Basic Description

Synonyms	AY-22989 \| CHEBI:9168 \| EC 610-965-5 \| HMS2089A21 \| RAPA \| (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-diox
Specifications & Purity	Moligand™, ≥98%
Biochemical and Physiological Mechanisms	Immunosuppressant and antifungal agent . Complexes with FKBP-12 and inhibits mTOR (mammalian target of rapamycin). In complex with its cellular receptor, the FK506-binding protein (FKBP12), rapamycin binds and inhibits the function of the mammalian target
Storage Temp	Protected from light,Store at -20°C,Desiccated
Shipped In	Ice chest + Ice pads
Grade	Moligand™
Action Type	INHIBITOR
Mechanism of action	Inhibitor of FKBP prolyl isomerase 1A
Note	Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
Product Description	Store at -20°C. Store In the Dark. Store under desiccating conditions. This product is air and light sensitive and impurities can occur as a result of air oxidation or due to metabolism by microbes.

Associated Targets(Human)

FKBP1A Tclin Peptidyl-prolyl cis-trans isomerase FKBP1A (10 Activities)

Discover Target: FKBP1A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FKBP1B Tchem Peptidyl-prolyl cis-trans isomerase FKBP1B (1 Activities)

Discover Target: FKBP1B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

FKBP5 Tchem Peptidyl-prolyl cis-trans isomerase FKBP5 (1 Activities)

Discover Target: FKBP5

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

EIF4E Tchem Eukaryotic translation initiation factor 4E (1 Activities)

Discover Target: EIF4E

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PDCD4 Tchem Programmed cell death protein 4 (1 Activities)

Discover Target: PDCD4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

MTOR Tclin Serine/threonine-protein kinase mTOR (7 Activities)

Discover Target: MTOR

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Names and Identifiers

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
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
InChi Key	QFJCIRLUMZQUOT-HPLJOQBZSA-N
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
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
RTECS	VE6250000
Molecular Weight	914.19
Reaxy-Rn	5848501

Database links

PubChem CID	5284616
CAS Registry No.	53123-88-9
ChEBI	CHEBI:9168
Wikipedia	Sirolimus
DrugBank Ligand	DB00877
ChEMBL Ligand	CHEMBL413
RCSB PDB Ligand	RAP
PEP	sirolimus
Immunopaedia Search	sirolimus
Reactome Reaction	R-HSA-9679044
Reactome Drug	R-ALL-9678687
DrugCentral Ligand	2446

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Chemical and Physical Properties

Solubility	Supplied in DMSO (5mM)
Sensitivity	air and light sensitive
Specific Rotation[α]	-150° (C=0.2,MeOH)
Melt Point(°C)	177 °C(dec.)

Safety and Hazards(GHS)

Pictogram(s)	GHS08
Signal	Danger
Hazard Statements	H351:Suspected of causing cancer H372:Causes damage to organs through prolonged or repeated exposure H361:Suspected of damaging fertility or the unborn child
Precautionary Statements	P280:Wear protective gloves/protective clothing/eye protection/face protection. P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P260:Do not breathe dust/fume/gas/mist/vapors/spray. P270:Do not eat, drink or smoke when using this product. P203:Obtain, read and follow all safety instructions before use. P318:if exposed or concerned, get medical advice. P319:Get medical help if you feel unwell.
RTECS	VE6250000
Reaxy-Rn	5848501
Merck Index	8114

