Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1489)
Drug Name
Sirolimus
Synonyms
Sirolimus; Supralimus; W36ZG6FT64; WY-090217; Wy 090217; sirolimusum; (-)-Rapamycin; 53123-88-9; AY 22989; AY-22989; C51H79NO13; Antibiotic AY 22989; Cypher; Rapammune; Rapamune; Rapamycin; Rapamycin (Sirolimus); SILA 9268A; CCRIS 9024; CHEBI:9168; DE-109; DSSTox_CID_3582; DSSTox_GSID_23582; DSSTox_RID_77091; HSDB 7284; MFCD00867594; NCGC00021305-05; NSC 226080; RAPA; UNII-W36ZG6FT64
Indication Lymphangioleiomyomatosis [ICD11: CB07] Approved [1]
Structure
3D MOL is unavailable 2D MOL
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
Cross-matching ID
PubChem CID
5284616
PubChem SID
636884 ; 830671 ; 7890221 ; 7982025 ; 8145920 ; 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
ChEBI ID
ChEBI:9168
CAS Number
53123-88-9
TTD Drug ID
D03LJR
Formula
C51H79NO13
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
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
11-OH-sirolimus DM006346 N. A. Oxidation - Aliphatic hydroxylation 1 [4]
12-OH-sirolimus DM006345 N. A. Oxidation - Aliphatic hydroxylation 1 [4]
16-O-Desmethylsirolimus DM006344
131874110
Oxidation - O-dealkylation 1 [4]
24-OH-sirolimus DM006348 N. A. Oxidation - Aliphatic hydroxylation 1 [4]
25-OH-sirolimus DM006347 N. A. Oxidation - Aliphatic hydroxylation 1 [4]
39-O-Desmethylsirolimus DM006343
434123693
Oxidation - O-dealkylation 1 [4]
41-O-demethylrapamycin DM006342
131770013
Oxidation - 41-O-Demethylation 1 [5]
46-OH-sirolimus DM006349 N. A. Oxidation - Aliphatic hydroxylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006808 Sirolimus 41-O-demethylrapamycin Oxidation - 41-O-Demethylation CYP3A4 [5]
MR006809 Sirolimus 39-O-Desmethylsirolimus Oxidation - O-dealkylation CYP3A4 [4]
MR006810 Sirolimus 16-O-Desmethylsirolimus Oxidation - O-dealkylation CYP3A4 [4]
MR006811 Sirolimus 12-OH-sirolimus Oxidation - Aliphatic hydroxylation CYP3A4 [4]
MR006812 Sirolimus 11-OH-sirolimus Oxidation - Aliphatic hydroxylation CYP3A4 [4]
MR006813 Sirolimus 25-OH-sirolimus Oxidation - Aliphatic hydroxylation CYP3A4 [4]
MR006814 Sirolimus 24-OH-sirolimus Oxidation - Aliphatic hydroxylation CYP3A4 [4]
MR006815 Sirolimus 46-OH-sirolimus Oxidation - Aliphatic hydroxylation CYP3A4 [4]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
References
1 Sirolimus was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
3 Drug Interactions Flockhart Table
4 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
5 FDA Approved Drug Products: RAPAMUNE (sirolimus) for oral use

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