WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 565100
CAS#: 1169829-40-6 (HCl)
Description: Patidegip, laos known as Saridegib and IPI-926, is an orally bioavailable, cyclopamine-derived (for structure comparison see Fig 1) inhibitor of the Hedgehog (Hh) pathway with potential antineoplastic activity. Specifically, Hedgehog pathway inhibitor IPI-926 binds to and inhibits the cell membrane-spanning G-protein coupled receptor SMO, which may result in the suppression of Hh pathway signaling and a decrease in tumor cell proliferation and survival. SMO is activated upon binding of Hh ligand to the cell surface receptor Patched (PTCH); inappropriate activation of Hh signaling and uncontrolled cellular proliferation may be associated with SMO mutations.
MedKoo Cat#: 565100
Name: Saridegib HCl
CAS#: 1169829-40-6 (HCl)
Chemical Formula: C29H49ClN2O3S
Exact Mass: 540.3152
Molecular Weight: 541.23
Elemental Analysis: C, 64.36; H, 9.13; Cl, 6.55; N, 5.18; O, 8.87; S, 5.92
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Related CAS #: 1037210-93-7 free base) 1169829-40-6 (HCl)
Synonym: Saridegib HCl; IPI 926; IPI-926; IPI926; Saridegib; Patidegip; Patidegib Free Base; WHO9619; WHO-9619; WHO 9619
IUPAC/Chemical Name: N-((2S,3R,3aR,4a'R,6R,6a'R,6b'R,7aR,12a'R,12b'S)-3,6,11',12b'-tetramethyl-2',3a,3',4,4',4a',5,5',6,6',6a',6b',7,7a,7',8',10',12',12a',12b'-icosahydro-1'H,3H-spiro[furo[3,2-b]pyridine-2,9'-naphtho[2,1-a]azulen]-3'-yl)methanesulfonamide hydrochloride
InChi Key: LICVMCOINZNZNW-ZMLHKANGSA-N
InChi Code: InChI=1S/C29H48N2O3S.ClH/c1-17-12-26-27(30-16-17)19(3)29(34-26)11-9-22-23-7-6-20-13-21(31-35(5,32)33)8-10-28(20,4)25(23)14-24(22)18(2)15-29;/h17,19-23,25-27,30-31H,6-16H2,1-5H3;1H/t17-,19-,20-,21?,22-,23+,25-,26-,27-,28+,29+;/m1./s1
SMILES Code: C[C@@H](CN1)C[C@H]([C@H]1[C@H]2C)O[C@@]32CC[C@@H]4[C@@H]5CC[C@@H]6CC(NS(C)(=O)=O)CC[C@]6(C)[C@@H]5CC4=C(C)C3.Cl
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: >3 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
The following data is based on the product molecular weight 541.23 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: Neelakantan D, Zhou H, Oliphant MUJ, Zhang X, Simon LM, Henke DM, Shaw CA, Wu MF, Hilsenbeck SG, White LD, Lewis MT, Ford HL. EMT cells increase breast cancer metastasis via paracrine GLI activation in neighbouring tumour cells. Nat Commun. 2017 Jun 12;8:15773. doi: 10.1038/ncomms15773. Erratum in: Nat Commun. 2018 Nov 12;9(1):4720. PubMed PMID: 28604738; PubMed Central PMCID: PMC5472791.
2: Ma H, Tian Y, Yu X. Targeting Smoothened Sensitizes Gastric Cancer to Chemotherapy in Experimental Models. Med Sci Monit. 2017 Mar 28;23:1493-1500. PubMed PMID: 28350784; PubMed Central PMCID: PMC5381338.
3: Lauressergues E, Heusler P, Lestienne F, Troulier D, Rauly-Lestienne I, Tourette A, Ailhaud MC, Cathala C, Tardif S, Denais-Laliève D, Calmettes MT, Degryse AD, Dumoulin A, De Vries L, Cussac D. Pharmacological evaluation of a series of smoothened antagonists in signaling pathways and after topical application in a depilated mouse model. Pharmacol Res Perspect. 2016 Mar 4;4(2):e00214. doi: 10.1002/prp2.214. eCollection 2016 Apr. PubMed PMID: 27069629; PubMed Central PMCID: PMC4804317.
