TANAPROGET

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H15N3OS
Molecular Weight	297.375
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN1C(=CC=C1C2=CC3=C(NC(=S)OC3(C)C)C=C2)C#N

InChI

InChIKey=PYVFWTPEBMRKSR-UHFFFAOYSA-N

InChI=1S/C16H15N3OS/c1-16(2)12-8-10(4-6-13(12)18-15(21)20-16)14-7-5-11(9-17)19(14)3/h4-8H,1-3H3,(H,18,21)

HIDE SMILES / InChI

Molecular Formula	C16H15N3OS
Molecular Weight	297.375
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

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

Description

Tanaproget (WAY-166989) is a nonsteroidal progesterone receptor agonist. It has been in Phase-II clinical trials as an oral contraceptive. The compound demonstrated a positive preclinical pharmacological profile in the treatment of endometriosis. The level of progesterone receptors in breast tumours can be used to guide the selection of endocrine therapies for breast cancer patients. Radiolabeled analogues of tanaproget have diagnostic potential as PET imaging agents for breast cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Progesterone receptor 61	Agonist 2,678		1.7 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Pregnancy 65	Preventing	Phase II 1,132	Unknown
Endometriosis 32	Primary	Preclinical	Unknown
Breast cancer 434	Diagnostic	Preclinical	Unknown

C_max

Value	Dose	Analyte	Population
0.3 ng/mL	0.1 mg single, oral	TANAPROGET plasma	Homo sapiens
12.63 ng/mL	7 mg single, oral	TANAPROGET plasma	Homo sapiens
10.04 ng/mL	7 mg single, oral	TANAPROGET plasma	Homo sapiens
1.99 ng/mL	1 mg single, oral	TANAPROGET plasma	Homo sapiens
16.21 ng/mL	15 mg single, oral	TANAPROGET plasma	Homo sapiens
0.64 ng/mL	0.3 mg single, oral	TANAPROGET plasma	Homo sapiens
3.93 ng/mL	3 mg single, oral	TANAPROGET plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
1.58 ng × h/mL	0.1 mg single, oral	TANAPROGET plasma	Homo sapiens
112.2 ng × h/mL	7 mg single, oral	TANAPROGET plasma	Homo sapiens
134.9 ng × h/mL	7 mg single, oral	TANAPROGET plasma	Homo sapiens
15.9 ng × h/mL	1 mg single, oral	TANAPROGET plasma	Homo sapiens
152.9 ng × h/mL	15 mg single, oral	TANAPROGET plasma	Homo sapiens
3.48 ng × h/mL	0.3 mg single, oral	TANAPROGET plasma	Homo sapiens
45.5 ng × h/mL	3 mg single, oral	TANAPROGET plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
4.6 h	0.1 mg single, oral	TANAPROGET plasma	Homo sapiens
20.4 h	7 mg single, oral	TANAPROGET plasma	Homo sapiens
30.2 h	7 mg single, oral	TANAPROGET plasma	Homo sapiens
11.7 h	1 mg single, oral	TANAPROGET plasma	Homo sapiens
16.5 h	15 mg single, oral	TANAPROGET plasma	Homo sapiens
4.3 h	0.3 mg single, oral	TANAPROGET plasma	Homo sapiens
18 h	3 mg single, oral	TANAPROGET plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 781 substrate 1,737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYPs 22	UGT2B7 389 UGT1A9 380

Drug as perpetrator

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1,925	inducer 1,573	no
CYPs 28	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity
UGT1A9 380	substrate 3,367	major
UGT2B7 389	substrate 3,367	major
CYP3A4 1,737	substrate 3,367	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0030QO	https://www.1pchem.com/search?query=1P0030QO
ApexBio Technology	A3857	https://www.apexbt.com/catalogsearch/result/?q=A3857
BLD Pharm	BD630626	http://www.bldpharm.com/search/Search.html?keyword=BD630626
Debye Scientific	DA-38867	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-38867
Lab Network	LN01342651	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342651

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PubMed

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Title	Date	PubMed
Synthesis and structure-activity relationship of novel 6-aryl-1,4-dihydrobenzo[d][1,3]oxazine-2-thiones as progesterone receptor modulators leading to the potent and selective nonsteroidal progesterone receptor agonist tanaproget.	2005 Aug 11	16078826

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Patents

Sample Use Guides

In Vivo Use Guide

A randomized, double-blind, placebo-controlled, sequential-group study of ascending single doses of tanaproget was conducted in healthy, 25- to 45-year-old women on cycle days 8 to 12. Eight subjects (six active, two placebo) per cohort received a dose of 0.1, 0.3, 1, 3, 7 (+/-high-fat meal) or 15 mg.

Route of Administration: Oral

In Vitro Use Guide

0.1 and 1 nM tanaproget effectively down-regulated matrix metalloproteinase 3 and 7 expression in vitro in endometrial stromal cells

Substance Class	Chemical
Record UNII	W9F9H8GXWR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TANAPROGET

Official Name

English

tanaproget [INN]

Common Name

English

5-(4,4-Dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-1-methyl-1H-pyrrole-2-carbonitrile

Systematic Name

English

TANAPROGET [USAN]

Common Name

English

NSP-989

Code

English

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Classification Tree

Code System

Code

Therapeutic Steroid Hormone

NCI_THESAURUS

C776

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Code System

Code

Type

Description

INN

8427

PRIMARY

EPA CompTox

DTXSID00184556

PRIMARY

MESH

C504446

PRIMARY

NCI_THESAURUS

C66578

PRIMARY

WIKIPEDIA

Tanaproget

PRIMARY

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Related Record

Type

Details


					Y9U552M5HL

Tanaproget C-11

LABELED -> NON-LABELED

Amount:


					DXN1OSB4IB

PROGESTERONE RECEPTOR

TARGET -> AGONIST

Qualification:

EC50

Amount:

0.1 NANOMOLAR (average)

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Related Record

Type

Details


					W9F9H8GXWR

TANAPROGET

ACTIVE MOIETY

Amount:

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator