Stampidine

Modify Date: 2024-01-10 01:30:57

Stampidine structure	Common Name	Stampidine
	CAS Number	217178-62-6	Molecular Weight	544.29000
	Density	N/A	Boiling Point	N/A
	Molecular Formula	C₂₀H₂₃BrN₃O₈P	Melting Point	N/A
	MSDS	N/A	Flash Point	N/A

Use of Stampidine

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].

Name	Stampidine
Synonym	More Synonyms

Description	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].
Related Catalog	Signaling Pathways >> Anti-infection >> HIV Research Areas >> Infection Signaling Pathways >> Anti-infection >> Reverse Transcriptase
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)[1]
In Vitro	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 has no effect on sperm motility and kinematics[2].
In Vivo	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]. Animal Model: SPF male or female domestic cats (2.9- 6.2 kg), with chronically FIV-infected[3] 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)[4] 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.
References	[1]. Fatih M Uckun. Stampidine as a Novel Nucleoside Reverse Transcriptase Inhibit With Potent anti-HIV Activity. Arzneimittelforschung. 2006 Feb;56(2A):121-35. [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. [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. [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.

Molecular Formula	C₂₀H₂₃BrN₃O₈P
Molecular Weight	544.29000
Exact Mass	543.04100
PSA	147.76000
LogP	2.80680

Hazard Codes	Xi

N-[p-(4-bromophenyl)-2'3'-didehydro-3'-deoxy-5'-thymidylyl]-L-alanine methyl ester

d4T-5'-[p-bromophenyl methoxyalaninyl phosphate]

Stampidine

Use of Stampidine

Names

Stampidine Biological Activity

Chemical & Physical Properties

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Synonyms