ORTERONEL

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H17N3O2
Molecular Weight	307.3465
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC(=O)C1=CC2=C(C=C1)C=C(C=C2)[C@@]3(O)CCN4C=NC=C34

InChI

InChIKey=OZPFIJIOIVJZMN-SFHVURJKSA-N

InChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)/t18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H17N3O2
Molecular Weight	307.3465
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21978946
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22249003

Orteronel (TAK-700) is a non-steroidal antiandrogen, discovered by Takeda Pharmaceutical Company Limited, that selectively inhibits the 17,20 lyase enzyme (CYP17A1). This enzyme, which is present in both the testes and adrenal glands, is central to the production of steroidal androgens. Synthesis of androgens outside the testes contributes to disease progression in castration-resistant prostate cancer (CRPC). In phase III of clinical trials for metastatic, hormone-refractory prostate cancer it wasn’t shown overall survival rates, and development was voluntarily terminated as a result.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cytochrome P450 17A1 8 Target ID: CHEMBL3522 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21978946	Inhibitor 8297		38.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Castrate-resistant prostate cancer 20 Sources: https://clinicaltrials.gov/ct2/show/NCT01193257	Primary		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
3.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25537627	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ORTERONEL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25537627	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ORTERONEL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.58 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25537627	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ORTERONEL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
1765 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27163497	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ORTERONEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2994 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27163497	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ORTERONEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: LOW-FAT
2832 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27163497	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ORTERONEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT

AUC

Value	Dose	Analyte	Population
14.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25537627	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ORTERONEL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
28.6 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25537627	400 mg 2 times / day multiple, oral dose: 400 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ORTERONEL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.64 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25537627	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	ORTERONEL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
17456 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27163497	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ORTERONEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
23019 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27163497	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ORTERONEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: LOW-FAT
24128 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27163497	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ORTERONEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT

T_1/2

Value	Dose	Analyte	Population
10.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27163497	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ORTERONEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
8.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27163497	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ORTERONEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: LOW-FAT
7.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27163497	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	ORTERONEL plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: HIGH-FAT

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY445289	https://www.001chemical.com/chem/search?q=DY445289
1PlusChem LLC	1P00ECV3	https://www.1pchem.com/search?query=1P00ECV3
AK Scientific	0218AP	https://aksci.com/item_detail.php?cat=0218AP
AK Scientific	W6233	https://aksci.com/item_detail.php?cat=W6233
AOBIOUS INC	AOB5917	http://aobious.com/aobious/search?search_query=AOB5917
ApexBio Technology	A3686	https://www.apexbt.com/catalogsearch/result/?q=A3686
ApexBio Technology	A4326	https://www.apexbt.com/catalogsearch/result/?q=A4326
AstaTech	40673	http://astatechinc.com/CPSResult.php?CRNO=40673
Axon MedChem	2124	https://www.axonmedchem.com/product/2124
BLD Pharm	BD630769	http://www.bldpharm.com/search/Search.html?keyword=BD630769
BOC Sciences	566939-85-3	http://www.bocsci.com/description.asp?cas=566939-85-3
BioSynth	J-501028	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-501028
BioSynth	J-502246	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-502246
Capot Chemical	22463	https://www.capotchem.com/search.do?q=22463
Capot Chemical	35483	https://www.capotchem.com/search.do?q=35483
Chem Scene	CS-0580	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0580
ChemShuttle	111882	https://www.chemshuttle.com/catalogsearch/result/?q=111882
ChemShuttle	169493	https://www.chemshuttle.com/catalogsearch/result/?q=169493
Debye Scientific	DA-42074	https://www.debyesci.com/index.php?id=product&ext[cno]=DA-42074
Debye Scientific	DB-070319	https://www.debyesci.com/index.php?id=product&ext[cno]=DB-070319
KeyOrganics	AS-74591	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-74591
Lab Network	LN01303663	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01303663
Lab Network	LN01342177	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342177
MedChem Express	HY-10505	https://www.medchemexpress.com/search.html?q=HY-10505&ft=&fa=&fp=
MolPort	MolPort-021-805-011	https://www.molport.com/shop/molecule-link/MolPort-021-805-011
MolPort	MolPort-028-720-386	https://www.molport.com/shop/molecule-link/MolPort-028-720-386
Molcore	MC445289	http://www.molcore.com/CatMC445289.html
Molnova	M15061	https://www.molnova.com/en/serch-list.html?keywords=M15061
Molnova	M17508	https://www.molnova.com/en/serch-list.html?keywords=M17508
MuseChem	I008489	https://www.musechem.com/product/I008489.html
Ryan Scientific	101-94099	https://ryansci.com/products?q=101-94099&list_q=&search_type=exact
ShangHai Biochempartner	BCP000166	http://www.biochempartner.com/search_BCP000166
ShangHai Biochempartner	BCP13183	http://www.biochempartner.com/search_BCP13183
Toronto Research Chemicals	O697600	https://www.trc-canada.com/product-detail/?CatNum=O697600
Wonderchem	WD064JY	http://www.wonder-chem.com/search.html?text=WD064JY
eMolecules	37153183	https://orderbb.emolecules.com/search/#?query=37153183
eMolecules	44786319	https://orderbb.emolecules.com/search/#?query=44786319
eMolecules	44786349	https://orderbb.emolecules.com/search/#?query=44786349
eNovation Chemicals	D372543	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372543&searchbtn.x=0&searchbtn.y=0
eNovation Chemicals	D766102	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D766102&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-1070454255	https://mcule.com/MCULE-1070454255/
mcule	MCULE-2580486234	https://mcule.com/MCULE-2580486234/
mcule	MCULE-7883591263	https://mcule.com/MCULE-7883591263/

PubMed

Title	Date	PubMed
		252160751

Sample Use Guides

In Vivo Use Guide

300 mg Orteronel twice daily

Route of Administration: Oral

In Vitro Use Guide

The reversibility of orteronel was further confirmed using a human adrenocortical tumor cell line. Orteronel also potently inhibits DHEA production in human adrenocortical tumor line H295R cells with IC50 of 37 nM. [2]

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:17:03 UTC 2023` Edited by `admin` on `Fri Dec 15 19:17:03 UTC 2023`
Record UNII	UE5K2FNS92
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ORTERONEL

Official Name

English

6-((7S)-7-HYDROXY-6,7-DIHYDRO-5H-PYRROLO(1,2-C)IMIDAZOL-7-YL)-N-METHYL-2-NAPHTHALENECARBOXAMIDE

Systematic Name

English

orteronel [INN]

Common Name

English

Orteronel [WHO-DD]

Common Name

English

ORTERONEL [JAN]

Common Name

English

2-NAPHTHALENECARBOXAMIDE, 6-((7S)-6,7-DIHYDRO-7-HYDROXY-5H-PYRROLO(1,2-C)IMIDAZOL-7-YL)-N-METHYL-

Systematic Name

English

TAK-700

Code

English

ORTERONEL [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C471