Stampidine

• CAT Number: I015354
• CAS Number: 217178-62-6
• Molecular Formula: C20H23BrN3O8P
• Molecular Weight: 544.29
• Purity: ≥95%
• Synonyms: methyl (2S)-2-[[(4-bromophenoxy)-[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphoryl]amino]propanoate
• 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?/m0/s1
• InChIKey: VPABMVYNSQRPBD-MIOXLMGNSA-N
• SMILES: CC1=CN(C(=O)NC1=O)C2C=CC(O2)COP(=O)(NC(C)C(=O)OC)OC3=CC=C(C=C3)Br

Stampidine is a nucleoside reverse transcriptase inhibitor (NRTI) with potent and broad-spectrum anti-HIV activity. Stampidine inhibits the laboratory HIV-1 strain HTLVIIIB (B-envelope subtype) and primary clinical isolates with IC50s of 1 nM and 2 nM, respectively. Stampidine also inhibits NRTI-resistant primary clinical isolates and NNRTI-resistant clinical isolates with IC50s of 8.7 nM and 11.2 nM, respectively[1].
Stampidine (7.8-1,000 μM; 24 hours) is not cytotoxic to genital tract epithelial cells[2].
Stampidine has no effect on sperm motility in cervical mucus[2].
Stampidine (50-100 mg/kg; p.o.) exhibits potent antiretroviral activity in chronically feline immunodeficiency virus (FIV)-infected cats[3].
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[4].
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[4].

Reference

[1]. Osmond J D’Cruz, et al. Stampidine: a selective oculo-genital microbicide. J Antimicrob Chemother. 2005 Jul;56(1):10-9.
 [Content Brief]

[2]. Osmond J D’Cruz, et al. Stampidine is a potential nonspermicidal broad-spectrum anti-human immunodeficiency virus microbicide. Fertil Steril. 2004 Mar;81 Suppl 1:831-41.
 [Content Brief]

[3]. Fatih M Uckun, et al. In Vivo Antiretroviral Activity of Stampidine in Chronically Feline Immunodeficiency Virus-Infected Cats. Antimicrob Agents Chemother. 2003 Apr;47(4):1233-40.
 [Content Brief]

[4]. Fatih M Uckun, et al. In Vivo Pharmacokinetics and Toxicity Profile of the anti-HIV Agent Stampidine in Dogs and Feline Immunodeficiency Virus-Infected Cats. Arzneimittelforschung. 2006 Feb;56(2A):176-92.
 [Content Brief]