycin, VETRANAL(TM), analytical standard; EC 610-965-5; Q32089; S-7759; 123R889; Q-201659; BRD-K84937637-001-04-0; BRD-K84937637-001-06-5; BRD-K89626439-001-01-0; 24,25,26,27,32,33,34,34a-hexadecahydro-3H-23,27-epoxypy; Rapamycin from Streptomyces hygroscopicus, >=95% (HPLC), powder; Rapamycin from Streptomyces hygroscopicus, Vetec(TM) reagent grade, >=95%
Clinical Status
Approved
Disease Indication Lymphangioleiomyomatosis ICD-11: CB07 [1]
PubChem CID
5284616
Formula
C51H79NO13
Canonical 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
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
InChIKey
QFJCIRLUMZQUOT-HPLJOQBZSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5284616"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 914.2 Topological Polar Surface Area 195
XlogP 6 Complexity 1760
Heavy Atom Count 65 Rotatable Bond Count 6
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 13
Full List of Drug Formulations (DFMs) Containing This API
          Sirolimus 2 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c red no. 40; Alpha-tocopherol; Magnesium stearate; Mannitol; Ammonia; Ferric oxide red; Ferric oxide yellow; Propylene glycol; Sucrose; Titanium dioxide; Poloxamer 188; Povidone; Carnauba wax; Cellulose, microcrystalline; Ethylcelluloses; Hypromellose 2910 (5 mpa.s); Polyethylene glycols; Shellac
                   Dosage Form Oral Tablet
                   Company Dr Reddy's Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
Alpha-tocopherol DIG Info Glutathione S-transferase P (IC50 = 500 nM) [3]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [4]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [5]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Calcium sulfate, unspecified form; Sucrose; Talc; Titanium dioxide; Poloxamer 188; Povidone k30; Alpha.-tocopherol acetate; Carnauba wax; Glyceryl oleate; Microcrystalline cellulose; Polyethylene glycol 8000
                   Dosage Form Oral Tablet
                   Company Pfizer
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Calcium sulfate, unspecified form; Sucrose; Talc; Titanium dioxide; Poloxamer 188; Alpha.-tocopherol acetate; Carnauba wax; Glyceryl oleate; Microcrystalline cellulose; Polyethylene glycol 8000; Povidone k29/32
                   Dosage Form Oral Tablet
                   Company Greenstone
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
          Sirolimus 1 mg tablet Click to Show/Hide the Full List of Formulation(s):          5 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c red no. 40; Alpha-tocopherol; Magnesium stearate; Mannitol; Ammonia; Propylene glycol; Sucrose; Titanium dioxide; Poloxamer 188; Povidone; Carnauba wax; Cellulose, microcrystalline; Ethylcelluloses; Hypromellose 2910 (5 mpa.s); Polyethylene glycols; Shellac
                   Dosage Form Oral Tablet
                   Company Dr Reddy's Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
Alpha-tocopherol DIG Info Glutathione S-transferase P (IC50 = 500 nM) [3]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [4]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [5]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c red no. 40; Alpha.-tocopherol; Magnesium stearate; Mannitol; Ammonia; Propylene glycol; Sucrose; Titanium dioxide; Poloxamer 188; Carnauba wax; Cellulose, microcrystalline; Diacetylated monoglycerides; Ethylcelluloses; Hypromellose 2910 (5 mpa.s); Polyethylene glycol 8000; Povidones; Shellac
                   Dosage Form Oral Tablet
                   Company American Health Packaging
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
Alpha-tocopherol DIG Info Glutathione S-transferase P (IC50 = 500 nM) [3]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [4]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [5]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [6]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose; Alpha-tocopherol; Magnesium stearate; Calcium sulfate; Sucrose; Talc; Titanium dioxide; Poloxamer 188; Povidone; 1-glyceryl monooleate; Carnauba wax; Cellulose, microcrystalline; Polyethylene glycol; Polyethylene glycol 8000; Shellac
                   Dosage Form Oral Tablet
                   Company Cardinal Health
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Alpha-tocopherol DIG Info Glutathione S-transferase P (IC50 = 500 nM) [3]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Calcium sulfate, unspecified form; Sucrose; Talc; Titanium dioxide; Poloxamer 188; Povidone k30; Alpha.-tocopherol acetate; Carnauba wax; Glyceryl oleate; Microcrystalline cellulose; Polyethylene glycol 8000
                   Dosage Form Oral Tablet
                   Company Pfizer
