Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H24FN5O4 |
| Molecular Weight | 441.4555 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(OC)=CC(=C1)N2CCN(CC2)C(=O)NC3=C(OC)N=C4C=CC(F)=CC4=N3
InChI
InChIKey=KAKPGJJRYRYSTP-UHFFFAOYSA-N
InChI=1S/C22H24FN5O4/c1-30-16-11-15(12-17(13-16)31-2)27-6-8-28(9-7-27)22(29)26-20-21(32-3)25-18-5-4-14(23)10-19(18)24-20/h4-5,10-13H,6-9H2,1-3H3,(H,24,26,29)
| Molecular Formula | C22H24FN5O4 |
| Molecular Weight | 441.4555 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
252 μg/L |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
226 μg/L |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
364 μg/L |
225 mg single, oral dose: 225 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
385 μg/L |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
660 μg/L |
425 mg single, oral dose: 425 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
707 μg/L |
575 mg single, oral dose: 575 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
571 μg/L |
775 mg single, oral dose: 775 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
394 μg/L |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
403 μg/L |
250 mg 3 times / week multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
288 μg/L |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
301 μg/L |
300 mg 3 times / week multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
347 μg/L |
150 mg 5 times / week multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
337 μg/L |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
440 μg/L |
200 mg 5 times / week multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
498 μg/L |
300.02 mg 5 times / week multiple, oral dose: 300.02 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2341 μg × h/L |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3280 μg × h/L |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4312 μg × h/L |
225 mg single, oral dose: 225 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5847 μg × h/L |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
14673 μg × h/L |
425 mg single, oral dose: 425 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
10098 μg × h/L |
575 mg single, oral dose: 575 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6570 μg × h/L |
775 mg single, oral dose: 775 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5211 μg × h/L |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7774 μg × h/L |
250 mg 3 times / week multiple, oral dose: 250 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4555 μg × h/L |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4143 μg × h/L |
300 mg 3 times / week multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3721 μg × h/L |
150 mg 5 times / week multiple, oral dose: 150 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
2752 μg × h/L |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4034 μg × h/L |
200 mg 5 times / week multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
4359 μg × h/L |
300.02 mg 5 times / week multiple, oral dose: 300.02 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11.4 h |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
12 h |
225 mg single, oral dose: 225 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
16 h |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
14 h |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
10.3 h |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
8.5 h |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SUPINOXIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Tue Apr 01 16:39:11 GMT 2025
by
admin
on
Tue Apr 01 16:39:11 GMT 2025
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| Record UNII |
ZU8OM8V5WF
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| Record Status |
Validated (UNII)
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| Record Version |
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Common Name | English | ||
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Preferred Name | English | ||
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Systematic Name | English |
| Code System | Code | Type | Description | ||
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C113293
Created by
admin on Tue Apr 01 16:39:11 GMT 2025 , Edited by admin on Tue Apr 01 16:39:11 GMT 2025
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PRIMARY | NCIT | ||
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888478-45-3
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11619093
Created by
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ZU8OM8V5WF
Created by
admin on Tue Apr 01 16:39:11 GMT 2025 , Edited by admin on Tue Apr 01 16:39:11 GMT 2025
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SUPINOXIN
Created by
admin on Tue Apr 01 16:39:11 GMT 2025 , Edited by admin on Tue Apr 01 16:39:11 GMT 2025
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PRIMARY | Description: Supinoxin, also known as RX-5902, is orally bioavailable small molecule inhibitor of phosphorylated-p68 RNA helicase (P-p68), with potential anti-proliferative and antineoplastic activity. Upon oral administration, P-p68 inhibitor RX-5902 may both inhibit the activity of the anti-apoptotic B-cell lymphoma 2 (Bcl-2) protein and facilitate the induction of cyclin-dependent kinase inhibitor 1 (p21). This may prevent G2/M cell cycle progression and lead to growth inhibition in tumor cells. P-p68 is overexpressed in various types of solid tumors but absent in normal tissues, and plays a role in tumor progression and metastasis. (last updated: 5/1/2016) |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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ACTIVE MOIETY |
Supinoxin (RX-5902) is an orally administered, potential first-in-class, small molecule inhibitor of a unique cancer protein phosphorylated-p68 (P-p68) which is selectively overexpressed in cancer cells and absent in normal tissue. P-p68 is believed to increase the activity of multiple cancer related genes including, cyclin D1, c-jun and c-myc, and play a prominent role in tumor progression and metastasis. Over-expression of P-p68 has been observed in many solid tumors, including, melanoma, colon, ovarian and lung tumors.
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ACTIVE MOIETY |
DEAD box RNA helicase DDX5/p68, and its phosphorylated form in particular, may play several important roles in cancer by means of cell transformation, epithelial mesenchymal transition (EMT), and cell migration, deeming it a promising target for novel anti-cancer therapeutics. We have previously shown that Supinoxin (RX-5902) interacts with phosphorylated p68 on Tyr593, interfering with the phosphorylated p68-.BETA.-catenin signaling pathway. Supinoxin also inhibits motility of MDA-MB231 breast cancer cell lines and could potentially prevent metastasis in cancer. In the MiaPaCa-2 model, at 50 and 70 mg/kg daily (oral, 5 days on/2 days off) for 3 weeks, both doses delayed tumor growth significantly (83% and 339% P < 0.001). All animals in the high dose showed complete regression (CR) and completing the study as tumor free survival (TFS-Day 65)one animal showed CR and TFS in the lower dose. Gemcitabine (120 mg/kg ip Q3D for 4 weeks) resulted in TGD of 71% (P < 0.001), with no CRs. Supinoxin did not result in a reduction in body weight gain, treatment related deaths, or clinical observations in this tumor model. These data support the potential therapeutic activity of Supinoxin in pancreatic cancer. A Phase 1 study of Supinoxin on relapse/refractory solid tumors is ongoing (NCT02003092).
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ACTIVE MOIETY |
Class: Antineoplastic, Piperazine, Quinoxaline, Small molecule; Mechanism of Action: RNA helicase inhibitor; Highest Development Phases: Phase I for Solid tumours, Preclinical for Breast cancer, Pancreatic cancer, Renal cancer; Most Recent Events: 06 Jun 2016 Rexahn Pharmaceuticals plans a phase Ib/IIa trial for Breast cancer and Ovarian cancer in USA, 24 Mar 2016 Pharmacodynamics data from a preclinical studies in Breast cancer released by Rexahn Pharmaceuticals, 25 Jan 2016 Pharmacodynamics data from a preclinical trial in Pancreatic cancer presented at the 51st Annual Meeting of the American Society for Clinical Oncology Gastrointestinal Cancers symposium (ASCO-GCS-2016)
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