PIMECROLIMUS HYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C43H68ClNO11.H2O
Molecular Weight	828.468
Optical Activity	( - )
Defined Stereocenters	14 / 14
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.[H][C@]12O[C@](O)([C@H](C)C[C@@H]1OC)C(=O)C(=O)N3CCCC[C@@]3([H])C(=O)O[C@@]([H])([C@H](C)[C@@H](O)CC(=O)[C@H](CC)\C=C(C)\C[C@H](C)C[C@@H]2OC)C(\C)=C\[C@@H]4CC[C@H](Cl)[C@@H](C4)OC

InChI

InChIKey=NZIZEODSJUZSHZ-MNZFELGNSA-N

InChI=1S/C43H68ClNO11.H2O/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)45-16-12-11-13-32(45)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-31(44)35(22-29)52-7;/h18,20,25,27-33,35-39,46,51H,10-17,19,21-23H2,1-9H3;1H2/b24-18+,26-20+;/t25-,27+,28+,29-,30+,31-,32-,33-,35+,36-,37-,38+,39+,43+;/m0./s1

HIDE SMILES / InChI

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

Molecular Formula	C43H68ClNO11
Molecular Weight	810.453
Charge	0
Count

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021302s018lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12113647 https://www.ncbi.nlm.nih.gov/pubmed/12090545

Pimecrolimus, an ascomycin macrolactam derivative, is an inhibitor of T-cell and mast-cell activation, developed and launched by Novartis for the potential treatment of psoriasis and allergic, irritant and atopic dermatitis. The topical formulation had been launched in the US by February 2002 for mild-to-moderate atopic dermatitis in patients aged two years and older. Pimecrolimus is an immunomodulating agent. The mechanism of action of pimecrolimus in atopic dermatitis is not known. While the following have been observed, the clinical significance of these observations in atopic dermatitis is not known. It has been demonstrated that pimecrolimus binds with high affinity to macrophilin-12 (FKBP-12) and inhibits the calcium dependent phosphatase, calcineurin. Therefore, it inhibits T cell activation by blocking the transcription of early cytokines. In particular, pimecrolimus inhibits at nanomolar concentrations Interleukin-2 and interferon gamma (Th1-type) and Interleukin-4 and Interleukin-10 (Th2-type) cytokine synthesis in human T-cells. In addition, pimecrolimus prevents the release of inflammatory cytokines and mediators from mast cells in vitro after stimulation by antigen/IgE. Following the administration of a single oral radiolabeled dose of pimecrolimus numerous circulating O-demethylation metabolites were seen. Studies with human liver microsomes indicate that pimecrolimus is metabolized in vitro by the CYP3A sub-family of metabolizing enzymes. No evidence of skin mediated drug metabolism was identified in vivo using the minipig or in vitro using stripped human skin.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
FK506-binding protein 1A 9 Target ID: CHEMBL1902 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12113647	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atopic dermatitis 43 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021302s018lbl.pdf	Palliative		Approved 8429	ELIDEL Approved Use ELIDEL ® (pimecrolimus) Cream 1% is indicated as second-line therapy for the short-term and non-continuous chronic treatment of mild to moderate atopic dermatitis in non-immunocompromised adults and children 2 years of age and older, who have failed to respond adequately to other topical prescription treatments, or when those treatments are not advisable. ELIDEL Cream is not indicated for use in children less than 2 years of age (see WARNINGS, boxed WARNING, and PRECAUTIONS, Pediatric Use). Launch Date 1.00820163E12

C_max

Value	Dose	Analyte	Population
0.89 ng/mL DRUG LABEL https://pubmed.ncbi.nlm.nih.gov/21099191	1 % 2 times / day multiple, topical dose: 1 % route of administration: Topical experiment type: MULTIPLE co-administered:	PIMECROLIMUS blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
43.3 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.5 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
79 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
147.5 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
18.57 ng × h/mL DRUG LABEL https://pubmed.ncbi.nlm.nih.gov/21099191	1 % 2 times / day multiple, topical dose: 1 % route of administration: Topical experiment type: MULTIPLE co-administered:	PIMECROLIMUS blood	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
159 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
24.4 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
377 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
966.1 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
10.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	15 mg single, oral dose: 15 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
11.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
42.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	30 mg single, oral dose: 30 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
35 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/14606933	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	PIMECROLIMUS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.5% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021302s018lbl.pdf			PIMECROLIMUS plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
30 mg 2 times / day steady, oral Highest studied dose Dose: 30 mg, 2 times / day Route: oral Route: steady Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14606933/	unhealthy, 18 - 40 years n = 8 Health Status: unhealthy Condition: psoriasis Age Group: 18 - 40 years Sex: M Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/14606933/	Sources: https://pubmed.ncbi.nlm.nih.gov/14606933/
60 mg single, oral Highest studied dose Dose: 60 mg Route: oral Route: single Dose: 60 mg Sources: https://pubmed.ncbi.nlm.nih.gov/14606933/	healthy, 18 - 40 years n = 6 Health Status: healthy Age Group: 18 - 40 years Sex: M Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/14606933/	Sources: https://pubmed.ncbi.nlm.nih.gov/14606933/
1 % 4 times / day steady, topical Recommended Dose: 1 %, 4 times / day Route: topical Route: steady Dose: 1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16605292/	unhealthy, 3 months to 81.2 years n = 947 Health Status: unhealthy Condition: atopic dermatitis Age Group: 3 months to 81.2 years Sex: M+F Population Size: 947 Sources: https://pubmed.ncbi.nlm.nih.gov/16605292/	Disc. AE: Hypersensitivity... AEs leading to discontinuation/dose reduction: Hypersensitivity (2.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/16605292/

