3D Mol Similar

Fingolimod hydrochloride

: Iupac Name：2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol;hydrochloride; CAS No.: 162359-56-0; Molecular Weight：343.936; Modify Date.: 2022-11-22 21:49; Introduction: Approved by the U.S. FDA in September 2010, fingolimod (also referredto as FTY720) is the first approved oral therapy for the relapsing-remittingform ofmultiple sclerosis (RRMS). Because of fingolimod’s structuralresemblance to sphingosine, a metabolite of sphingolipids that constitutesthe cell membrane of all eukaryotic cells, it was hypothesized thatfingolimod may be affecting sphingolipid metabolism in cells. A series ofelegant in vitro and in vivo studies confirmed that fingolimod isconverted to (S)-fingolimod phosphate primarily by sphingosine kinase-2 and that (S)-fingolimod phosphate mediates multiple biological processesby binding to novel GPCR’s referred to as sphingosine-1-phosphate (S1P)receptors. S1P receptors are divided into five subtypes, S1P1–5, which havevarying tissue and cellular distribution. S1P1–3 receptors are ubiquitouslyexpressed in the immune, cardiovascular, and central nervous systems, S1P4is restricted to the hematopoietic system, and S1P5 is mostly localized in thewhite matter of CNS. S1P1–3 receptors play important roles in endothelialbarrier function, maintaining vascular tone, regulating heart rate and allowingfor lymphocyte egress fromsecondary lymphoid organs. The functionalrole of S1P4 is unknown,while the S1P5 receptor is thought to be involved innatural killer cell trafficking and oligodendrocyte function. View more+

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1. Names and Identifiers

: 1.1 Name; Fingolimod hydrochloride; 1.2 Synonyms; 1,3-Propanediol, 2-amino-2-[2-(4-octylphenyl)ethyl]-, hydrochloride (1:1) 2-amino-2-(2-(4-octylphenyl)ethyl)propane-1,3-diol hydrochloride 2-Amino-2-(4-octylphenethyl)propane-1,3-diol hydrochloride 2-Amino-2-[2-(4-n-octylphenyl)ethyl]propane-1,3-diol Hydrochloride 2-Amino-2-[2-(4-octylphényl)éthyl]-1,3-propanediol chlorhydrate 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol hydrochloride 2-Amino-2-[2-(4-octylphenyl)ethyl]-1,3-propandiolhydrochlorid 2-Amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol hydrochloride 2-Amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol hydrochloride (1:1) 2-AMINO-2-[2-(4-OCTYLPHENYL)ETHYL]-1,3-PROPANEDIOL, HYDROCHLORIDE 2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride 2-Amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol hydrochloride (1:1) 2-Amino-2-[2-(4-octyl-phenyl)-ethyl]-propane-1,3-diol hydrochloride Fingolimod hydrochloride Fin Fingolimod (FTY720) hydrochloride Fingolimod (hydrochloride) Fingolimod HCl FTY720 FTY720 Hydrochloride limod hydrochloride MFCD00939512; View all

1.3 CAS No.: 162359-56-0

1.4 CID: 107969

1.5 EINECS(EC#): 1308068-626-2

1.6 Molecular Formula: C19H34ClNO2 (isomer)

1.7 Inchi: InChI=1S/C19H33NO2.ClH/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-22;/h9-12,21-22H,2-8,13-16,20H2,1H3;1H

1.8 InChIkey: SWZTYAVBMYWFGS-UHFFFAOYSA-N

1.9 Canonical Smiles: CCCCCCCCC1=CC=C(C=C1)CCC(CO)(CO)N.Cl

1.10 Isomers Smiles: CCCCCCCCC1=CC=C(C=C1)CCC(CO)(CO)N.Cl

2. Properties

2.1 Density: 1.016

2.1 Melting point: 102-107°C

2.1 Boiling point: 479.5°C at 760 mmHg

2.1 Refractive index: 1.531

2.1 Flash Point: 243.8°C

2.1 Precise Quality: 343.22800

2.1 PSA: 66.48000

2.1 logP: 4.70660

2.1 Solubility: water: soluble10mg/mL, clear

2.2 Appearance: white to beige

2.3 Storage: -20°C Freezer

2.4 Chemical Properties: White Solid

2.5 Color/Form: Powder

2.6 Water Solubility: water: soluble10mg/mL, clear

2.7 StorageTemp: -20°C

3. Use and Manufacturing

3.1 Definition: ChEBI: The hydrochloride salt of 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol (fingolimod).

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 70 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 70 companies. For more detailed information, please visit ECHA C&L website

Of the 8 notification(s) provided by 69 of 70 companies with hazard statement code(s):

H315 (84.06%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (85.51%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (84.06%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
H361 (11.59%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H362 (10.14%): May cause harm to breast-fed children [Reproductive toxicity, effects on or via lactation]
H412 (84.06%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P260, P261, P263, P264, P270, P271, P273, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501; View all

3.3 Usage: A derivative of ISP-1 (myriocin), a fungal metabolite of the Chinese herb Iscaria sinclarii as well as a structural analogue of Sphingosine. It is a novel immune modulator that prolongs allograft transplant survival in numberour models by inhibitin

