Page last updated: 2024-12-07
opc 21268
Description
Research Excerpts
Clinical Trials
Roles
Classes
Pathways
Study Profile
Bioassays
Related Drugs
Related Conditions
Protein Interactions
Research Growth
Market Indicators
Description
OPC 21268: structure given in first source; vasopressin V1 receptor antagonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
Cross-References
| ID Source | ID |
|---|---|
| PubMed CID | 114904 |
| CHEMBL ID | 296908 |
| SCHEMBL ID | 3504368 |
| MeSH ID | M0187639 |
Synonyms (36)
| Synonym |
|---|
| n-(3-{4-[4-(2-oxo-3,4-dihydro-2h-quinolin-1-yl)-piperidine-1-carbonyl]-phenoxy}-propyl)-acetamide |
| bdbm50029644 |
| n-(3-(4-(4-(2-oxo-3,4-dihydroquinolin-1(2h)-yl)piperidine-1-carbonyl)phenoxy)propyl)acetamide |
| gtpl2196 |
| opc-21268 |
| 1-(1-(4-(3-acetylaminopropoxy)benzoyl)-4-piperidyl)-3,4-dihydro-2(1h)-quinolinone |
| opc 21268 |
| acetamide, n-(3-(4-((4-(3,4-dihydro-2-oxo-1(2h)-quinolinyl)-1-piperidinyl)carbonyl)phenoxy)propyl)- |
| opc-1268 |
| CHEMBL296908 , |
| L001417 |
| n-[3-[4-[4-(2-oxo-3,4-dihydroquinolin-1-yl)piperidine-1-carbonyl]phenoxy]propyl]acetamide |
| 131631-89-5 |
| opc-21268 hydrate |
| SCHEMBL3504368 |
| n-[3-[4-[[4-(3,4-dihydro-2-oxo-1(2h)quinolinyl)-1-piperidinyl]carbonyl]phenoxy]propyl]-acetamide |
| AKOS024457877 |
| EX-A593 |
| J-006031 |
| n-[3-[4-[[4-(3,4-dihydro-2-oxo-1(2h)-quinolinyl)-1-piperidinyl]carbonyl]phenoxy]propyl]acetamide |
| NCGC00370961-01 |
| n-(3-{4-[4-(2-oxo-3,4-dihydroquinolin-1(2h)-yl)piperidine-1-carbonyl]phenoxy}propyl)ethanimidic acid |
| DTXSID70927295 |
| fuscoside |
| FT-0700164 |
| Q27088205 |
| 1262770-69-3 |
| BCP14853 |
| opc-21268;opc21268 |
| CS-0003694 |
| HY-15009 |
| acetamide, n-[3-[4-[[4-(3,4-dihydro-2-oxo-1(2h)-quinolinyl)-1-piperidinyl]carbonyl]phenoxy]propyl]- |
| MS-28145 |
| 1-[1-[4-(3-acetylaminopropoxy)benzoyl]-4-piperidyl]-3,4-dihydroquinolin-2(1h)-one |
| A856968 |
| AC-35504 |
Research Excerpts
Bioavailability
| Excerpt | Reference | Relevance |
|---|---|---|
| " These compounds are structurally related to the 1-(4-piperidyl)-2(1H)-quinolinones, including OPC-21268, an orally bioavailable AVP V1 antagonist with high V1 specificity." | ( Orally active, nonpeptide vasopressin V1 antagonists. A novel series of 1-(1-substituted 4-piperidyl)-3,4-dihdyro-2(1H)-quinolinone. Chihara, T; Kondo, K; Miyamoto, H; Mori, T; Nakaya, K; Ogawa, H; Tominaga, M; Yabuuchi, Y; Yamamura, Y; Yamashita, H, 1993) | 0.29 |
| "The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs." | ( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019) | 0.51 |
Dosage Studied
| Excerpt | Relevance | Reference |
|---|---|---|
| " The dose-response curve for AVP was shifted to the right in parallel by OPC-31260 but not by OPC-21268." | ( Potent antagonistic action of OPC-31260, a vasopressin V2 receptor antagonist, on [Arg8]vasopressin-induced vasoconstriction in isolated simian femoral arteries. Chiba, S; Tsukada, M, 1992) | 0.28 |
| " produced a rightward parallel shift of the dose-response curves for AVP in a dose-dependent manner." | ( OPC-21268 antagonizes arginine vasopressin-induced vasoconstrictor response in the spinally-anesthetized dog. Chihara, T; Mori, T; Nakamura, S; Onogawa, T; Tominaga, M; Yabuuchi, Y; Yamamura, Y; Yamashita, T, 1995) | 0.29 |
| " Brain tissue sodium content was significantly reduced at the dosage of 300 mg/kg (P<0." | ( Treatment of brain edema with a nonpeptide arginine vasopressin V1 receptor antagonist OPC-21268 in rats. Bemana, I; Nagao, S, 1999) | 0.3 |
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
Protein Targets (8)
Potency Measurements
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| cytochrome P450 family 3 subfamily A polypeptide 4 | Homo sapiens (human) | Potency | 10.6840 | 0.0123 | 7.9835 | 43.2770 | AID1645841 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Inhibition Measurements
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Vasopressin V2 receptor | Homo sapiens (human) | Ki | 45.5000 | 0.0004 | 0.4345 | 3.9811 | AID217391; AID513686 |
| Oxytocin receptor | Homo sapiens (human) | Ki | 0.1700 | 0.0001 | 0.0718 | 0.9780 | AID151801 |
