SIROLIMUS

U.S. Department of Health & Human Services Divider Arrow

National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C51H79NO13
Molecular Weight	914.1719
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of SIROLIMUS

Structure Search

SMILES

[H][C@@]12CC[C@@H](C)[C@@](O)(O1)C(=O)C(=O)N3CCCC[C@@]3([H])C(=O)O[C@@]([H])(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(C)\[C@H](C2)OC)[C@H](C)C[C@@H]4CC[C@@H](O)[C@@H](C4)OC

InChI

InChIKey=QFJCIRLUMZQUOT-HPLJOQBZSA-N

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

HIDE SMILES / InChI

Molecular Formula	C51H79NO13
Molecular Weight	914.1719
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	15 / 15
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:41:41 UTC 2023` Edited by `admin` on `Fri Dec 15 15:41:41 UTC 2023`
Record UNII	W36ZG6FT64
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SIROLIMUS

Official Name

English

SIROLIMUS [VANDF]

Common Name

English

EVEROLIMUS IMPURITY A [EP IMPURITY]

Common Name

English

AY-22989

Code

English

SM-88 COMPONENT SIROLIMUS

Code

English

Sirolimus [WHO-DD]

Common Name

English

WY-090217

Code

English

RAPAMYCIN [MI]

Common Name

English

SIROLIMUS [JAN]

Common Name

English

NSC-226080

Code

English

NAB-RAPAMYCIN COMPONENT RAPAMYCIN

Common Name

English

SIROLIMUS [HSDB]

Common Name

English

RPM

Common Name

English

L04AA10

Code

English

RAPA

Common Name

English

sirolimus [INN]

Common Name

English

SIROLIMUS [ORANGE BOOK]

Common Name

English

NPC-12G

Common Name

English

FYARRO

Brand Name

English

SIROLIMUS [USP-RS]

Common Name

English

RAPAMYCIN

Common Name

English

HYFTOR

Brand Name

English

SIROLIMUS [USAN]

Common Name

English

RAPAMUNE

Brand Name

English

SIROLIMUS [EMA EPAR]

Common Name

English

RAPALIMUS

Brand Name

English

SIROLIMUS [MART.]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

434114

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

568416

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

524916

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

616217

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

453114

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

WHO-VATC

QL04AA10

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

327210

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

NCI_THESAURUS

C261

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

698619

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

379312

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

NDF-RT

N0000175624

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

NCI_THESAURUS

C574

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

828521

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

184304

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

EU-Orphan Drug

EU/3/17/1910

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

237007

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

NDF-RT

N0000175605

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

391013

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

LIVERTOX

NBK548028

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

540516

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

NDF-RT

N0000175550

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

678319

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

469915

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

628918

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

508515

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

833821

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

EMA ASSESSMENT REPORTS

RAPAMUNE (AUTHORIZED: GRAFT REJECTION)

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

829421

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

NDF-RT

N0000175625

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

WHO-ATC

S01XA23

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

CFR

21 CFR 862.3840

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

EMA ASSESSMENT REPORTS

RAPAMUNE (AUTHORIZED: KINDEY TRANSPLANTATION)

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

FDA ORPHAN DRUG

555516

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

WHO-ATC

L04AA10

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

Code System Code Type Description

MESH

D020123

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

MERCK INDEX

m9502

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

Merck Index

DAILYMED

W36ZG6FT64

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

IUPHAR

6031

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

NSC

226080

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

RS_ITEM_NUM

1612765

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

USAN

DD-70

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

SMS_ID

100000089170

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

EVMPD

SUB10537MIG

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

INN

7104

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

NCI_THESAURUS

C1212

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

CHEBI

9168

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

ChEMBL

CHEMBL413

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

RXCUI

35302

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

RxNorm

HSDB

7284

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

LACTMED

Sirolimus

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

PUBCHEM

5284616

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

FDA UNII

W36ZG6FT64

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

WIKIPEDIA

SIROLIMUS

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

DRUG BANK

DB00877

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

JAPANESE REVIEW

RAPALIMUS

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

APPROVED JULY 2014

DRUG CENTRAL

2446

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

CAS

53123-88-9

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

EPA CompTox

DTXSID5023582

Created by admin on Fri Dec 15 15:41:41 UTC 2023 , Edited by admin on Fri Dec 15 15:41:41 UTC 2023

PRIMARY

Related Record Type Details


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Amount:


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Comments:

Sirolimus is extensively bound (approximately 92%) to human plasma proteins, mainly serum albumin (97%), α1-acid glycoprotein, and lipoproteins.

Interaction Type:

BINDING

Amount:


					W36ZG6FT64

SIROLIMUS

EXCRETED UNCHANGED

Qualification:

URINE

Amount:


					4I7AHS3FPJ

TARGET -> INHIBITOR

Amount:


					IGL4DTS8F8

DERIVATIVE -> PARENT

Amount:


					1788PW098Q

SERINE/THREONINE-PROTEIN KINASE MTOR

TARGET -> INHIBITOR

Amount:


					HRJ300HC9W

TARGET -> INHIBITOR

Amount:


					6NP3XSMIP3

MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1

TRANSPORTER -> INHIBITOR


					FNO32LO217

HUMAN INTERLEUKIN-2

TARGET -> INHIBITOR

Amount:


					U36PGF65JH

DERIVATIVE -> PARENT

Amount:


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE

Amount:

Related Record Type Details


					2719UAHUA8

NOVOLIMUS

METABOLITE ACTIVE -> PARENT

Amount:

Related Record Type Details


					ZVF9AF2S67

SECORAPAMYCIN A

IMPURITY -> PARENT

Amount:


					9HW64Q8G6G

PARENT -> IMPURITY

Amount:

Related Record Type Details


					W36ZG6FT64

SIROLIMUS

ACTIVE MOIETY

Amount:

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Volume of Distribution	PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC

Tmax	PHARMACOKINETIC				ORAL ADMINISTRATION