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MedKoo Cat#: 558303 | Name: Valspodar
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Description:

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

Valspodar, also known as PSC-833, is an analogue of cyclosporin-A. Valspodar inhibits p-glycoprotein, the multidrug resistance efflux pump, thereby restoring the retention and activity of some drugs in some drug-resistant tumor cells. This agent also induces caspase-mediated apoptosis.

Chemical Structure

Valspodar
Valspodar
CAS#121584-18-7

Theoretical Analysis

MedKoo Cat#: 558303

Name: Valspodar

CAS#: 121584-18-7

Chemical Formula: C63H111N11O12

Exact Mass: 1213.8414

Molecular Weight: 1214.62

Elemental Analysis: C, 62.30; H, 9.21; N, 12.68; O, 15.81

Price and Availability

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1mg USD 550.00 2 Weeks
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Synonym
PSC833; PSC833; PSC833; SDZ PSC 833; Sdz-psc-833; Valspodar
IUPAC/Chemical Name
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-6,9,18,24-tetraisobutyl-3,21,30-triisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-33-((R,E)-2-methylhex-4-enoyl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone
InChi Key
YJDYDFNKCBANTM-QCWCSKBGSA-N
InChi Code
InChI=1S/C63H111N11O12/c1-26-27-28-41(16)53(76)52-57(80)67-49(38(10)11)61(84)68(19)33-48(75)69(20)44(29-34(2)3)56(79)66-50(39(12)13)62(85)70(21)45(30-35(4)5)55(78)64-42(17)54(77)65-43(18)58(81)71(22)46(31-36(6)7)59(82)72(23)47(32-37(8)9)60(83)73(24)51(40(14)15)63(86)74(52)25/h26-27,34-47,49-52H,28-33H2,1-25H3,(H,64,78)(H,65,77)(H,66,79)(H,67,80)/b27-26+/t41-,42+,43-,44+,45+,46+,47+,49+,50+,51+,52+/m1/s1
SMILES Code
O=C([C@H](C(C)C)N(C)C([C@H](CC(C)C)N(C)C([C@H](CC(C)C)N(C)C([C@@H](C)NC([C@H](C)NC([C@H](CC(C)C)N(C)C([C@H](C(C)C)NC([C@H](CC(C)C)N(C)C(CN(C)C([C@H](C(C)C)N1)=O)=O)=O)=O)=O)=O)=O)=O)=O)N(C)[C@@H](C([C@H](C)C/C=C/C)=O)C1=O
Appearance
White to beige 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
>5 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
PSC-833 is a non-immunosuppressive cyclosporin derivative that potently and specifically inhibits P-gp.  In vitro experiments indicate that PSC-833 interacts directly with P-gp with high affinity and probably interferes with the ATPase activity of P-gp. Studies in multidrug resistant tumor models confirm P-gp as the in vivo target of PSC-833 and demonstrate the ability of PSC-833 to reverse MDR leukemias and solid tumors in mice. Presently, PSC-833 is being evaluated in the clinic.   According to wikipedia.com. Previous studies in animal models have found it to be effective at preventing cancer cell resistance to chemotherapeutics, but these findings did not translate to clinical success. (http://en.wikipedia.org/wiki/Psc833).        

