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MedKoo Cat#: 317587 | Name: Delavirdine
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Description:

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

Delavirdine is a non-nucleoside reverse transcriptase inhibitor (NNRTI). It is used as part of highly active antiretroviral therapy (HAART) for the treatment of human immunodeficiency virus (HIV) type 1. Although delavirdine was approved by the U.S. Food and Drug Administration in 1997, its efficacy is lower than other NNRTIs, especially efavirenz, and it also has an inconvenient schedule. These factors have led the U.S. DHHS not to recommend its use as part of initial therapy. (Source: https://en.wikipedia.org/wiki/Delavirdine).

Chemical Structure

Delavirdine
Delavirdine
CAS#136817-59-9 (free base)

Theoretical Analysis

MedKoo Cat#: 317587

Name: Delavirdine

CAS#: 136817-59-9 (free base)

Chemical Formula: C22H28N6O3S

Exact Mass: 456.1944

Molecular Weight: 456.56

Elemental Analysis: C, 57.88; H, 6.18; N, 18.41; O, 10.51; S, 7.02

Price and Availability

Size Price Availability Quantity
5mg USD 250.00 Ready to ship
10mg USD 450.00 2 Weeks
25mg USD 750.00 2 Weeks
100mg USD 1,050.00 2 Weeks
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Related CAS #
147221-93-0 (mesylate) 136817-59-9 (free base)
Synonym
Delavirdine; Rescriptor; BHAP-U 90152; DLV; U 90152; U90152; U-90152;
IUPAC/Chemical Name
N-[2-[4-[3-(propan-2-ylamino)pyridin-2-yl]piperazine-1-carbonyl]-1H-indol-5-yl]methanesulfonamide
InChi Key
WHBIGIKBNXZKFE-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H28N6O3S/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20/h4-8,13-15,24-26H,9-12H2,1-3H3
SMILES Code
CC(C)NC1=C(N=CC=C1)N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(=C4)NS(=O)(=O)C
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, not in water
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
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot# A9M06C12
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Delavirdine (U 90152) is a non-nucleoside reverse transcriptase inhibitor (NNRTI) that selectively inhibits HIV-1 reverse transcriptase (RT) (IC50=0.26 μM) over DNA polymerase α (IC50=440 μM) and polymerase δ (IC50>550 μM)
In vitro activity:
A novel bisheteroarylpiperazine, U-90152 [1-(5-methanesulfonamido-1H-indol-2-yl-carbonyl)-4-[3-(1-methyl eth ylamino)pyridinyl]piperazine] inhibited recombinant HIV-1 RT at a 50% inhibitory concentration (IC50) of 0.26 microM (compared with IC50s of > 440 microM for DNA polymerases alpha and delta). U-90152 blocked the replication in peripheral blood lymphocytes of 25 primary HIV-1 isolates, including variants that were highly resistant to 3'-azido-2',3'-dideoxythymidine (AZT) or 2',3'dideoxyinosine, with a mean 50% effective dose of 0.066 +/- 0.137 microM. U-90152 had low cellular cytotoxicity, causing less than 8% reduction in peripheral blood lymphocyte viability at 100 microM. In experiments assessing inhibition of the spread of HIV-1IIIB in cell cultures, U-90152 was much more effective than AZT. 3 microM U-90152 totally prevented the spread of HIV-1, and death and/or dilution of the original inoculum of infected cells prevented renewed viral growth after U-90152 was removed at day 24. U90152 drug retains significant activity against these mutant RTs (K103N and Y181C) in vitro (IC50s, approximately 8 microgramM). Reference: Antimicrob Agents Chemother. 1993 May;37(5):1127-31. https://pubmed.ncbi.nlm.nih.gov/7685995/