| Vasopressin V1a receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 0.4400 | 0.0820 | 1.0477 | 5.0000 | AID217060 |
| Vasopressin V1a receptor | Rattus norvegicus (Norway rat) | Ki | 0.0299 | 0.0008 | 0.0300 | 0.1100 | AID217234; AID217235; AID217238; AID513685 |
| Vasopressin V2 receptor | Sus scrofa (pig) | Ki | 10.0000 | 0.2850 | 0.2850 | 0.2850 | AID217688 |
| Vasopressin V1a receptor | Homo sapiens (human) | Ki | 25.6700 | 0.0002 | 0.6235 | 7.0300 | AID217085; AID217088; AID217091; AID337610; AID513684 |
| Oxytocin receptor | Rattus norvegicus (Norway rat) | Ki | 0.2300 | 0.0009 | 0.0489 | 0.2300 | AID151933 |
| Vasopressin V2 receptor | Rattus norvegicus (Norway rat) | IC50 (µMol) | 100.0000 | 0.0005 | 0.0638 | 0.5700 | AID213927 |
| Vasopressin V2 receptor | Rattus norvegicus (Norway rat) | Ki | 16.6667 | 0.0003 | 0.9791 | 9.7000 | AID217688; AID513687 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (63)
Molecular Functions (7)
| Process | via Protein(s) | Taxonomy |
|---|---|---|
| vasopressin receptor activity | Vasopressin V2 receptor | Homo sapiens (human) |
| protein binding | Vasopressin V2 receptor | Homo sapiens (human) |
| peptide binding | Vasopressin V2 receptor | Homo sapiens (human) |
| peptide hormone binding | Oxytocin receptor | Homo sapiens (human) |
| peptide binding | Oxytocin receptor | Homo sapiens (human) |
| vasopressin receptor activity | Oxytocin receptor | Homo sapiens (human) |
| oxytocin receptor activity | Oxytocin receptor | Homo sapiens (human) |
| vasopressin receptor activity | Vasopressin V1a receptor | Homo sapiens (human) |
| protein kinase C binding | Vasopressin V1a receptor | Homo sapiens (human) |
| protein binding | Vasopressin V1a receptor | Homo sapiens (human) |
| peptide hormone binding | Vasopressin V1a receptor | Homo sapiens (human) |
| V1A vasopressin receptor binding | Vasopressin V1a receptor | Homo sapiens (human) |
| peptide binding | Vasopressin V1a receptor | Homo sapiens (human) |
| [Information is prepared from geneontology information from the June-17-2024 release] | ||
Ceullar Components (11)
Bioassays (36)
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID217239 | Evaluated for the binding affinity towards Vasopressin V1a receptor in rat liver membrane using [3H]AVP as radioligand | 2002 | Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2 | N-Methylbenzanilide derivatives as a novel class of selective V(1A) receptor antagonists. |
| AID513685 | Displacement of [3H]vasopressin from vasopressin V1a receptor in rat liver tissue | 2010 | Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18 | Oral oxytocin antagonists. |
| AID182931 | In vivo dose required to inhibit AVP-induced pressor response in pithed rats by 50% | 2002 | Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2 | N-Methylbenzanilide derivatives as a novel class of selective V(1A) receptor antagonists. |
| AID217688 | Binding affinity at Vasopressin V2 receptor, performed using [3H]AVP on rat kidney | 2002 | Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12 | Synthesis and pharmacological evaluation of 5-(4-biphenyl)-3-methyl-4-phenyl-1,2,4-triazole derivatives as a novel class of selective antagonists for the human vasopressin V(1A) receptor. |
| AID217060 | Ability to displace [3H]- Arginine Vasopressin (AVP) from its specific binding sites in rat liver (V1 receptor) | 1993 | Journal of medicinal chemistry, Jul-09, Volume: 36, Issue:14 | Orally active, nonpeptide vasopressin V1 antagonists. A novel series of 1-(1-substituted 4-piperidyl)-3,4-dihdyro-2(1H)-quinolinone. |
| AID217694 | Selectivity ratio Vasopressin V2 receptor/Vasopressin V1 receptor of the compound | 2002 | Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2 | N-Methylbenzanilide derivatives as a novel class of selective V(1A) receptor antagonists. |
| AID217091 | Binding affinity was evaluated by measuring the displacement of [3H]AVP (arginine vasopressin) from specific binding sites in human platelets. | 1995 | Journal of medicinal chemistry, Nov-10, Volume: 38, Issue:23 | 1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist. |