4. Safety and Handling

4.1 Symbol: GHS07;

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: 36/37/38-52/53

4.1 Safety Statements: 26-61

4.1 Hazard Declaration: H315; H319; H335; H412

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261; P273; P305 + P351 + P338

4.1 WGK Germany: 3

4.1 RTECS: TY3130000

4.1 Specification: ? 1,3-Propanediol,2-amino-2-[2-(4-octylphenyl)ethyl]-, hydrochloride (1:1) , its cas register number is 162359-56-0. It also can be called?2-Amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride ; FTY-720 ; FTY720 ; Fingolimod HCl ;
?Fingolimod hydrochloride ; UNII-G926EC510T . 1,3-Propanediol,2-amino-2-[2-(4-octylphenyl)ethyl]-, hydrochloride (1:1) (CAS NO.162359-56-0) is a?white Solid.

4.2 Toxicity: LD50 orally in rats: 300-600 mg/kg (Troncoso)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation H412 Harmful to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P273 Avoid release to the environment.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Other Information

7.0 Merck: 14,4083

7.1 Oral drug for the treatment of multiple sclerosis: Fingolimod hydrochloride is the first oral drug for the treatment of multiple sclerosis. It is successfully developed by the pharmaceutical company Novartis, and it has been approved for marketing by the US Food and Drug Administration (FDA). The recommended dose is 0.5mg once a day for oral administration.
Multiple sclerosis is a debilitating neurological disease that can cause the patient to lose a sense of balance, appear muscle spasms and other movement disorders. The disease has been treated with injectable drugs. This kind of medication brought great inconvenience to patients.
Fingolimod is a sphingosine-l-phosphate (S1PR) receptor modulator. After phosphorylation, It is bound to s1P receptor that is on the surface of lymphocyte, which will change lymphocyte migration, and promote cells into the lymphatic tissue, and prevent lymphocytes from leaving the lymphoid tissue and get into the graft. Thereby, it will prevent these cells from infiltrating the central nervous system (CNS), which achieves the effect of immunosuppression. According to the drug's introduction, drugmaker Novartis said that this process of pharmacological effects is reversible. If medication is stopped, the level of lymphocytes in circulating system will return to normal.; View all

7.2 Chemical Properties: White Solid

7.3 Uses: A derivative of ISP-1 (myriocin), a fungal metabolite of the Chinese herb Iscaria sinclarii as well as a structural analogue of Sphingosine. It is a novel immune modulator that prolongs allograft transplant survival in numberour models by inhibitin

7.4 Uses: A derivative of ISP-1 (myriocin), a fungal metabolite of the Chinese herb Iscaria sinclarii as well as a structural analogue of Sphingosine. t is a novel immune modulator that prolongs allograft transplant survival in numberour models by inhibiting lymphocyte emigration from lymphoid organs. Reported to be phosphorylated by sphingosine kinase to FTY720-P, which has been shown to potently stimulate GTPgS binding activity in S1P-transfected CHO cells (EC50 = 210 pM, 4.9 nM, 4.3 nM, and 1 nM for S1P1, S1P3, S1P4 and S1P5, respectively).

7.5 Target: Value

7.6 S1P receptor (K562, NK cells ): 0.033 nM

7.7 Description: Approved by the U.S. FDA in September 2010, fingolimod (also referred to as FTY720) is the first approved oral therapy for the relapsing-remitting form ofmultiple sclerosis (RRMS). Because of fingolimod’s structural resemblance to sphingosine, a metabolite of sphingolipids that constitutes the cell membrane of all eukaryotic cells, it was hypothesized that fingolimod may be affecting sphingolipid metabolism in cells. A series of elegant in vitro and in vivo studies confirmed that fingolimod is converted to (S)-fingolimod phosphate primarily by sphingosine kinase- 2 and that (S)-fingolimod phosphate mediates multiple biological processes by binding to novel GPCR’s referred to as sphingosine-1-phosphate (S1P) receptors. S1P receptors are divided into five subtypes, S1P_1–5, which have varying tissue and cellular distribution. S1P_1–3 receptors are ubiquitously expressed in the immune, cardiovascular, and central nervous systems, S1P4 is restricted to the hematopoietic system, and S1P₅ is mostly localized in the white matter of CNS. S1P_1–3 receptors play important roles in endothelial barrier function, maintaining vascular tone, regulating heart rate and allowing for lymphocyte egress fromsecondary lymphoid organs. The functional role of S1P₄ is unknown,while the S1P5 receptor is thought to be involved in natural killer cell trafficking and oligodendrocyte function.; View all

7.8 Originator: Yoshitomi Pharmaceutical Industries (now Mitsubishi Tanabe Pharma) (United States)

7.9 Uses: Fingolimod Hydrochloride is a derivative of ISP-1 (myriocin), a fungal metabolite of the Chinese herb Iscaria sinclarii as well as a structural analogue of Sphingosine. Fingolimod is a novel immune modulator that prolongs allograft transplant survival in numerous models by inhibiting lymphocyte emigration from lymphoid organs. Fingolimod is reported to be phosphorylated by sphingosine kinase to FTY720-P, which has been shown to potently stimulate GTPgS binding activity in S1P-transfected CHO cells (EC50 = 210 pM, 4.9 nM, 4.3 nM, and 1 nM for S1P1, S1P3, S1P4 and S1P5, respectively).

