Tafluprost acid

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H28F2O5
Molecular Weight	410.4515
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@H]1C[C@@H](O)[C@H](\C=C\C(F)(F)COC2=CC=CC=C2)[C@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=KIQXRQVVYTYYAZ-VKVYFNERSA-N

InChI=1S/C22H28F2O5/c23-22(24,15-29-16-8-4-3-5-9-16)13-12-18-17(19(25)14-20(18)26)10-6-1-2-7-11-21(27)28/h1,3-6,8-9,12-13,17-20,25-26H,2,7,10-11,14-15H2,(H,27,28)/b6-1-,13-12+/t17-,18-,19+,20-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H28F2O5
Molecular Weight	410.4515
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15037111http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202514s003s004lbl.pdf
Curator's Comment: http://www.merck.com/licensing/our-partnership/santen-partnership.html

Tafluprost acid is a prostanoid selective FP receptor agonist that is believed to reduce the intraocular pressure (IOP) by increasing the outflow of aqueous humor. Studies in animals and humans suggest that the main mechanism of action is increased uveoscleral outflow. A prostaglandin analogue ester prodrug used topically (as eye drops) to control the progression of glaucoma and in the management of ocular hypertension. Tafluprost was approved for use in the U.S. on February 10, 2012. Tafluprost, preserved and preservative-free formulations, received marketing approval for the reduction of elevated intraocular pressure (IOP) in open-angle glaucoma and ocular hypertension in several European and Nordic countries as well as Japan, and some other Asia Pacific markets.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostanoid FP receptor 21 Target ID: CHEMBL1987 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202514s003s004lbl.pdf	Agonist 2678		0.5 nM [IC50]
Prostanoid FP receptor 21 Target ID: CHEMBL1987 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15037111	Agonist 2678		0.4 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2578
Glaucoma 57 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202514s003s004lbl.pdf	Secondary	Approved 8429	ZIOPTAN Approved Use Indicated for reducing elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Launch Date 2012
Ocular hypertension 50 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202514s003s004lbl.pdf	Secondary	Approved 8429	ZIOPTAN Approved Use Is indicated for reducing elevated intraocular pressure in patients with open-angle glaucoma or ocular hypertension. Launch Date 2012

C_max

Value	Dose	Co-administered	Analyte	Population
24.4 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18752509	1 drop single, topical dose: 1 drop route of administration: Topical experiment type: SINGLE co-administered:		TAFLUPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
26 pg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202514s000lbl.pdf	1 drop single, topical dose: 1 drop route of administration: Topical experiment type: SINGLE co-administered:		TAFLUPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
405.9 pg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/18752509	1 drop single, topical dose: 1 drop route of administration: Topical experiment type: SINGLE co-administered:		TAFLUPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
394 pg × min/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/202514s000lbl.pdf	1 drop single, topical dose: 1 drop route of administration: Topical experiment type: SINGLE co-administered:		TAFLUPROST ACID plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	Disc. AE: Eye irritation, Abnormal sensation in eye... AEs leading to discontinuation/dose reduction: Eye irritation (3 patients) Abnormal sensation in eye (1 patient) Lacrimation increased (1 patient) Eye pruritus (3 patients) Blepharitis (1 patient) Intraocular pressure increased (2 patients) Pulmonary fibrosis (1 patient) Scleritis (1 patient) Dry skin (1 patient) Conjunctival disorder (2 patients) Ocular hyperemia (2 patients) Headache (2 patients) Hypertrichosis (1 patient) Cough (1 patient) Eye pain (2 patients) Vision blurred (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
0.0003 % 1 times / day multiple, ophthalmic Dose: 0.0003 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0003 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 60 years n = 1 Health Status: unhealthy Age Group: 60 years Sex: M Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	Disc. AE: Blood pressure increased... AEs leading to discontinuation/dose reduction: Blood pressure increased (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 270

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000ClinPharmR.pdf#page=12 Page: 12.0	no

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000PharmR.pdf#page=29 Page: 29.0		AFP-172 2