| AID513687 | Displacement of [3H]vasopressin from vasopressin V2 receptor in rat kidney tissue | 2010 | Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18 | Oral oxytocin antagonists. |
| AID217693 | Selectivity ratio (Ki) of affinity at rat Vasopressin V2 receptor to that of rat Vasopressin V1a receptor | 2002 | Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12 | Synthesis and pharmacological evaluation of 5-(4-biphenyl)-3-methyl-4-phenyl-1,2,4-triazole derivatives as a novel class of selective antagonists for the human vasopressin V(1A) receptor. |
| AID217085 | Binding affinity at cloned human Vasopressin V1a receptor stably expressed in CHO cells, using [3H]AVP as radioligand | 2002 | Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12 | Synthesis and pharmacological evaluation of 5-(4-biphenyl)-3-methyl-4-phenyl-1,2,4-triazole derivatives as a novel class of selective antagonists for the human vasopressin V(1A) receptor. |
| AID217519 | Binding affinity was evaluated by measuring the displacement of [3H]AVP (arginine vasopressin) from specific binding sites in kidney medulla obtained from early postmortem human donors. | 1995 | Journal of medicinal chemistry, Nov-10, Volume: 38, Issue:23 | 1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist. |
| AID513686 | Displacement of [3H]vasopressin from vasopressin V2 receptor in human kidney tissue | 2010 | Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18 | Oral oxytocin antagonists. |
| AID217235 | Binding affinity towards Vasopressin V1a receptor in rat liver | 2000 | Journal of medicinal chemistry, Nov-16, Volume: 43, Issue:23 | Novel design of nonpeptide AVP V(2) receptor agonists: structural requirements for an agonist having 1-(4-aminobenzoyl)-2,3,4, 5-tetrahydro-1H-1-benzazepine as a template. |
| AID513683 | Displacement of [3H]-oxytocin from oxytocin receptor in rat uterus tissue | 2010 | Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18 | Oral oxytocin antagonists. |
| AID513684 | Displacement of [3H]vasopressin from vasopressin V1a receptor in human liver tissue | 2010 | Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18 | Oral oxytocin antagonists. |
| AID213767 | Inhibition expressed as percent change in diastolic blood pressure increased by AVP (30 milliunits / kg, iv) before and after oral administration at 22 uM/kg | 1993 | Journal of medicinal chemistry, Jul-09, Volume: 36, Issue:14 | Orally active, nonpeptide vasopressin V1 antagonists. A novel series of 1-(1-substituted 4-piperidyl)-3,4-dihdyro-2(1H)-quinolinone. |
| AID217691 | Binding affinity was evaluated by measuring the displacement of [3H]AVP (arginine vasopressin) from specific binding sites in kidney medulla obtained from rats. | 1995 | Journal of medicinal chemistry, Nov-10, Volume: 38, Issue:23 | 1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist. |
| AID337610 | Binding affinity to vasopressin V1a receptor | 1994 | Journal of natural products, Oct, Volume: 57, Issue:10 | Khusimol, a non-peptide ligand for vasopressin V1a receptors. |
| AID513682 | Displacement of [3H]-oxytocin from oxytocin receptor in human uterus tissue | 2010 | Journal of medicinal chemistry, Sep-23, Volume: 53, Issue:18 | Oral oxytocin antagonists. |
| AID213927 | Ability to displace [3H]- Arginine Vasopressin (AVP) from its specific binding sites in rat liver (V2 receptor) | 1993 | Journal of medicinal chemistry, Jul-09, Volume: 36, Issue:14 | Orally active, nonpeptide vasopressin V1 antagonists. A novel series of 1-(1-substituted 4-piperidyl)-3,4-dihdyro-2(1H)-quinolinone. |
| AID217088 | Binding affinity towards Vasopressin V1a receptor in human liver | 2000 | Journal of medicinal chemistry, Nov-16, Volume: 43, Issue:23 | Novel design of nonpeptide AVP V(2) receptor agonists: structural requirements for an agonist having 1-(4-aminobenzoyl)-2,3,4, 5-tetrahydro-1H-1-benzazepine as a template. |
| AID217692 | Evaluated for the binding affinity towards Vasopressin V2 receptor in rat kidney membrane using [3H]-AVP as radioligand | 2002 | Bioorganic & medicinal chemistry letters, Jan-21, Volume: 12, Issue:2 | N-Methylbenzanilide derivatives as a novel class of selective V(1A) receptor antagonists. |
