| Synonyms |
2',3'-Didehydro-2',3'-dideoxythymidine-5'-p-bromophenyl methoxy-L-alaninyl phosphate; HI 113; L-Alanine, N-(P-(4-bromophenyl)-2',3'-didehydro-3'-deoxy-5'-thymidylyl)-, methyl ester |
| IUPAC Name |
methyl (2R)-2-[[(4-bromophenoxy)-[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphoryl]amino]propanoate |
| Molecular Weight |
544.29 |
| Molecular Formula |
C20H23BrN3O8P |
| Canonical SMILES |
CC1=CN(C(=O)NC1=O)C2C=CC(O2)COP(=O)(NC(C)C(=O)OC)OC3=CC=C(C=C3)Br |
| InChI |
InChI=1S/C20H23BrN3O8P/c1-12-10-24(20(27)22-18(12)25)17-9-8-16(31-17)11-30-33(28,23-13(2)19(26)29-3)32-15-6-4-14(21)5-7-15/h4-10,13,16-17H,11H2,1-3H3,(H,23,28)(H,22,25,27)/t13-,16+,17-,33?/m1/s1 |
| InChIKey |
VPABMVYNSQRPBD-AOJMVMDXSA-N |
| Purity |
99% |
| Solubility |
In vitro:
10 mM in DMSO |
| Appearance |
White to off-white (Solid) |
| Storage |
Store at -20°C |
| Complexity |
873 |
| Exact Mass |
543.04061 |
| In Vitro |
Stampidine (7.8-1,000 μM; 24 hours) is not cytotoxic to genital tract epithelial cells. Stampidine has no effect on sperm motility in cervical mucus. Stampidine has no effect on sperm motility and kinematics. |
| In Vivo |
Stampidine (50-100 mg/kg; p.o.) exhibits potent antiretroviral activity in chronically feline immunodeficiency virus (FIV)-infected cats. Stampidine (100 mg/kg; p.o.) shows the average plasma Cmax, AUC, half-life (t1/2), and mean residence time (MRT) values of 15.4 µM, 23.1 µM·h, 108.6 min and 119.4 min, respectively, in dogs. Stampidine does not cause anemia, thrombocytopenia, neutropenia, or lymphopenia suggestive of hematologic toxicity, elevations of BUN or creatinine or electrolyte disturbances suggestive of renal toxicity or Metabolic abnormalities, elevations of ALT, AST, Alk in adult beagle dogs. Animal Model: SPF male or female domestic cats (2.9- 6.2 kg), with chronically FIV-infected Dosage: 50 mg/kg, 100 mg/kg Administration: Oral administration (oral bolus dose) Result: Exhibited potent antiretroviral activity. Animal Model: Male beagle dogs (10-12 kg) Dosage: 100 mg/kg (Pharmacokinetic Analysis) Administration: Oral administration Result: The estimated average plasma Cmax and AUC values were 15.4 ± 6.1 µM and 23.1 ± 5.4 µM·h, respectively. The average elimination half-life (t1/2) and mean residence time (MRT) were 108.6 ± 28.8 and 119.4 ± 24.6 min, respectively. |
| PSA |
147.76000 |
| Target |
IC50: 1 nM (HTLVIIIB), 2 nM (primary clinical isolates), 8.7 nM (NRTI-resistant primary clinical isolates), 11.2 nM (NRTI-resistant primary clinical isolates) |
| XLogP3-AA |
1.7 |
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