In vivo activity:
The excretion, disposition, brain penetration, and metabolism of delavirdine were investigated in CD-1 mice after oral administration of [14C]delavirdine mesylate at single doses of 10 and/or 250 mg/kg and multiple doses of 200 mg/kg/day. Delavirdine was absorbed and metabolized rapidly, that it constituted a minor component in circulation, that its pharmacokinetics were nonlinear, and that its metabolism to desalkyl delavirdine was capacity limited or inhibitable. Delavirdine did not significantly cross the blood-brain barrier; however, itsN-isopropylpyridinepiperazine metabolite—arising from amide bond cleavage—was present in brain at levels 2- to 3-fold higher than in plasma. The metabolism of delavirdine in the mouse was extensive and involved amide bond cleavage,N-desalkylation, hydroxylation at the C-6′ position of the pyridine ring, and pyridine ring-cleavage as determined by MS and/or1H and 13C NMR spectroscopies. N-desalkylation and amide bond cleavage were the primary metabolic pathways at low drug doses and, as the biotransformation of delavirdine to desalkyl delavirdine reached saturation or inhibition, amide bond cleavage became the predominant pathway at higher doses and after multiple doses. Reference: . Drug Metab Dispos. 1997 Jul;25(7):828-39. https://dmd.aspetjournals.org/content/25/7/828.long
Solvent mg/mL mM
Solubility
H2O 30.0 65.71
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 456.56 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
Formulation protocol:
1. Dueweke TJ, Poppe SM, Romero DL, Swaney SM, So AG, Downey KM, Althaus IW, Reusser F, Busso M, Resnick L, et al. U90152, a potent inhibitor of human immunodeficiency virus type 1 replication. Antimicrob Agents Chemother. 1993 May;37(5):112731. doi: 10.1128/AAC.37.5.1127. PMID: 7685995; PMCID: PMC187915. 2. Romero MA, Mobley CB, Mumford PW, Roberson PA, Haun CT, Kephart WC, Healy JC, Beck DT, Young KC, Martin JS, Lockwood CM, Roberts MD. Acute and chronic resistance training downregulates select LINE-1 retrotransposon activity markers in human skeletal muscle. Am J Physiol Cell Physiol. 2018 Mar 1;314(3):C379-C388. doi: 10.1152/ajpcell.00192.2017. Epub 2017 Dec 20. PMID: 29351416. 3. Chang M, Sood VK, Wilson GJ, Kloosterman DA, Sanders PE, Hauer MJ, Zhang W, Branstetter DG. Metabolism of the HIV-1 reverse transcriptase inhibitor delavirdine in mice. Drug Metab Dispos. 1997 Jul;25(7):828-39. PMID: 9224777.
In vitro protocol:
1. Dueweke TJ, Poppe SM, Romero DL, Swaney SM, So AG, Downey KM, Althaus IW, Reusser F, Busso M, Resnick L, et al. U90152, a potent inhibitor of human immunodeficiency virus type 1 replication. Antimicrob Agents Chemother. 1993 May;37(5):112731. doi: 10.1128/AAC.37.5.1127. PMID: 7685995; PMCID: PMC187915. 2. Romero MA, Mobley CB, Mumford PW, Roberson PA, Haun CT, Kephart WC, Healy JC, Beck DT, Young KC, Martin JS, Lockwood CM, Roberts MD. Acute and chronic resistance training downregulates select LINE-1 retrotransposon activity markers in human skeletal muscle. Am J Physiol Cell Physiol. 2018 Mar 1;314(3):C379-C388. doi: 10.1152/ajpcell.00192.2017. Epub 2017 Dec 20. PMID: 29351416.
In vivo protocol:
1. Chang M, Sood VK, Wilson GJ, Kloosterman DA, Sanders PE, Hauer MJ, Zhang W, Branstetter DG. Metabolism of the HIV-1 reverse transcriptase inhibitor delavirdine in mice. Drug Metab Dispos. 1997 Jul;25(7):828-39. PMID: 9224777.