Citations of This Product

1. Xiaowei Wang, Wenjun Zhang, Sheng Zeng, Liudi Wang, Bin Wang. (2023) Collagenase Type I and Probucol-Loaded Nanoparticles Penetrate the Extracellular Matrix to Target Hepatic Stellate Cells for Hepatic Fibrosis Therapy. Acta Biomaterialia, [PMID:38141933]
2. Xie Xu, Nana Tao, Caihua Sun, Robert D. Hoffman, Dongling Shi, Yuyuan Ying, Shujie Dong, Jianli Gao. (2023) Ligustilide prevents thymic immune senescence by regulating Thymosin β15-dependent spatial distribution of thymic epithelial cells. PHYTOMEDICINE, (155216). [PMID:38061285]
3. Xiaolin Zhang, Zhen Dong, Yuanmiao Yang, Chaolong Liu, Jisheng Li, Wenli Sun, Yikang Zhu, Yang Shen, Zhi Wang, Muhan Lü, Hongjuan Cui. (2023) Morusinol Extracted from Morus alba Inhibits Cell Proliferation and Induces Autophagy via FOXO3a Nuclear Accumulation-Mediated Cholesterol Biosynthesis Obstruction in Colorectal Cancer. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, (19): [PMID:37870273]
4. Kangjia Ding, Xueke Yu, Dongfang Wang, Xiaofeng Wang, Qian Li. (2023) Small diameter expanded polytetrafluoroethylene vascular graft with differentiated inner and outer biomacromolecules for collaborative endothelialization, anti-thrombogenicity and anti-inflammation. COLLOIDS AND SURFACES B-BIOINTERFACES, 229 (113449). [PMID:37506438]
5. Minghui Cai, Haijuan Sun, Yujia Huang, Haixu Yao, Chen Zhao, Jiao Wang, Hui Zhu. (2023) Resveratrol Protects Rat Ovarian Luteinized Granulosa Cells from H2O2-Induced Dysfunction by Activating Autophagy. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 24 (13): (10914). [PMID:37446088]
6. Xiaoqian Jiang, Xinxin Xu, Hua Kuang, Liqiang Liu, Liguang Xu, Aihua Qu, Chuanlai Xu. (2023) A gold-based immunochromatographic strip for the specific detection of tacrolimus in whole blood. Journal of Materials Chemistry B, 11 (20): (4464-4474). [PMID:37159048]
7. Caihua Wang, Xiaofang Li, Wei Zhang, Wenxuan Liu, Ziwei Lv, Runlin Gui, Man Li, Yujia Li, Xiaomin Sun, Ping Liu, Xiaobin Fan, Shiyao Yang, Yuyan Xiong, Lu Qian. (2023) ETNPPL impairs autophagy through regulation of the ARG2-ROS signaling axis, contributing to palmitic acid-induced hepatic insulin resistance. FREE RADICAL BIOLOGY AND MEDICINE, 199 (126). [PMID:36841363]
8. Xueyao Yang, Xin Zhao, Yanfei Liu, Yue Liu, Libo Liu, Ziyu An, Haoran Xing, Jinfan Tian, Xiantao Song. (2023) Ginkgo biloba extract protects against diabetic cardiomyopathy by restoring autophagy via adenosine monophosphate-activated protein kinase/mammalian target of the rapamycin pathway modulation. PHYTOTHERAPY RESEARCH, 37 (4): (1377-1390). [PMID:36751963]
9. Han Chengzhi, Qian Xinyi, Ren Xiaorong, Zhang Shutian, Hu Li, Li Jingyao, Huang Yijun, Huang Renhui, Ooi Kokwin, Lin Hong, Xia Chunmei. (2022) Inhibition of cGAS in Paraventricular Nucleus Attenuates Hypertensive Heart Injury Via Regulating Microglial Autophagy. MOLECULAR NEUROBIOLOGY, 59 (11): (7006-7024). [PMID:36070120]
10. Pan-Pan Hong, Cang Li, Guo-Juan Niu, Xiao-Fan Zhao, Jin-Xing Wang. (2022) White spot syndrome virus directly activates mTORC1 signaling to facilitate its replication via polymeric immunoglobulin receptor-mediated infection in shrimp. PLoS Pathogens, 18 (9): (e1010808). [PMID:36067252]
11. Rui Wang, Jian Lu, Jiasheng Yin, Han Chen, Hongmei Liu, Fei Xu, Tongtong Zang, Rende Xu, Chenguang Li, Yizhe Wu, Qilin Wu, Xiang Fei, Meifang Zhu, Li Shen, Junbo Ge. (2023) A TEMPOL and rapamycin loaded nanofiber-covered stent favors endothelialization and mitigates neointimal hyperplasia and local inflammation. Bioactive Materials, 19 (666). [PMID:35600979]
12. Qiang Chen, Chunjing Guo, Xiudi Zhou, Yanguo Su, Huimin Guo, Min Cao, Jing Li, Yue Zhang, Weiyi Zhao, Xin Gao, Shuqi Mi, Daquan Chen. (2022) N-acetylneuraminic acid and chondroitin sulfate modified nanomicelles with ROS-sensitive H2S donor via targeting E-selectin receptor and CD44 receptor for the efficient therapy of atherosclerosis. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 211 (259). [PMID:35513096]
13. Yanzhen Han, Yan Zhou, Liyuan Zhou, Xiaoyan Jia, Xiangjun Yu, Xiaohong An, Zhe Shi. (2022) Blockade of chloride channel-3 enhances cisplatin sensitivity of cholangiocarcinoma cells though inhibiting autophagy. CANADIAN JOURNAL OF PHYSIOLOGY AND PHARMACOLOGY, 100 (7): [PMID:35413227]
14. Miaomiao Qi, Xiang Liu, Ying Zhou, Haoyu Wang, Ying Zhao, Jing Ren, Jin Xiang. (2021) Berberine Inhibits MDA-MB-231 Cells as an Agonist of G Protein-Coupled Estrogen Receptor 1. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 22 (21): (11466). [PMID:34768896]

