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MedKoo Cat#: 584428 | Name: Stampidine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Stampidine is a possible next-generation Pre-exposure prophylaxis (PrEP) candidate to prevent the sexual transmission of HIV-1. The compound exhibited remarkable subnanomolar to low nanomolar in vitro antiretroviral potency against genotypically and phenotypically nucleoside reverse transcriptase inhibitor (NRTI)-resistant primary clinical HIV isolates, non-nucleoside RT-resistant HIV-1 isolates and did not cause any maternal toxicity, developmental toxicity or teratogenicity in rabbits treated at 10 - 40 mg/kg/day dose levels

Chemical Structure

Stampidine
Stampidine
CAS#217178-62-6

Theoretical Analysis

MedKoo Cat#: 584428

Name: Stampidine

CAS#: 217178-62-6

Chemical Formula: C20H23BrN3O8P

Exact Mass: 543.0406

Molecular Weight: 544.29

Elemental Analysis: C, 44.13; H, 4.26; Br, 14.68; N, 7.72; O, 23.52; P, 5.69

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Stampidine; HI 113; HI-113; HI113
IUPAC/Chemical Name
L-Alanine, N-(P-(4-bromophenyl)-2',3'-didehydro-3'-deoxy-5'-thymidylyl)-, methyl ester
InChi Key
VPABMVYNSQRPBD-MIOXLMGNSA-N
InChi Code
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
SMILES Code
C[C@@H](C(OC)=O)NP(OC[C@@H]1C=C[C@H](N2C(NC(C(C)=C2)=O)=O)O1)(OC3=CC=C(Br)C=C3)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 544.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Uckun FM, Cahn P, Qazi S, D'Cruz O. Stampidine as a promising antiretroviral drug candidate for pre-exposure prophylaxis against sexually transmitted HIV/AIDS. Expert Opin Investig Drugs. 2012 Apr;21(4):489-500. doi: 10.1517/13543784.2012.664635. Epub 2012 Feb 24. Review. PubMed PMID: 22360744. 2: Agrahari V, Meng J, Zhang T, Youan BB. Application of Design of Experiment and Simulation Methods to Liquid Chromatography Analysis of Topical HIV Microbicides Stampidine and HI443. J Anal Bioanal Tech. 2014 Feb;5(1). pii: 180. PubMed PMID: 25767739; PubMed Central PMCID: PMC4354943. 3: D'Cruz OJ, Samuel P, Waurzyniak B, Uckun FM. Development and evaluation of a thermoreversible ovule formulation of stampidine, a novel nonspermicidal broad-spectrum anti-human immunodeficiency virus microbicide. Biol Reprod. 2003 Dec;69(6):1843-51. Epub 2003 Jul 30. PubMed PMID: 12890726. 4: D'Cruz OJ, Uckun FM. Stampidine is a potential nonspermicidal broad-spectrum anti-human immunodeficiency virus microbicide. Fertil Steril. 2004 Mar;81 Suppl 1:831-41. PubMed PMID: 15019817. 5: D'Cruz OJ, Uckun FM. Stampidine: a selective oculo-genital microbicide. J Antimicrob Chemother. 2005 Jul;56(1):10-9. Epub 2005 May 26. Review. PubMed PMID: 15919769. 6: Chen CL, Yu G, Venkatachalam TK, Uckun FM. Metabolism of stavudine-5'-[p-bromophenyl methoxyalaninyl phosphate], stampidine, in mice, dogs, and cats. Drug Metab Dispos. 2002 Dec;30(12):1523-31. PubMed PMID: 12433828. 7: Uckun FM, Petkevich AS, Vassilev AO, Tibbles HE, Titov L. Stampidine prevents mortality in an experimental mouse model of viral hemorrhagic fever caused by lassa virus. BMC Infect Dis. 2004 Jan 13;4:1. Corrected and republished in: BMC Infect Dis. 2004 Jun 1;4:14. PubMed PMID: 14720304; PubMed Central PMCID: PMC331410. 