Drug Information
| General Information | ||||||
|---|---|---|---|---|---|---|
| Drug ID |
DR00262
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| Drug Name |
Sirolimus
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| Synonyms |
(-)-Rapamycin; 23,27-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine; 23,27-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine; 23,27-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclohentriacontine-1,5,11,28,29; 3H-pyrido(2,1-c)(1,4)oxaazacyclohentriacontine-1,5,11,28,29(4H,6H,31H)-pentone; AY 22989; AY-22989; Antibiotic AY 22989; DE-109; Heptadecahydro-9,27-dihydroxy-3-[(1R)-2-[(1S,3R,4R)-4-hydroxy; LCP-Siro; MS-R001; Perceiva; RAP; RAPA; RPM; Rapammune; Rapamune; Rapamune (TN); Rapamycin; Rapamycin (TN); Rapamycin C-7, analog 4; Rapamycin Immunosuppressant Drug; Rapamycin from Streptomyces hygroscopicus; SIIA 9268A; SILA 9268A; Sirolimus (MTOR inhibitor); Sirolimus (RAPAMUNE); Sirolimus (USAN/INN); Sirolimus [USAN:BAN:INN]; Sirolimus, Rapamune,Rapamycin; WY-090217; Wy 090217
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| Drug Type |
Small molecular drug
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| Indication | Organ transplant rejection [ICD11:NE84] | Approved | [1] | |||
| Therapeutic Class |
Immunosuppressive Agents
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| Structure |
|
 |
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| 3D MOL | 2D MOL | |||||
| Formula |
C51H79NO13
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| 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
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| 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
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| InChIKey |
QFJCIRLUMZQUOT-HPLJOQBZSA-N
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| CAS Number |
CAS 53123-88-9
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| Pharmaceutical Properties | Molecular Weight | 914.2 | Topological Polar Surface Area | 195 | ||
| Heavy Atom Count | 65 | Rotatable Bond Count | 6 | |||
| Hydrogen Bond Donor Count | 3 | Hydrogen Bond Acceptor Count | 13 | |||
| XLogP |
6
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| PubChem CID | ||||||
| PubChem SID |
11110132
,11110134
,11110139
,11528741
,12014635
,14816423
,14816426
,24430811
,24899339
,26701762
,26705530
,26705537
,26709840
,26713306
,37101833
,46391895
,46392864
,47289337
,48416541
,49635682
,49815675
,50103901
,50139515
,56310631
,56310880
,56311583
,56311585
,56311714
,56311827
,56311949
,56311983
,56312137
,56312183
,56312184
,56312185
,56312186
,56312645
,56312887
,56313330
,56313354
,56313375
,56313498
,56313803
,56313974
,56314022
,636884
,7890221
,7982025
,8145920
,830671
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| ChEBI ID |
ChEBI:9168
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| TTD Drug ID | ||||||
| DT(s) Transporting This Drug | OATP1B1 | Transporter Info | Organic anion transporting polypeptide 1B1 | Substrate | [2] | |
| P-GP | Transporter Info | P-glycoprotein 1 | Substrate | [3] | ||
| References | ||||||
| 1 | Sirolimus was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019) | |||||
| 2 | Pharmacokinetic and pharmacodynamic interactions between the immunosuppressant sirolimus and the lipid-lowering drug ezetimibe in healthy volunteers. Clin Pharmacol Ther. 2010 Jun;87(6):663-7. | |||||
| 3 | Pharmacogenetics of tacrolimus and sirolimus in renal transplant patients: from retrospective analyses to prospective studies. Transplant Proc. 2007 Sep;39(7):2142-4. | |||||
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