| AID213762 | Inhibition dose for AVP (30 milliunits/kg, iv) induced vasoconstriction when orally administarted | 1993 | Journal of medicinal chemistry, Jul-09, Volume: 36, Issue:14 | Orally active, nonpeptide vasopressin V1 antagonists. A novel series of 1-(1-substituted 4-piperidyl)-3,4-dihdyro-2(1H)-quinolinone. |
| AID217234 | Binding affinity at Vasopressin V1a receptor, performed using [3H]AVP on rat liver | 2002 | Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12 | Synthesis and pharmacological evaluation of 5-(4-biphenyl)-3-methyl-4-phenyl-1,2,4-triazole derivatives as a novel class of selective antagonists for the human vasopressin V(1A) receptor. |
| AID151801 | Binding affinity was evaluated by measuring the displacement of [3H]-OT (oxytocin) from specific binding sites in uterine tissue obtained from human. | 1995 | Journal of medicinal chemistry, Nov-10, Volume: 38, Issue:23 | 1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist. |
| AID217238 | Binding affinity was evaluated by measuring the displacement of [3H]AVP (arginine vasopressin) from specific binding sites in rat liver. | 1995 | Journal of medicinal chemistry, Nov-10, Volume: 38, Issue:23 | 1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist. |
| AID151933 | Binding affinity was evaluated by measuring the displacement of [3H]-OT (oxytocin) from specific binding sites in uterine tissue obtained from rats | 1995 | Journal of medicinal chemistry, Nov-10, Volume: 38, Issue:23 | 1-(1-[4-[(N-acetyl-4-piperidinyl)oxy]-2-methoxybenzoyl]piperidin-4- yl)-4H-3,1-benzoxazin-2(1H)-one (L-371,257): a new, orally bioavailable, non-peptide oxytocin antagonist. |
| AID217391 | Binding affinity at cloned human Vasopressin V2 receptor stably expressed in CHO cells, using [3H]AVP as radioligand | 2002 | Journal of medicinal chemistry, Jun-06, Volume: 45, Issue:12 | Synthesis and pharmacological evaluation of 5-(4-biphenyl)-3-methyl-4-phenyl-1,2,4-triazole derivatives as a novel class of selective antagonists for the human vasopressin V(1A) receptor. |
| AID1296008 | Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening | 2020 | SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1 | Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening. |
| AID1347160 | Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1347159 | Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
| AID1346986 | P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346987 | P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen | 2019 | Molecular pharmacology, 11, Volume: 96, Issue:5 | A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. |
| AID1346469 | Human OT receptor (Vasopressin and oxytocin receptors) | 1995 | Life sciences, , Volume: 57, Issue:24 | Characterization of the human oxytocin receptor stably expressed in 293 human embryonic kidney cells. |
| AID1346453 | Human V2 receptor (Vasopressin and oxytocin receptors) | 1997 | Endocrinology, Oct, Volume: 138, Issue:10 | The human V3 pituitary vasopressin receptor: ligand binding profile and density-dependent signaling pathways. |
| AID1346432 | Human V1A receptor (Vasopressin and oxytocin receptors) | 1997 | Endocrinology, Oct, Volume: 138, Issue:10 | The human V3 pituitary vasopressin receptor: ligand binding profile and density-dependent signaling pathways. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
Research
Studies (129)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 90 (69.77) | 18.2507 |
| 2000's | 31 (24.03) | 29.6817 |
| 2010's | 6 (4.65) | 24.3611 |
| 2020's | 2 (1.55) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
Market Indicators
Research Demand Index: 14.39
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (14.39) All Compounds (24.57) |
Study Types
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 3 (2.26%) | 5.53% |
| Reviews | 6 (4.51%) | 6.00% |
| Case Studies | 3 (2.26%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 121 (90.98%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||