1: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Delavirdine. 2023 Apr 15. PMID: 30000604. 2: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Delavirdine. 2017 Dec 27. PMID: 31643235. 3: Tran JQ, Gerber JG, Kerr BM. Delavirdine: clinical pharmacokinetics and drug interactions. Clin Pharmacokinet. 2001;40(3):207-26. doi: 10.2165/00003088-200140030-00005. PMID: 11327199. 4: Scott LJ, Perry CM. Delavirdine: a review of its use in HIV infection. Drugs. 2000 Dec;60(6):1411-44. doi: 10.2165/00003495-200060060-00013. PMID: 11152019. 5: Freimuth WW. Delavirdine mesylate, a potent non-nucleoside HIV-1 reverse transcriptase inhibitor. Adv Exp Med Biol. 1996;394:279-89. doi: 10.1007/978-1-4757-9209-6_25. PMID: 8815692. 6: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Antiviral Agents. 2022 Dec 2. PMID: 31643973. 7: Zhou SF. Drugs behave as substrates, inhibitors and inducers of human cytochrome P450 3A4. Curr Drug Metab. 2008 May;9(4):310-22. doi: 10.2174/138920008784220664. PMID: 18473749. 8: Gilden D. Delavirdine/protease inhibitor interactions. GMHC Treat Issues. 1996 Sep;10(9):11-2. PMID: 11363839. 9: Mascolini M. Delavirdine data: skewed or skewered? J Int Assoc Physicians AIDS Care. 1997 Feb;3(2):42-6. PMID: 11364099. 10: James JS. Delavirdine (Rescriptor) approved. AIDS Treat News. 1997 Apr 18;(No 269):1-3. PMID: 11364252. 11: Adams WJ, Aristoff PA, Jensen RK, Morozowich W, Romero DL, Schinzer WC, Tarpley WG, Thomas RC. Discovery and development of the BHAP nonnucleoside reverse transcriptase inhibitor delavirdine mesylate. Pharm Biotechnol. 1998;11:285-312. doi: 10.1007/0-306-47384-4_13. PMID: 9760685. 12: Shelton MJ, Hewitt RG, Adams JM, Cox SR, Chambers JH, Morse GD. Delavirdine malabsorption in HIV-infected subjects with spontaneous gastric hypoacidity. J Clin Pharmacol. 2003 Feb;43(2):171-9. doi: 10.1177/0091270002239826. PMID: 12616670. 13: Smith PF, Dicenzo R, Forrest A, Shelton M, Friedland G, Para M, Pollard R, Fischl M, DiFrancesco R, Morse GD. Population pharmacokinetics of delavirdine and N-delavirdine in HIV-infected individuals. Clin Pharmacokinet. 2005;44(1):99-109. doi: 10.2165/00003088-200544010-00004. PMID: 15634033. 14: Ming W, Lu WL, Pannecouque C, Chen J, Wang HF, Xiao YQ, Hu S, Gu SX, Zhu YY, Chen FE. Hybrids of delavirdine and piperdin-4-yl-aminopyrimidines (DPAPYs) as potent HIV-1 NNRTIs: Design, synthesis and biological activities. Eur J Med Chem. 2023 Feb 15;248:115114. doi: 10.1016/j.ejmech.2023.115114. Epub 2023 Jan 11. PMID: 36640458. 15: Delavirdine (Rescriptor). Res Initiat Treat Action. 2000 Mar;6(1):20-1. PMID: 11708180. 16: Tran JQ, Petersen C, Garrett M, Hee B, Kerr BM. Pharmacokinetic interaction between amprenavir and delavirdine: evidence of induced clearance by amprenavir. Clin Pharmacol Ther. 2002 Dec;72(6):615-26. doi: 10.1067/mcp.2002.128868. PMID: 12496743. 17: Temesgen Z, Wright AJ. Antiretrovirals. Mayo Clin Proc. 1999 Dec;74(12):1284-301. doi: 10.4065/74.12.1284. PMID: 10593358. 18: Borin MT, Chambers JH, Carel BJ, Gagnon S, Freimuth WW. Pharmacokinetic study of the interaction between rifampin and delavirdine mesylate. Clin Pharmacol Ther. 1997 May;61(5):544-53. doi: 10.1016/S0009-9236(97)90134-X. PMID: 9164416. 19: Voorman RL, Maio SM, Payne NA, Zhao Z, Koeplinger KA, Wang X. Microsomal metabolism of delavirdine: evidence for mechanism-based inactivation of human cytochrome P450 3A. J Pharmacol Exp Ther. 1998 Oct;287(1):381-8. PMID: 9765359. 20: Adkins JC, Noble S. Efavirenz. Drugs. 1998 Dec;56(6):1055-64; discussion 1065-6. doi: 10.2165/00003495-199856060-00014. PMID: 9878993.