LP-184 | CAS#924835-67-6 | acylfulvene-derived prodrug

MedKoo Cat#: 145189 | Name: LP-184

Description:

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

LP-184 is an acylfulvene-derived prodrug activated by the oxidoreductase PTGR1 that alkylates at N3-adenine. Cytotoxicity of LP-184 is solely dependent on prostaglandin reductase 1 (PTGR1). LP-184 metabolizes to an active compound by the oxidoreductase activity of enzyme prostaglandin reductase 1 (PTGR1), which is frequently elevated in multiple solid tumor types.

Chemical Structure

LP-184

CAS#924835-67-6

Theoretical Analysis

MedKoo Cat#: 145189

Name: LP-184

CAS#: 924835-67-6

Chemical Formula: C16H20N2O4

Exact Mass: 304.1423

Molecular Weight: 304.35

Elemental Analysis: C, 63.14; H, 6.62; N, 9.20; O, 21.03

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

LP-184; LP184; LP 184;

IUPAC/Chemical Name

(R)-1-hydroxy-1-((6'-hydroxy-2',4',6'-trimethyl-7'-oxo-6',7'-dihydrospiro[cyclopropane-1,5'-inden]-3'-yl)methyl)urea

InChi Key

VWMPVAZEBAKLFR-HNNXBMFYSA-N

InChi Code

1S/C16H20N2O4/c1-8-6-10-12(11(8)7-18(22)14(17)20)9(2)16(4-5-16)15(3,21)13(10)19/h6,21-22H,4-5,7H2,1-3H3,(H2,17,20)/t15-/m0/s1

SMILES Code

CC1=C(CN(O)C(N)=O)C2=C(C)C3(CC3)[C@@](C)(O)C(=O)C2=C1

Appearance

To be determined

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 304.35 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.

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: Lal B, Kulkarni A, McDermott J, Rais R, Alt J, Wu Y, Lopez-Bertoni H, Sall S, Kathad U, Zhou J, Slusher BS, Bhatia K, Laterra J. Preclinical Efficacy of LP-184, a Tumor Site Activated Synthetic Lethal Therapeutic, in Glioblastoma. Clin Cancer Res. 2023 Oct 13;29(20):4209-4218. doi: 10.1158/1078-0432.CCR-23-0673. PMID: 37494541. 2: Restifo D, McDermott JR, Cvetkovic D, Dos Santos T, Ogier C, Surumbayeva A, Handorf EA, Schimke C, Ma C, Cai KQ, Olszanski AJ, Kathad U, Bhatia K, Sharma P, Kulkarni A, Astsaturov I. Conditional Dependency of LP-184 on Prostaglandin Reductase 1 is Synthetic Lethal in Pancreatic Cancers with DNA Damage Repair Deficiencies. Mol Cancer Ther. 2023 Oct 2;22(10):1182-1190. doi: 10.1158/1535-7163.MCT-22-0818. PMID: 37552607; PMCID: PMC10592171. 3: Kulkarni A, Zhou J, Biyani N, Kathad U, Banerjee PP, Srivastava S, Prucsi Z, Solarczyk K, Bhatia K, Ewesuedo RB, Sharma P. LP-184, a Novel Acylfulvene Molecule, Exhibits Anticancer Activity against Diverse Solid Tumors with Homologous Recombination Deficiency. Cancer Res Commun. 2024 May 6;4(5):1199-1210. doi: 10.1158/2767-9764.CRC-23-0554. PMID: 38630886; PMCID: PMC11072798. 4: Kulkarni A, McDermott JR, Kathad U, Modali R, Richard JP, Sharma P, Bhatia K. The acylfulvene alkylating agent, LP-184, retains nanomolar potency in non-small cell lung cancer carrying otherwise therapy-refractory mutations. Oncotarget. 2021 Apr 13;12(8):791-806. doi: 10.18632/oncotarget.27943. PMID: 33889302; PMCID: PMC8057270. 5: Kathad U, Kulkarni A, McDermott JR, Wegner J, Carr P, Biyani N, Modali R, Richard JP, Sharma P, Bhatia K. A machine learning-based gene signature of response to the novel alkylating agent LP-184 distinguishes its potential tumor indications. BMC Bioinformatics. 2021 Mar 2;22(1):102. doi: 10.1186/s12859-021-04040-8. PMID: 33653269; PMCID: PMC7923321. 6: Staake MD, Kashinatham A, McMorris TC, Estes LA, Kelner MJ. Hydroxyurea derivatives of irofulven with improved antitumor efficacy. Bioorg Med Chem Lett. 2016 Apr 1;26(7):1836-8. doi: 10.1016/j.bmcl.2016.02.028. Epub 2016 Feb 13. PMID: 26922141. 7: Sung ES, Kim JH. The difference effect of estrogen on muscle tone of medial and lateral thigh muscle during ovulation. J Exerc Rehabil. 2018 Jun 30;14(3):419-423. doi: 10.12965/jer.1836110.055. PMID: 30018928; PMCID: PMC6028216.