Details of the Drug

General Information of Drug (ID: DMTXHJ9)

Drug Name

Sirolimus

Synonyms

Rapammune; Sirolimus; Rapamycin; I2190A; 53123-88-9; (-)-Rapamycin; Wy 090217; SIIA 9268A; Rapamune; I-2190A; AY-22989; RAPA; NSC 226080; I 2190A; AY 22989; Rapamycin (Sirolimus); WY-090217; Antibiotic AY 22989; UNII-W36ZG6FT64; SILA 9268A; CHEBI:9168; CCRIS 9024; W36ZG6FT64; HSDB 7284; C51H79NO13; DE-109; NCGC00021305-05; DSSTox_CID_3582; DSSTox_RID_77091; DSSTox_GSID_23582; Supralimus; Sirolimus

Indication

Disease Entry	ICD 11	Status	REF
Lymphangioleiomyomatosis	CB07	Approved	[1]
Coronavirus Disease 2019 (COVID-19)	1D6Y	Phase 2	[2]

Therapeutic Class

Antiviral Agents

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

914.2

Topological Polar Surface Area (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 14.4 +/- 5.3 mcg/L [3]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 2.1 +/- 0.8 h [3]
Clearance: The apparent oral clearance of drug is 173 +/- 50 mL/h/kg [3]
Elimination: Following oral administration of [14C] sirolimus in healthy subjects, about 91% of the radioactivity was recovered from feces and only 2.2% of the radioactivity was detected in urine [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 62 +/- 16 hours [3]
Metabolism: The drug is metabolized via the liver [3]
Vd: The volume of distribution (Vd) of drug is 12 +/- 8 L/kg [3]

Chemical Identifiers

Formula: C51H79NO13
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
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: 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

Cross-matching ID

PubChem CID: 5284616
ChEBI ID: CHEBI:9168
CAS Number: 53123-88-9
DrugBank ID: DB00877
TTD ID: D07ALX
ACDINA ID: D00627

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
HUMAN mammalian target of rapamycin (mTOR)	TT7HQAF	MTOR_HUMAN	Inhibitor	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	FDA Approved Drug Products from FDA Official Website. 2019. Application Number: (ANDA) 201578.
2	ClinicalTrials.gov (NCT04341675) Sirolimus Treatment in Hospitalized Patients With COVID-19 Pneumonia. U.S. National Institutes of Health.
3	FDA Approved Drug Products: RAPAMUNE (sirolimus) for oral use
4	Network-based drug repurposing for novel coronavirus 2019-nCoV/SARS-CoV-2. Cell Discov. 2020 Mar 16;6:14.
5	Coronaviruses - drug discovery and therapeutic options. Nat Rev Drug Discov. 2016 May;15(5):327-47.
6	Prevent COVID-19 Severity by Repurposing mTOR Inhibitors. 2 April 2020