60414-06-4, Amiprilose, CAS: 60414-06-4

60414-06-4, Amiprilose,
CAS: 60414-06-4
C14H27NO6 / 305.37

Amiprilose , 氨普立糖

Amiprilose is a nonsteroidal anti-inflammatory drug that inhibits the production of IL-2. Amiprilose has been shown to inhibit IL-17a, which is an inflammatory cytokine, in skin cells and mononuclear cells. It also inhibits cell proliferation by binding to the il-2 receptor on muscle cells. Amiprilose has been shown to be effective as a pharmacological agent for treating autoimmune diseases such as rheumatoid arthritis and psoriasis.

Title: Amiprilose

CAS Registry Number: 60414-06-4

CAS Name: 3-O-[3-(Dimethylamino)propyl]-1,2-O-(1-methylethylidene)-a-D-glucofuranose

Additional Names: 1,2-O-isopropylidene-3-O-[3¢-(N,N-dimethylamino)propyl]-a-D-glucofuranose

Molecular Formula: C14H27NO6

Molecular Weight: 305.37

Percent Composition: C 55.06%, H 8.91%, N 4.59%, O 31.44%

Literature References: Synthetic, substituted monosaccharide with immunomodulatory activity. Prepn: BE 823313; P. Gordon, US 3939146 (1975, 1976 both to Strategic Med. Res.); E. R. Garrett et al., J. Pharm. Sci. 71, 387 (1982). Absolute configuration: R. J. Linhardt et al., ibid. 79, 158 (1990). HPLC determn in plasma: S. T. Wu et al., J. Chromatogr. B 692, 149 (1997). Clinical pharmacokinetics: E. R. Garrett et al., J. Pharmacokinet. Biopharm. 10, 247 (1982). Clinical trial in rheumatoid arthritis: W. G. Riskin et al., Ann. Intern. Med. 111, 455 (1989). Review of immunoregulatory effects: D. M. Chang, Immunopharmacol. Immunotoxicol. 17, 437-450 (1995).

Properties: Colorless, viscous oil. n25 1.4687.

Index of refraction: n25 1.4687

Derivative Type: Hydrochloride

CAS Registry Number: 60414-06-4

Manufacturers' Codes: SM-1213

Trademarks: Therafectin (BLS)

Molecular Formula: C14H27NO6.HCl

Molecular Weight: 341.83

Percent Composition: C 49.19%, H 8.26%, N 4.10%, O 28.08%, Cl 10.37%

Properties: Crystals from methanol, mp 181-183°. Sol in water, methanol, hot ethanol.

Melting point: mp 181-183°

Therap-Cat: Immunomodulator; anti-inflammatory.

Keywords: Immunomodulator.

CAS Number	60414-06-4
Product Name	Amiprilose
IUPAC Name	(1R)-1-[(3aR,5R,6S,6aR)-6-[3-(dimethylamino)propoxy]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol;hydrochloride
Molecular Formula	C14H27NO6
Molecular Weight	305.37 g/mol
InChI	InChI=1S/C14H27NO6.ClH/c1-14(2)20-12-11(18-7-5-6-15(3)4)10(9(17)8-16)19-13(12)21-14;/h9-13,16-17H,5-8H2,1-4H3;1H/t9-,10-,11+,12-,13-;/m1./s1
InChI Key	YXBQLONCIPUQKO-UJPOAAIJSA-N
SMILES	CC1(OC2C(C(OC2O1)C(CO)O)OCCCN(C)C)C.Cl
Solubility	Soluble in DMSO
Synonyms	1,2-O-isopropylidene-3-O-3'-(N',N'-dimethylamino-N-propyl)-D-glucofuranose, amiprilose, amiprilose hydrochloride, amprilose, SM 1213, SM-1213, Therafectin
Canonical SMILES	CC1(OC2C(C(OC2O1)C(CO)O)OCCCN(C)C)C
Isomeric SMILES	CC1(O[C@@H]2[C@H]([C@H](O[C@@H]2O1)[C@@H](CO)O)OCCCN(C)C)C

COA:

Name: Amiprilose CAS: 60414-06-4 M.F.: C₁₄H₂₇NO6 M.W.: 305.37

Items	Standards	Results
Appearance	Yellowish or colorless viscous oil.	Positive
NMR and MS	Should comply	Complies
Identification	IR and TLC	Positive
Water Content	0.5%	0.12%
Residue On Ignition	Max. 0.2%	0.02%
Heavy metal	Max. 20ppm	Complies
TLC	Should be one spot	one spot
Assay (HPLC)	Min. 98%	98.5%