TACROLIMUS

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

National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C44H69NO12.H2O
Molecular Weight	822.0334
Optical Activity	( - )
Defined Stereocenters	14 / 14
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of TACROLIMUS

Structure Search

SMILES

O.[H][C@]1(CC[C@@H](O)[C@@H](C1)OC)\C=C(/C)[C@@]2([H])OC(=O)[C@]3([H])CCCCN3C(=O)C(=O)[C@]4(O)O[C@@]([H])([C@H](C[C@H]4C)OC)[C@H](C[C@@H](C)C\C(C)=C\[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)OC

InChI

InChIKey=NWJQLQGQZSIBAF-MLAUYUEBSA-N

InChI=1S/C44H69NO12.H2O/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7;/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3;1H2/b25-19+,27-21+;/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C44H69NO12
Molecular Weight	804.0182
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	14 / 14
E/Z Centers	1
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:46:51 UTC 2023` Edited by `admin` on `Fri Dec 15 15:46:51 UTC 2023`
Record UNII	WM0HAQ4WNM
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TACROLIMUS

Official Name

English

FK 506

Code

English

TACROLIMUS [ORANGE BOOK]

Common Name

English

TACROLIMUS [USP-RS]

Common Name

English

TACROLIMUS HYDRATE [JAN]

Common Name

English

NSC-758659

Code

English

MODIGRAF

Brand Name

English

TACROLIMUS MONOHYDRATE

Common Name

English

TACROLIMUS [EMA EPAR]

Common Name

English

PROTOPIC

Brand Name

English

FK-506

Code

English

FK506

Code

English

TACROLIMUS HYDRATE

Common Name

English

TACROLIMUS [VANDF]

Common Name

English

TACROLIMUS MONOHYDRATE [MI]

Common Name

English

TACROLIMUS [USAN]

Common Name

English

PROGRAF

Brand Name

English

ADVAGRAF

Brand Name

English

Tacrolimus monohydrate [WHO-DD]

Common Name

English

15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-t

Systematic Name

English

TACROLIMUS MONOHYDRATE [EP MONOGRAPH]

Common Name

English

ENVARSUS XR

Brand Name

English

(−)-(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-Allyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylvinyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3

Systematic Name

English

FR-900506

Code

English

FR900506

Code

English

TACROLIMUS [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

472815

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

743220

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

534516

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

WHO-VATC

QD11AH01

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

407113

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

EMA ASSESSMENT REPORTS

ADVAGRAF (AUTHORIZED: GRAFT REJECTION)

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

314310

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

LIVERTOX

NBK548545

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

WHO-ATC

L04AD02

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

NCI_THESAURUS

C2201

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

EMA ASSESSMENT REPORTS

ENVARSUS (AUTHORIZED: GRAFT REJECTION)

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

EMA ASSESSMENT REPORTS

MODIGRAF (AUTHORIZED: GRAFT REJECTION)

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

468214

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

849321

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

NDF-RT

N0000175457

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

701319

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

753620

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

203305

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

EU-Orphan Drug

EU/3/03/185

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

WHO-ATC

D11AH01

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

EMA ASSESSMENT REPORTS

PROTOPIC (AUTHORIZED: PSORIASIS)

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

FDA ORPHAN DRUG

111398

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

NCI_THESAURUS

C146638

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

WHO-VATC

QL04AD02

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

EMA ASSESSMENT REPORTS

PROTOPY (AUTHORIZED: DERMATATIS, ATOPIC)

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

Code System Code Type Description

NSC

758659

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

ChEMBL

CHEMBL269732

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

EVMPD

SUB23141

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

NCI_THESAURUS

C1311

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

DRUG CENTRAL

2552

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

RXCUI

484288

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

CHEBI

61049

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

WIKIPEDIA

TACROLIMUS

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

CAS

109581-93-3

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

IUPHAR

6784

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

PUBCHEM

5282315

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

RXCUI

42316

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

ALTERNATIVE

SMS_ID

100000087996

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

EVMPD

SUB25193

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

DRUG BANK

DB00864

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

MESH

D016559

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

DAILYMED

WM0HAQ4WNM

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

LACTMED

Tacrolimus

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

MERCK INDEX

m10425

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

Merck Index

FDA UNII

WM0HAQ4WNM

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

CHEBI

61057

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

RS_ITEM_NUM

1642802

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

USAN

EE-43

Created by admin on Fri Dec 15 15:46:51 UTC 2023 , Edited by admin on Fri Dec 15 15:46:51 UTC 2023

PRIMARY

Related Record Type Details


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE


					AIN96D6SGL

OATP1B1

TRANSPORTER -> INHIBITOR


					Y5L2157C4J

TACROLIMUS ANHYDROUS

PARENT -> SALT/SOLVATE

Amount:


					Y5L2157C4J

TACROLIMUS ANHYDROUS

ANHYDROUS->SOLVATE

Amount:


					RYF5TU3245

PEPTIDYL-PROLYL CIS-TRANS ISOMERASE FKBP1A

TARGET -> INHIBITOR


					WM0HAQ4WNM

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

Related Record Type Details


					94K77BR6AT

ASCOMYCIN 19-EPIMER

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					LOS6YV3B9N

TACROLIMUS DIENE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					CJ99AS37NC

TACROLIMUS IMPURITY F

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					0SDH06DWVW

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					CN64Z1Q9FN

TACROLIMUS ANHYDROUS 19-EPIMER

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					AUF4U5NSJK

ASCOMYCIN

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					94K77BR6AT

ASCOMYCIN 19-EPIMER

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					69S4289688

10-DESMETHYL TACROLIMUS

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					XB5YB7L8RD

TACROLIMUS IMPURITY H

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					294O3172M2

TACROLIMUS ANHYDROUS 8-EPIMER

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					294O3172M2

TACROLIMUS ANHYDROUS 8-EPIMER

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					LOS6YV3B9N

TACROLIMUS DIENE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					4LZ5DLK79R

Tacrolimus open ring

IMPURITY -> PARENT

Amount:


					0SDH06DWVW

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:


					AP3VG6M3W4

IMPURITY -> PARENT

Interaction Type:

MINOR

Amount:


					H4HLP8PW27

TELMISARTAN TERT-BUTYL ESTER

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:


					AUF4U5NSJK

ASCOMYCIN

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

Related Record Type Details


					Y5L2157C4J

TACROLIMUS ANHYDROUS

ACTIVE MOIETY

Amount: