U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ORTERONEL

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
38.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.1 μg/mL
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
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
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
14.5 μg × h/mL
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
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
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
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
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10.5 h
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
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
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

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed

Sample Use Guides

300 mg Orteronel twice daily
Route of Administration: Oral
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]
Name Type Language
ORTERONEL
INN   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
Code System Code Type Description
EVMPD
SUB126331
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
SMS_ID
100000151906
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
USAN
YY-51
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
CAS
426219-18-3
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
FDA UNII
UE5K2FNS92
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID001319121
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
MESH
C571806
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
CAS
566939-85-3
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
INN
9332
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
PUBCHEM
9796590
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
WIKIPEDIA
ORTERONEL
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
ChEMBL
CHEMBL1921976
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
DRUG BANK
DB12066
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY
NCI_THESAURUS
C90582
Created by admin on Fri Dec 15 19:17:03 GMT 2023 , Edited by admin on Fri Dec 15 19:17:03 GMT 2023
PRIMARY