AEs

AE	Significance	Dose	Population
Hypersensitivity	2.3% Disc. AE	1 % 4 times / day steady, topical Recommended Dose: 1 %, 4 times / day Route: topical Route: steady Dose: 1 %, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/16605292/	unhealthy, 3 months to 81.2 years n = 947 Health Status: unhealthy Condition: atopic dermatitis Age Group: 3 months to 81.2 years Sex: M+F Population Size: 947 Sources: https://pubmed.ncbi.nlm.nih.gov/16605292/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1037 inhibitor 1767	substrate 1217 inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2B6 810 CYP2E1 882 CYP4A9/11 37 CYP3A4/5 278 CYP2C19 1478	CYP3A 191 CYP2C19 991 CYP3A4/5 85

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 8.0	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 8.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 8.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 8.0	no
CYP4A9/11 37	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 8.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 8.0	yes [IC50 13 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 8.0	yes [IC50 15 uM]
CYP3A4/5 335	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 8.0	yes [Ki 1 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 8.0	yes [Ki 22 uM]

Drug as victim

Target	Modality	Activity
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_biopharmr_P1.pdf Page: 18.0	yes
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_biopharmr_P1.pdf Page: 18.0	yes
CYP2D6 1217	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_biopharmr_P1.pdf Page: 18.0	yes
CYP3A 191	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_biopharmr_P1.pdf Page: 18.0	yes
CYP3A4/5 85	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-302_ELIDEL_pharmr_P3.pdf Page: 4.0	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY520265	https://www.001chemical.com/chem/137071-32-0
AA Blocks	AA00705J	https://www.aablocks.com/goods/Goods/detail?id=AA00705J
AK Scientific, Inc. (AKSCI)	X7261	http://www.aksci.com/item_detail.php?cat=X7261
Aaron Chemicals	AR0070XB	http://www.aaronchem.com/137071-32-0
AbMole Bioscience	M2221	http://www.abmole.com/products/pimecrolimus.html
Achemtek	0104-012822	http://www.achemtek.com/137071-32-0
Acorn PharmaTech	ACN-046371	http://www.acornpharmatech.com/
Active Biopharma	ABP000224	http://www.activebiopharma.com/137071-32-0
Allbio Pharm Co., Ltd	AB00031	http://www.allbiopharm.com/product/n/AB00031
Ambeed	A944531	https://www.ambeed.com/products/137071-32-0.html
Ambinter	Amb17619420	http://www.ambinter.com/reference/17619420
Angene	AGN-PC-0PL7YZ	http://www.angenechemical.com/productshow/AGN-PC-0PL7YZ.html
ApexBio Technology	B1817	http://www.apexbt.com/pimecrolimus.html
Ark Pharm	AK104470	http://www.arkpharminc.com/products/137071-32-0.html
Ark Pharma Scientific Limited	A-0276	http://www.arkpharmtech.com/product/32227.html
Aurora Fine Chemicals LLC	A13.108.748	http://online.aurorafinechemicals.com/info?ID=A13.108.748
Aurora Fine Chemicals LLC	K16.774.687	http://online.aurorafinechemicals.com/info?ID=K16.774.687
AvaChem Scientific	2188	http://www.avachem.com/productSearch.asp?2188
BLD Pharm	BD157907	http://www.bldpharm.com/products/137071-32-0.html
BioChemPartner	BCP01403	http://www.biochempartner.com/137071-32-0-BCP01403
BioCrick	BCC4703	http://www.biocrick.com/Pimecrolimus-BCC4703.html
BioSynth	Q-201579	https://www.biosynth.com/en/products/chemical-intermediates/advanced-intermediates/products/Q-201579.html
Boerchem	BC622572	http://www.boerchem.com/?product_43079.html
CSNpharm	CSN12264	https://www.csnpharm.com/products/pimecrolimus.html
Chem Scene	CS-2691	http://www.chemscene.com/137071-32-0.html
ChemFish Tokyo co.,ltd	CF00254	http://www.chemfish.com/index.php?c=msg&id=3766&
ChemMol	2100064	http://www.chemmol.com/chemmol/2100064.html
ChemMol	30111179	http://www.chemmol.com/chemmol/30111179.html
ChemMol	49400129	http://www.chemmol.com/chemmol/49400129.html
ChemMol	99042588	http://www.chemmol.com/chemmol/99042588.html
Chemodex	P0598	http://www.chemodex.com/products/P0598
Chemspace	CSSB00016990164	https://chem-space.com/CSSB00016990164
Chemspace	CSSB02125554488	https://chem-space.com/CSSB02125554488
Combi-Blocks	QJ-4456	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-4456
DC Chemicals	DC8243	http://www.dcchemicals.com/product_show-Pimecrolimus.html
Excenen	EX-A2138	https://www.excenen.com/searchresultlist.php?id=137071-32-0
Hairui	HR124110	http://www.hairuichem.com/en/product/137071-32-0.html
Matrix Scientific	95362	https://www.matrixscientific.com/095362.html
MedChem Express	HY-13723	https://www.medchemexpress.com/Pimecrolimus.html
MolPort	MolPort-003-666-749	https://www.molport.com/shop/molecule-link/MolPort-003-666-749
MolPort	MolPort-008-155-973	https://www.molport.com/shop/molecule-link/MolPort-008-155-973
MolPort	MolPort-044-193-674	https://www.molport.com/shop/molecule-link/MolPort-044-193-674
MolPort	MolPort-046-684-033	https://www.molport.com/shop/molecule-link/MolPort-046-684-033
Molcore	MC520265	https://www.molcore.com/product/137071-32-0
MuseChem	A000429	https://www.musechem.com/product/A000429.html
OChem	23988	http://www.ocheminc.com/index.php?act=psearch&pid=071P320
Parchem	18230	http://www.parchem.com/chemical-supplier-distributor/Pimecrolimus-008230.aspx
Sigma-Aldrich	SML1437_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/sml1437?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S539689	http://www.smolecule.com/products/s539689
Sun-shine Chemical	Pimecrolimus	http://www.sun-shinechem.com/Details/Pimecrolimus/1219/137071-32-0.html
THE BioTek	bt-278354	https://www.thebiotek.com/product/inhibitors/bt-278354
abcr GmbH	AB452187	http://www.abcr.com/shop/en/AB452187
eNovation Chemicals	D371356	http://www.enovationchem.com/productDetails.asp?productID=D371356
eNovation Chemicals	D501827	http://www.enovationchem.com/productDetails.asp?productID=D501827
eNovation Chemicals	D618610	https://www.enovationchem.com/ProductDetails.asp?ProductID=D618610
eNovation Chemicals	Y0974019	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0974019
iChemical	EBD21291	http://www.ichemical.com/products/137071-32-0.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Ascomycin macrolactam derivative SDZ ASM 981 inhibits the release of granule-associated mediators and of newly synthesized cytokines in RBL 2H3 mast cells in an immunophilin-dependent manner.	1998 Sep	9808344