References

1. Vasquez EM. (2000) Sirolimus: a new agent for prevention of renal allograft rejection.. Am J Health Syst Pharm, 57 (5): (437-48; quiz 449-51). [PMID:10711524]
2. McCormack FX, Inoue Y, Moss J, Singer LG, Strange C, Nakata K, Barker AF, Chapman JT, Brantly ML, Stocks JM et al.. (2011) Efficacy and safety of sirolimus in lymphangioleiomyomatosis.. N Engl J Med, 364 (17): (1595-606). [PMID:21410393]
3. Li J, Kim SG, Blenis J. (2014) Rapamycin: one drug, many effects.. Cell Metab, 19 (3): (373-9). [PMID:24508508]
4. Kindrachuk J, Ork B, Hart BJ, Mazur S, Holbrook MR, Frieman MB, Traynor D, Johnson RF, Dyall J, Kuhn JH et al.. (2015) Antiviral potential of ERK/MAPK and PI3K/AKT/mTOR signaling modulation for Middle East respiratory syndrome coronavirus infection as identified by temporal kinome analysis.. Antimicrob Agents Chemother, 59 (2): (1088-99). [PMID:25487801]
5. Dyall J, Gross R, Kindrachuk J, Johnson RF, Olinger Jr GG, Hensley LE, Frieman MB, Jahrling PB. (2017) Middle East Respiratory Syndrome and Severe Acute Respiratory Syndrome: Current Therapeutic Options and Potential Targets for Novel Therapies.. Drugs, 77 (18): (1935-1966). [PMID:29143192]
6. Kopparthy P, Murphy M. (2021) Rapid and Durable Response With Nab-Sirolimus After Everolimus Failure in a Patient With Perivascular Epithelioid Cell Tumors (PEComas) of the Uterus.. Cureus, 13 (5): (e14951). [PMID:34123648]
7. Wagner AJ, Ravi V, Riedel RF, Ganjoo K, Van Tine BA, Chugh R, Cranmer L, Gordon EM, Hornick JL, Du H et al.. (2021) nab-Sirolimus for Patients With Malignant Perivascular Epithelioid Cell Tumors.. J Clin Oncol, 129 (3): (JCO2101728). [PMID:34637337]
8. Chen J, Zheng XF, Brown EJ, Schreiber SL. (1995) Identification of an 11-kDa FKBP12-rapamycin-binding domain within the 289-kDa FKBP12-rapamycin-associated protein and characterization of a critical serine residue.. Proc Natl Acad Sci USA, 92 (11): (4947-51). [PMID:7539137]
9. Chiu MI, Katz H, Berlin V. (1994) RAPT1, a mammalian homolog of yeast Tor, interacts with the FKBP12/rapamycin complex.. Proc Natl Acad Sci USA, 91 (26): (12574-8). [PMID:7809080]
10. Kelly PA, Gruber SA, Behbod F, Kahan BD. (1997) Sirolimus, a new, potent immunosuppressive agent.. Pharmacotherapy, 17 (6): (1148-56). [PMID:9399599]
11. Vilella-Bach M, Nuzzi P, Fang Y, Chen J. (1999) The FKBP12-rapamycin-binding domain is required for FKBP12-rapamycin-associated protein kinase activity and G1 progression.. J Biol Chem, 274 (7): (4266-72). [PMID:9933627]
12. Pollen AA et al.. (2019) Establishing Cerebral Organoids as Models of Human-Specific Brain Evolution.. Cell, 176 (4): (743-756.e17). [PMID:30735633]
13. Yazdankhah M et al.. (2020) Modulating EGFR-MTORC1-autophagy as a potential therapy for persistent fetal vasculature (PFV) disease.. Autophagy, 16 (6): (1130-1142). [PMID:31462148]
14. Xiaowei Wang, Wenjun Zhang, Sheng Zeng, Liudi Wang, Bin Wang. (2023) Collagenase Type I and Probucol-Loaded Nanoparticles Penetrate the Extracellular Matrix to Target Hepatic Stellate Cells for Hepatic Fibrosis Therapy. Acta Biomaterialia, [PMID:38141933]
15. Xie Xu, Nana Tao, Caihua Sun, Robert D. Hoffman, Dongling Shi, Yuyuan Ying, Shujie Dong, Jianli Gao. (2023) Ligustilide prevents thymic immune senescence by regulating Thymosin β15-dependent spatial distribution of thymic epithelial cells. PHYTOMEDICINE, (155216). [PMID:38061285]
16. Xiaolin Zhang, Zhen Dong, Yuanmiao Yang, Chaolong Liu, Jisheng Li, Wenli Sun, Yikang Zhu, Yang Shen, Zhi Wang, Muhan Lü, Hongjuan Cui. (2023) Morusinol Extracted from Morus alba Inhibits Cell Proliferation and Induces Autophagy via FOXO3a Nuclear Accumulation-Mediated Cholesterol Biosynthesis Obstruction in Colorectal Cancer. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, (19): [PMID:37870273]
17. Kangjia Ding, Xueke Yu, Dongfang Wang, Xiaofeng Wang, Qian Li. (2023) Small diameter expanded polytetrafluoroethylene vascular graft with differentiated inner and outer biomacromolecules for collaborative endothelialization, anti-thrombogenicity and anti-inflammation. COLLOIDS AND SURFACES B-BIOINTERFACES, 229 (113449). [PMID:37506438]
18. Minghui Cai, Haijuan Sun, Yujia Huang, Haixu Yao, Chen Zhao, Jiao Wang, Hui Zhu. (2023) Resveratrol Protects Rat Ovarian Luteinized Granulosa Cells from H2O2-Induced Dysfunction by Activating Autophagy. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 24 (13): (10914). [PMID:37446088]
19. Xiaoqian Jiang, Xinxin Xu, Hua Kuang, Liqiang Liu, Liguang Xu, Aihua Qu, Chuanlai Xu. (2023) A gold-based immunochromatographic strip for the specific detection of tacrolimus in whole blood. Journal of Materials Chemistry B, 11 (20): (4464-4474). [PMID:37159048]
20. Caihua Wang, Xiaofang Li, Wei Zhang, Wenxuan Liu, Ziwei Lv, Runlin Gui, Man Li, Yujia Li, Xiaomin Sun, Ping Liu, Xiaobin Fan, Shiyao Yang, Yuyan Xiong, Lu Qian. (2023) ETNPPL impairs autophagy through regulation of the ARG2-ROS signaling axis, contributing to palmitic acid-induced hepatic insulin resistance. FREE RADICAL BIOLOGY AND MEDICINE, 199 (126). [PMID:36841363]
21. Xueyao Yang, Xin Zhao, Yanfei Liu, Yue Liu, Libo Liu, Ziyu An, Haoran Xing, Jinfan Tian, Xiantao Song. (2023) Ginkgo biloba extract protects against diabetic cardiomyopathy by restoring autophagy via adenosine monophosphate-activated protein kinase/mammalian target of the rapamycin pathway modulation. PHYTOTHERAPY RESEARCH, 37 (4): (1377-1390). [PMID:36751963]
22. Han Chengzhi, Qian Xinyi, Ren Xiaorong, Zhang Shutian, Hu Li, Li Jingyao, Huang Yijun, Huang Renhui, Ooi Kokwin, Lin Hong, Xia Chunmei. (2022) Inhibition of cGAS in Paraventricular Nucleus Attenuates Hypertensive Heart Injury Via Regulating Microglial Autophagy. MOLECULAR NEUROBIOLOGY, 59 (11): (7006-7024). [PMID:36070120]
23. Pan-Pan Hong, Cang Li, Guo-Juan Niu, Xiao-Fan Zhao, Jin-Xing Wang. (2022) White spot syndrome virus directly activates mTORC1 signaling to facilitate its replication via polymeric immunoglobulin receptor-mediated infection in shrimp. PLoS Pathogens, 18 (9): (e1010808). [PMID:36067252]
24. Rui Wang, Jian Lu, Jiasheng Yin, Han Chen, Hongmei Liu, Fei Xu, Tongtong Zang, Rende Xu, Chenguang Li, Yizhe Wu, Qilin Wu, Xiang Fei, Meifang Zhu, Li Shen, Junbo Ge. (2023) A TEMPOL and rapamycin loaded nanofiber-covered stent favors endothelialization and mitigates neointimal hyperplasia and local inflammation. Bioactive Materials, 19 (666). [PMID:35600979]
25. Qiang Chen, Chunjing Guo, Xiudi Zhou, Yanguo Su, Huimin Guo, Min Cao, Jing Li, Yue Zhang, Weiyi Zhao, Xin Gao, Shuqi Mi, Daquan Chen. (2022) N-acetylneuraminic acid and chondroitin sulfate modified nanomicelles with ROS-sensitive H2S donor via targeting E-selectin receptor and CD44 receptor for the efficient therapy of atherosclerosis. INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 211 (259). [PMID:35513096]
26. Yanzhen Han, Yan Zhou, Liyuan Zhou, Xiaoyan Jia, Xiangjun Yu, Xiaohong An, Zhe Shi. (2022) Blockade of chloride channel-3 enhances cisplatin sensitivity of cholangiocarcinoma cells though inhibiting autophagy. CANADIAN JOURNAL OF PHYSIOLOGY AND PHARMACOLOGY, 100 (7): [PMID:35413227]
27. Miaomiao Qi, Xiang Liu, Ying Zhou, Haoyu Wang, Ying Zhao, Jing Ren, Jin Xiang. (2021) Berberine Inhibits MDA-MB-231 Cells as an Agonist of G Protein-Coupled Estrogen Receptor 1. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 22 (21): (11466). [PMID:34768896]

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Rapamycin (DMSO solution) - ≥98%, high purity , CAS No.53123-88-9, Inhibitor of FKBP prolyl isomerase 1A