SIROLIMUS

Search structure
Trade Names:
Synonyms:
Status: Approved (1999)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L04AA10
UNII: W36ZG6FT64

Structure
InChI Key QFJCIRLUMZQUOT-HPLJOQBZSA-N
Smile CO[C@H]1C[C@@H]2CC[C@@H](C)[C@@](O)(O2)C(=O)C(=O)N2CCCC[C@H]2C(=O)O[C@H]([C@H](C)C[C@@H]2CC[C@@H](O)[C@H](OC)C2)CC(=O)[C@H](C)/C=C(\C)[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)/C=C/C=C/C=C/1C
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C51H79NO13
Molecular Weight 914.19
AlogP 6.18
Hydrogen Bond Acceptor 13.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 6.0
Polar Surface Area 195.43
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 65.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR FK506-binding protein 1A inhibitor DailyMed
Primary Target
FKBP prolyl isomerase 1A
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 77000 - - 19
Enzyme Isomerase
36 1-20 0 0-1 -
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase AKT family
- - - - 91
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase DMPK family AGC protein kinase ROCK subfamily
- - - - 92
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC alpha subfamily
- - - - 99
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase RSK family AGC protein kinase MSK subfamily
- - - - 104
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase RSK family AGC protein kinase p70 subfamily
- - - - 109
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase SGK family
- - - - 108
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PDHK subfamily
- - - - 110
Enzyme Kinase Protein Kinase Atypical protein kinase group Atypical protein kinase PIKK family Atypical protein kinase FRAP subfamily
- 0-430 1 - 95
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase CAMK1 family CAMK protein kinase CHK1 subfamily
- - - - 102
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase MAPKAPK family CAMK protein kinase MAPKAPK subfamily
- - - - 125
Enzyme Kinase Protein Kinase CAMK protein kinase group CAMK protein kinase RSKb family CAMK protein kinase MSKb subfamily
- - - - 104
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase GSK family
- - - - 89
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase ERK subfamily
- - - - 90
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase JNK subfamily
- - - - 98
Enzyme Kinase Protein Kinase CMGC protein kinase group CMGC protein kinase MAPK family CMGC protein kinase p38 subfamily
- - - - 100
Enzyme Kinase Protein Kinase Other protein kinase group Other protein kinase CK2 family
- - - - 104
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Src family
- - - - 102
Enzyme Kinase Protein kinase regulatory subunit
- - - - 104
Enzyme
36 0-430 0 0-1 100
Other nuclear protein
- - 1 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
890-10000 - - - -
Transporter Primary active transporter P-type ATPase Calcium ATPase
- 77000 - - -
Unclassified protein
50 - - - -

Metabolites

visNetwork

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hodgkin Disease 3 D006689 ClinicalTrials
Fibroma 3 D005350 ClinicalTrials
Diabetes Mellitus, Type 1 3 D003922 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Birt-Hogg-Dube Syndrome 3 D058249 ClinicalTrials
Breast Neoplasms 3 D001943 ClinicalTrials
Carcinoma, Hepatocellular 3 D006528 ClinicalTrials
Skin Neoplasms 3 D012878 ClinicalTrials
Lymphangioleiomyomatosis 3 D018192 ClinicalTrials
Cardiovascular Abnormalities 3 D018376 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Lichen Planus, Oral 3 D017676 ClinicalTrials
Polycystic Kidney, Autosomal Dominant 3 D016891 ClinicalTrials
Myositis, Inclusion Body 3 D018979 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Urinary Bladder Neoplasms 3 D001749 ClinicalTrials
Lymphoma, Non-Hodgkin 3 D008228 ClinicalTrials
Graft vs Host Disease 3 D006086 ClinicalTrials
Skin Neoplasms 3 D012878 ClinicalTrials
Diabetic Nephropathies 3 D003928 ClinicalTrials
Osteosarcoma 2 D012516 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Glomerulonephritis, IGA 2 D005922 ClinicalTrials
Glomerulosclerosis, Focal Segmental 2 D005923 ClinicalTrials
Vascular Malformations 2 D054079 ClinicalTrials
Anemia, Aplastic 2 D000741 ClinicalTrials
Retroperitoneal Fibrosis 2 D012185 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Neoplasms 2 D009369 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Hypertension 2 D006973 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Macular Degeneration 2 D008268 ClinicalTrials
Lupus Erythematosus, Systemic 2 D008180 ClinicalTrials
Lymphoma, T-Cell, Cutaneous 2 D016410 ClinicalTrials
Dry Eye Syndromes 2 D015352 ClinicalTrials
Scleroderma, Systemic 2 D012595 ClinicalTrials
Aging 2 D000375 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Neuroblastoma 2 D009447 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Amyotrophic Lateral Sclerosis 2 D000690 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 2 D016403 ClinicalTrials
Neoplasms, Germ Cell and Embryonal 2 D009373 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Pinealoma 2 D010871 ClinicalTrials
Uveitis, Intermediate 2 D015867 ClinicalTrials
Uveitis, Posterior 2 D015866 ClinicalTrials
Gliosarcoma 2 D018316 ClinicalTrials
Lymphoma, Mantle-Cell 2 D020522 ClinicalTrials
Hematologic Diseases 2 D006402 ClinicalTrials
Anemia, Aplastic 2 D000741 ClinicalTrials
Severe Combined Immunodeficiency 2 D016511 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Sturge-Weber Syndrome 2 D013341 ClinicalTrials
Intracranial Arteriovenous Malformations 2 D002538 ClinicalTrials
Neurofibromatosis 1 2 D009456 ClinicalTrials
Adenomatous Polyposis Coli 2 D011125 ClinicalTrials
Fanconi Anemia 2 D005199 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Bronchitis 2 D001991 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Renal Insufficiency 2 D051437 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Intracranial Aneurysm 2 D002532 ClinicalTrials
Wet Macular Degeneration 2 D057135 ClinicalTrials
Polycystic Kidney Diseases 2 D007690 ClinicalTrials
Anemia 2 D000740 ClinicalTrials
Liver Neoplasms 2 D008113 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Castleman Disease 2 D005871 ClinicalTrials
Liver Neoplasms 2 D008113 ClinicalTrials
beta-Thalassemia 2 D017086 ClinicalTrials
Graves Ophthalmopathy 2 D049970 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Depressive Disorder 2 D003866 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Lupus Nephritis 2 D008181 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Granulomatous Disease, Chronic 1 D006105 ClinicalTrials
Fibromatosis, Aggressive 1 D018222 ClinicalTrials
Neurilemmoma 1 D009442 ClinicalTrials
Kidney Diseases 1 D007674 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 1 D002289 ClinicalTrials
Rectal Neoplasms 1 D012004 ClinicalTrials
Sarcopenia 1 D055948 ClinicalTrials
Uveitis, Anterior 1 D014606 ClinicalTrials
Parkinson Disease 1 D010300 ClinicalTrials
Acute Lung Injury 1 D055371 ClinicalTrials
Central Nervous System Neoplasms 1 D016543 ClinicalTrials
Multiple Sclerosis, Relapsing-Remitting 1 D020529 ClinicalTrials
Carcinoma, Squamous Cell 1 D002294 ClinicalTrials
Hyperinsulinism 1 D006946 ClinicalTrials
Respiratory Distress Syndrome 1 D012128 ClinicalTrials
Hypercholesterolemia 1 D006937 ClinicalTrials
Scleritis 1 D015423 ClinicalTrials
HIV Infections 1 D015658 ClinicalTrials
Hypertension, Pulmonary 1 D006976 ClinicalTrials
Glycogen Storage Disease Type II 1 D006009 ClinicalTrials
Pachyonychia Congenita 1 D053549 ClinicalTrials
Frontotemporal Dementia 1 D057180 ClinicalTrials
Lung Neoplasms 1 D008175 ClinicalTrials
Diabetic Retinopathy 1 D003930 ClinicalTrials
Prostatic Neoplasms 1 D011471 ClinicalTrials
Adenocarcinoma of Lung 1 D000077192 ClinicalTrials
Port-Wine Stain 1 D019339 ClinicalTrials
Alcoholism 1 D000437 ClinicalTrials
Leukemia, Plasma Cell 1 D007952 ClinicalTrials
Small Cell Lung Carcinoma 1 D055752 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Gaucher Disease 1 D005776 ClinicalTrials
Neoplasm Metastasis 1 D009362 ClinicalTrials
Fallopian Tube Neoplasms 1 D005185 ClinicalTrials
Hematologic Neoplasms 1 D019337 ClinicalTrials
Gangliosidoses 1 D005733 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 1 D015464 ClinicalTrials
Pemphigus 0 D010392 ClinicalTrials

Related Entries

Scaffolds

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Injury, poisoning and procedural complications
15.61
General disorders and administration site conditions
10.69
Infections and infestations
8.05
Respiratory, thoracic and mediastinal disorders
8.04
Gastrointestinal disorders
6.72
Nervous system disorders
6.64
Investigations
6.44
Cardiac disorders
4.54
Vascular disorders
4.39
Metabolism and nutrition disorders
3.77
Skin and subcutaneous tissue disorders
3.58
Musculoskeletal and connective tissue disorders
3.45
Renal and urinary disorders
3.21
Psychiatric disorders
2.87
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.49
Immune system disorders
2.42
Blood and lymphatic system disorders
2.09

Cross References

Resources Reference
CAS NUMBER 53123-88-9
ChEBI 9168
ChEMBL CHEMBL413
DrugBank DB00877
DrugCentral 2446
EPA CompTox DTXSID5023582
FDA SRS W36ZG6FT64
Guide to Pharmacology 6031
KEGG C07909
PDB RAP
PubChem 5284616
SureChEMBL SCHEMBL3463
ZINC ZINC000169289388
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