Preparing Stock Solutions

The following data is based on the product molecular weight 1,214.62 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
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Comparative study on ABCB1-dependent efflux of anthracyclines and their metabolites: consequences for cancer resistance. Xenobiotica. 2023 Dec;53(6-7):507-514. doi: 10.1080/00498254.2023.2264391. Epub 2023 Nov 3. PMID: 37753851. 5: Kumar AR, Sheikh ED, Monson JW, Ligon SE, Talley RL, Dornisch EM, Howitz KJ, Damicis JR, Ieronimakis N, Unadkat JD. Understanding the Mechanism and Extent of Transplacental Transfer of (-)-∆9 -Tetrahydrocannabinol (THC) in the Perfused Human Placenta to Predict In Vivo Fetal THC Exposure. Clin Pharmacol Ther. 2023 Aug;114(2):446-458. doi: 10.1002/cpt.2964. Epub 2023 Jul 3. PMID: 37278090. 6: Fracasso PM, Fisher GA Jr, Goodner SA, Beumer JH, Egorin MJ, Fears CL, Wildi JD, Jones GJ, Pearce TE, Sikic BI. A Phase I Trial of the ABCB1 Inhibitor, Oral Valspodar, in Combination With Paclitaxel in Patients With Advanced Solid Tumors. Am J Clin Oncol. 2023 Aug 1;46(8):353-359. doi: 10.1097/COC.0000000000001014. Epub 2023 Jun 2. PMID: 37264515; PMCID: PMC10524540. 7: Frye WJE, Huff LM, Dalmasy JMG, Salazar P, Carter RM, Gensler RT, Esposito D, Robey RW, Ambudkar SV, Gottesman MM. The Multidrug Resistance Transporter P-glycoprotein Confers Resistance to Ferroptosis Inducers. bioRxiv [Preprint]. 2023 Feb 23:2023.02.23.529736. doi: 10.1101/2023.02.23.529736. Update in: Cancer Drug Resist. 2023 Jul 27;6(6):468-480. doi: 10.20517/cdr.2023.29. PMID: 36945397; PMCID: PMC10028811. 8: Ibrahim MAA, Abdeljawaad KAA, Jaragh-Alhadad LA, Oraby HF, Atia MAM, Alzahrani OR, Mekhemer GAH, Moustafa MF, Shawky AM, Sidhom PA, Abdelrahman AHM. Potential drug candidates as P-glycoprotein inhibitors to reverse multidrug resistance in cancer: an in silico drug discovery study. J Biomol Struct Dyn. 2023;41(23):13977-13992. doi: 10.1080/07391102.2023.2176360. Epub 2023 Mar 8. PMID: 36883864. 9: Shono K, Mizobuchi Y, Yamaguchi I, Nakajima K, Fujiwara Y, Fujihara T, Kitazato K, Matsuzaki K, Uto Y, Sampetrean O, Saya H, Takagi Y. Elevated cellular PpIX potentiates sonodynamic therapy in a mouse glioma stem cell- bearing glioma model by downregulating the Akt/NF-κB/MDR1 pathway. Sci Rep. 2021 Jul 23;11(1):15105. doi: 10.1038/s41598-021-93896-0. PMID: 34301977; PMCID: PMC8302615. 10: Parsons AJ, Cohen T, Schwarz TM, Stein KR, Ophir SI, Casado JP, Tortorella D. Valspodar limits human cytomegalovirus infection and dissemination. Antiviral Res. 2021 Sep;193:105124. doi: 10.1016/j.antiviral.2021.105124. Epub 2021 Jun 28. PMID: 34197862; PMCID: PMC9157689. 11: Onuma S, Manabe A, Yoshino Y, Matsunaga T, Asai T, Ikari A. Upregulation of Chemoresistance by Mg2+ Deficiency through Elevation of ATP Binding Cassette Subfamily B Member 1 Expression in Human Lung Adenocarcinoma A549 Cells. Cells. 2021 May 12;10(5):1179. doi: 10.3390/cells10051179. PMID: 34066059; PMCID: PMC8150369. 12: Yin W, Xiang D, Wang T, Zhang Y, Pham CV, Zhou S, Jiang G, Hou Y, Zhu Y, Han Y, Qiao L, Tran PH, Duan W. The inhibition of ABCB1/MDR1 or ABCG2/BCRP enables doxorubicin to eliminate liver cancer stem cells. Sci Rep. 2021 May 24;11(1):10791. doi: 10.1038/s41598-021-89931-9. PMID: 34031441; PMCID: PMC8144399. 13: Larrazabal C, Silva LMR, Pervizaj-Oruqaj L, Herold S, Hermosilla C, Taubert A. P-Glycoprotein Inhibitors Differently Affect Toxoplasma gondii, Neospora caninum and Besnoitia besnoiti Proliferation in Bovine Primary Endothelial Cells. Pathogens. 2021 Mar 25;10(4):395. doi: 10.3390/pathogens10040395. PMID: 33806177; PMCID: PMC8065907. 14: Bernecic NC, de Graaf SP, Leahy T, Gadella BM. HDL mediates reverse cholesterol transport from ram spermatozoa and induces hyperactivated motility. Biol Reprod. 2021 Jun 4;104(6):1271-1281. doi: 10.1093/biolre/ioab035. PMID: 33674849; PMCID: PMC8181994. 15: Rowbottom C, Pietrasiewicz A, Tuczewycz T, Grater R, Qiu D, Kapadnis S, Trapa P. Optimization of dose and route of administration of the P-glycoprotein inhibitor, valspodar (PSC-833) and the P-glycoprotein and breast cancer resistance protein dual-inhibitor, elacridar (GF120918) as dual infusion in rats. Pharmacol Res Perspect. 2021 Apr;9(2):e00740. doi: 10.1002/prp2.740. PMID: 33660938; PMCID: PMC7931226. 16: Glitscher M, Martín DH, Woytinek K, Schmidt B, Tabari D, Scholl C, Stingl JC, Seelow E, Choi M, Hildt E. Targeting Cholesterol Metabolism as Efficient Antiviral Strategy Against the Hepatitis E Virus. Cell Mol Gastroenterol Hepatol. 2021;12(1):159-180. doi: 10.1016/j.jcmgh.2021.02.002. Epub 2021 Feb 15. PMID: 33601063; PMCID: PMC8099564. 17: Cao Y, Cao Y, Shi Y, Cai Y, Chen L, Wang D, Liu Y, Chen X, Zhu Z, Hong Z, Chai Y. Surface plasmon resonance biosensor combined with lentiviral particle stabilization strategy for rapid and specific screening of P-Glycoprotein ligands. Anal Bioanal Chem. 2021 Mar;413(7):2021-2031. doi: 10.1007/s00216-021-03170-5. Epub 2021 Feb 2. PMID: 33528601. 18: Bajza Á, Kocsis D, Berezvai O, Laki AJ, Lukács B, Imre T, Iván K, Szabó P, Erdő F. Verification of P-Glycoprotein Function at the Dermal Barrier in Diffusion Cells and Dynamic "Skin-On-A-Chip" Microfluidic Device. Pharmaceutics. 2020 Aug 25;12(9):804. doi: 10.3390/pharmaceutics12090804. PMID: 32854319; PMCID: PMC7559210. 19: Mai Y, Ashiru-Oredope DAI, Yao Z, Dou L, Madla CM, Taherali F, Murdan S, Basit AW. Boosting drug bioavailability in men but not women through the action of an excipient. Int J Pharm. 2020 Sep 25;587:119678. doi: 10.1016/j.ijpharm.2020.119678. Epub 2020 Jul 22. PMID: 32710919. 20: Kabeya T, Mima S, Imakura Y, Miyashita T, Ogura I, Yamada T, Yasujima T, Yuasa H, Iwao T, Matsunaga T. Pharmacokinetic functions of human induced pluripotent stem cell-derived small intestinal epithelial cells. Drug Metab Pharmacokinet. 2020 Aug;35(4):374-382. doi: 10.1016/j.dmpk.2020.04.334. Epub 2020 May 16. PMID: 32651148.

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