Patents

Sample Use Guides

In Vivo Use Guide

Apply a thin layer of ELIDEL (pimecrolimus) Cream, 1% to the affected skin twice daily.

Route of Administration: Topical

In Vitro Use Guide

Primary human basophils pre-treated or not with 0.5-50 μMol pimecrolimus were exposed to various concentrations of recombinant Bet v 1a allergen, bee or wasp venom extracts and anti-IgE for 20 min, and then examined for the expression of CD45, CD193, CD203c, CD63 and CD164 using flow cytometry. The inhibition was concentration-dependent; approximately half of the basophils were inhibited in the presence of 2.5 mMol pimecrolimus.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:08:19 UTC 2023` Edited by `admin` on `Sat Dec 16 19:08:19 UTC 2023`
Record UNII	89GTE436P6
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PIMECROLIMUS HYDRATE

Common Name

English

15,19-EPOXY-3H-PYRIDO(2,1-C)(1,4)OXAAZACYCLOTRICOSINE-1,7,20,21(4H,23H)-TETRONE, 3-((1E)-2-((1R,3R,4S)-4-CHLORO-3-METHOXYCYCLOHEXYL)-1-METHYLETHENYL)-8-ETHYL-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26A-HEXADECAHYDRO-5,19-DIHYDROXY-14,16-DIMETHOXY-4,10,

Systematic Name

English

Code System Code Type Description

SMS_ID

100000174203

Created by admin on Sat Dec 16 19:08:19 UTC 2023 , Edited by admin on Sat Dec 16 19:08:19 UTC 2023

PRIMARY

CAS

1000802-56-1

Created by admin on Sat Dec 16 19:08:19 UTC 2023 , Edited by admin on Sat Dec 16 19:08:19 UTC 2023

PRIMARY

FDA UNII

89GTE436P6

Created by admin on Sat Dec 16 19:08:19 UTC 2023 , Edited by admin on Sat Dec 16 19:08:19 UTC 2023

PRIMARY

PUBCHEM

91886159

Created by admin on Sat Dec 16 19:08:19 UTC 2023 , Edited by admin on Sat Dec 16 19:08:19 UTC 2023

PRIMARY

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ANHYDROUS->SOLVATE

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					7KYV510875

PIMECROLIMUS

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021302s018lbl.pdfCurator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12113647 https://www.ncbi.nlm.nih.gov/pubmed/12090545

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/021302s018lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12113647 https://www.ncbi.nlm.nih.gov/pubmed/12090545

C_max

T_1/2

F_unbound

Drug as perpetrator