8: Venkatachalam TK, Samuel P, Uckun FM. Enzymatic hydrolysis of stampidine and other stavudine phosphoramidates in the presence of mammalian proteases. Bioorg Med Chem. 2005 Apr 1;13(7):2651-5. PubMed PMID: 15755664. 9: Uckun FM, Chen CL, Samuel P, Pendergrass S, Venkatachalam TK, Waurzyniak B, Qazi S. In vivo antiretroviral activity of stampidine in chronically feline immunodeficiency virus-infected cats. Antimicrob Agents Chemother. 2003 Apr;47(4):1233-40. PubMed PMID: 12654652; PubMed Central PMCID: PMC152500. 10: D'Cruz OJ, Uckun FM. Mucosal safety of PHI-443 and stampidine as a combination microbicide to prevent genital transmission of HIV-1. Fertil Steril. 2007 Oct;88(4 Suppl):1197-206. Epub 2007 May 11. PubMed PMID: 17498709. 11: Uckun FM, Petkevich AS, Vassilev AO, Tibbles HE, Titov L. Correction: Stampidine prevents mortality in an experimental mouse model of viral hemorrhagic fever caused by lassa virus. BMC Infect Dis. 2004 Jun 1;4:14. PubMed PMID: 15171793; PubMed Central PMCID: PMC428577. 12: Uckun FM, Qazi S, Venkatachalam TK. In vitro anti-HIV potency of stampidine alone and in combination with standard anti-HIV drugs. Arzneimittelforschung. 2005;55(4):223-31. PubMed PMID: 15901046. 13: Uckun FM, Chen CL, Lisowski E, Mitcheltree GC, Venkatachalam TK, Erbeck D, Chen H, Waurzyniak B. Toxicity and pharmacokinetics of stampidine in mice and rats. Arzneimittelforschung. 2003;53(5):357-67. PubMed PMID: 12854363. 14: Uckun FM. Stampidine as a novel nucleoside reverse transcriptase inhibit with potent anti-HIV activity. Arzneimittelforschung. 2006 Feb;56(2A):121-35. Review. PubMed PMID: 16570821. 15: Venkatachalam TK, Qazi S, Uckun FM. Site-specific enzymatic activation of the anti-HIV agent stampidine. Arzneimittelforschung. 2006 Feb;56(2A):167-75. PubMed PMID: 16570825. 16: Venkatachalam TK, Samuel P, Li G, Qazi S, Mao C, Pendergrass S, Uckun FM. Lipase-mediated stereoselective hydrolysis of stampidine and other phosphoramidate derivatives of stavudine. Bioorg Med Chem. 2004 Jun 15;12(12):3371-81. PubMed PMID: 15158806. 17: Uckun FM, Qazi S, Pendergrass S, Lisowski E, Waurzyniak B, Chen CL, Venkatachalam TK. In vivo toxicity, pharmacokinetics, and anti-human immunodeficiency virus activity of stavudine-5'-(p-bromophenyl methoxyalaninyl phosphate) (stampidine) in mice. Antimicrob Agents Chemother. 2002 Nov;46(11):3428-36. PubMed PMID: 12384347; PubMed Central PMCID: PMC128716. 18: D'Cruz OJ, Erbeck D, Uckun FM. Developmental safety profile of the anti-HIV agent stampidine in rabbits. Arzneimittelforschung. 2006 Feb;56(2A):159-66. PubMed PMID: 16570824. 19: Uckun FM, Waurzyniak B, Tibbles H, Venkatachalam TK, Erbeck D. 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. PubMed PMID: 16570826. 20: DuMez D, Venkatachalam TK, Uckun FM. Large-scale synthesis and formulation of GMP-grade stampidine, a new anti-HIV agent. Arzneimittelforschung. 2006 Feb;56(2A):136-51. PubMed PMID: 16570822.a