4: Bowles DW, Keysar SB, Eagles JR, Wang G, Glogowska MJ, McDermott JD, Le PN, Gao D, Ray CE, Rochon PJ, Roop DR, Tan AC, Serracino HS, Jimeno A. A pilot study of cetuximab and the hedgehog inhibitor IPI-926 in recurrent/metastatic head and neck squamous cell carcinoma. Oral Oncol. 2016 Feb;53:74-9. doi: 10.1016/j.oraloncology.2015.11.014. Epub 2015 Dec 15. PubMed PMID: 26705064; PubMed Central PMCID: PMC5676309.
5: Ko AH, LoConte N, Tempero MA, Walker EJ, Kate Kelley R, Lewis S, Chang WC, Kantoff E, Vannier MW, Catenacci DV, Venook AP, Kindler HL. A Phase I Study of FOLFIRINOX Plus IPI-926, a Hedgehog Pathway Inhibitor, for Advanced Pancreatic Adenocarcinoma. Pancreas. 2016 Mar;45(3):370-5. doi: 10.1097/MPA.0000000000000458. PubMed PMID: 26390428; PubMed Central PMCID: PMC5908466.
6: Sasaki K, Gotlib JR, Mesa RA, Newberry KJ, Ravandi F, Cortes JE, Kelly P, Kutok JL, Kantarjian HM, Verstovsek S. Phase II evaluation of IPI-926, an oral Hedgehog inhibitor, in patients with myelofibrosis. Leuk Lymphoma. 2015 Jul;56(7):2092-7. doi: 10.3109/10428194.2014.984703. Epub 2015 Feb 17. PubMed PMID: 25641433; PubMed Central PMCID: PMC4919663.
7: Campbell VT, Nadesan P, Ali SA, Wang CY, Whetstone H, Poon R, Wei Q, Keilty J, Proctor J, Wang LW, Apte SS, McGovern K, Alman BA, Wunder JS. Hedgehog pathway inhibition in chondrosarcoma using the smoothened inhibitor IPI-926 directly inhibits sarcoma cell growth. Mol Cancer Ther. 2014 May;13(5):1259-69. doi: 10.1158/1535-7163.MCT-13-0731. Epub 2014 Mar 14. PubMed PMID: 24634412.
8: Peluso MO, Campbell VT, Harari JA, Tibbitts TT, Proctor JL, Whitebread N, Conley JM, White KF, Kutok JL, Read MA, McGovern K, Faia KL. Impact of the Smoothened inhibitor, IPI-926, on smoothened ciliary localization and Hedgehog pathway activity. PLoS One. 2014 Mar 7;9(3):e90534. doi: 10.1371/journal.pone.0090534. eCollection 2014. PubMed PMID: 24608250; PubMed Central PMCID: PMC3946503.
9: Jimeno A, Weiss GJ, Miller WH Jr, Gettinger S, Eigl BJ, Chang AL, Dunbar J, Devens S, Faia K, Skliris G, Kutok J, Lewis KD, Tibes R, Sharfman WH, Ross RW, Rudin CM. Phase I study of the Hedgehog pathway inhibitor IPI-926 in adult patients with solid tumors. Clin Cancer Res. 2013 May 15;19(10):2766-74. doi: 10.1158/1078-0432.CCR-12-3654. Epub 2013 Apr 10. PubMed PMID: 23575478; PubMed Central PMCID: PMC3694426.
10: Smith S, Hoyt J, Whitebread N, Manna J, Peluso M, Faia K, Campbell V, Tremblay M, Nair S, Grogan M, Castro A, Campbell M, Ferguson J, Arsenault B, Nevejans J, Carter B, Lee J, Dunbar J, McGovern K, Read M, Adams J, Constan A, Loewen G, Sydor J, Palombella V, Soglia J. The pre-clinical absorption, distribution, metabolism and excretion properties of IPI-926, an orally bioavailable antagonist of the hedgehog signal transduction pathway. Xenobiotica. 2013 Oct;43(10):875-85. doi: 10.3109/00498254.2013.780671. Epub 2013 Mar 25. PubMed PMID: 23527529.
11: Lee MJ, Hatton BA, Villavicencio EH, Khanna PC, Friedman SD, Ditzler S, Pullar B, Robison K, White KF, Tunkey C, LeBlanc M, Randolph-Habecker J, Knoblaugh SE, Hansen S, Richards A, Wainwright BJ, McGovern K, Olson JM. Hedgehog pathway inhibitor saridegib (IPI-926) increases lifespan in a mouse medulloblastoma model. Proc Natl Acad Sci U S A. 2012 May 15;109(20):7859-64. doi: 10.1073/pnas.1114718109. Epub 2012 May 1. PubMed PMID: 22550175; PubMed Central PMCID: PMC3356655.