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Calcium sulfate, unspecified form; Sucrose; Talc; Titanium dioxide; Poloxamer 188; Alpha.-tocopherol acetate; Carnauba wax; Glyceryl oleate; Microcrystalline cellulose; Polyethylene glycol 8000; Povidone k29/32
                   Dosage Form Oral Tablet
                   Company Greenstone
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
          Sirolimus 0.5 mg tablet Click to Show/Hide the Full List of Formulation(s):          5 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c yellow no. 5; Alpha-tocopherol acetate; Glyceryl monooleate; Citric acid monohydrate; Ferric oxide yellow; Sucrose; Talc; Titanium dioxide; Crospovidone; Poloxamer 188; Povidone; Cellulose, microcrystalline; Hypromelloses; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Zydus Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrazine yellow DIG Info GABA(A) receptor alpha-1 (IC50 = 13 uM) [2]
Glyceryl monooleate DIG Info Diacylglycerol kinase alpha (Ki = 91000 nM) [9]
Tocopheryl acetate DIG Info Prostate cancer LNCaP cells (EC50 = 38000 nM) [10]
Tocopheryl acetate DIG Info Breast cancer MCF7 cells (IC50 > 500000 nM) [11]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [7]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c yellow no. 5; Alpha-tocopherol acetate; Citric acid monohydrate; Ferric oxide yellow; Sucrose; Talc; Titanium dioxide; Poloxamer 188; Povidone; Cellulose, microcrystalline; Crospovidone (15 mpa.s at 5%); Glyceryl oleate; Hypromelloses; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Cadila Healthcare
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrazine yellow DIG Info GABA(A) receptor alpha-1 (IC50 = 13 uM) [2]
Tocopheryl acetate DIG Info Prostate cancer LNCaP cells (EC50 = 38000 nM) [10]
Tocopheryl acetate DIG Info Breast cancer MCF7 cells (IC50 > 500000 nM) [11]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Povidone DIG Info Cholesterol 25-hydroxylase (IC50 = 78.3 uM) [7]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c yellow no. 5; Citric acid monohydrate; Ferric oxide yellow; Sucrose; Talc; Titanium dioxide; Poloxamer 188; Alpha.-tocopherol acetate; Crospovidone (15 mpa.s at 5%); Glyceryl oleate; Hypromellose, unspecified; Microcrystalline cellulose; Polyethylene glycol, unspecified; Povidone, unspecified
                   Dosage Form Oral Tablet
                   Company American Health Packaging
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hydrazine yellow DIG Info GABA(A) receptor alpha-1 (IC50 = 13 uM) [2]
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
             Drug Formulation 4 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Calcium sulfate, unspecified form; Ferric oxide yellow; Sucrose; Talc; Titanium dioxide; Poloxamer 188; Povidone k30; Alpha.-tocopherol acetate; Carnauba wax; Glyceryl oleate; Microcrystalline cellulose; Polyethylene glycol 8000
                   Dosage Form Oral Tablet
                   Company Pfizer
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
             Drug Formulation 5 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Calcium sulfate, unspecified form; Ferric oxide yellow; Sucrose; Talc; Titanium dioxide; Poloxamer 188; Alpha.-tocopherol acetate; Carnauba wax; Glyceryl oleate; Microcrystalline cellulose; Polyethylene glycol 8000; Povidone k29/32
                   Dosage Form Oral Tablet
                   Company Greenstone
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Poloxamer 188 DIG Info Albendazole monooxygenase (IC50 = 60 uM) [7]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [8]
References
1 FDA label for approved sirolimus from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Reviewing Hit Discovery Literature for Difficult Targets: Glutathione Transferase Omega-1 as an Example. J Med Chem. 2018 Sep 13; 61(17):7448-7470.
4 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
5 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
6 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.
7 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
8 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
9 Identification of a novel DGKalpha inhibitor for XLP-1 therapy by virtual screening. Eur J Med Chem. 2019; 164:378-390.
10 First pharmacophore-based identification of androgen receptor down-regulating agents: discovery of potent anti-prostate cancer agents. Bioorg Med Chem. 2007 May 15; 15(10):3413-21.
11 Design and synthesis of analogs of vitamin E: antiproliferative activity against human breast adenocarcinoma cells. Bioorg Med Chem Lett. 1998 Sep 22; 8(18):2433-8.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.