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:66899	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:66899
ChemicalBook	CB3401660	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3401660
MolPort	MolPort-020-006-049	https://www.molport.com/shop/molecule-link/MolPort-020-006-049
ZINC	ZINC000013912394	http://zinc15.docking.org/substances/ZINC000013912394

PubMed

Title	Date	PubMed
Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug.	2004 Apr	15037111
Disposition and metabolism of a novel prostanoid antiglaucoma medication, tafluprost, following ocular administration to rats.	2009 Aug	19477946
Tafluprost for glaucoma.	2011 Oct	21916788
Tafluprost: a novel prostaglandin analog for treatment of glaucoma.	2011 Sep	21858491

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

The affinity for the FP receptor shown by AFP-172 (Ki : 0.4 nm) was 12 times that of PhXA85 ( Ki : 4.7 nm), a carboxylic acid of latanoprost. For the prostanoid FP receptor-binding study, it was used a clonal cell line that stably expresses the recombinant human prostanoid FP receptor. The AFP-172 showed a high afﬁnity for the human prostanoid FP receptor, with an EC50 of 0,53 nM.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:12:33 GMT 2023` Edited by `admin` on `Sat Dec 16 09:12:33 GMT 2023`
Record UNII	WTV8EPZ396
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Tafluprost acid

Common Name

English

5-Heptenoic acid, 7-[(1R,2R,3R,5S)-2-[(1E)-3,3-difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-, (5Z)-

Systematic Name

English

Tafluprost free acid

Common Name

English

(5Z)-7-[(1R,2R,3R,5S)-2-[(1E)-3,3-Difluoro-4-phenoxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid

Systematic Name

English

AFP-172

Code

English

Code System Code Type Description

FDA UNII

WTV8EPZ396

Created by admin on Sat Dec 16 09:12:33 GMT 2023 , Edited by admin on Sat Dec 16 09:12:33 GMT 2023

PRIMARY

PUBCHEM

9978917

Created by admin on Sat Dec 16 09:12:33 GMT 2023 , Edited by admin on Sat Dec 16 09:12:33 GMT 2023

PRIMARY

CAS

209860-88-8

Created by admin on Sat Dec 16 09:12:33 GMT 2023 , Edited by admin on Sat Dec 16 09:12:33 GMT 2023

PRIMARY

EPA CompTox

DTXSID60694020

Created by admin on Sat Dec 16 09:12:33 GMT 2023 , Edited by admin on Sat Dec 16 09:12:33 GMT 2023

PRIMARY

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Tafluprost acid

ACTIVE MOIETY

Amount:

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Tmax	PHARMACOKINETIC

AE	Significance	Dose	Population
Abnormal sensation in eye	1 patient Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Blepharitis	1 patient Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Cough	1 patient Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Dry skin	1 patient Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Hypertrichosis	1 patient Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Lacrimation increased	1 patient Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Pulmonary fibrosis	1 patient Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Scleritis	1 patient Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Vision blurred	1 patient Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Conjunctival disorder	2 patients Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Eye pain	2 patients Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Headache	2 patients Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Intraocular pressure increased	2 patients Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Ocular hyperemia	2 patients Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Eye irritation	3 patients Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Eye pruritus	3 patients Disc. AE	0.0015 % 1 times / day multiple, ophthalmic Recommended Dose: 0.0015 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0015 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 27-72 years n = 18 Health Status: unhealthy Condition: open-angle glaucoma \| ocular hypertension Age Group: 27-72 years Sex: M+F Population Size: 18 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66
Blood pressure increased	1 patient Disc. AE	0.0003 % 1 times / day multiple, ophthalmic Dose: 0.0003 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.0003 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66	unhealthy, 60 years n = 1 Health Status: unhealthy Age Group: 60 years Sex: M Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/202514Orig1s000MedR.pdf Page: p.66

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15037111http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202514s003s004lbl.pdfCurator's Comment: http://www.merck.com/licensing/our-partnership/santen-partnership.html

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

Doses

AEs

Overview

OverviewOther

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15037111http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/202514s003s004lbl.pdf
Curator's Comment: http://www.merck.com/licensing/our-partnership/santen-partnership.html

C_max