Cyclopamine CAS 4449-51-8 Steroidal Jerveratrum Alkaloid from Veratrum californicum
Product Identification
| Item | Detail |
|---|---|
| Synonyms | Cyclopamine; 11-Deoxojervine; Cyclopia alkaloid; HSDB-3505 |
| CAS RN | 4449-51-8 |
| Molecular Formula | C₂₇H₄₁NO₂ |
| MW | 411.62 |
| Botanical (source) | Veratrum californicumJeps. (Melanthiaceae, corn lily) — NOT V. nigrum(TCM Li-Lu, different alkaloids) |
| Related in plant | Cycloposine (= cyclopamine-3-O-glucoside, precursor in plant, more water-soluble, can co-occur in crude) |
| HS Code (ref) | 2939 / 2942 (alkaloid derivative) |
| RTECS | GY0750000 (Teratogenic / Carcinogenic D) |
| Clinical successors | Vismodegib (GDC-0449) / Sonidegib (LDE225) — synthetic Smo inhibitors inspired by cyclopamine |
Description
Cyclopamine is the prototype natural Smo antagonist — the molecule that definedHedgehog signaling in teratology and launchedthe Hh/Smo oncology drug class (Vismodegib/Sonidegib).
Three commercial buckets (all B2B R&D, zero DTC):
- Hh/Smo Probe R&D (main): Pure cyclopamine ≥98% as natural Smo antagonist reference — (a) Hh pathway assays (Shh-light2, PTCH reporter), (b) BCC / medulloblastoma / PDAC cell lines (SMOhigh vs SMOlow differential, e.g. L3.6pl vs Panc-1), (c) comparator to synthetic Smo inhibitors (Vismodegib/Sonidegib/PF-5274857) in MOA studies. Inner-link: if Taima stocks Vismodegib/Sonidegib intermediates (unlikely, pure pharma API), else “cyclopamine = natural probe, Vismodegib = clinical synthetic” narrative. Search: “cyclopamine Hh Smo IC50”, “cyclopamine BCC PDAC”
- PROTAC / Chimer Ligand (emerging): Cyclopamine’s Smo-binding pocket (transmembrane helices, distinct from Vismodegib’s binding site — Chen 2002 PNAS notes cyclopamine vs Vismodegib bind differently) makes it a tool ligand for Hh-PROTAC (Smo degrader concepts 2023–2025 lit). Small but growing R&D PO: CROs building “Hh degrader toolkit” need cyclopamine 98%+ as warhead candidate. Taima: cyclopamine ≥98% small-pack (1/5/10/25 mg) for PROTAC screening.
- Teratology / Developmental Biology Teaching: Cyclopia sheep story = textbook case (Hh signaling, teratogen screening, FDA teratogen assessment workflows). University biology/dev-bio depts + tox-screening CROs. Not high-volume but steady reference-standard PO.
Applications
Hh/Smo Natural Probe R&D – Cyclopamine ≥98% (IC₅₀ TM3Hh12 ~46 nM, [³H]Hh-Ag CHO-K1 ~280 nM); BCC / medulloblastoma / PDAC SMOhigh models; comparator to Vismodegib/Sonidegib; “natural Smo antagonist” reference (vs synthetic successors); Tomatidine as negative control lit-pair
PROTAC / Chimer Ligand (emerging) – Cyclopamine Smo-binding warhead candidate for Hh-degrader toolkit; CRO PROTAC library screening; differentiates from Vismodegib-binding site (literature notes distinct pockets) → “dual-warhead PROTAC” R&D angle
Teratology / Dev-Bio Teaching – Cyclopia sheep case (1950s Idaho V. californicum); Hh signaling embryology; tox-screening CRO reference; university procurement
Reference Standard (≥98%) – for V. californicumcrude P.E. QC (cyclopamine + cycloposine dual-peak optional), Hh assay, PROTAC screen; pack size 1 mg–100 mg (high-ticket R&D only, no kg bulk — teratogenic D)
