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ID: ALA574852
Max Phase: Preclinical
Molecular Formula: C18H21ClF2N4O3
Molecular Weight: 414.84
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COC[C@H](C1CC1)n1cc(Cl)nc(Nc2cc(C)c(OC(F)F)nc2C)c1=O
Standard InChI: InChI=1S/C18H21ClF2N4O3/c1-9-6-12(10(2)22-16(9)28-18(20)21)23-15-17(26)25(7-14(19)24-15)13(8-27-3)11-4-5-11/h6-7,11,13,18H,4-5,8H2,1-3H3,(H,23,24)/t13-/m1/s1
Standard InChI Key: CBVDPVDNACOCTI-CYBMUJFWSA-N
Associated Targets(Human)
Serum 1292 Activities
Liver microsomes 16955 Activities
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Associated Targets(non-human)
Liver microsomes 8692 Activities
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Rattus norvegicus 775804 Activities
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Corticotropin releasing factor receptor 1 741 Activities
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 414.84 | Molecular Weight (Monoisotopic): 414.1270 | AlogP: 3.85 | #Rotatable Bonds: 8 |
| Polar Surface Area: 78.27 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 7 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 1.72 | CX LogP: 3.49 | CX LogD: 3.49 |
| Aromatic Rings: 2 | Heavy Atoms: 28 | QED Weighted: 0.71 | Np Likeness Score: -0.98 |
References
| 1. Hartz RA, Ahuja VT, Zhuo X, Mattson RJ, Denhart DJ, Deskus JA, Vrudhula VM, Pan S, Ditta JL, Shu YZ, Grace JE, Lentz KA, Lelas S, Li YW, Molski TF, Krishnananthan S, Wong H, Qian-Cutrone J, Schartman R, Denton R, Lodge NJ, Zaczek R, Macor JE, Bronson JJ.. (2009) A strategy to minimize reactive metabolite formation: discovery of (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-[6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylamino]-5-oxo-4,5-dihydropyrazine-2-carbonitrile as a potent, orally bioavailable corticotropin-releasing factor-1 receptor antagonist., 52 (23): [PMID:19954247] [10.1021/jm900716v] |
| 2. Hartz RA, Ahuja VT, Schmitz WD, Molski TF, Mattson GK, Lodge NJ, Bronson JJ, Macor JE.. (2010) Synthesis and structure-activity relationships of N3-pyridylpyrazinones as corticotropin-releasing factor-1 (CRF1) receptor antagonists., 20 (6): [PMID:20176478] [10.1016/j.bmcl.2010.01.129] |
| 3. Ahuja VT, Hartz RA, Molski TF, Mattson GK, Lentz KA, Grace JE, Lodge NJ, Bronson JJ, Macor JE.. (2016) Synthesis and evaluation of carbamate and aryl ether substituted pyrazinones as corticotropin releasing factor-1 (CRF₁) receptor antagonists., 26 (9): [PMID:27020524] [10.1016/j.bmcl.2016.03.067] |
Source
Source(1):