7.10 Brand name: Gilenya

7.11 Biochem/physiol Actions: FTY720 is an immunomodulating drug and sphingosine 1-phosphate (S1P) receptor modulator. Phosphorylation of FTY270 by sphingosine kinase causes S1P1R internalization, which sequesters lymphocytes in lymph nodes, preventing them from taking part in an autoimmune response. Clinically, it has been approved for the treatment of multiple sclerosis (MS). It has also been shown to block and reverse paclitaxel-induced chemotherapy induced peripheral neuropathy (CIPN) through S1PR inhibition as well as inhibit the activity of histone deacetylases in the hippocampus of mouse brains, thereby modulating memory.

7.12 Clinical Use: Fingolimod hydrochloride is an immunosuppressive drug developed by Novartis and approved in the U.S., Europe, and Australia in 2010 for the treatment of multiple sclerosis. The structure of fingolimod derives from the naturally-occurring myriocin (ISP-1) metabolite of the fungus I. sinclairii and the aminoalcohol functionality within the drug possesses structural similarity to the sphingosine family of natural products.

7.13 Chemical Synthesis: Although several convenient preparations of fingolimod (FTY720) have been reported in the literature, the route most closely resembling the process-scale approach is described in the scheme. Friedel-Crafts acylation of commercial toluene derivative 89 with bromoacetyl chloride followed by ethoxide-mediated N-acylated aminomalonate (91) attack onto the resulting -bromoketone 90 gave rise to ketoamide 92 in good overall yield. Next, separate hydride reduction protocols were employed to furnish diol 93. Presumably, triethylsilyl hydride reduced the ketone and both ethyl esters within 92 to the corresponding diacid, which then underwent lithium aluminum hydride treatment to arrive at diol 93. Careful attention to stoichiometry was required to avoid over reduction of amide 93, which was critical to achieve high-yielding (76%) salt formation of fingolimod HCl (VI) through the use of 6 N ethanolic hydrochloric acid.; View all

7.14 Mesh: Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)|Agents that affect the function of G-protein coupled SPHINGOSINE 1-PHOSPHATE RECEPTORS. Their binding to the receptors blocks lymphocyte migration and are often used as IMMUNOSUPPRESSANTS. (See all compounds classified as Sphingosine 1 Phosphate Receptor Modulators.)

7.15 Mesh Entry Terms: 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride

7.16 Use Classification: Human drugs -> Gilenya -> EMA Drug Category|Immunosuppressants -> Human pharmacotherapeutic group|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

7.17 Uses: Oral medicine for the treatment of multiple sclerosis

7.18 Uses: FTY720 is a derivative of ISP-1 (myriocin), a fungal metabolite of the Chinese herb Iscaria sinclarii as well as a structural analogue of Sphingosine. FTY720 is a novel immune modulator that prolong s allograft transplant survival in numberour models by inhibiting lymphocyte emigration from lymphoid organs. FTY720 us reported to be phosphorylated by sphingosine kinase to FTY720-P, which has been shown to potently stimulate GTPgS binding activity in S1P-transfected CHO cells (EC50 = 210 pM, 4.9 nM, 4.3 nM, and 1 nM for S1P1, S1P3, S1P4 and S1P5, respectively).

7.19 Uses: A cell-permeable aminopropanediol immunosuppressive agent that displays lymphocyte sequestration properties.

7.20 Definition: ChEBI: The hydrochloride salt of 2-amino-2-[2-(4-octylphenyl) ethyl]-1,3-propanediol (fingolimod).

8. Computational chemical data

Molecular Weight: 343.936g/mol
Molecular Formula: C₁₉H₃₄ClNO₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 343.2278070
Monoisotopic Mass: 343.2278070
Complexity: 258
Rotatable Bond Count: 12
Hydrogen Bond Donor Count: 4
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 66.5
Heavy Atom Count: 23
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADcfB6MAAEAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgAQCAAADIihmAIyAIBAAgCAAiBCAAACAAAgAAAIiAAAAIgKMCKAkRCAYAAlkAAIiAeQwPAOQAAAAAAAAACAAAAAAAAAAAAAAAAAAA==

9. Question & Answer

How is Fingolimod Hydrochloride Synthesized? Mar 19 2023
Fingolimod hydrochloride is a novel immunosuppressant that can be administered orally for the treatment of relapsing-remitting multiple sclerosis. It has two main mechanisms of action: promoting the m..
What is Fingolimod hydrochloride and how should it be taken? Jul 24 2021
Fingolimod hydrochloride, a relatively unknown product to many, is commonly used as an immunosuppressant and has a wide range of clinical applications. However, there is still limited understanding a..

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Pharmaceutical intermediates Fingolimod hydrochloride cas 162359-56-0